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Seller is motivated! Welcome to Bay Oaks Estates—your quiet Florida retreat! This 3-bed, 2-bath + den home offers a true indoor-outdoor lifestyle with a private pool featuring a beautiful ocean-inspired mosaic. With no houses in front and none behind, you’ll appreciate the peace and privacy. Enjoy cozy winter nights with your wood-burning fireplace, and peace of mind with a new roof (2022) and newer water heater. You’re only 10 minutes from Siesta Key and Nokomis Beach and just steps from the Legacy Trail for biking and jogging. Shopping and dining are all close by as well! If you’ve been searching for a spacious pool home in a secluded neighborhood—this one checks all the boxes.

3 Beds ⋅ 2 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34229 Zip Code

Seller is motivated! Welcome to Bay Oaks Estates—your quiet Florida retreat! This 3-bed, 2-bath + den home offers a true indoor-outdoor lifestyle with a private pool featuring a beautiful ocean-inspired mosaic. With no houses in front and none behind, you’ll appreciate the peace and privacy. Enjoy cozy winter nights with your wood-burning fireplace, and peace of mind with a new roof (2022) and newer water heater. You’re only 10 minutes from Siesta Key and Nokomis Beach and just steps from the Legacy Trail for biking and jogging. Shopping and dining are all close by as well! If you’ve been searching for a spacious pool home in a secluded neighborhood—this one checks all the boxes.

566 Oak Bay Drive, Osprey

$520,000

This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm with elegant living. The desirable Willow floor plan with a sparkling pool and lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases meticulous attention to detail with features such as high ceilings, architectural details like arches and insets, sconce lighting, crown molding, tray ceilings and shutters. The layout promotes a refined atmosphere where the subtle color palette, which is newly painted, fosters a seamless transition between indoor and outdoor spaces, ideal for enjoying Florida's unique climate. Stylish den at front of the home while the living and dining areas flow into a spacious family room adjacent to the open kitchen. The kitchen is functional and stylish, equipped with solid wood cabinets, granite, ample storage options and a breakfast room with tranquil pool views. Natural gas cooking for the chef of the residence. A practical entry from the garage leads to a large laundry room that includes additional storage. The owner’s suite is a retreat, featuring dual closets, a separate linen closet, a luxurious walk-in shower, glass brick accents, dual sinks with separate vanities and a relaxing soaker tub. Convenient direct pool access as well. Guests will appreciate the two-bedroom suite with its dedicated hallway and bath, which allows for privacy from the owner’s suite. The community boasts low fees that cover ground maintenance, irrigation, access to the pool and spa, gym facilities, pickleball courts, and high-speed internet and DirecTV streaming. Families will benefit from the nearby top-rated Pine View School, while the Intracoastal Waterway, beautiful beaches, Legacy Trail, shopping, dining, grocery stores, coffee shops and vibrant tiki bars are all just minutes away. New water heater in 2025, Interior freshly painted in 2025, storm shutters on lanai in 2020 and accordion storm shutter on front door.

3 Beds ⋅ 2 Baths ⋅ Willowbend SubDv. ⋅ 34229 Zip Code

This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm with elegant living. The desirable Willow floor plan with a sparkling pool and lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases meticulous attention to detail with features such as high ceilings, architectural details like arches and insets, sconce lighting, crown molding, tray ceilings and shutters. The layout promotes a refined atmosphere where the subtle color palette, which is newly painted, fosters a seamless transition between indoor and outdoor spaces, ideal for enjoying Florida's unique climate. Stylish den at front of the home while the living and dining areas flow into a spacious family room adjacent to the open kitchen. The kitchen is functional and stylish, equipped with solid wood cabinets, granite, ample storage options and a breakfast room with tranquil pool views. Natural gas cooking for the chef of the residence. A practical entry from the garage leads to a large laundry room that includes additional storage. The owner’s suite is a retreat, featuring dual closets, a separate linen closet, a luxurious walk-in shower, glass brick accents, dual sinks with separate vanities and a relaxing soaker tub. Convenient direct pool access as well. Guests will appreciate the two-bedroom suite with its dedicated hallway and bath, which allows for privacy from the owner’s suite. The community boasts low fees that cover ground maintenance, irrigation, access to the pool and spa, gym facilities, pickleball courts, and high-speed internet and DirecTV streaming. Families will benefit from the nearby top-rated Pine View School, while the Intracoastal Waterway, beautiful beaches, Legacy Trail, shopping, dining, grocery stores, coffee shops and vibrant tiki bars are all just minutes away. New water heater in 2025, Interior freshly painted in 2025, storm shutters on lanai in 2020 and accordion storm shutter on front door.

1337 Copperwood Drive, Osprey

$520,000

Florida’s perfect floor plan! Built in 2002, this home features soaring ceilings and a thoughtfully designed layout for both living and entertaining. Large and bright great room flows seamlessly into a formal dining room, a spacious eat-in kitchen, and a versatile office. The serene primary suite is complemented by two generously sized guest bedrooms. Recent updates include a 2025 tankless water heater, a newer roof, AC, and Hurricane impact windows. Within a brick-paver lanai that enjoys southern exposure for abundant natural light. The lush quarter-acre lot ensures privacy, while the oversized 2-car garage provides ample parking and storage. Ideally situated in desirable flood zone X. This home provides the perfect combination of comfort, style, and convenience.

3 Beds ⋅ 2 Baths ⋅ Rivendell SubDv. ⋅ 34229 Zip Code

Florida’s perfect floor plan! Built in 2002, this home features soaring ceilings and a thoughtfully designed layout for both living and entertaining. Large and bright great room flows seamlessly into a formal dining room, a spacious eat-in kitchen, and a versatile office. The serene primary suite is complemented by two generously sized guest bedrooms. Recent updates include a 2025 tankless water heater, a newer roof, AC, and Hurricane impact windows. Within a brick-paver lanai that enjoys southern exposure for abundant natural light. The lush quarter-acre lot ensures privacy, while the oversized 2-car garage provides ample parking and storage. Ideally situated in desirable flood zone X. This home provides the perfect combination of comfort, style, and convenience.

708 Anna Hope Lane, Osprey

$520,000

Prepare to be impressed as you enter this bright and spacious maintenance-free townhome with soaring ceilings, an abundance of natural light, and surrounded by nature in a wooded setting. Nestled near Casey Key, this coveted West of the Trail subdivision with only 44 single-family, attached homes, is walking distance to Casey Key, Blackburn Point Marina, and Blackburn Point Park, which features a boat ramp, canoe/kayak launch and fishing pier. “BPW” is perfect for condo owners eager to move up to better construction & space for guests & cars, as well as for typical single-family homeowners ready for a maintenance free lifestyle. HOA fees include exterior building (including roof!), grounds maintenance, exterior insurance, and a membership to Pine Run amenities. You will enjoy the spacious great room floor plan with vaulted ceilings, hardwood flooring, a wood burning fireplace, and glass solarium with screens off the main living space. It is truly magical! Also on the first level is one of two primary suites with a generously sized ensuite bath and an entire wall of closets, another full bath which adjoins the den/ 4th bedroom. The spacious dine in kitchen with 2 pantries, laundry room and two car garage, with built in storage also reside on the first level. The staircase leads you to the upper-level primary suite, boasting spacious closets, high ceilings, a connected, full bath, and balcony with an amazing view of your beautiful landscaping and a protected preserve area. The second floor also contains a large, multi-use loft space and bonus room, either of which can be used as the 3rd bedroom. It is all about flexibility and whether you want to use the spaces for guest accommodation, an exercise room, artist’s studio or storage. There is tons of storage throughout, electric and hand crank hurricane shutters and shared walls are solid-poured concrete block for sound-proof privacy. Lovely backyard with paved patio, walking path over bridge to small pond (Association green space) and more green space across the street w/pond and fountain. The community is proximate to Nokomis, Venice and Siesta Key beaches, restaurants, shopping and Oscar Scherer State Park, and shares neighboring Pine Run The community is proximate to Nokomis, Venice and siesta Key beaches, restaurants, shopping and Oscar Scherer State Park, and shares Pine Run's many amenities, including two heated pools, tennis and pickleball courts, fitness center and clubhouse.

4 Beds ⋅ 3 Baths ⋅ Blackburn Point Woods SubDv. ⋅ 34229 Zip Code

Prepare to be impressed as you enter this bright and spacious maintenance-free townhome with soaring ceilings, an abundance of natural light, and surrounded by nature in a wooded setting. Nestled near Casey Key, this coveted West of the Trail subdivision with only 44 single-family, attached homes, is walking distance to Casey Key, Blackburn Point Marina, and Blackburn Point Park, which features a boat ramp, canoe/kayak launch and fishing pier. “BPW” is perfect for condo owners eager to move up to better construction & space for guests & cars, as well as for typical single-family homeowners ready for a maintenance free lifestyle. HOA fees include exterior building (including roof!), grounds maintenance, exterior insurance, and a membership to Pine Run amenities. You will enjoy the spacious great room floor plan with vaulted ceilings, hardwood flooring, a wood burning fireplace, and glass solarium with screens off the main living space. It is truly magical! Also on the first level is one of two primary suites with a generously sized ensuite bath and an entire wall of closets, another full bath which adjoins the den/ 4th bedroom. The spacious dine in kitchen with 2 pantries, laundry room and two car garage, with built in storage also reside on the first level. The staircase leads you to the upper-level primary suite, boasting spacious closets, high ceilings, a connected, full bath, and balcony with an amazing view of your beautiful landscaping and a protected preserve area. The second floor also contains a large, multi-use loft space and bonus room, either of which can be used as the 3rd bedroom. It is all about flexibility and whether you want to use the spaces for guest accommodation, an exercise room, artist’s studio or storage. There is tons of storage throughout, electric and hand crank hurricane shutters and shared walls are solid-poured concrete block for sound-proof privacy. Lovely backyard with paved patio, walking path over bridge to small pond (Association green space) and more green space across the street w/pond and fountain. The community is proximate to Nokomis, Venice and Siesta Key beaches, restaurants, shopping and Oscar Scherer State Park, and shares neighboring Pine Run The community is proximate to Nokomis, Venice and siesta Key beaches, restaurants, shopping and Oscar Scherer State Park, and shares Pine Run's many amenities, including two heated pools, tennis and pickleball courts, fitness center and clubhouse.

447 Oak Point Road, Osprey

$515,000

Immaculate and truly move-in ready! This turnkey-furnished, spacious 2-bedroom + den, 2-bath home offers an open floor plan with gorgeous wood flooring throughout the living areas and den. The kitchen features marble countertops, an oversized island, large pantry, and quality finishes, while additional highlights include crown molding, plantation shutters, a private heated pool, electric roll-down hurricane shutters for the lanai, and stored hurricane shutters conveniently kept in the garage for storm protection. Recent upgrades include a new A/C (2022), roof replaced in 2022, and a brand-new pool cage in 2024, along with a reverse-osmosis water filtration system serving the kitchen sink and refrigerator. Located in Rivendell, one of Sarasota County’s most cherished communities spanning over 400 acres of protected nature preserves, residents enjoy scenic walking and biking trails, a heated community pool, and a peaceful, park-like atmosphere. Ideally situated just 2 miles from Oscar Scherer State Park, 2.5 miles from the Legacy Trail, 5 miles to Nokomis Beach, and under 7 miles to world-famous Siesta Key Beach, the home is approximately 1.4 miles (walkable and bikeable) to Pine View School for the Gifted (grades 2–12), consistently ranked among the top public schools in the nation. With no CDD fees and a low HOA, this home offers an exceptional combination of comfort, location, and long-term value in one of Osprey’s most desirable neighborhoods.

2 Beds ⋅ 2 Baths ⋅ Rivendell SubDv. ⋅ 34229 Zip Code

Immaculate and truly move-in ready! This turnkey-furnished, spacious 2-bedroom + den, 2-bath home offers an open floor plan with gorgeous wood flooring throughout the living areas and den. The kitchen features marble countertops, an oversized island, large pantry, and quality finishes, while additional highlights include crown molding, plantation shutters, a private heated pool, electric roll-down hurricane shutters for the lanai, and stored hurricane shutters conveniently kept in the garage for storm protection. Recent upgrades include a new A/C (2022), roof replaced in 2022, and a brand-new pool cage in 2024, along with a reverse-osmosis water filtration system serving the kitchen sink and refrigerator. Located in Rivendell, one of Sarasota County’s most cherished communities spanning over 400 acres of protected nature preserves, residents enjoy scenic walking and biking trails, a heated community pool, and a peaceful, park-like atmosphere. Ideally situated just 2 miles from Oscar Scherer State Park, 2.5 miles from the Legacy Trail, 5 miles to Nokomis Beach, and under 7 miles to world-famous Siesta Key Beach, the home is approximately 1.4 miles (walkable and bikeable) to Pine View School for the Gifted (grades 2–12), consistently ranked among the top public schools in the nation. With no CDD fees and a low HOA, this home offers an exceptional combination of comfort, location, and long-term value in one of Osprey’s most desirable neighborhoods.

811 Shadow Bay Way, Osprey

$511,500

Virtually Staged. Beautiful home in the desirable Bay Oaks neighborhood, known for its winding roads, mature landscaping, and minimal traffic. Perfectly situated between The Oaks Golf Course and Stoneybrook Golf & Country Club, this home offers the lifestyle and views without the high price tag or association fees. The property welcomes you with a circular driveway, new roof (2018), fenced yard, and freshly pressure-washed exterior(2026) with updated landscaping (2026). Double French doors open to a grand foyer with soaring ceilings and immediate views of the family room, pool, and backyard, creating a Florida grand entrance. The entire interior of the home was repainted (2026). A dedicated office with French doors and a formal dining room, both overlook the front yard. The spacious primary suite features new porcelain tile flooring, two walk-in closets, and pocket sliders that open to the newly rescreened lanai (2026), perfect for enjoying stunning west coast sunsets year-round. The primary bathroom includes a new double-sink vanity, a private water closet with a pocket door, and a separate tub and shower. The kitchen offers a built-in pantry, space for a breakfast table, and uniquely angled countertops and bar that maximize outdoor views. Enjoy peekaboo views of The Oaks golf course through the third set of sliding glass doors and corner windows. The second living area continues the vaulted ceilings and is filled with southwest-facing natural light. An updated half bath with direct pool access adds convenience. A pocket door separates the split floor plan, leading to two additional bedrooms and a full bathroom with tub/shower combo, new vanity, and porcelain flooring. At the heart of the home is the covered and newly rescreened lanai. The recently refinished pool (2025) pool pump (2026) with water features, completed by award-winning Platinum Pools, create a relaxed setting. The fenced backyard offers privacy, with the option to open up more golf course views at the owner’s request (through The Oaks Club and at no additional expense). Additional features include an interior laundry room with a sink, located just off the two-car garage with refinished floors (2026), an exterior access door, and whole house replumbed (2018). This home offers a highly functional layout, with many major updates already completed for peace of mind and quick move-in, while still allowing room for your personal touch. Located just 6 miles from Siesta Key (#1 beach in America), 4 miles to Casey Key, and close to multiple local marinas, golf courses, and the Legacy Trail. Also conveniently located near major shopping, including Costco, grocery stores, pharmacies, pet stores, restaurants, Starbucks, and Nordstrom Rack, as well as an upcoming development featuring Whole Foods, Chipotle, Sprouts, and more. This is a home you need to experience in person. Schedule your private showing today!

3 Beds ⋅ 3 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34229 Zip Code

Virtually Staged. Beautiful home in the desirable Bay Oaks neighborhood, known for its winding roads, mature landscaping, and minimal traffic. Perfectly situated between The Oaks Golf Course and Stoneybrook Golf & Country Club, this home offers the lifestyle and views without the high price tag or association fees. The property welcomes you with a circular driveway, new roof (2018), fenced yard, and freshly pressure-washed exterior(2026) with updated landscaping (2026). Double French doors open to a grand foyer with soaring ceilings and immediate views of the family room, pool, and backyard, creating a Florida grand entrance. The entire interior of the home was repainted (2026). A dedicated office with French doors and a formal dining room, both overlook the front yard. The spacious primary suite features new porcelain tile flooring, two walk-in closets, and pocket sliders that open to the newly rescreened lanai (2026), perfect for enjoying stunning west coast sunsets year-round. The primary bathroom includes a new double-sink vanity, a private water closet with a pocket door, and a separate tub and shower. The kitchen offers a built-in pantry, space for a breakfast table, and uniquely angled countertops and bar that maximize outdoor views. Enjoy peekaboo views of The Oaks golf course through the third set of sliding glass doors and corner windows. The second living area continues the vaulted ceilings and is filled with southwest-facing natural light. An updated half bath with direct pool access adds convenience. A pocket door separates the split floor plan, leading to two additional bedrooms and a full bathroom with tub/shower combo, new vanity, and porcelain flooring. At the heart of the home is the covered and newly rescreened lanai. The recently refinished pool (2025) pool pump (2026) with water features, completed by award-winning Platinum Pools, create a relaxed setting. The fenced backyard offers privacy, with the option to open up more golf course views at the owner’s request (through The Oaks Club and at no additional expense). Additional features include an interior laundry room with a sink, located just off the two-car garage with refinished floors (2026), an exterior access door, and whole house replumbed (2018). This home offers a highly functional layout, with many major updates already completed for peace of mind and quick move-in, while still allowing room for your personal touch. Located just 6 miles from Siesta Key (#1 beach in America), 4 miles to Casey Key, and close to multiple local marinas, golf courses, and the Legacy Trail. Also conveniently located near major shopping, including Costco, grocery stores, pharmacies, pet stores, restaurants, Starbucks, and Nordstrom Rack, as well as an upcoming development featuring Whole Foods, Chipotle, Sprouts, and more. This is a home you need to experience in person. Schedule your private showing today!

562 Oak Bay Drive, Osprey

$510,000

This end unit in The Meridian has been thoughtfully updated and carefully maintained. Offering 3 bedrooms and 3 full baths, it also has a dedicated study/den with pocket doors. Light and bright, this 2,594 square foot residence is spacious and offers room for comfortable and elegant living. The large master suite has a large bathroom with a walk-in shower, dual vanities and sinks and tons of cabinetry. The southern facing screened balcony, with electric Kelvin hurricane shutters, affords a lovely view of the Preserve. This unit has 2 parking spaces. Don’t pass up on the opportunity to live a carefree, country club lifestyle. The unit is ready for you to come and make it your own. Residents of The Oaks have use of their own pool, spa and workout room, and can take advantage of all The Oaks Club has to offer with 2 championship golf courses, a world-class tennis facility, a state-of-the art wellness center and a wide variety of club amenities, including dining options and social offerings. Club membership is required with homeownership.

3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code

This end unit in The Meridian has been thoughtfully updated and carefully maintained. Offering 3 bedrooms and 3 full baths, it also has a dedicated study/den with pocket doors. Light and bright, this 2,594 square foot residence is spacious and offers room for comfortable and elegant living. The large master suite has a large bathroom with a walk-in shower, dual vanities and sinks and tons of cabinetry. The southern facing screened balcony, with electric Kelvin hurricane shutters, affords a lovely view of the Preserve. This unit has 2 parking spaces. Don’t pass up on the opportunity to live a carefree, country club lifestyle. The unit is ready for you to come and make it your own. Residents of The Oaks have use of their own pool, spa and workout room, and can take advantage of all The Oaks Club has to offer with 2 championship golf courses, a world-class tennis facility, a state-of-the art wellness center and a wide variety of club amenities, including dining options and social offerings. Club membership is required with homeownership.

393 N Point Road Unit 301, Osprey

$505,025

Enjoy Maintenance Free Living in Beautiful Willowbend - 3-Bedroom, 2-Bath, 2-Car Garage, Pool Home ! LEE WETHERINGTON Opal Model ~Featuring Open Plan Very Private Pool on the Screen Enclosed Deck and Lanai. Complete w/ Extensive Upgrades Including: Crown Molding & Tray Ceilings in the Great Room w/ Special Lighting Features, also a Tray Ceiling in a Spacious Master Bedroom w/ Sitting area & 2-Walk-in Closets; Master Bathroom has Solid Surface Dual Vanities + Tub & Separate Shower. Second Bedroom has an Additional 2 foot Extension. Neutral Colors throughout with Plantation Shutters, Designer Window Treatments, 6 ceiling fans with lights, granite countertops in kitchen, Newer SS Refrigerator + SS Appliances in the Kitchen Large Pantry, Washer and Natural Gas Dryer Included- Hurricane Windows + a Generator too. Willowbend has a Beautiful Community Swimming Pool w/ Heated Spa, Fitness Center, Tennis + Basket Ball Court & Playground Area. Very Close to Pineview Top Rated "A" School! Oscar Scherer State Park is just Short Stroll or Bicycle ride down a Paved Sidewalk. Nokomis Beach on the Gulf is just a 10 minute drive away and there are Excellent Shops and Restaurants to choose from. Great location !!

3 Beds ⋅ 2 Baths ⋅ Willow Bend SubDv. ⋅ 34229 Zip Code

Enjoy Maintenance Free Living in Beautiful Willowbend - 3-Bedroom, 2-Bath, 2-Car Garage, Pool Home ! LEE WETHERINGTON Opal Model ~Featuring Open Plan Very Private Pool on the Screen Enclosed Deck and Lanai. Complete w/ Extensive Upgrades Including: Crown Molding & Tray Ceilings in the Great Room w/ Special Lighting Features, also a Tray Ceiling in a Spacious Master Bedroom w/ Sitting area & 2-Walk-in Closets; Master Bathroom has Solid Surface Dual Vanities + Tub & Separate Shower. Second Bedroom has an Additional 2 foot Extension. Neutral Colors throughout with Plantation Shutters, Designer Window Treatments, 6 ceiling fans with lights, granite countertops in kitchen, Newer SS Refrigerator + SS Appliances in the Kitchen Large Pantry, Washer and Natural Gas Dryer Included- Hurricane Windows + a Generator too. Willowbend has a Beautiful Community Swimming Pool w/ Heated Spa, Fitness Center, Tennis + Basket Ball Court & Playground Area. Very Close to Pineview Top Rated "A" School! Oscar Scherer State Park is just Short Stroll or Bicycle ride down a Paved Sidewalk. Nokomis Beach on the Gulf is just a 10 minute drive away and there are Excellent Shops and Restaurants to choose from. Great location !!

570 Crane Prairie Way, Osprey

$500,000

PRICE TO SELL. One or more photo(s) has been virtually staged. Exceptional opportunity in highly sought-after Rivendell, one of Osprey’s most desirable communities known for its scenic lakes, preserves, walking trails, and beautiful natural surroundings. Ideally located just steps from top-rated Pine View School, offering the rare convenience to walk or bike to one of Florida’s most acclaimed schools. This beautifully maintained home features a durable tile roof, tranquil lake views, and a spacious lanai overlooking the water, perfect for relaxing or entertaining. Enjoy stunning lake views from the dining room, creating a bright and inviting everyday setting. HOA maintained lawn care adds convenience and low maintenance living. The backyard is a tropical retreat with fruit trees including sugar apple, guava, and plum. Prime location near Oscar Scherer State Park, Casey Key beaches, shopping, dining, and the Legacy Trail. Rare combination of location, lifestyle, views, and school district appeal.

3 Beds ⋅ 2 Baths ⋅ Rivendell The Woodlands SubDv. ⋅ 34229 Zip Code

PRICE TO SELL. One or more photo(s) has been virtually staged. Exceptional opportunity in highly sought-after Rivendell, one of Osprey’s most desirable communities known for its scenic lakes, preserves, walking trails, and beautiful natural surroundings. Ideally located just steps from top-rated Pine View School, offering the rare convenience to walk or bike to one of Florida’s most acclaimed schools. This beautifully maintained home features a durable tile roof, tranquil lake views, and a spacious lanai overlooking the water, perfect for relaxing or entertaining. Enjoy stunning lake views from the dining room, creating a bright and inviting everyday setting. HOA maintained lawn care adds convenience and low maintenance living. The backyard is a tropical retreat with fruit trees including sugar apple, guava, and plum. Prime location near Oscar Scherer State Park, Casey Key beaches, shopping, dining, and the Legacy Trail. Rare combination of location, lifestyle, views, and school district appeal.

1361 New Forest Lane, Osprey

$500,000

Welcome to this attractive St. Charles floor plan found in the desirable Woodlands at Rivendell community! This charming home sits on a large corner lot directly across from the heated community pool and is within easy reach of the highly ranked Pine View School for the Gifted (Grades:2-12). Built in 2001, this well-maintained home features four bedrooms, or three bedrooms plus den with closet, and two full baths. The spacious great room includes living and dining areas, elegant crown moldings, tray ceilings, built-ins and plantation shutters for timeless style. The open kitchen offers a breakfast bar, Corian countertops, and a bright breakfast nook with bay windows ideal for casual dining. Go outside to enjoy a large, fenced-in backyard with exotic palm and fruit trees, and a screened-in lanai featuring roll-down sun protection and westerly exposure, ideal for relaxing sunsets or entertaining guests. Recent updates include new roof and paint from July 2023 (transferable warranty) and a new air conditioner in May 2024. Well for irrigation. Woodlands at Rivendell is in Osprey near the top-rated Pine View School, the Legacy Trail, shopping, dining, Casey Key, kayaking, boating, and the beautiful Gulf beaches. In a preferred X flood zone with low HOA dues (only $721 semi-annually), and no CDD fees.

4 Beds ⋅ 2 Baths ⋅ Rivendell SubDv. ⋅ 34229 Zip Code

Welcome to this attractive St. Charles floor plan found in the desirable Woodlands at Rivendell community! This charming home sits on a large corner lot directly across from the heated community pool and is within easy reach of the highly ranked Pine View School for the Gifted (Grades:2-12). Built in 2001, this well-maintained home features four bedrooms, or three bedrooms plus den with closet, and two full baths. The spacious great room includes living and dining areas, elegant crown moldings, tray ceilings, built-ins and plantation shutters for timeless style. The open kitchen offers a breakfast bar, Corian countertops, and a bright breakfast nook with bay windows ideal for casual dining. Go outside to enjoy a large, fenced-in backyard with exotic palm and fruit trees, and a screened-in lanai featuring roll-down sun protection and westerly exposure, ideal for relaxing sunsets or entertaining guests. Recent updates include new roof and paint from July 2023 (transferable warranty) and a new air conditioner in May 2024. Well for irrigation. Woodlands at Rivendell is in Osprey near the top-rated Pine View School, the Legacy Trail, shopping, dining, Casey Key, kayaking, boating, and the beautiful Gulf beaches. In a preferred X flood zone with low HOA dues (only $721 semi-annually), and no CDD fees.

1036 Oak Meadow Ln, Osprey

$492,500

Bring your BOAT or RV and store ON YOUR LOT. West of the Trail! Welcome home to Sorrento Shores, nestled perfectly between the vibrant communities of Sarasota and Venice, yet tucked away from the hustle and bustle of city life in the charming town of Osprey. This sought-after neighborhood offers spacious lots, a relaxed atmosphere, and the added bonus of low HOA fees and no CDD to worry about. Discover the possibilities in this home that sits on a generous 19,500 (ALMOST ½ ACRE) square foot lot, providing ample space to stretch out, play, and grow. Step outside and enjoy the expansive, enclosed over-sized lanai and host gatherings all while overlooking your own backyard paradise. Inside, multiple large sliding glass doors effortlessly blend the indoor and outdoor spaces, inviting the sunshine to fill your home. The home features three spacious bedrooms, 2 bathrooms, multiple living spaces, and 2-car attached garage. Recent updates bring peace of mind: NEW ROOF (2025) and HVAC SYSTEM (2025). Also, enjoy the IRRIGATION SYSTEM that runs off a private well to keep your lawn green. This home is also perfectly positioned to enjoy the best local amenities. You’ll find the stunning Oscar Scherer State Park just moments away, offering miles of trails for hiking and birdwatching. The famous Legacy Trail is nearby, ideal for cycling or a leisurely stroll through the scenic landscape. When you're ready to soak up the sun, Nokomis Beach is just a short drive away, perfect for sand, surf, and sunsets. And when it’s time to dine out, you’re surrounded by a variety of waterfront restaurants offering delicious meals with views to match. It’s the ultimate blend of peaceful living and easy access to everything you need for relaxation and adventure.

3 Beds ⋅ 2 Baths ⋅ Sorrento Shores SubDv. ⋅ 34229 Zip Code

Bring your BOAT or RV and store ON YOUR LOT. West of the Trail! Welcome home to Sorrento Shores, nestled perfectly between the vibrant communities of Sarasota and Venice, yet tucked away from the hustle and bustle of city life in the charming town of Osprey. This sought-after neighborhood offers spacious lots, a relaxed atmosphere, and the added bonus of low HOA fees and no CDD to worry about. Discover the possibilities in this home that sits on a generous 19,500 (ALMOST ½ ACRE) square foot lot, providing ample space to stretch out, play, and grow. Step outside and enjoy the expansive, enclosed over-sized lanai and host gatherings all while overlooking your own backyard paradise. Inside, multiple large sliding glass doors effortlessly blend the indoor and outdoor spaces, inviting the sunshine to fill your home. The home features three spacious bedrooms, 2 bathrooms, multiple living spaces, and 2-car attached garage. Recent updates bring peace of mind: NEW ROOF (2025) and HVAC SYSTEM (2025). Also, enjoy the IRRIGATION SYSTEM that runs off a private well to keep your lawn green. This home is also perfectly positioned to enjoy the best local amenities. You’ll find the stunning Oscar Scherer State Park just moments away, offering miles of trails for hiking and birdwatching. The famous Legacy Trail is nearby, ideal for cycling or a leisurely stroll through the scenic landscape. When you're ready to soak up the sun, Nokomis Beach is just a short drive away, perfect for sand, surf, and sunsets. And when it’s time to dine out, you’re surrounded by a variety of waterfront restaurants offering delicious meals with views to match. It’s the ultimate blend of peaceful living and easy access to everything you need for relaxation and adventure.

437 S Shore Drive, Osprey

$480,000

Beautifully renovated and move-in ready, this exceptional property offers the perfect blend of privacy, comfort, and investment potential. Situated on over half an acre along a private, tree-lined street, the home is surrounded by lush tropical landscaping, creating a peaceful oasis just minutes from everything Sarasota has to offer. Step inside to discover a spacious, thoughtfully updated interior featuring modern finishes and an effortless flow between indoor and outdoor living spaces. The heated pool and expansive screened lanai provide the perfect setting for relaxing, entertaining, and enjoying Florida’s year-round sunshine. This turnkey home has been meticulously maintained and boasts a proven track record as a successful income-producing rental. Major upgrades offer peace of mind, including a complete interior renovation, new roof, and pool cage rescreening (2021), pool pump (2022), HVAC system (2023), and a new water heater, well pump, and garage door opener (2024). Additional recent improvements include an automated pool cleaner and septic system flush (2025). Perfectly positioned between Sarasota and Venice, you’ll enjoy easy access to world-class beaches, waterfront dining, shopping, and entertainment. Nature lovers will appreciate having Oscar Scherer State Park directly across the street, offering scenic trails, kayaking, and renowned birdwatching, while the Osprey Junction Trailhead provides quick access to the Legacy Trail just minutes away for biking, walking, and outdoor recreation. With NO HOA restrictions and ample room for a boat, RV, or other recreational vehicles, this property offers a rare combination of flexibility and freedom. Whether you’re seeking a full-time residence, seasonal retreat, or income-producing investment, this beautifully updated home delivers the Florida lifestyle you’ve been looking for.

3 Beds ⋅ 2 Baths ⋅ Harms Sub SubDv. ⋅ 34229 Zip Code

Beautifully renovated and move-in ready, this exceptional property offers the perfect blend of privacy, comfort, and investment potential. Situated on over half an acre along a private, tree-lined street, the home is surrounded by lush tropical landscaping, creating a peaceful oasis just minutes from everything Sarasota has to offer. Step inside to discover a spacious, thoughtfully updated interior featuring modern finishes and an effortless flow between indoor and outdoor living spaces. The heated pool and expansive screened lanai provide the perfect setting for relaxing, entertaining, and enjoying Florida’s year-round sunshine. This turnkey home has been meticulously maintained and boasts a proven track record as a successful income-producing rental. Major upgrades offer peace of mind, including a complete interior renovation, new roof, and pool cage rescreening (2021), pool pump (2022), HVAC system (2023), and a new water heater, well pump, and garage door opener (2024). Additional recent improvements include an automated pool cleaner and septic system flush (2025). Perfectly positioned between Sarasota and Venice, you’ll enjoy easy access to world-class beaches, waterfront dining, shopping, and entertainment. Nature lovers will appreciate having Oscar Scherer State Park directly across the street, offering scenic trails, kayaking, and renowned birdwatching, while the Osprey Junction Trailhead provides quick access to the Legacy Trail just minutes away for biking, walking, and outdoor recreation. With NO HOA restrictions and ample room for a boat, RV, or other recreational vehicles, this property offers a rare combination of flexibility and freedom. Whether you’re seeking a full-time residence, seasonal retreat, or income-producing investment, this beautifully updated home delivers the Florida lifestyle you’ve been looking for.

742 Harms Drive, Osprey

$480,000

A rare, light-filled, meticulously-maintained tranquil sanctuary with an estate-sized .28-Acre Zone X Preserve- backed lot in the coveted The Woodlands at Rivendell! Maintenance-free Living, Low HOA Fees, and No Required Flood Insurance saves you thousands yearly. Newly Priced at $529,900 Elegance, privacy, and peace of mind come together effortlessly as you enter this amazing 400-acre community of lakes, preserves, and walking trails, that provide residents a peaceful, park-like setting just minutes from everything. From the moment you step inside, sunlight pours through 15-foot sliding glass doors, connecting the refined interior to a large covered lanai and lush natural vistas. Double tray ceilings, crown molding, custom plantation shutters, and rich cherry hardwoods create a refined atmosphere. The flexible home office features dual pocket doors, easily serving as a nursery or third bedroom. The open floor plan enhances both everyday living and entertaining, with expansive sightlines that keep nature's views front and center. The kitchen offers generous Corian countertops, abundant cabinetry, two breakfast bars, and newer quality appliances — all complemented by a reverse-osmosis drinking water system. A bright dining-area bump-out bathes the kitchen and living spaces in natural light throughout the day. The primary suite is a peaceful retreat, featuring a sunlit bay-window bump-out, private sliding-door access to the lanai, and two walk-in closets. The spa-inspired ensuite bath includes a large walk-in shower, a soaking tub, and a dual-sink vanity designed for both comfort and function. The guest bedroom is equally inviting with its own bay windows, ample closet space, and a full bath conveniently located just outside the door. Exceptional Infrastructure & Reliability: HVAC (2022): High-efficiency with UV air purification. Water Heater (2023): Dual-element electric for rapid heating. Kinetico System: Whole-home softening, carbon filtration, and UV treatment for "bottle-quality" water from every tap. Outdoor living is both serene and cost-efficient. The oversized lawn is supported by a private irrigation well with a new six-zone controller that will save you thousands every year in water bills, while affordable professional landscaping is included through an HOA. The over-sized 2-car garage adds practical flexibility with built-in storage, a utility sink, and a second refrigerator/freezer. Ideally positioned between the hustle and bustle of Sarasota and Venice, Rivendell in Osprey is next door to Florida’s #1-ranked Pine View School, the Legacy Trail, and Gulf beaches. Offering brilliant morning sun, dazzling sunset views over the preserve, and a sense of calm that’s increasingly hard to find, this move-in ready sanctuary is ready for its next chapter.

2 Beds ⋅ 2 Baths ⋅ Rivendell SubDv. ⋅ 34229 Zip Code

A rare, light-filled, meticulously-maintained tranquil sanctuary with an estate-sized .28-Acre Zone X Preserve- backed lot in the coveted The Woodlands at Rivendell! Maintenance-free Living, Low HOA Fees, and No Required Flood Insurance saves you thousands yearly. Newly Priced at $529,900 Elegance, privacy, and peace of mind come together effortlessly as you enter this amazing 400-acre community of lakes, preserves, and walking trails, that provide residents a peaceful, park-like setting just minutes from everything. From the moment you step inside, sunlight pours through 15-foot sliding glass doors, connecting the refined interior to a large covered lanai and lush natural vistas. Double tray ceilings, crown molding, custom plantation shutters, and rich cherry hardwoods create a refined atmosphere. The flexible home office features dual pocket doors, easily serving as a nursery or third bedroom. The open floor plan enhances both everyday living and entertaining, with expansive sightlines that keep nature's views front and center. The kitchen offers generous Corian countertops, abundant cabinetry, two breakfast bars, and newer quality appliances — all complemented by a reverse-osmosis drinking water system. A bright dining-area bump-out bathes the kitchen and living spaces in natural light throughout the day. The primary suite is a peaceful retreat, featuring a sunlit bay-window bump-out, private sliding-door access to the lanai, and two walk-in closets. The spa-inspired ensuite bath includes a large walk-in shower, a soaking tub, and a dual-sink vanity designed for both comfort and function. The guest bedroom is equally inviting with its own bay windows, ample closet space, and a full bath conveniently located just outside the door. Exceptional Infrastructure & Reliability: HVAC (2022): High-efficiency with UV air purification. Water Heater (2023): Dual-element electric for rapid heating. Kinetico System: Whole-home softening, carbon filtration, and UV treatment for "bottle-quality" water from every tap. Outdoor living is both serene and cost-efficient. The oversized lawn is supported by a private irrigation well with a new six-zone controller that will save you thousands every year in water bills, while affordable professional landscaping is included through an HOA. The over-sized 2-car garage adds practical flexibility with built-in storage, a utility sink, and a second refrigerator/freezer. Ideally positioned between the hustle and bustle of Sarasota and Venice, Rivendell in Osprey is next door to Florida’s #1-ranked Pine View School, the Legacy Trail, and Gulf beaches. Offering brilliant morning sun, dazzling sunset views over the preserve, and a sense of calm that’s increasingly hard to find, this move-in ready sanctuary is ready for its next chapter.

827 Placid Lake Drive, Osprey

$475,000

Investor / Developer / Builder ALERT. Great potential awaits with this exceptional opportunity to purchase just over one acre in a central location. Lot was previously platted as 7 lots and is zoned RSF3. Location has great proximity to many amenities; Oscar Scherer State Park, Legacy Trail, Old Spanish Point, Shopping, I75 Access, beaches and Pineview School. There have been some new homes built in the immediate area demonstrating stability. Property would be ideal to replat into several lots and build multiple single family homes or build a multi generational estate. There are existing older improvements on the property. Seller may consider 30% financing for well qualified borrower.

Ogburns T B Add To Town Of Osprey SubDv. ⋅ 34229 Zip Code

Investor / Developer / Builder ALERT. Great potential awaits with this exceptional opportunity to purchase just over one acre in a central location. Lot was previously platted as 7 lots and is zoned RSF3. Location has great proximity to many amenities; Oscar Scherer State Park, Legacy Trail, Old Spanish Point, Shopping, I75 Access, beaches and Pineview School. There have been some new homes built in the immediate area demonstrating stability. Property would be ideal to replat into several lots and build multiple single family homes or build a multi generational estate. There are existing older improvements on the property. Seller may consider 30% financing for well qualified borrower.

34 Washington Avenue, Osprey

$470,000

Welcome to The Woodlands At Rivendell! This beautiful home is on a large corner lot in the Patio Section of the Woodlands. It has TWO Bedrooms + a DEN, Great Room, double tray ceilings w/ crown molding. The den has double pocket doors! The kitchen is central in the house for entertaining, with plenty of storage, pull-out shelves, and 2 pantries! The Lanai has glimmering water views! Some nice features of the home: New Interior Paint! New Carpet! New Microwave! Irrigation System! Don't worry about maintaining the lawn/landscaping, that is included! Enjoy everything that surrounds you outside as well, such as the Legacy Trail just east of this home for walking, jogging, biking, rollerblading, strolling with your pets or whatever your outdoor activity of choice is. Just south of you is Oscar Scherer State Park for even more outdoor adventures. Just west of you is the beautiful Intracoastal Waterway & Gulf of Mexico with super soft white sandy beaches! You’re also in the company of the best schools around such as Pineview, next door to this neighborhood. Rivendell, a picturesque community known for its extensive green spaces, parks and 24 serene lakes!

2 Beds ⋅ 2 Baths ⋅ Rivendell The Woodlands SubDv. ⋅ 34229 Zip Code

Welcome to The Woodlands At Rivendell! This beautiful home is on a large corner lot in the Patio Section of the Woodlands. It has TWO Bedrooms + a DEN, Great Room, double tray ceilings w/ crown molding. The den has double pocket doors! The kitchen is central in the house for entertaining, with plenty of storage, pull-out shelves, and 2 pantries! The Lanai has glimmering water views! Some nice features of the home: New Interior Paint! New Carpet! New Microwave! Irrigation System! Don't worry about maintaining the lawn/landscaping, that is included! Enjoy everything that surrounds you outside as well, such as the Legacy Trail just east of this home for walking, jogging, biking, rollerblading, strolling with your pets or whatever your outdoor activity of choice is. Just south of you is Oscar Scherer State Park for even more outdoor adventures. Just west of you is the beautiful Intracoastal Waterway & Gulf of Mexico with super soft white sandy beaches! You’re also in the company of the best schools around such as Pineview, next door to this neighborhood. Rivendell, a picturesque community known for its extensive green spaces, parks and 24 serene lakes!

1363 New Forest Lane, Osprey

$445,000

Perfectly positioned West of the Trail near Blackburn Point and Casey Key, this turnkey furnished 3 bedroom, 2 bathroom attached single family residence offers nearly 1,800 square feet of vaulted, light-filled interiors framed by lush preserve views. Set within an exclusive enclave of just 44 homes, this residence delivers the privacy and proportions of single-family living with the ease of a fully maintained community. The HOA provides exterior building maintenance including the roof, exterior insurance, and comprehensive grounds care, along with access to Pine Run amenities, creating a refined lock-and-leave lifestyle ideal for seasonal or full-time ownership. Inside, soaring ceilings and expansive living spaces create an immediate sense of openness and comfort. Tile flooring flows throughout the main areas, while a triple hurricane-rated sliding glass door seamlessly connects the living room to the screened lanai. Surrounded by mature palms and natural greenery, the outdoor space feels tranquil and secluded. The kitchen has been thoughtfully updated with new countertops, upgraded drawer systems with interior lighting, white cabinetry, and a striking blue tile backsplash that adds a distinctive coastal elegance. The primary suite is a true retreat, featuring arched windows, a custom walk-in closet, and a spa-inspired bath with freestanding soaking tub, oversized walk-in shower, and dual vessel sinks. Two additional bedrooms offer versatility for guests, office, or creative space. An air-conditioned two car garage, tile roof, new lanai structure, and full turnkey furnishings complete this exceptional offering. Moments from waterfront dining, marina access, kayak launches, and the beaches of Casey Key, this is elevated West of the Trail living defined by privacy, convenience, and understated sophistication. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

3 Beds ⋅ 2 Baths ⋅ Blackburn Point Woods SubDv. ⋅ 34229 Zip Code

Perfectly positioned West of the Trail near Blackburn Point and Casey Key, this turnkey furnished 3 bedroom, 2 bathroom attached single family residence offers nearly 1,800 square feet of vaulted, light-filled interiors framed by lush preserve views. Set within an exclusive enclave of just 44 homes, this residence delivers the privacy and proportions of single-family living with the ease of a fully maintained community. The HOA provides exterior building maintenance including the roof, exterior insurance, and comprehensive grounds care, along with access to Pine Run amenities, creating a refined lock-and-leave lifestyle ideal for seasonal or full-time ownership. Inside, soaring ceilings and expansive living spaces create an immediate sense of openness and comfort. Tile flooring flows throughout the main areas, while a triple hurricane-rated sliding glass door seamlessly connects the living room to the screened lanai. Surrounded by mature palms and natural greenery, the outdoor space feels tranquil and secluded. The kitchen has been thoughtfully updated with new countertops, upgraded drawer systems with interior lighting, white cabinetry, and a striking blue tile backsplash that adds a distinctive coastal elegance. The primary suite is a true retreat, featuring arched windows, a custom walk-in closet, and a spa-inspired bath with freestanding soaking tub, oversized walk-in shower, and dual vessel sinks. Two additional bedrooms offer versatility for guests, office, or creative space. An air-conditioned two car garage, tile roof, new lanai structure, and full turnkey furnishings complete this exceptional offering. Moments from waterfront dining, marina access, kayak launches, and the beaches of Casey Key, this is elevated West of the Trail living defined by privacy, convenience, and understated sophistication. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

288 Woods Point Road, Osprey

1102 Jessie Harbor Drive Unit 1102, Osprey

$435,000

Welcome home! This GULF ACCESS, WATERFRONT condo is ready for its new owners. Fully updated, this 2 BED, 2 BATH residence with a 1 CAR GARAGE is ideally positioned at the END OF A CANAL, offering privacy, open water views, and MILLION-DOLLAR SUNSET VIEWS every night. Located within a GATED community spanning approximately 11 acres, this home delivers both serenity and an active Florida lifestyle. Lush tropical landscaping leads to a private side entrance with an additional parking space, in addition to your one-car garage—making this one of the most special and uniquely positioned units in all of Blackburn. This intimate building of only four units sits at the end of the community marina, placing you just steps from your boat and offering a front-row seat to breathtaking sunsets. A BONUS LANAI DOOR provides direct sidewalk access, making trips to the pool, marina, or clubhouse quick and convenient. Designed for effortless coastal living, this condo has been thoughtfully updated with FRESH NEUTRAL PAINT, LUXURY VINYL PLANK FLOORING installed in 2023, 5” BASEBOARDS, CROWN MOLDING throughout (including the lanai), PLANTATION SHUTTERS throughout (excluding sliders), and STAINLESS STEEL APPLIANCES, including a NEW MAYTAG DISHWASHER (Oct 2025). The primary suite offers exceptional storage with THREE CLOSETS, including a BONUS WALK-IN CLOSET located within the primary bathroom. Additional upgrades include REMOTE-CONTROL CEILING FANS, an EPOXIED (granite-style) garage and lanai floor, and a ONE-CAR GARAGE with BUILT-IN OVERHEAD STORAGE SHELVING. This FINANCIALLY SOUND community offers boat slips available to rent behind the unit and a resort-style amenity package including a POOL, CLUBHOUSE, FITNESS ROOM, TENNIS COURT, PICKLEBALL COURTS, KAYAK LAUNCH & STORAGE, and beautifully maintained grounds. Residents also enjoy an active social calendar featuring water aerobics, monthly happy hours, bingo and game nights, monthly girls’ nights out, pickleball club, book club, and more. Spend your days boating to the jetty, visiting nearby tiki bars, or beaching the boat at Snake Island—this is true FLORIDA WATERFRONT LIVING. Conveniently located near US-41, with easy access to numerous beaches, Downtown Sarasota, Downtown Venice, I-75, Sarasota Memorial Hospital Venice Campus, and all the Florida charm you could imagine. Call today to schedule your private showing and experience this exceptional waterfront lifestyle firsthand.

2 Beds ⋅ 2 Baths ⋅ Blackburn Harbor SubDv. ⋅ 34229 Zip Code

Welcome home! This GULF ACCESS, WATERFRONT condo is ready for its new owners. Fully updated, this 2 BED, 2 BATH residence with a 1 CAR GARAGE is ideally positioned at the END OF A CANAL, offering privacy, open water views, and MILLION-DOLLAR SUNSET VIEWS every night. Located within a GATED community spanning approximately 11 acres, this home delivers both serenity and an active Florida lifestyle. Lush tropical landscaping leads to a private side entrance with an additional parking space, in addition to your one-car garage—making this one of the most special and uniquely positioned units in all of Blackburn. This intimate building of only four units sits at the end of the community marina, placing you just steps from your boat and offering a front-row seat to breathtaking sunsets. A BONUS LANAI DOOR provides direct sidewalk access, making trips to the pool, marina, or clubhouse quick and convenient. Designed for effortless coastal living, this condo has been thoughtfully updated with FRESH NEUTRAL PAINT, LUXURY VINYL PLANK FLOORING installed in 2023, 5” BASEBOARDS, CROWN MOLDING throughout (including the lanai), PLANTATION SHUTTERS throughout (excluding sliders), and STAINLESS STEEL APPLIANCES, including a NEW MAYTAG DISHWASHER (Oct 2025). The primary suite offers exceptional storage with THREE CLOSETS, including a BONUS WALK-IN CLOSET located within the primary bathroom. Additional upgrades include REMOTE-CONTROL CEILING FANS, an EPOXIED (granite-style) garage and lanai floor, and a ONE-CAR GARAGE with BUILT-IN OVERHEAD STORAGE SHELVING. This FINANCIALLY SOUND community offers boat slips available to rent behind the unit and a resort-style amenity package including a POOL, CLUBHOUSE, FITNESS ROOM, TENNIS COURT, PICKLEBALL COURTS, KAYAK LAUNCH & STORAGE, and beautifully maintained grounds. Residents also enjoy an active social calendar featuring water aerobics, monthly happy hours, bingo and game nights, monthly girls’ nights out, pickleball club, book club, and more. Spend your days boating to the jetty, visiting nearby tiki bars, or beaching the boat at Snake Island—this is true FLORIDA WATERFRONT LIVING. Conveniently located near US-41, with easy access to numerous beaches, Downtown Sarasota, Downtown Venice, I-75, Sarasota Memorial Hospital Venice Campus, and all the Florida charm you could imagine. Call today to schedule your private showing and experience this exceptional waterfront lifestyle firsthand.

1102 Jessie Harbor Drive Unit 1102, Osprey

$430,000

Welcome to this beautifully updated home on a half acre lot. Presenting a modern comfort in a county-like setting. Only 10 minutes from Siesta Key Beach, 8 minutes from Nokomis Beach, within a mile from a highly sought-after Pine View Elementary School, and close to shopping and dining! Inside you will find a fully remodeled interior featuring a custom kitchen with shaker cabinets, subway tile backsplash, and quartz countertops. You will also find new Samsung Bespoke appliances including a refrigerator, range, microwave, dishwasher, washer and dryer. High-end laminate flooring throughout, an updated bathroom with new tile, modern shower with a glass enclosure, and a custom vanity with a touch to illuminate mirror. Outside enjoy a 12x24 screened in lanai, a large yard for entertaining, gardening, or just room to relax. This property has generous parking with room for a RV, boat, and multiple additional vehicles, along with a 16x10 powered shed for storage, hobbies, or workshop.

2 Beds ⋅ 1 Baths ⋅ Bay Acres Sub SubDv. ⋅ 34229 Zip Code

Welcome to this beautifully updated home on a half acre lot. Presenting a modern comfort in a county-like setting. Only 10 minutes from Siesta Key Beach, 8 minutes from Nokomis Beach, within a mile from a highly sought-after Pine View Elementary School, and close to shopping and dining! Inside you will find a fully remodeled interior featuring a custom kitchen with shaker cabinets, subway tile backsplash, and quartz countertops. You will also find new Samsung Bespoke appliances including a refrigerator, range, microwave, dishwasher, washer and dryer. High-end laminate flooring throughout, an updated bathroom with new tile, modern shower with a glass enclosure, and a custom vanity with a touch to illuminate mirror. Outside enjoy a 12x24 screened in lanai, a large yard for entertaining, gardening, or just room to relax. This property has generous parking with room for a RV, boat, and multiple additional vehicles, along with a 16x10 powered shed for storage, hobbies, or workshop.

328 E Bay Street, Osprey

$425,000

Nestled on a generous 0.74-acre lot, this 2-bedroom, 1-bath residence offers 1,211 square feet of living space in a peaceful, private setting just moments from Sarasota Bay. Set back on a semi-private driveway and surrounded by mature landscaping and fruit trees, this property provides a rare opportunity to enjoy the charm and character of Old Florida living while remaining close to all of Sarasota’s modern conveniences. The expansive lot offers ample space for outdoor living, gardening, recreation, or future improvements. Whether you’re seeking a private retreat, a renovation project, an investment opportunity, or the ideal site to build your dream home, this property presents endless possibilities. The existing home is livable and full of potential, offering a solid foundation for updates and customization to suit your vision. Enjoy the serenity of a large homesite with the added benefit of being just minutes from Sarasota Bay, local parks, shopping, dining, entertainment, and the area’s renowned Gulf Coast beaches. Properties with this combination of lot size, privacy, location, and potential are becoming increasingly difficult to find. Whether you’re an investor, builder, or buyer looking to create something special, this unique property is ready for its next chapter.

2 Beds ⋅ 1 Baths ⋅ Harms Sub SubDv. ⋅ 34229 Zip Code

Nestled on a generous 0.74-acre lot, this 2-bedroom, 1-bath residence offers 1,211 square feet of living space in a peaceful, private setting just moments from Sarasota Bay. Set back on a semi-private driveway and surrounded by mature landscaping and fruit trees, this property provides a rare opportunity to enjoy the charm and character of Old Florida living while remaining close to all of Sarasota’s modern conveniences. The expansive lot offers ample space for outdoor living, gardening, recreation, or future improvements. Whether you’re seeking a private retreat, a renovation project, an investment opportunity, or the ideal site to build your dream home, this property presents endless possibilities. The existing home is livable and full of potential, offering a solid foundation for updates and customization to suit your vision. Enjoy the serenity of a large homesite with the added benefit of being just minutes from Sarasota Bay, local parks, shopping, dining, entertainment, and the area’s renowned Gulf Coast beaches. Properties with this combination of lot size, privacy, location, and potential are becoming increasingly difficult to find. Whether you’re an investor, builder, or buyer looking to create something special, this unique property is ready for its next chapter.

811 Sarabay Road, Osprey

$425,000

One or more photo(s) has been virtually staged. Fresh paint is done, and new carpet is coming. SELLER WILL CONSIDER LEASE PURCHASE. Try it before you buy it. Price reflects the need to update property interior. With expected ARV (after repair value) of +/- $600k, $91 per square foot under the most recent sale in the neighborhood, and less than a mile from the beach this is a great opportunity to find your Florida getaway. Experience maintenance free Florida living, just a short walk, bike or drive to Casey Key in this large villa situated in the rarely available neighborhood of Blackburn Point Woods. The home greets visitors with a large welcoming paver patio providing a place to relax and greet your neighbors in this close-knit community. Entering the home, you will be find an expansive space ready for entertaining. Natural light abounds throughout, aided by the home’s soaring cathedral ceilings allowing you to enjoy a favorite book while enjoying nature in the preserve showcased through the enclosed lanai. The kitchen abounds with counter and cabinet space including a breakfast area overlooking the front patio. The main bedroom features an en-suite bath, preserve views and access to the lanai. A second bath and newly floored den complete the ground floor features. A loft overlooking the first floor, a second bedroom with an en-suite bath and separate office/storage room provides plenty of space for easy living. This home is located in one of the most desirable communities in Osprey. You are less than one mile from the beach, Blackburn point with its marina and boat launch, Casey Key Fish House, Deep Lagoon Seafood, Publix is just around the corner. Great healthcare is available at the new Sarasota Memorial Hospital in Venice. Easy access to I-75 can get you to 5 airports, extended shopping and more. Don’t let this one get away.

2 Beds ⋅ 3 Baths ⋅ Blackburn Point Woods SubDv. ⋅ 34229 Zip Code

One or more photo(s) has been virtually staged. Fresh paint is done, and new carpet is coming. SELLER WILL CONSIDER LEASE PURCHASE. Try it before you buy it. Price reflects the need to update property interior. With expected ARV (after repair value) of +/- $600k, $91 per square foot under the most recent sale in the neighborhood, and less than a mile from the beach this is a great opportunity to find your Florida getaway. Experience maintenance free Florida living, just a short walk, bike or drive to Casey Key in this large villa situated in the rarely available neighborhood of Blackburn Point Woods. The home greets visitors with a large welcoming paver patio providing a place to relax and greet your neighbors in this close-knit community. Entering the home, you will be find an expansive space ready for entertaining. Natural light abounds throughout, aided by the home’s soaring cathedral ceilings allowing you to enjoy a favorite book while enjoying nature in the preserve showcased through the enclosed lanai. The kitchen abounds with counter and cabinet space including a breakfast area overlooking the front patio. The main bedroom features an en-suite bath, preserve views and access to the lanai. A second bath and newly floored den complete the ground floor features. A loft overlooking the first floor, a second bedroom with an en-suite bath and separate office/storage room provides plenty of space for easy living. This home is located in one of the most desirable communities in Osprey. You are less than one mile from the beach, Blackburn point with its marina and boat launch, Casey Key Fish House, Deep Lagoon Seafood, Publix is just around the corner. Great healthcare is available at the new Sarasota Memorial Hospital in Venice. Easy access to I-75 can get you to 5 airports, extended shopping and more. Don’t let this one get away.

264 Woods Point Road, Osprey

$420,000

PRICE IMPROVEMENT!! The Cottages of Rivendell are highly desirable residences, offering an exclusive community with only 84 homes. Each home is surrounded by lush landscaping and tree-lined streets, contributing to the area's charm and appeal. This home features 2 bedrooms and 2 bathrooms, as well as a versatile den or office space. It is an ideal choice for those seeking a seasonal residence in Florida, or for anyone looking to downsize without sacrificing comfort or style. Residents enjoy the best of the Florida lifestyle, with close proximity to beautiful beaches-just 2 stoplights away. Additionally, the community is near parks, arts venues, shopping, and restaurants, making it perfect for both active living and peaceful retreat. This home has been thoughtfully updated with new porcelain "wood-look" tile throughout most of the living space, a renovated guest bathroom featuring a walk-in shower, fresh interior paint, and a new roof installed in 2021. The neighborhood is located in one of Sarasota County's top school districts, with Pine View School just a few minutes away. Just a short walk up the street, the community clubhouse offers a generously sized pool, perfect for swimming and social gatherings. Whether you're seeking tranquil relaxation or active outdoor adventures, this exceptional property and community provide the perfect balance. Notice- Some photos of the property have been Virtually Staged.

2 Beds ⋅ 2 Baths ⋅ Rivendell SubDv. ⋅ 34229 Zip Code

PRICE IMPROVEMENT!! The Cottages of Rivendell are highly desirable residences, offering an exclusive community with only 84 homes. Each home is surrounded by lush landscaping and tree-lined streets, contributing to the area's charm and appeal. This home features 2 bedrooms and 2 bathrooms, as well as a versatile den or office space. It is an ideal choice for those seeking a seasonal residence in Florida, or for anyone looking to downsize without sacrificing comfort or style. Residents enjoy the best of the Florida lifestyle, with close proximity to beautiful beaches-just 2 stoplights away. Additionally, the community is near parks, arts venues, shopping, and restaurants, making it perfect for both active living and peaceful retreat. This home has been thoughtfully updated with new porcelain "wood-look" tile throughout most of the living space, a renovated guest bathroom featuring a walk-in shower, fresh interior paint, and a new roof installed in 2021. The neighborhood is located in one of Sarasota County's top school districts, with Pine View School just a few minutes away. Just a short walk up the street, the community clubhouse offers a generously sized pool, perfect for swimming and social gatherings. Whether you're seeking tranquil relaxation or active outdoor adventures, this exceptional property and community provide the perfect balance. Notice- Some photos of the property have been Virtually Staged.

508 Meadow Sweet Circle, Osprey

$416,000

Virtually Staged. Welcome to your private poolside retreat in the desirable coastal community of Osprey— perfectly situated on a premium corner lot with NO HOA and NO CDD fees! This beautiful 3-bedroom, 2-bath home offers a bright, open-concept layout designed for both everyday comfort and effortless entertaining. The spacious living area features sliding glass doors that lead directly to your screened-in lanai and sparkling inground pool, creating seamless indoor-outdoor living. The well-equipped kitchen boasts abundant cabinetry and generous counter space, making it ideal for preparing meals and hosting gatherings. Each of the three bedrooms includes a walk- in closet, providing ample storage and convenience. Retreat to the primary suite, where you’ll find a spa-like jetted tub—perfect for unwinding after a long day. Step outside and enjoy the added bonus of an outdoor shower, ideal for rinsing off after a swim. Additional highlights include a two-car garage, functional layout, and a yard that offers both privacy and potential. With its corner lot location and private pool this home delivers the ultimate Florida lifestyle. Opportunities like this don’t last—schedule your private showing today and make this Osprey gem yours!

3 Beds ⋅ 2 Baths ⋅ Ogburns T B Add To Town Of Osprey SubDv. ⋅ 34229 Zip Code

Virtually Staged. Welcome to your private poolside retreat in the desirable coastal community of Osprey— perfectly situated on a premium corner lot with NO HOA and NO CDD fees! This beautiful 3-bedroom, 2-bath home offers a bright, open-concept layout designed for both everyday comfort and effortless entertaining. The spacious living area features sliding glass doors that lead directly to your screened-in lanai and sparkling inground pool, creating seamless indoor-outdoor living. The well-equipped kitchen boasts abundant cabinetry and generous counter space, making it ideal for preparing meals and hosting gatherings. Each of the three bedrooms includes a walk- in closet, providing ample storage and convenience. Retreat to the primary suite, where you’ll find a spa-like jetted tub—perfect for unwinding after a long day. Step outside and enjoy the added bonus of an outdoor shower, ideal for rinsing off after a swim. Additional highlights include a two-car garage, functional layout, and a yard that offers both privacy and potential. With its corner lot location and private pool this home delivers the ultimate Florida lifestyle. Opportunities like this don’t last—schedule your private showing today and make this Osprey gem yours!

212 Washington Avenue, Osprey

$400,000

Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater, and stainless steel appliances—all completed in 2022. Yard was completely fenced in 2024. With ample square footage, there’s even potential to add a third bedroom, offering flexibility for your needs. All major systems have been upgraded; now this home is waiting for your personal touch. The oversized garage with over 500 SF has sliding doors leading to the backyard and side-yard. Large 15,500 SF of land there is ample space to add a pool. This home has a split bedroom layout and 2 bathrooms (one en-suite; other could be made en-suite). Not located in a high risk flood zone. The Bay Acres community features a private waterfront park on a protected bay with dockage for boats up to 22 feet, a kayak launch, and storage for kayaks and paddleboards. There’s also a shaded picnic area for relaxing or entertaining. Boaters will love the direct access to the water from the 12-slip community boat basin, with slips available by waitlist. For larger vessels, Blackburn Point Park Boat Ramp is just 1.5 miles away. Located just minutes from Casey Key, Siesta Key, and the A+ rated Pine View School, this property is ideal for boaters, beachgoers, and families alike. Nearby attractions include Oscar Scherer State Park, Selby’s Historic Spanish Point, and The Legacy Trail, while Downtown Sarasota and Venice have plenty of shopping, dining, and entertainment options. Bay Acres is a non-deed-restricted neighborhood, giving you the freedom to park your boat, trailer, or RV without the hassle of HOA restrictions. All the hard work has been done—now it’s time to make this your own piece of paradise.

2 Beds ⋅ 2 Baths ⋅ Bay Acres Sub SubDv. ⋅ 34229 Zip Code

Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater, and stainless steel appliances—all completed in 2022. Yard was completely fenced in 2024. With ample square footage, there’s even potential to add a third bedroom, offering flexibility for your needs. All major systems have been upgraded; now this home is waiting for your personal touch. The oversized garage with over 500 SF has sliding doors leading to the backyard and side-yard. Large 15,500 SF of land there is ample space to add a pool. This home has a split bedroom layout and 2 bathrooms (one en-suite; other could be made en-suite). Not located in a high risk flood zone. The Bay Acres community features a private waterfront park on a protected bay with dockage for boats up to 22 feet, a kayak launch, and storage for kayaks and paddleboards. There’s also a shaded picnic area for relaxing or entertaining. Boaters will love the direct access to the water from the 12-slip community boat basin, with slips available by waitlist. For larger vessels, Blackburn Point Park Boat Ramp is just 1.5 miles away. Located just minutes from Casey Key, Siesta Key, and the A+ rated Pine View School, this property is ideal for boaters, beachgoers, and families alike. Nearby attractions include Oscar Scherer State Park, Selby’s Historic Spanish Point, and The Legacy Trail, while Downtown Sarasota and Venice have plenty of shopping, dining, and entertainment options. Bay Acres is a non-deed-restricted neighborhood, giving you the freedom to park your boat, trailer, or RV without the hassle of HOA restrictions. All the hard work has been done—now it’s time to make this your own piece of paradise.

32 Bay Avenue, Osprey

$399,000

Welcome to 329 Bay Vista Ave., Osprey, FL 34229—a rare opportunity to own a beautifully renovated 2-bedroom, 2-bathroom home on an expansive lot (0.47 acre!!!) with no HOA, no deed restrictions, and endless possibilities. Inside, you'll find a thoughtfully updated interior that's move-in ready, offering the perfect blend of comfort and style. Whether you're looking for a full-time residence, seasonal retreat, or investment property, this charming home provides easy, low-maintenance living in one of Osprey's most desirable locations. Situated on a generously sized homesite, this property offers the flexibility that's becoming increasingly difficult to find. Whether you've been dreaming of adding a pool, building a detached garage or workshop, parking your RV or boat, creating a garden oasis, or expanding the existing home, the space is here to bring your vision to life. Without the limitations of an association, you have the freedom to truly make this property your own. For those who love the Florida waterfront lifestyle, this location is hard to beat. Enjoy being just minutes from the Intracoastal Waterway, public boat ramps, Casey Key, Nokomis Beach, and waterfront dining, while having the added peace of mind of being outside of a flood zone. It's the best of both worlds—close to the water without the added concerns that often come with waterfront living. Conveniently located near the Legacy Trail, Oscar Scherer State Park, shopping, dining, top-rated schools, and with easy access to both Sarasota and Venice, this home combines location, flexibility, and lifestyle. Whether you're looking for your first home, a winter escape, or a property with room to grow, 329 Bay Vista Ave. delivers a unique combination of updated living, land, and freedom that's becoming increasingly rare to find. Bring your boat, your RV, your ideas, and your vision—because with this oversized lot, no HOA, and endless potential, the possibilities are truly limitless.

2 Beds ⋅ 2 Baths ⋅ Bay Acres Sub SubDv. ⋅ 34229 Zip Code

Welcome to 329 Bay Vista Ave., Osprey, FL 34229—a rare opportunity to own a beautifully renovated 2-bedroom, 2-bathroom home on an expansive lot (0.47 acre!!!) with no HOA, no deed restrictions, and endless possibilities. Inside, you'll find a thoughtfully updated interior that's move-in ready, offering the perfect blend of comfort and style. Whether you're looking for a full-time residence, seasonal retreat, or investment property, this charming home provides easy, low-maintenance living in one of Osprey's most desirable locations. Situated on a generously sized homesite, this property offers the flexibility that's becoming increasingly difficult to find. Whether you've been dreaming of adding a pool, building a detached garage or workshop, parking your RV or boat, creating a garden oasis, or expanding the existing home, the space is here to bring your vision to life. Without the limitations of an association, you have the freedom to truly make this property your own. For those who love the Florida waterfront lifestyle, this location is hard to beat. Enjoy being just minutes from the Intracoastal Waterway, public boat ramps, Casey Key, Nokomis Beach, and waterfront dining, while having the added peace of mind of being outside of a flood zone. It's the best of both worlds—close to the water without the added concerns that often come with waterfront living. Conveniently located near the Legacy Trail, Oscar Scherer State Park, shopping, dining, top-rated schools, and with easy access to both Sarasota and Venice, this home combines location, flexibility, and lifestyle. Whether you're looking for your first home, a winter escape, or a property with room to grow, 329 Bay Vista Ave. delivers a unique combination of updated living, land, and freedom that's becoming increasingly rare to find. Bring your boat, your RV, your ideas, and your vision—because with this oversized lot, no HOA, and endless potential, the possibilities are truly limitless.

329 Bay Vista Avenue, Osprey

$380,000

Incredible opportunity with a $10,000 credit to buyers at closing for costs or a rate buy-down! This low-maintenance gem is fully updated with a NEW AC, brand-new ductwork, stylish new counters/backsplash, new dishwasher, and a beautifully refreshed bathroom. The backyard is a private oasis boasting a brand-new 2025 heated saltwater pool and spa. Location is unbeatable: just .4 miles from the ocean, 10~ minutes to Venice and world-famous Siesta Key, and just a couple miles to Sarasota Square where the upcoming Sarasota Square Mall is located. Walking distance to local ice cream shop, restaurants, Walmart, and dog park! Bring the toys—no HOA and plenty of boat parking. Dog friendly buyers will appreciate the custom made dog wash station! NO FLOOD INSURANCE REQUIRED!

3 Beds ⋅ 1 Baths ⋅ Osprey Park SubDv. ⋅ 34229 Zip Code

Incredible opportunity with a $10,000 credit to buyers at closing for costs or a rate buy-down! This low-maintenance gem is fully updated with a NEW AC, brand-new ductwork, stylish new counters/backsplash, new dishwasher, and a beautifully refreshed bathroom. The backyard is a private oasis boasting a brand-new 2025 heated saltwater pool and spa. Location is unbeatable: just .4 miles from the ocean, 10~ minutes to Venice and world-famous Siesta Key, and just a couple miles to Sarasota Square where the upcoming Sarasota Square Mall is located. Walking distance to local ice cream shop, restaurants, Walmart, and dog park! Bring the toys—no HOA and plenty of boat parking. Dog friendly buyers will appreciate the custom made dog wash station! NO FLOOD INSURANCE REQUIRED!

429 Patterson Avenue, Osprey

$375,000

Virtually Staged. Perfectly positioned west of the Trail in the desirable coastal community of Towns-End Shores, this versatile property offers an exceptional opportunity to enjoy the Florida lifestyle while generating income. This home provides both peace of mind and outstanding value in one of Sarasota County’s most sought-after areas. Designed with flexibility in mind, the property features a unique two-level layout that allows you to live upstairs while renting the lower-level in-law suite, currently producing $1,500 per month on a month-to-month lease. The private suite includes its own entrance, bedroom, bathroom, kitchen, and living area, creating an ideal setup for rental income, guests, or multigenerational living. Upstairs, the two bedroom and two bathroom primary residence offers an open and inviting layout filled with natural light. The kitchen features granite countertops, solid wood cabinetry, and a functional layout that flows easily into the living and dining areas. Crown molding, tray ceilings, wood flooring, and thoughtful design elements add character and comfort throughout the home. Recent updates provide valuable peace of mind, including a new air conditioning system and water heater installed in 2024, while the air-conditioned garage adds versatility for storage, hobbies, or a workshop. Plus, NEW ROOF 2026 with 10 year warranty! NO FLOOD ZONE — meaning flood insurance is not required. Outdoor living is just as appealing. Residents enjoy low HOA dues and access to the sunny community pool, along with the rare convenience of a private kayak launch, allowing you to explore nearby waterways and mangroves with ease. The location truly sets this property apart. Bike to the beach, explore nearby Oscar Scherer State Park, or access the Legacy Trail just minutes away for miles of scenic biking and walking. You are also conveniently located near South Bay and the beautiful beaches of Casey Key, along with local dining, shopping, and coastal attractions. Whether you are seeking a primary residence with income potential, a coastal retreat, or an investment property in a prime west-of-the-trail location, this home delivers flexibility, lifestyle, and value all in one. Schedule your private showing today and experience the possibilities this unique property offers.

3 Beds ⋅ 3 Baths ⋅ Towns-End Shores SubDv. ⋅ 34229 Zip Code

Virtually Staged. Perfectly positioned west of the Trail in the desirable coastal community of Towns-End Shores, this versatile property offers an exceptional opportunity to enjoy the Florida lifestyle while generating income. This home provides both peace of mind and outstanding value in one of Sarasota County’s most sought-after areas. Designed with flexibility in mind, the property features a unique two-level layout that allows you to live upstairs while renting the lower-level in-law suite, currently producing $1,500 per month on a month-to-month lease. The private suite includes its own entrance, bedroom, bathroom, kitchen, and living area, creating an ideal setup for rental income, guests, or multigenerational living. Upstairs, the two bedroom and two bathroom primary residence offers an open and inviting layout filled with natural light. The kitchen features granite countertops, solid wood cabinetry, and a functional layout that flows easily into the living and dining areas. Crown molding, tray ceilings, wood flooring, and thoughtful design elements add character and comfort throughout the home. Recent updates provide valuable peace of mind, including a new air conditioning system and water heater installed in 2024, while the air-conditioned garage adds versatility for storage, hobbies, or a workshop. Plus, NEW ROOF 2026 with 10 year warranty! NO FLOOD ZONE — meaning flood insurance is not required. Outdoor living is just as appealing. Residents enjoy low HOA dues and access to the sunny community pool, along with the rare convenience of a private kayak launch, allowing you to explore nearby waterways and mangroves with ease. The location truly sets this property apart. Bike to the beach, explore nearby Oscar Scherer State Park, or access the Legacy Trail just minutes away for miles of scenic biking and walking. You are also conveniently located near South Bay and the beautiful beaches of Casey Key, along with local dining, shopping, and coastal attractions. Whether you are seeking a primary residence with income potential, a coastal retreat, or an investment property in a prime west-of-the-trail location, this home delivers flexibility, lifestyle, and value all in one. Schedule your private showing today and experience the possibilities this unique property offers.

1795 Highland Road, Osprey

$365,000

This well-maintained first-floor condominium offers an ideal opportunity for full-time living or a seasonal Florida retreat. Featuring the desirable Osprey floor plan, this open-concept residence includes two bedrooms, two bathrooms both with granite vanity tops, and a bonus room/office. The unit is conveniently located on the first floor with no stairs and provides easy access to the community’s heated resort-style pool, fitness center, and clubhouse. The kitchen is appointed with 42-inch cabinetry and granite countertops. The primary bathroom features a tiled walk-in shower and dual vanity. Additional highlights include a screened lanai, Huge 2.5-car garage, and two-car driveway, offering ample parking and storage. The condominium has been meticulously maintained and is move-in ready. Located in the gated, maintenance-free community of Bay Street Village, the property is ideally situated between Sarasota and Venice, with convenient access to dining, shopping, the Legacy Trail, Pine View School, and nearby beaches including Siesta Key, Nokomis, Casey Key, and Venice Beach. Additional features include concrete block construction, impact-resistant windows and doors, tile roof, and paver driveway. Water and sewer are included in the HOA fee, and there is no CDD fee. Furniture is available under a separate contract between buyer and seller.

2 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code

This well-maintained first-floor condominium offers an ideal opportunity for full-time living or a seasonal Florida retreat. Featuring the desirable Osprey floor plan, this open-concept residence includes two bedrooms, two bathrooms both with granite vanity tops, and a bonus room/office. The unit is conveniently located on the first floor with no stairs and provides easy access to the community’s heated resort-style pool, fitness center, and clubhouse. The kitchen is appointed with 42-inch cabinetry and granite countertops. The primary bathroom features a tiled walk-in shower and dual vanity. Additional highlights include a screened lanai, Huge 2.5-car garage, and two-car driveway, offering ample parking and storage. The condominium has been meticulously maintained and is move-in ready. Located in the gated, maintenance-free community of Bay Street Village, the property is ideally situated between Sarasota and Venice, with convenient access to dining, shopping, the Legacy Trail, Pine View School, and nearby beaches including Siesta Key, Nokomis, Casey Key, and Venice Beach. Additional features include concrete block construction, impact-resistant windows and doors, tile roof, and paver driveway. Water and sewer are included in the HOA fee, and there is no CDD fee. Furniture is available under a separate contract between buyer and seller.

4235 Expedition Way Unit 102, Osprey

$362,500

The only available home in the community with a 2 Car Garage! Welcome to Bay Street Village, a charming, beach-close, gated community in sought-after Osprey. This rarely available First-Floor residence features an oversized two-car garage with exceptional space for vehicles, bikes, kayaks, and all your Florida adventure gear. Ideally situated on a quiet cul-de-sac with peaceful pond views, this light-filled, move-in-ready home offers tranquil water vistas from both the interior and the screened lanai. The open-concept floor plan flows effortlessly, creating a comfortable and inviting living space. The owner’s suite enjoys serene pond views, while the guest bedroom is thoughtfully positioned on the opposite side of the home, adjacent to a well-appointed full bath. A stylish office/den with double-door entry provides flexible space for working from home or accommodating overnight guests. The kitchen features, stainless appliances, granite countertops along with an island with seating, and a walk-in pantry. Built with solid concrete block construction, this home includes impact windows for added peace of mind and a new (Oct 2025) HVAC system. Additional highlights include water and sewer included in the low HOA fee, no CDD fees, and a pet-friendly community. Bay Street Village offers resort-style amenities, including a heated pool, fitness room, and clubhouse—all just a short walk from your front door. Ideally located between Sarasota and Venice, you’ll enjoy easy access to shopping, dining, theater, fishing piers, kayak launches, and the Legacy Bike Trail. World-famous beaches and resorts, including Siesta Key, are just minutes away. This is a rare opportunity to own a beautiful, affordable Florida lifestyle retreat.

2 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code

The only available home in the community with a 2 Car Garage! Welcome to Bay Street Village, a charming, beach-close, gated community in sought-after Osprey. This rarely available First-Floor residence features an oversized two-car garage with exceptional space for vehicles, bikes, kayaks, and all your Florida adventure gear. Ideally situated on a quiet cul-de-sac with peaceful pond views, this light-filled, move-in-ready home offers tranquil water vistas from both the interior and the screened lanai. The open-concept floor plan flows effortlessly, creating a comfortable and inviting living space. The owner’s suite enjoys serene pond views, while the guest bedroom is thoughtfully positioned on the opposite side of the home, adjacent to a well-appointed full bath. A stylish office/den with double-door entry provides flexible space for working from home or accommodating overnight guests. The kitchen features, stainless appliances, granite countertops along with an island with seating, and a walk-in pantry. Built with solid concrete block construction, this home includes impact windows for added peace of mind and a new (Oct 2025) HVAC system. Additional highlights include water and sewer included in the low HOA fee, no CDD fees, and a pet-friendly community. Bay Street Village offers resort-style amenities, including a heated pool, fitness room, and clubhouse—all just a short walk from your front door. Ideally located between Sarasota and Venice, you’ll enjoy easy access to shopping, dining, theater, fishing piers, kayak launches, and the Legacy Bike Trail. World-famous beaches and resorts, including Siesta Key, are just minutes away. This is a rare opportunity to own a beautiful, affordable Florida lifestyle retreat.

124 Revolution Way, Osprey

$362,500

RARELY AVAILABLE FIRST FLOOR END-UNIT in the 12-acre waterfront resort-style gated community of Hidden Bay - move-in ready and fully furnished for an easy Florida lifestyle. This open-concept 2-bedroom, 2-bath home with a flex space offers newer luxury vinyl flooring, a bright and spacious kitchen and a large pantry, and a charming breakfast nook framed by a bay window. The primary suite offers beautiful water views and private access to the enclosed lanai - perfect for morning coffee or unwinding at the end of the day. Inside, you’ll find dual vanities, a soaking tub, walk-in shower, and a private water closet for a true spa-like retreat. The guest suite, thoughtfully positioned on the opposite side of the home, provides comfort and privacy with its own en-suite bath and walk-in closet. Hidden Bay offers resort-style amenities: a newly updated clubhouse, tiki bar, fitness center, heated pool and spa, nature trails, tennis, pickleball and a scenic boardwalk for sunset views. The community is in the process of rebuilding the fishing pier as well, so fishing the intracoastal waterway and a kayak launch is in your future! Quarterly HOA fees include exterior maintenance, water, sewer, trash, and basic cable - making ownership simple and carefree. Just minutes from an assortment of breathtaking beaches, golf courses, Legacy Trail, Siesta Key, and downtown Sarasota’s dining and arts scene, this condo blends relaxation, recreation, and convenience. Move-in ready and waiting for you - hurry and schedule your showing today!

2 Beds ⋅ 2 Baths ⋅ Lake Vista SubDv. ⋅ 34229 Zip Code

RARELY AVAILABLE FIRST FLOOR END-UNIT in the 12-acre waterfront resort-style gated community of Hidden Bay - move-in ready and fully furnished for an easy Florida lifestyle. This open-concept 2-bedroom, 2-bath home with a flex space offers newer luxury vinyl flooring, a bright and spacious kitchen and a large pantry, and a charming breakfast nook framed by a bay window. The primary suite offers beautiful water views and private access to the enclosed lanai - perfect for morning coffee or unwinding at the end of the day. Inside, you’ll find dual vanities, a soaking tub, walk-in shower, and a private water closet for a true spa-like retreat. The guest suite, thoughtfully positioned on the opposite side of the home, provides comfort and privacy with its own en-suite bath and walk-in closet. Hidden Bay offers resort-style amenities: a newly updated clubhouse, tiki bar, fitness center, heated pool and spa, nature trails, tennis, pickleball and a scenic boardwalk for sunset views. The community is in the process of rebuilding the fishing pier as well, so fishing the intracoastal waterway and a kayak launch is in your future! Quarterly HOA fees include exterior maintenance, water, sewer, trash, and basic cable - making ownership simple and carefree. Just minutes from an assortment of breathtaking beaches, golf courses, Legacy Trail, Siesta Key, and downtown Sarasota’s dining and arts scene, this condo blends relaxation, recreation, and convenience. Move-in ready and waiting for you - hurry and schedule your showing today!

291 Hidden Bay Drive Unit 101, Osprey

$358,000

This charming home located in the heart of Osprey checks ALL the boxes. With over 1,500+ sq ft of living space, this well maintained 2 bed/2 bath home with bonus Florida room and 2 car garage is priced to sell. A NEW ROOF is scheduled for installation the 1st week of December and will be paid for by the Seller. Equipped with over $50,000 worth of brand-new energy-saving solar panels*, the monthly electric bill averages $30. Home has a new A/C in 2021, garage door in 2018 and freshly painted exterior. New range in 2021, and new washer, dryer and disposal in 2024. Brand new fridge and dishwasher in September 2025. The spilt plan layout is ideal for family and friends, with a family room, a separate living room and a dining area, as well as a sunny bonus Florida room. The Primary Suite has an oversized walk-in closet, and the large ensuite bath features dual sinks and linen closets. The laundry room with washer, dryer and utility sink is conveniently located off the kitchen, with direct access to the 2 car garage. With a spacious, private fenced backyard perfect for entertaining, and a cozy side yard complete with a hot tub and romantic peekaboo views of the sunset, every day’s a vacation. A free-standing air-conditioned shed measuring 14 x 8 is perfect as a workshop or for storage. Located just south of Sarasota, the home is on City water with a well for irrigation. No HOA, no deed restrictions, and NOT in a flood zone. Nestled in a quiet neighborhood with great neighbors, this home is positioned on a corner lot and is conveniently located to the best of everything that Sarasota, Osprey and Venice have to offer. With Marie Selby Botanical Gardens at Historic Spanish Point directly across the road, as well as the Osprey Conservancy at Bay Preserve, evening strolls to watch sunset are yours for the taking. Ideally situated, the house sits just a 15-minute drive - 7.5 miles to the crystalline sands of world-famous Siesta Key Beach, with Nokomis Beach just 6.5 miles away. Nearby you will find an abundance of outdoor activities including waterfront dining, golfing, boating, hiking and fishing, with a dog park and a library a stone’s throw from the house. A kayak launch is conveniently located across the street, and a public boat ramp is just 3 miles away. A 20-minute drive to Downtown Sarasota offers world-class shopping, dining, and cultural events. Easy access to the interstate and state-of-the-art medical facilities, the home is under 2 miles from Pine View School, consistently ranked as one of the top ten schools in the United States. The Legacy Biking Trail is practically outside your door and Oscar Scherer State Park is just 4 miles south. Wal-Mart and the Post Office are under a mile away. Costco, Lowes, Publix & Target are 2 miles north, and a new nearby Trader Joe’s and Whole Foods are in the works. Come! Live, work and play in paradise! *Solar panels will not be mounted after the new roof is installed in the event the Buyer does not wish to use them. They will be left for the benefit of the buyer to install should they choose.

2 Beds ⋅ 2 Baths ⋅ Osprey Park SubDv. ⋅ 34229 Zip Code

This charming home located in the heart of Osprey checks ALL the boxes. With over 1,500+ sq ft of living space, this well maintained 2 bed/2 bath home with bonus Florida room and 2 car garage is priced to sell. A NEW ROOF is scheduled for installation the 1st week of December and will be paid for by the Seller. Equipped with over $50,000 worth of brand-new energy-saving solar panels*, the monthly electric bill averages $30. Home has a new A/C in 2021, garage door in 2018 and freshly painted exterior. New range in 2021, and new washer, dryer and disposal in 2024. Brand new fridge and dishwasher in September 2025. The spilt plan layout is ideal for family and friends, with a family room, a separate living room and a dining area, as well as a sunny bonus Florida room. The Primary Suite has an oversized walk-in closet, and the large ensuite bath features dual sinks and linen closets. The laundry room with washer, dryer and utility sink is conveniently located off the kitchen, with direct access to the 2 car garage. With a spacious, private fenced backyard perfect for entertaining, and a cozy side yard complete with a hot tub and romantic peekaboo views of the sunset, every day’s a vacation. A free-standing air-conditioned shed measuring 14 x 8 is perfect as a workshop or for storage. Located just south of Sarasota, the home is on City water with a well for irrigation. No HOA, no deed restrictions, and NOT in a flood zone. Nestled in a quiet neighborhood with great neighbors, this home is positioned on a corner lot and is conveniently located to the best of everything that Sarasota, Osprey and Venice have to offer. With Marie Selby Botanical Gardens at Historic Spanish Point directly across the road, as well as the Osprey Conservancy at Bay Preserve, evening strolls to watch sunset are yours for the taking. Ideally situated, the house sits just a 15-minute drive - 7.5 miles to the crystalline sands of world-famous Siesta Key Beach, with Nokomis Beach just 6.5 miles away. Nearby you will find an abundance of outdoor activities including waterfront dining, golfing, boating, hiking and fishing, with a dog park and a library a stone’s throw from the house. A kayak launch is conveniently located across the street, and a public boat ramp is just 3 miles away. A 20-minute drive to Downtown Sarasota offers world-class shopping, dining, and cultural events. Easy access to the interstate and state-of-the-art medical facilities, the home is under 2 miles from Pine View School, consistently ranked as one of the top ten schools in the United States. The Legacy Biking Trail is practically outside your door and Oscar Scherer State Park is just 4 miles south. Wal-Mart and the Post Office are under a mile away. Costco, Lowes, Publix & Target are 2 miles north, and a new nearby Trader Joe’s and Whole Foods are in the works. Come! Live, work and play in paradise! *Solar panels will not be mounted after the new roof is installed in the event the Buyer does not wish to use them. They will be left for the benefit of the buyer to install should they choose.

115 Green Street, Osprey