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2141 Cordes Street, Osprey
$350,000
2 Beds ⋅ 2 Baths ⋅ Cordes Cove SubDv. ⋅ 34229 Zip Code
Nestled in a peaceful setting with views of the Oaks Golf Course, this charming 2-bedroom, 2-bath home offers the perfect blend of comfort and natural beauty. The thoughtfully designed split floor plan provides privacy, while the open-concept living area creates a bright and inviting space for everyday living and entertaining. The primary suite features its own private porch, offering a quiet place to enjoy morning coffee or unwind while taking in the serene garden surroundings. A bonus office area provides the perfect space for working from home or hobbies. Step outside to a large screened lanai with a pool, ideal for relaxing and enjoying Florida’s year-round sunshine. A separate outdoor entertaining area offers additional space for gatherings, dining, or simply unwinding while surrounded by the home’s beautifully landscaped gardens. With its tranquil garden setting, scenic golf course views, and wonderful indoor-outdoor flow, this home provides a peaceful retreat in a highly desirable location only minutes to Siesta Key, shopping areas and premier restaurants.

2141 Cordes Street, Osprey

240 Patterson Avenue, Osprey
$350,000
3 Beds ⋅ 2 Baths ⋅ Osprey Park SubDv. ⋅ 34229 Zip Code
Charming 3-bedroom, 2-bath bungalow with no HOA or deed restrictions—perfect for boaters, RV owners, or anyone seeking freedom and flexibility. Situated in a prime location close to beaches, waterfront dining, the Legacy Trail, Selby Botanical Gardens, Pine View school is 1 mile away (this high school is ranked numbr 18 nationwide and number 1 in Florida), shopping (Walmart Super Center) and Oscar Scherer Park. A kayak launch is conveniently located across the street, and a public boat ramp is just 3 miles away. This well-maintained home features a spacious under-roof lanai added in 2020, newer septic system (2022), newer AC (2023 with 10 year warranty) and a roof replaced in 2016. The lush yard is a tropical oasis with mature fruit trees including lemon, dragon fruit, sapodilla, and loquat. Don’t miss this opportunity to enjoy Florida living at its best with space to store your toys and easy access to the area's top attractions.

240 Patterson Avenue, Osprey

291 Hidden Bay Drive Unit 102, Osprey
$335,000
2 Beds ⋅ 2 Baths ⋅ Lake Vista SubDv. ⋅ 34229 Zip Code
In the lush and serene grounds of this private and peaceful community is a best-kept secret with a name that says it all. Within Hidden Bay, this condominium gem resides in a spot on the community lake with a stunning view and soothing sound of waterfalls from your own enclosed lanai. Fully furnished with mostly all new furniture in the owners’ suite, including a new king-size mattress, living room, guest bedroom and the office/den, this turnkey treasure is move-in ready! Loaded with many new upgrades which include new kitchen appliances such as refrigerator, microwave and dishwasher (2025), new laminate flooring in both bedrooms (2025), a new water heater (2024), new faucets and toilets (2025), new air conditioner (2020), all new screens (2025), all new slider wheels (2025) and interior painted (2025). The home offers two bedrooms, two baths and an office/den, a one- car detached garage and an etched glass front door. The flooring consists of new laminate in both bedrooms, laminate in the office/den and ceramic tile throughout the rest of the home. Beautiful lake views can be seen from the living room, kitchen and owner’s suite. The owner’s suite bath has dual vanities, a soaking tub and a walk-in shower while the guest bath has a soaking tub. This unique waterfront community exudes an awesome Florida lifestyle that boasts many amenities with a newly renovated heated pool and spa, a clubhouse with a full kitchen, a tiki bar, game rooms, a library, a fitness center, a large sundeck, grilling stations, two lit pickleball courts, tennis, a kayak launch, a dog park, a car wash area and a 500-yard elevated boardwalk that winds through mangroves and palms offering scenic sunset watching. And coming soon is a 150-foot fishing pier all for your enjoyment. HOA fees include exterior maintenance, water, sewer, trash and basic cable. Centrally located between Sarasota and Venice, Hidden Bay is on Little Sarasota Bay in Osprey, an ideal location just minutes from the award-winning beaches of Siesta Key and Venice Beach, Sarasota with its many cultural venues, golfing and a variety of casual and fine dining restaurants. Make this special home your own piece of paradise!

291 Hidden Bay Drive Unit 102, Osprey

172 Explorer Drive, Osprey
$335,000
2 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code
Welcome to Bay Street Village, a gated community in the heart of Osprey offering maintenance-free Florida living in an ideal Sarasota County location. This beautifully maintained condo features two bedrooms, two bathrooms, a versatile den, and a private extended one-car garage with interior access, creating a layout that is both functional and inviting. Inside, the open-concept living and dining areas are filled with natural light and flow seamlessly into the kitchen, making the space perfect for everyday living and entertaining. The kitchen is well appointed with stainless steel appliances including a double oven, generous counter space, a center island with seating, and a walk-in pantry. The primary suite offers a peaceful retreat with a walk-in closet and an ensuite bathroom featuring dual sinks, a makeup vanity, and a walk-in shower. With a split bedroom floorplan, the spacious guest bedroom and flexible den provide plenty of options for a home office, study, or additional guest space. Step out onto the screened lanai to enjoy calming water views and the soothing sound of the fountain, an ideal spot to relax and unwind. Bay Street Village offers resort-style amenities including a heated pool with a year round temperature of 85, fitness center, and clubhouse, all just steps away. Offering gated and secured access for both vehicles and pedestrians, each building includes four dedicated guest parking spaces for guests. The community is pet friendly and located directly across from Bay Street Park, which features a dog park and playground. Outdoor enthusiasts will love the easy access to the Legacy Trail right on Bay Street, perfect for biking, jogging, or leisurely walks. The location is truly exceptional. Osprey sits between Sarasota and Venice, offering convenient access to US 41 and I-75. Nokomis Beach is just 6.5 miles away, while the world-famous Siesta Key Beach is a short drive north. Nature lovers will appreciate being close to Oscar Scherer State Park, known for its hiking trails, wildlife, and kayaking opportunities. Shopping, dining, marinas, golf courses, and healthcare are all nearby, making everyday errands and weekend plans effortless. Pine View School for the Gifted, one of the area’s most highly regarded schools serving grades 2 through 12, is located just minutes away. A low monthly fee covers exterior maintenance, insurance, roof, landscaping, gated entry, water, trash, recycling, and community amenities. With no flood insurance required, this home works beautifully as a full-time residence, seasonal retreat, or investment opportunity. Bay Street Village offers the perfect blend of location, lifestyle, and low-maintenance living in one of Osprey’s most desirable communities.

172 Explorer Drive, Osprey

85 Navigation Circle, Osprey
$329,000
3 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code
The luxury Florida lifestyle you’ve been dreaming of is here! Step into carefree, maintenance-free living in this exceptional 3-bed, 2-bath walk-up condo, perfectly positioned in a highly desirable location. Originally a model home, this 2015 residence is loaded with upgrades and has been meticulously maintained by its one and only owner. Fully furnished and thoughtfully appointed, it’s truly turnkey just bring your suitcase and start living. Built for peace of mind, the community features solid concrete block construction and hurricane-impact windows for added safety and durability. A private, ground-level garage beneath the residence offers unmatched convenience when arriving or heading out. Inside, the open-concept layout feels bright and spacious thanks to high ceilings, crown molding, beautiful tile floors, plantation shutters, and custom drapery. The chef-inspired kitchen is a standout, featuring quartz countertops, stainless steel appliances, a stylish backsplash, walk-in pantry, and upgraded fixtures, perfect for both everyday cooking and entertaining. The primary suite provides a peaceful retreat with a walk-in closet and a spa-like ensuite bathroom with double vanity and walk-in shower. Two additional bedrooms on the opposite side of the home, along with a second well-appointed bathroom, offers comfort and privacy for family or guests. Relax on the screened-in lanai overlooking tranquil water views, making it an ideal spot for morning coffee or evening cocktails. All of this is set in a prime location between Sarasota and Venice, with quick access to US-41, I-75, Siesta Key, and Nokomis Beach. Enjoy a short stroll to Bay Street Park with its playground and dog park, or walk to Pine View School, Walmart, and the Legacy Trail’s Osprey Junction trailhead. Vibrant dining, shopping, golf courses, coastal recreation, and top-rated medical facilities are all within minutes. Residents of Bay Street Village enjoy resort-style amenities including a heated pool, fitness center and clubhouse. With a reasonable monthly condo fee (no flood insurance required) covering exterior maintenance, roof, water, sewer, and two gated entrances, this property offers ease of ownership whether you're looking for full-time living, a seasonal retreat, or a smart investment. Grab your swimsuit and flip-flops, your Florida lifestyle awaits!

85 Navigation Circle, Osprey

116 Navigation Circle Unit 106, Osprey
$318,000
3 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code
Location, Lifestyle, and Peace of Mind — All in One! Welcome home to this beautifully appointed 3-bedroom, 2-bath end-unit condo in one of the area's most desirable pet-friendly gated communities. Built with lasting quality in mind, this home offers solid block stucco construction paired with hurricane-impact windows and doors — giving you the comfort of security and the ease of low maintenance living. Step inside and be greeted by an inviting open-concept floor plan designed for modern living. Soaring ceilings, abundant natural light, and a thoughtful split-bedroom layout create the perfect blend of spaciousness and privacy. The heart of the home — a stunning chef’s kitchen — features granite countertops, stainless steel appliances, and a center island with seating, making it ideal for everyday meals or casual entertaining. Enjoy the convenience of an in-unit laundry room and the luxury of a primary suite retreat complete with a walk-in closet and a spa-inspired en-suite bath with dual vanities. Added bonuses include a whole-house water softener and a covered, screened patio overlooking lush gardens and swaying palm trees — your personal oasis. And for those with little ones or furry friends? The spacious side yard offers the perfect spot for play and relaxation. Resort-style living is yours with amenities including a heated pool, fitness center, and clubhouse. The attached garage with the longest driveway in the community, easily accommodating up to 4 cars, plus extra guest parking conveniently located right across the street. Even better — Bay Street Park, complete with a dog park and playground, is just steps away from the entrance. Unbeatable Sarasota/Venice Location! Ideally located between Sarasota and Venice, with easy access to US 41, I-75, Siesta Key, Nokomis Beach (just 6.5 miles!), the Legacy Trail, and Oscar Scherer State Park. Top-rated schools, golf courses, marinas, shopping, dining, and healthcare are all close by. With a low $460 monthly fee that covers exterior maintenance, insurance, roof, landscaping, gates, water, and amenities — and NO flood insurance required — this home is a smart choice for full-time living, a seasonal escape, or a savvy investment. Don’t miss your chance — schedule your private tour today!

116 Navigation Circle Unit 106, Osprey

2251 Jessie Harbor Drive Unit 2101, Osprey
$310,000
2 Beds ⋅ 2 Baths ⋅ Blackburn Harbor Waterfront Villas SubDv. ⋅ 34229 Zip Code
INCREDIBLE VIEWS!....INCREDIBLE LOCATION!...You Will be Wowed by the LONG WATER & SUNSET VIEWS in this Bright and Spacious (2) Bedroom (2) Bath Corner Unit with PRIVATE GARAGE located in Blackburn Harbor Waterfront Villas, a PET FRIENDLY Gated 11 acre Waterfront Resort-Style Community with: HeatedPool; Fitness Center; Kayak Storage & Launch; BBQ Gazebo; Dog Park; Walking Trails; Pickleball/Tennis and****BOAT SLIPS****for easy "no bridges" access to Intracoastal & Gulf......Abundance of Storage; Ideal Split Bedroom Floor Plan; TILE THROUGHOUT & Expansive Screened Lanai---providing the Ultimate Indoor/Outdoor Living and PERFECT for Morning Coffees, Enjoying Your Favorite Podcast and of course, SUNSET COCKTAILS!....Blackburn Harbor is Conveniently Located to EVERYTHING: Shopping; Dining; Recreation; the New Sarasota Memorial Hospital; Legacy Bike Trail and just minutes to MULTIPLE BEACHES, including TOP RATED SIESTA KEY!....Ideal as Year-Round; Vacation or Investment Property!

2251 Jessie Harbor Drive Unit 2101, Osprey

764 Sarabay Road Unit 8, Osprey
$310,000
2 Beds ⋅ 2 Baths ⋅ Heron Bay Club SubDv. ⋅ 34229 Zip Code
Virtually Staged. BOAT SLIP-KAYAK LAUNCH-FISHING STATION!!! Live the Florida dream on the water! Wake up to shimmering bay views, spend your days boating and fishing, and end every evening with breathtaking sunsets over Little Sarasota Bay, all from this rarely available, maintenance-free waterfront villa. In the exclusive Heron Bay Club, an intimate bayfront enclave of just 25 villas set across 10 beautifully manicured acres, this home offers the ultimate Florida lifestyle. Enjoy resort-style amenities including a heated waterfront pool, tennis courts, kayak launch, fishing pier, and community docks with water and electric. Best of all, there are 10 free boat slips with no fixed bridges to the Gulf, making this a boater’s paradise, so bring your boat and go! This spacious two-bedroom, two-bath villa features sweeping views of Little Sarasota Bay, the Intracoastal Waterway, the community pond and pool. The open concept floor plan is enhanced by 15-foot ceilings, abundant natural light, and seamless indoor-outdoor living. Relax on the screened lanai, cool off in your heated waterfront pool and enjoy nightly sunsets that never get old. A private gated courtyard entry sets the tone for this unique home, complete with a new paved walkway and pet-friendly artificial turf, completely maintenance-free. Inside, enjoy ES Prestige impact-rated windows and sliding glass doors, all-new kitchen appliances, and an eat-in kitchen overlooking the courtyard. The primary suite offers lanai access through sliding glass doors and features two custom walk-in closets. The second bedroom also opens to the private courtyard and includes its covered lanai, perfect for guests or a home office retreat. Conveniently with quick access to Interstate 75, shopping, dining and beaches, this exceptional waterfront villa delivers boating, fishing, views and effortless Florida living in one remarkable package. A rare opportunity, this is waterfront living at its finest. Schedule your private showing today.

764 Sarabay Road Unit 8, Osprey

4304 Expedition Way Way Unit 105, Osprey
$309,000
3 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code
Virtually Staged. Spectacular water views from most windows in this immaculate, lightly used 3BR/2BA condo, built in 2018 and located in the gated community of Bay Street Villages. The popular Ibis floor plan offers an open-concept kitchen, dining, and great room with designer finishes, including white 42” cabinetry, light granite countertops, custom backsplash and stainless-steel appliances. Enjoy peaceful pond views with birds and wildlife from the screened lanai. Quality construction and peace of mind are provided by hurricane-impact windows and doors, concrete block construction, tile roof, and a paver driveway. The primary suite features plantation shutters, a custom ceiling fan with light, custom closet system, linen closet, lighted 10× makeup mirror, and a bidet-ready outlet. The second and third bedrooms also include custom ceiling fans and 2" blinds. The dining area is accented by a custom light fixture and accordion blinds on the balcony sliding doors. The balcony is enhanced with a tropical palm-leaf ceiling fan and outdoor curtains for added shade and comfort. The great room is fitted with plantation shutters for added elegance. A spacious laundry room includes a washer and dryer. Added features-Ring Doorbell, Keyless Entry on Front Door as well as an Exterior Garage door keypad. The monthly condo fee includes water, sewer, exterior and grounds maintenance, gated entry, heated resort-style pool, cabana, fitness center, and club room. No CDD fees. Ideally located near Nokomis Beach, Casey Key, Siesta Key Beach, the Legacy Trail, Sarasota and Venice dining and shopping, Oscar Scherer Park, and A-rated Pine View School. Maintenance-free Florida living at its best.

4304 Expedition Way Way Unit 105, Osprey

173 Navigation Circle Unit 107, Osprey
$305,000
3 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code
Immaculate and lightly lived-in 3BR/2BA condo in the gated community of Bay Street Village, offering beautiful water views with a fountain from the main living areas, the primary suite, and the screened lanai. The popular Ibis floor plan features an open-concept kitchen, dining, and great room with 42" upper cabinets, granite countertops, a custom tile backsplash, and stainless-steel appliances. The designer-level, fully customized laundry room includes soft-close custom cabinets, a laundry sink, a custom backsplash, and a stacking washer and dryer, providing exceptional storage and functionality. The primary suite offers a water view, a barn-door entry to the bath, a custom frameless glass shower enclosure with stone flooring, a linen closet, custom closet organizers, and a designer ceiling fan with light. Bedroom two also features custom closet organizers, while bedrooms two and three include custom ceiling fans. Ceiling fans are additionally installed in the great room and the lanai for enhanced comfort. Plantation shutters are installed in the entry foyer, primary bedroom, bedrooms 2 and 3, and the family room, adding style, privacy, and a cohesive look throughout the home. Additional upgrades include upgraded carpet on the stairs and in the primary bedroom, keyless front-door entry, keyless man-door entry, and an exterior garage door keypad. Quality construction provides peace of mind with hurricane-impact windows and doors, concrete block construction, a tile roof, and a paver driveway. The monthly condo fee covers water, sewer, exterior maintenance, landscaping, gated entry, a heated resort-style pool, cabana, fitness center, and clubhouse. No CDD fees. Ideally located near Nokomis Beach, Casey Key, Siesta Key, the Legacy Trail, Oscar Scherer Park, Sarasota and Venice shopping and dining, and A-rated Pine View School. Maintenance-free Florida living at its best.

173 Navigation Circle Unit 107, Osprey

4213 Expedition Way Unit 107, Osprey
$300,000
3 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code
"Location, Location, Location" The luxury Florida lifestyle you’ve been dreaming. Welcome to this beautifully appointed 3-bed, 2-bath walk-up condo in a highly desirable location in a pet-friendly gated community. Built for peace of mind, the community features solid concrete block construction and hurricane-impact windows for added safety and durability. The attached ground-level garage beneath the residence offers convenience when arriving or heading out. The open-concept layout floor plan, soaring ceilings, and split-bedroom layout create perfect privacy. Stunning chef’s kitchen, granite countertops, stainless steel appliances, and a center island with seating, walk-in pantry, and upgraded fixtures. The primary suite features a walk-in closet, a spa, a double vanity, and a walk-in shower. Two other bedrooms on the opposite side, along with a second full bathroom, gives comfort and privacy for families or guests. Relax on the screened-in lanai overlooking beautiful water views for morning coffee or evening cocktails. The Tesla charger installed in the garage is a bonus. The community is located in a prime location with quick access to US-41, I-75, Siesta Key Beach, and Nokomis Beach, Bay Street Park with its playground and dog park, and walking distance to renowned Pine View School, Walmart, and the Legacy Trail. Bay Street Village resort-style amenities include a heated pool, fitness center, and clubhouse. The monthly condo fee covering exterior maintenance, roof, water, sewer, and two gated entrances… Don’t miss this rare opportunity – call the listing agent now to schedule a private viewing.

4213 Expedition Way Unit 107, Osprey

222 Glenwood Avenue, Osprey
$300,000
2 Beds ⋅ 2 Baths ⋅ Ogburns T B Add To Town Of Osprey SubDv. ⋅ 34229 Zip Code
Take advantage of a RARE OPPORTUNITY in real estate with the current owners ASSUMABLE MORTGAGE at 2.75%! Step out your french doors and wake up to the songs of birds, as you sip coffee in your lanai. The day ahead is whatever you want! What"s your pleasure? Beach? Siesta Key (#1 in US multiple times) is minutes away. Nature Hiking? Oscar Scherer State Park is even closer to your front door. The same goes for Restaurants, Shopping, Golfing and even Tiki Bars. Or maybe a day in Sarasota, at the Ringling Museum, Mote Marine Laboratory, or Jungle Gardens. And that night you can catch a show at the Van Wezel, Asolo Reperatory, or Florida Studio Theater. Afterwards return home to the charm of your bungalow in the sun. Beautiful rosewood floors sparkle to welcome you as you head to a stainless steel decked kitchen for a snack to bring into the open living/dining room and once again visit the french doors. NEWER A/C 2018. NEW LONG LASTING METAL ROOF AND NEW BEAUTIFUL GARAGE DOOR (2025). This home is surrounded by everything you could ever want at an AMAZING Price!

222 Glenwood Avenue, Osprey

100 Navigation Circle Unit NA, Osprey
$295,000
2 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code
Welcome to Bay Street Village in Osprey, where maintenance-free Florida living awaits in this gorgeous gated community. This immaculate end-unit condo features 2 bedrooms, 2 bathrooms, and a 1-car garage. The garage is located beneath the unit and offers a private interior stairway leading to your second-floor residence. Enjoy an open-concept living and dining area perfect for entertaining that flows seamlessly into the beautiful kitchen, complete with a walk-in pantry, stainless steel appliances, and ample seating around a center island. The peaceful primary suite offers a walk-in closet and an ensuite bathroom with dual sinks, a makeup vanity, and a walk-in shower. Bay Street Village provides resort-style amenities, including a sparkling pool and a fitness center, along with plenty of guest parking. The community is dog-friendly, with a fantastic dog park just a short walk outside the gate. Outdoor enthusiasts will appreciate the easy access to the Legacy Trail right on Bay Street. Pine View School for the Gifted (grades 2-12) is conveniently located on the next street. Ideally situated, Osprey is just south of Sarasota and offers easy access to Nokomis Beach and the world-famous Siesta Key Beach.

100 Navigation Circle Unit NA, Osprey

4267 Expedition Way, Osprey
$295,000
2 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code
Welcome to Bay Street Village, Osprey - Perfectly nestled between the vibrant cities of Sarasota and Venice - only minutes to the pristine shoreline of Nokomis Beach. This desirable gated community features a resort style heated pool, clubhouse and a fitness center designed to enhance your Florida life style. Enjoy local dining, shopping, and many arts and cultural attractions. This second floor meticulously maintained 2-bedroom/2-bathroom condo has an open floor plan and has an abundance of natural light. The kitchen is a chef's delight with rich dark wood cabinetry, granite countertops, stainless steel appliances, a walk-in pantry and a ample breakfast bar. The spacious dining area is adjacent and is perfect for casual dining or entertaining. The living room is comfortable for relaxing. Step onto a screened lanai; perfect for a peaceful morning or a wind down at the end of the day. Primary suite includes a walk-in, linen closet and an ensuite bathroom. Bathroom is complete with dual sinks, makeup vanity and a large shower. The second bedroom has a sizable closet and full bathroom nearby. The second bathroom comes complete with a shower/tub combo. The laundry room is conveniently located in the hallway near bedrooms. Included is an attached one car garage with an additional storage room. Perfect for full time residence, seasonal enjoyment or as an investment property.

4267 Expedition Way, Osprey

120 Woodland Place Unit 120, Osprey
$285,900
2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
Over $80,000 in upgrades and designer renovations by renowned Murray Homes, a symbol of luxury in Sarasota. The team included an architect, designer, and contractors to transform this Pine Run end-unit, second-floor condo into a stunning modern coastal retreat. Featuring a completely reimagined light and bright open floor plan and custom kitchen with quartz countertops, custom cabinetry, floating shelves, designer tile backsplash, stainless appliances, and workstation sink, this move-in-ready home also offers luxury wide-plank flooring throughout, beautifully updated bathrooms, newer HVAC, fresh interior paint, contemporary lighting, new trim, doors, hardware, and window treatments, new ceiling fans, new stackable washer and dryer. Primary bedroom is ensuite with a walk-in closet and both bedrooms enjoy a private balcony. The spacious screened lanai is private and overlooks lush tropical landscaping, creating the perfect setting to relax and enjoy Florida living. There is an abundance of storage closets and attic space. Covered end-unit parking with storage and guest parking. Walk to shopping and waterfront bars and restaurants. Ideally located just minutes by bike to Nokomis Beach, Casey Key, Oscar Sherer State Park, and the Legacy Trail, Pine Run offers resort-style amenities including two pools, tennis and pickleball courts, kayak storage and launch, a clubhouse, and gym. Luxury, location, and lifestyle—all in one exceptional, and updated-to-like-new condo ready for you to call home.

120 Woodland Place Unit 120, Osprey

4173 Frontier Lane Unit 4173, Osprey
$285,000
2 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code
INCREDIBLE CHARM!....INCREDIBLE LOCATION!.....You will be ENAMORED by this Highly Sought After (2) Bedroom (2) Bath Heron Floor Plan with PRIVATE GARAGE in the PET FRIENDLY Gated Community, Bay Street Village. This Meticulously Maintained One Owner corner unit residence features BRIGHT SPACIOUS INTERIORS; Hurricane Impact Windows and a Generous Screened Lanai---perfect for enjoying Morning Coffee while listening to your Favorite Podcast or just relaxing with Evening Cocktails.....Meal Prep is Easy with OVER-SIZED KITCHEN ISLAND; Stainless Steel Appliances and Pantry for Extra Storage....Bay Street is Conveniently Located to EVERYTHING: Shopping; Dining; Recreation; the New Sarasota Memorial Hospital; Legacy Bike Trail and just minutes to MULTIPLE BEACHES, including TOP RATED SIESTA KEY!.....Ideal as Year-Round, Vacation or Investment Property.

4173 Frontier Lane Unit 4173, Osprey

2043 Cordes Street, Osprey
$285,000
3 Beds ⋅ 2 Baths ⋅ Cordes Cove SubDv. ⋅ 34229 Zip Code
Charming & Versatile Home Near the Beaches! This cute and cozy, well-maintained 3-bedroom, 2-bath residence offers exceptional flexibility including a private-entrance 1-bedroom, 1-bath suite plus den—perfect for an in-law suite, guest quarters, extra bedroom or home office setup. The home features durable tile and vinyl flooring throughout, updated bathrooms with newer showers, and a bright, comfortable layout. Enjoy Florida living year-round from the screened-in lanai overlooking a spacious backyard complete with a storage shed. Additional highlights include a metal roof, exterior paint completed last year, and peace of mind knowing the home did not flood. Home has been repiped, AC Changed in (2021) Metal Roof is (2014). Ideally located 6 miles to Siesta Key or 7 miles to Nokomis Beach, Boat launch at Blackburn only 3 miles away, shopping, dining, and everyday conveniences—this charming property offers comfort, versatility, and location all in one. Cash only.

2043 Cordes Street, Osprey

232 Explorer Drive Unit 15, Osprey
$280,000
2 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code
Charming 2 Bedroom 2 Bath corner end unit( which provides extra natural light) condominium with attached 1 car Garage. Open floor plan, Kitchen features granite counter tops and stainless steel appliances, master bedroom suite has walk-in closet private bath with double vanity. Dining Room opens to enclosed balcony. Quality construction concrete block building with impact resistant glass windows, tile roof,and paver brick driveway. Bay Street Village is a Gated maintenance free complex featuring a Resort style Swimming Pool , fitness room, and Clubhouse This pet friendly complex is located across the street from Osprey Dog Park and easy access to the Legacy Trail great for biking, jogging, and leisurely walks. Fantastic location near shopping , dining, Oscar Scherer Park, and just a short drive to Siesta Key and Nokomis Beaches and A+ Pineview School is just 1 Minute away. A Great Place to spend the Season or a Lifetime. Welcome Home!!!

232 Explorer Drive Unit 15, Osprey

108 Woodland Place Unit 108, Osprey
$275,000
2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
Bring your furniture and move right in to this popular Pine Run neighborhood. No need to worry about remodeling this condo! New coastal look ceramic tile throughout the entire home! New kitchen and appliances, new guest bathroom, new doors throughout, new light fixtures, and newly painted. Wow! First floor condo offers more outdoor living space. The patio off the main entry offers privacy and has access from the dinette area. A spacious center atrium feels like a peaceful retreat. The main covered lanai off the living room and dining room is screened in with a door to the back yard. Each bedroom has it’s own small patio with privacy fence. Kitchen is nicely equipped with washer and dryer in the dinette closet area. The hallway has large almost floor to ceiling windows looking onto the center atrium for a very open feel. Pine Run is an active community nestled between mature landscaping and trees, with many activities including pickleball, tennis, kayak storage and two swimming pools! Launch your kayaks in the Blackburn Point Park and boat launch just down the road. Pine Run is conveniently located near shopping, restaurants, major roads and Casey Key Fish House and Tiki Bar. Sarasota is about 13 miles away, Venice about 7 miles. Area beaches are close at hand with Nokomis Beach just 5 miles and Siesta Key Beach is 9 miles. You are in the heart of paradise! Come see for yourself!

108 Woodland Place Unit 108, Osprey

135 Woodland Place, Osprey
$260,000
2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
Ideally located in the heart of Osprey, this private corner, first floor condo offers effortless Florida living just minutes from pristine Gulf beaches and less than half a mile from the Intracoastal Waterway. The sought after community at the entrance to Casey Key was designed to live in harmony with nature by Frank Folsum Smith of the Sarasota School of Architecture. This unit features a garden view with four patios that includes a rear lanai enclosed with sliding vinyl windows. A unique inner atrium with aquarium style glass windows adds architectural interest and abundant natural light while maintaining privacy. The unit features easy to maintain custom tile floors on the diagonal throughout with wood floor inspired ceramic tiles in the bedrooms. Since 2023, unit updates include all new kitchen appliances, new faucets, new PEX water lines, a new water heater as well as new paint inside and out. The unit also includes a deeded carport parking space and two storage closets. Onsite resort style amenities include two heated pools (one overlooking a lagoon), two cedar saunas, a fitness room, Florida style clubhouse, walking trails, BBQ gas grill, outdoor gas fireplace, kayak storage, pickleball and tennis courts. Within a mile is the Pine View School (the only standalone public gifted school in the state), Oscar Scherer State Park, 2 kayak launches, a public boat ramp, Casey Key Fish House, Walmart and a Post Office. Easily walk to Publix, Ace Hardware, CVS, shops and restaurants or bike to the Legacy Trail and Nokomis Beach. Exceptional privacy, easy access, and a premier location make this residence an outstanding opportunity. Priced to sell!

135 Woodland Place, Osprey

761 Pine Run Drive Unit 761, Osprey
$260,000
2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
As you step through the gate and into the private courtyard, you’ll immediately feel at home in this beautifully maintained 2-bedroom, 2-bathroom ground-level condominium. Located in one of Sarasota’s most desirable areas west of the trail, this residence offers a perfect blend of comfort, convenience, and timeless architectural design by renowned Frank Folsom Smith. Inside, an open and inviting living space flows seamlessly into a bright Florida room, offering the perfect spot to relax and unwind. Just beyond, an outdoor patio provides a peaceful retreat, surrounded by lush tropical vegetation, creating a serene and private backyard oasis. Whether you're enjoying your morning coffee or entertaining guests, this space offers a tranquil escape. A covered carport with extra storage ensures you have space for all your essentials. This vibrant community features two pools, tennis and pickle ball courts, kayak storage, a small gym, and club house, making it easy to enjoy an active and social lifestyle. This vibrant community features two sparkling pools, tennis and pickleball courts, kayak storage, a small gym, and a clubhouse, making it easy to enjoy an active and social lifestyle. Don't miss this rare opportunity to own a charming condo in an unbeatable location! Schedule your private showing today.

761 Pine Run Drive Unit 761, Osprey

232 Woodland Drive Unit 232, Osprey
$259,900
2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
This condo has the 3 L's! Location Location Location! Located in the central area of Osprey making it an easy drive to area beaches, downtown Venice or Sarasota. Located about a half mile to the Inter Coastal, making for a great walking area on Casey Key. Located close to the well known Casey Key Fish House and Tiki Bar. Shopping and restaurants are all nearby! The location of this condo within the Pine Run community is also good with an abundance of trees and landscaping creating a private setting from your lanai off the livingroom. You will feel like you are living in a tree house! This condo has had extensive work done in the last 6 years including ELECTRIC ON-DEMAND TANKLESS HOT WATER HEATER, NEW CUSTOM KITCHEN WITH DOVE TAIL DRAWER CHERRY CABINETS, FLOORING, PAINT, LIGHT FIXTURES, NEW BATHROOMS AND PLUMBING. Unique frosted glass sliding doors in the dinette area open to washer dryer combo plus a pantry area! Crown molding in the living and dining area give an elegant feel to the rooms, The roof, maintained by the HOA was replaced about 3 years ago. Pine run is an active, vibrant community with small clubhouse with fitness room, pickle ball, tennis and other activities just waiting for you. Come take a look! If you are comparing other condo's, this one has much to like!

232 Woodland Drive Unit 232, Osprey

480 Blackburn Point Road Unit 6, Osprey
$250,000
Wet Slips At Bellagio Harbor Village SubDv. ⋅ 34229 Zip Code
A rare find in Sarasota, 1 of 6 total with only 2 that haven't recently sold, this covered 50 ft x 15 x 15 wet slip at Osprey Harbor Village offers the perfect blend of protection, convenience, and value. Eligible for boat lift! Located at 480 Blackburn Point Road in Osprey, just off the Intracoastal Waterway, this sheltered slip keeps your yacht out of the Florida sun with quick access north to Sarasota Bay or south to Venice and the Gulf of Mexico beyond. Enjoy the benefits of ownership without the million-dollar price tag of waterfront real estate, complete with water, electric, cable, pump-out services, a fuel dock, on-site restaurant, and secure, well-lit docks. Low $200 monthly fee and rental potential of $1600/month makes this an exceptional opportunity for any serious boater or investor!

480 Blackburn Point Road Unit 6, Osprey

4271 Expedition Way Unit 103, Osprey
$250,000
2 Beds ⋅ 2 Baths ⋅ Bay Street Village & Towncenter Land Condo SubDv. ⋅ 34229 Zip Code
Virtually Staged. Live where everyday life feels simple, connected, and close to everything you love. Located in the gated community of Bay Street Village in Osprey, this beautifully maintained second-floor condo offers the perfect blend of comfort, convenience, and a relaxed Florida lifestyle. Just minutes from Nokomis Beach, Siesta Key, the Legacy Trail, Oscar Scherer State Park, and an abundance of shopping and dining options, everything you need is right at your fingertips. This 2-bedroom, 2-bathroom condo welcomes you with a private entry and interior stairway leading to a bright and open main living space. Positioned on the second floor, the home enjoys added privacy along with elevated views and an abundance of natural light. The layout lives effortlessly, with high ceilings and neutral finishes creating an inviting and airy feel throughout. An attached garage with direct interior access adds everyday ease and practicality. The kitchen is both functional and stylish, featuring granite countertops, stainless steel appliances, a large island with seating, and a walk-in pantry. It opens seamlessly to the dining and living areas, making it easy to host, relax, or simply enjoy day-to-day living without feeling closed off. The spacious primary suite offers a comfortable retreat with a large walk-in closet and an en-suite bathroom complete with dual sinks and a walk-in shower. A second bedroom and full bath provide flexibility for guests, a home office, or additional living space. Enjoy your morning coffee or unwind in the evening on the screened lanai, where you can take in the Florida breeze and peaceful surroundings from your elevated position. Whether you're heading out to the beach, meeting friends for dinner, or enjoying the nearby parks and trails, this location makes it all feel effortless. Bay Street Village enhances the lifestyle even further with resort-style amenities including a community pool, fitness center, scenic ponds, and beautifully landscaped grounds, all within a gated and well-maintained setting. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

4271 Expedition Way Unit 103, Osprey

207 Woodland Drive Unit 207, Osprey
$250,000
2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
Welcome to this beautifully appointed, well-cared for and fully furnished 2-bedroom, 2-bath condo located in the sought-after Pine Run community. It is completely turnkey; all you need to bring are your clothes! This second-floor unit has been tastefully updated and comes equipped with everything you need to move right in, including all furniture, beds, bedding, all kitchenware, appliances, and even recreational items like beach chairs, coolers, and two bicycles. The 9-ft high ceiling gives you an open, airy feel. The unit has been updated throughout and re-plumbed for peace of mind. The two separate en-suite bedrooms are spacious and have their own patio decks and patio furniture for added privacy. The kitchen boasts solid wood cabinets, granite countertops, a cozy dinette area and it opens to a formal dining room, along with a comfortable living room that opens to a covered screened porch. Elegant upgrades include engineered hardwood scraped hickory flooring, designer light fixtures and fans, profiled baseboards and custom blinds. There’s ample storage with a deeded covered carport, two storage lockers and an easily accessible attic. Pine Run spans 20 acres of lush, tropical landscaping and offers an array of amenities to enhance your lifestyle. There are two heated pools, with one conveniently located just steps from the unit, pickle ball, tennis courts, walking trails, kayak rack storage for easy access to water adventures, and a main clubhouse with a fitness center for social gatherings. Situated just a mile from the iconic Casey Key Road and only two miles from Nokomis Beach, this condo offers the perfect blend of tranquility and convenience. Sarasota Airport is just 17 miles away, making travel a breeze. Across the street, you’ll find everything you need for daily living, including a Publix grocery store, hardware, salon, specialty retailers, fitness center, bike rental store & medical services. For dinner and entertainment take a leisurely stroll to the new Deep Lagoon restaurant or enjoy live music at the popular Casey Key Fish House and Tiki Bar. Six additional restaurants are within walking distance, offering a variety of dining options. The Legacy Bike Trail, area state parks and public beaches are all nearby. Whether you’re looking for a vacation retreat or a full-time residence, this condo offers everything you need to enjoy Florida living at its best. Do not miss out on this incredible opportunity to own a piece of paradise in one of the most desirable locations on the Gulf coast. Pine Run is nestled between Sarasota and Downtown Venice and is 7 miles away from the famous Siesta Key Beach, voted the #1 beach in the U.S.

207 Woodland Drive Unit 207, Osprey

754 Pine Run Drive Unit 754, Osprey
$249,000
2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
Virtually Staged. Rarely available and truly one-of-a-kind, this beautifully updated ground-floor 2-bedroom, 2-bath residence offers an exceptional combination of privacy, architectural character, and an unbeatable location. Designed around a stunning private open-air atrium, the home features 8-foot glass doors on three sides, flooding the interior with natural light and creating a seamless indoor-outdoor connection rarely found in condominium living. The thoughtfully designed floorplan delivers a tranquil, nature-inspired experience—particularly from the south bedroom wing, where walls of glass frame peaceful wooded views, offering a remarkable sense of serenity and privacy. Beautifully modernized for today’s lifestyle, the kitchen and living spaces have been opened into a sophisticated great-room design, ideal for entertaining and everyday comfort. Timeless Saltillo Mexican tile flooring runs throughout, adding warmth, texture, and character. Additional conveniences include covered carport parking, a large private storage closet, and tasteful updates that make this residence completely move-in ready. Residents enjoy an impressive collection of resort-style amenities, including two heated pools—one dramatically overlooking a wildlife-filled lagoon—along with two cedar saunas, a fitness center, a Florida-style clubhouse, scenic walking trails, BBQ gas grills, an outdoor gas fireplace, kayak storage, and tennis and pickleball courts. Perfectly positioned for an active coastal lifestyle, this premier location places you just minutes from Nokomis Beach, Oscar Scherer State Park, multiple kayak launches, a public boat ramp, and the Legacy Trail, offering miles of biking and recreation connecting Venice and Sarasota. Nearby favorites include Casey Key Fish House, Historic Spanish Point, waterfront dining, medical facilities, and endless local conveniences. Everyday living couldn’t be easier—walk to Publix, CVS, Ace Hardware, shops, restaurants, fitness centers, Walmart, and the Post Office, or enjoy quick access to everything the area has to offer without needing a car. Families will appreciate proximity to the highly acclaimed Pine View School for the Gifted—the only standalone public gifted school in Florida and consistently ranked among the state’s best. Combining exceptional privacy, thoughtful design, resort-style amenities, and unmatched convenience, this is a rare opportunity to own a distinctive, beautifully updated home in one of the area’s most desirable locations—perfect for those seeking the ideal balance of nature, accessibility, and modern coastal living.

754 Pine Run Drive Unit 754, Osprey

Sarabay Road, Osprey
$241,000
Bay Acres Sub SubDv. ⋅ 34229 Zip Code
One or more photo(s) has been virtually staged. Rare corner lot opportunity in the highly sought-after waterfront community of Bay Acres in Osprey. Zoned RSF-2, this oversized 0.32-acre homesite offers the flexibility to build a custom approximately 4,500 sq ft pool home or design a smaller primary residence with a detached guest cottage/ADU for guests, multigenerational living, or additional flexibility. Public water and sewer are available, and a private well is already in place for future irrigation. Survey available. Bay Acres is a hidden gem for boating and outdoor enthusiasts, offering optional HOA access to a private 12-slip marina, community boat ramp, paddleboard and kayak launch, with dockage available for qualifying vessels up to 22 feet. Surrounded by million-dollar homes and new luxury construction, this location blends lifestyle, boating access, and long-term value in one of Sarasota County’s most desirable coastal corridors. Ideally located near Nokomis Beach, Casey Key, Oscar Scherer State Park, Legacy Trail, Pine View School, Downtown Venice, and Downtown Sarasota’s dining, shopping, marinas, and arts scene. Walk the property, envision your future home, and experience why vacant land west of the Trail is becoming increasingly hard to find.

Sarabay Road, Osprey

139 Woodland Place Unit 139, Osprey
$235,000
1 Beds ⋅ 2 Baths ⋅ Wood Ridge At The Meadows SubDv. ⋅ 34229 Zip Code
Here’s a polished real estate listing you can use: --- **Stunning Fully Remodeled 1-Bed / 2-Bath Ground-Floor Condo with Designer Finishes + $15,000 Custom Golf Cart Included** Step into luxury and comfort in this beautifully remodeled ground-floor condo, professionally designed from top to bottom. Every detail has been thoughtfully crafted to create a modern, open-concept living experience surrounded by natural beauty. **Property Highlights:** * **1 bedroom, 2 bathrooms** — spacious layout perfect for full-time living or a serene seasonal retreat * **Professional designer remodel** — high-end finishes, updated fixtures, new appliances, and a cohesive modern aesthetic throughout * **Nature views from all sliding glass doors** — enjoy peaceful, scenic greenery no matter where you are in the home * **Open floor plan** — seamless flow between living, dining, and kitchen areas * **Large enclosed lanai** — accessible from both the living room and bedroom, perfect for relaxing, entertaining, or enjoying morning coffee * **Expansive front courtyard** — a welcoming outdoor space as you enter the home * **Exceptional storage** — 2 interior storage closets plus 2 additional exterior-access storage areas * **Covered carport** — convenient, protected parking right at your doorstep * **BONUS: Custom $15,000 golf cart included** — a fantastic added value for lifestyle, leisure, or getting around the community This ground-floor showpiece blends luxury, practicality, and unmatched natural surroundings. Move-in ready and designed to impress, it’s the perfect opportunity for buyers seeking a unique, beautifully remodeled home with exceptional extras.

139 Woodland Place Unit 139, Osprey

111 Woodland Place, Osprey
$227,000
2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
Hidden away in Osprey is the private oasis of Pine Run. You could not find a more natural setting and fantastic location, convenient to Sarasota, Venice and Gulf beaches. This immaculate, ground floor condo is being sold furnished so settling in will be easy. The updated kitchen with stainless appliances is large enough to incorporate dine-in eating, and a laundry closet with full size washer and dryer. A generously proportioned living/dining area leads to the private covered lanai with garden view. The master bedroom has a private en-suite bath and walk-in closet. Other outdoor spaces include a paved courtyard just off of the kitchen and a private interior courtyard with gazebo that can be accessed from the living room and master bedroom. Large sliders in every room allow lots of light in and you'll love the feel of sea breezes passing through when all are opened. Two exterior storage closets provide ample storage. Pine Run is a pet friendly haven for artists and the active; sitting on 20+ lushly vegetated acres, with 2 heated pools; clubhouse overlooking a lagoon teeming with wildlife; tennis; pickle ball; brick patio with fire pit; kayak storage; saunas and fitness room. The community's location is ideal: West of the Trail, near shopping/banking/medical services, parks, public beaches, nationally acclaimed Pine View School, and casual and fine dining. The Legacy Bike Trail and Blackburn Point Park with a kayak launch are minutes away and Nokomis Public Beach is a quick, convenient drive. The popular Casey Key Fish House & Tiki Bar and other waterfront dining, all within a short distance.

111 Woodland Place, Osprey