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438 Camille Drive, Osprey
$1,800,000
3 Beds ⋅ 3 Baths ⋅ South Creek Point SubDv. ⋅ 34229 Zip Code
EXCEPTIONAL WATERFRONT LIVING . . . PRIVATE DOCK & BOAT LIFT . . . HEATED SALTWATER POOL . . . EXTENSIVE 2025–2026 UPGRADES! Experience the ultimate Florida waterfront lifestyle at 438 Camille Drive, where timeless elegance, exceptional craftsmanship by Pruett and thoughtful upgrades come together in a private, tropical setting. Nestled within an exclusive five-lot cul-de-sac community, this extraordinary residence offers tranquil mangrove-lined water views, lush landscaping and exceptional indoor-outdoor living. Inside, beautiful tile flooring with protective cork underlayment, plantation shutters, granite countertops, a stunning aquarium window with a gas fireplace creates an inviting atmosphere. The outdoor living spaces are truly spectacular! Enjoy the beautifully renovated heated saltwater pool, resurfaced and rebuilt in 2025 with new tile, filtration equipment and a new pool enclosure. An outdoor gas fireplace, shower, expansive entertaining areas and remote-controlled patio storm shutter enhance this exceptional retreat. Boating enthusiasts will appreciate the approximately 200-foot decked walkway leading to a private 30-foot Trex dock with an elevator boat lift, surrounded by peaceful water views and natural mangroves. Plumbing is already in place for a future outdoor kitchen and the dock and pool have separate water plumbing. Extensive improvements provide added comfort, efficiency and peace of mind, including a new roof (2025), driveway (2026), and two new air-conditioning systems (2026). Additional features include glued and mechanically fastened cement barrel roof tiles, spray-foam attic insulation, WindGuard windows and doors, a reinforced garage door, and a whole-house Kohler generator. A drinking H2O purification system, tankless water heater, buried 500-gallon propane tank owned by Detweiler's and new dishwasher (2026) complete the impressive list of amenities. Meticulously maintained and thoughtfully improved, this exceptional waterfront residence offers the perfect combination of privacy, luxury, boating convenience and Florida coastal living. All property information and improvements are provided by the seller and deemed reliable but not guaranteed. Buyers are encouraged to independently verify all details, including permits, water access, and dock specifications.

438 Camille Drive, Osprey
47 Shoreland Drive, Osprey
$1,299,000
2 Beds ⋅ 2 Baths ⋅ Towns-End Shores SubDv. ⋅ 34229 Zip Code
Exceptional Key West-Style Waterfront Living in Osprey, Florida! Welcome to 47 Shoreland Drive, where beautifully appointed interiors, extensive upgrades, and an exceptional waterfront setting come together to create a truly remarkable Key West-style Florida residence. Meticulously maintained and thoughtfully improved, this stunning home shows like a model and offers the perfect combination of elegance, comfort, and coastal living. From the moment you arrive, you’ll appreciate the home’s impressive curb appeal and charming Key West-style architecture, enhanced by updated exterior siding, a durable metal roof, and newly replaced front steps. Inside, beautifully maintained living spaces and thoughtful details create a warm, inviting atmosphere ideal for both everyday living and entertaining. Step outside and embrace the Florida waterfront lifestyle! Enjoy peaceful water views, refreshing breezes, and the convenience of your own private dock and boat lift, providing boating access to the Intracoastal Waterway and the Gulf of America. Watch dolphins swimming by and kayakers paddling along the waterways, adding to the natural beauty and charm of this waterfront setting. Whether you’re spending an afternoon on the water, entertaining family and friends, or simply relaxing and taking in the surroundings, this property offers an exceptional opportunity to enjoy coastal living. The inviting swimming pool features a PebbleTec finish, creating the perfect setting for outdoor relaxation and entertaining. An outdoor lift provides additional convenience. Additional RV or boat parking along the side of the home offers even more flexibility for enjoying the Florida lifestyle. The home’s many improvements reflect years of care and pride of ownership. Please see or request the list of improvements that have been made through the years. Ideally situated in desirable Osprey, this waterfront retreat offers convenient access to Sarasota, Venice, beautiful Gulf Coast beaches, shopping, and recreation. Enjoy nearby waterfront dining at popular local favorites such as Deep Lagoon Seafood & Oyster House and Casey Key Fish House, where you can relax at the waterfront tiki bar, enjoy fresh seafood, and take in the beautiful coastal atmosphere. Everyday conveniences are equally appealing, with Publix grocery shopping nearby, making errands and daily essentials easily accessible. Beautifully maintained, extensively improved, and offering the waterfront lifestyle you’ve been dreaming of, 47 Shoreland Drive is a property you won’t want to miss. Schedule your private showing today!

47 Shoreland Drive, Osprey
172 Sea Anchor Drive, Osprey
$875,000
3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
What’s old is new again! This Southbay home built in 1977 has been extensively renovated since 2024 and feels like new! With 2,283 square feet this pool home sits on a landscaped corner lot just one block from the clubhouse and marina. Both are an easy walk or golf cart ride away! Recent upgrades and improvements include: TILE ROOF APRIL 2024 * RENOVATED KITCHEN WITH NEW CABINETS AND COUNTERTOPS OCT. 2024 * NEW KITCHEN APPLIANCES NOV. 2024 * NEW LUXURY VINYL FLOORING THROUGHOUT SEPT. 2024 * NEW INTERIOR PAINT 2024 * NEW PRIMARY BATH SEPT. 2024 * NEW HURRICANE IMPACT FRONT DOOR JUNE 2024 * NEW BLINDS AND PLANTATION SHUTTERS MAY 2024 * NEW POOL SCREEN MAY 2025 * IRRIGATION UPGRADES SEPT. 2026 * POOL BATH SHOWER APRIL 2026 * PVC PLUMBING IN THE FLOOR FOR TOILETS, SHOWERS AND SINKS, COPPER PLUMBING IN THE ATTIC AND NO CAST-IRON PLUMBING IN THE HOUSE * NEW HVAC SYSTEM 2026 * HEATED SALT WATER POOL WITH NEW SALT CELL JULY 2026 * HURRICANE-IMPACT WINDOWS AND DOORS THROUGHOUT * WATER FILTRATION SYSTEM WITH REVERSE OSMOSIS * NEW MINI-SPLIT IN PRIMARY BEDROOM NOV. 2024 * NEW GARAGE DOOR OPENER JUNE 2024 * EXTENSIVE LANDSCAPING WITH NEW SOD MARCH 2024 * NEW ARECA PALMS AND PITCH APPLES APRIL 2026 AND NEW FRONT YARD LANDSCAPING SEPT. 2026 * BROCHURE PACKET WITH ALL DETAILS AVAILABLE. Now, on to other details about the house! Just inside the entry is a cozy den and a separate office (currently an in-home gym) features siding glass pocket doors. The living room opens to the kitchen and overlooks the pool through a large full view sliding glass door. The gourmet kitchen has seating in three locations, cabinets and counter space galore. The kitchen and dining area flow into a vaulted family room with sliders to the lanai. The primary suite features two closets, a renovated bath and direct acccess to the lanai with a sliding glass door. A pocket doors allows the second bedroom and pool bath to function as a private suite, while the third bedroom has a full bath just steps away. Trees and lush greenery add privacy to the corner lot. Southbay residents-only Marina accommodates a wide range of boat sizes, with many slips available now. The renovated clubhouse offers a ballroom, card room, fitness center, lounge and two kitchens for community gatherings. Residents also enjoy tennis, pickleball, bocce, a kayak launch and playground. From this Osprey location, Pine View School, the Publix plaza, local shops and restaurants, well known Casey Key Fish House & Tiki Bar, are close by - most by golf cart! Nokomis Beach, Siesta Key, downtown Sarasot and Venice island are all within easy reach. Come see the home, then take a stroll down to the marina - you’ll see what makes this home and Southbay Yacht & Racquet Club so special!

172 Sea Anchor Drive, Osprey
320 Bay Vista Avenue, Osprey
$989,000
4 Beds ⋅ 4 Baths ⋅ Bay Acres Sub SubDv. ⋅ 34229 Zip Code
Virtually Staged. Experience the ultimate blend of luxury, functionality, and coastal living iin this modernized 4 large bedroom, 3.5 bath sanctuary located West of the trail on a beautifully landscaped, spacious lot. Designed for year-round outdoor entertainment, this bright and airy residence seamlessly transitions to lovely generous outdoor living spaces complete with a sparkling pool, hot tub, large patio, and a fully equipped outdoor kitchen. Water enthusiasts will love the rare opportunity of a private boat slip, while non-deed restricted grounds offer ample space to park your boat, RV, and toys. A key feature of this home is the private-entrance in-law suite-offering complete independence for extended family, guests, or those teenagers you occasionally pretend aren't yours! Ideally Located in Osprey-Sarasota County's hidden gem, just minutes from Siesta Key, Downtown Sarasota, Venice, and the exceptional Pine View School. Enjoy world-class beaches, restaurants, and premier shopping! This home truly has it all.

320 Bay Vista Avenue, Osprey
472 Park Trace Boulevard, Osprey
$595,000
4 Beds ⋅ 2 Baths ⋅ Park Place Estates SubDv. ⋅ 34229 Zip Code
Welcome to desirable Park Trace Estates in Osprey, where spacious living, thoughtful upgrades, and the Florida lifestyle come together! This beautifully maintained 4-bedroom, 2-bath pool home offers 2,217 square feet of living space, 2,895 total square feet, and an oversized 2-car garage. Major improvements include a NEW ROOF IN 2025, impact-resistant windows, and a whole-house water filtration system! Best of all, enjoy NO CDD fees and LOW HOA dues of just $695 ANNUALLY! From the moment you step inside, you'll appreciate the soaring ceilings, elegant architectural columns, crown molding, and abundant natural light. The thoughtfully designed floor plan features separate living and dining areas, along with a spacious family room that opens to the kitchen, creating an inviting atmosphere for everyday living and entertaining. The kitchen offers granite countertops, white cabinetry, ample storage, a breakfast bar with seating, and a casual dining area overlooking the tropical surroundings. Step outside to your own private Florida retreat! The expansive screened lanai features a sparkling saltwater swimming pool with a raised spillover feature, surrounded by lush tropical landscaping. Whether enjoying your morning coffee, relaxing poolside, or entertaining friends and family, this outdoor space is designed for year-round enjoyment. The spacious primary suite provides a comfortable retreat, while three additional bedrooms offer flexibility for guests, a home office, or hobbies. Additional features include tile flooring throughout the main living areas, decorative lighting, ceiling fans, and an oversized 2-car garage with extra storage space. Ideally located in sought-after Park Trace Estates, this home is just minutes from Pine View School and The Legacy Trail, with convenient access to shopping, dining, beautiful Gulf Coast beaches, and everything Sarasota and Venice have to offer. With its generous living spaces, beautiful outdoor setting, significant upgrades, and exceptionally affordable community fees, this home offers an outstanding opportunity to enjoy the best of Florida living. Schedule your private showing today!

472 Park Trace Boulevard, Osprey
452 Blue Garden Lane, Osprey
$1,925,000
3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Experience exceptional luxury and privacy in this Updated, custom Bo MacEwen residence, ideally situated on a beautifully landscaped cul-de-sac homesite in the prestigious gated community of Oaks Bayside. A welcoming approach features a long paver driveway, side-entry garage, and generous guest parking. Inside, architectural details take center stage with a dramatic two-story domed foyer, 11-foot ceilings, custom millwork, crown molding, tray ceilings, travertine flooring, abundant natural light, and oversized doors throughout. Designed for both elegant entertaining and comfortable everyday living, the open great room features a fireplace and flows seamlessly into a chef-inspired kitchen appointed with custom wood cabinetry, granite countertops, induction cooktop, double wall ovens, microwave drawer, and premium built-in appliances, including a wine cooler. The expansive primary suite offers a private retreat with ample sitting space, generous walk-in closets, and a beautifully appointed bath featuring dual vanities, dressing area, soaking tub, and glass-enclosed shower overlooking a secluded garden. Two additional guest suites, each with private en-suite baths, are thoughtfully positioned on the opposite side of this split floor plan. Outdoors, a recently renovated private courtyard creates an exceptional setting for relaxation and entertaining, featuring more than 1,500 square feet of covered and open-air space, a heated pool and spa, and convenient access to the main living areas and pool bath. Additional features include central vacuum, zoned HVAC with enhanced air filtration, hardwired security, integrated pool controls, and a Sonos/Sonance theater system. A distinctive combination of craftsmanship, architectural character, and private outdoor living in one of The Oaks' most desirable neighborhoods. The nearby, Private Dock on the Intracoastal Waterway is a cherished amenity of the Oaks-Bayside residents. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **Please Enjoy Viewing the 3D VIRTUAL TOUR**

452 Blue Garden Lane, Osprey
312 Yacht Harbor Drive, Osprey
$2,250,000
3 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
Virtually Staged. Directly across the street from one of the most exceptional community-owned marinas on Florida’s west coast, this beautifully renovated waterfront residence offers remarkable views and an extraordinary boating lifestyle in Southbay Yacht and Racquet Club. Recent exterior enhancements include a brand-new tile roof, fresh exterior paint, a redesigned front vestibule with a more modern aesthetic and updated outdoor lighting at the front of the home. Considered one of the region’s finest private residential marinas, Southbay’s seven-acre deep-water basin accommodates kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet. With six feet of water at mean low tide, the marina offers slips for 175 resident-owned boats. Southbay’s HOA fees are just $218.87 per month, and marina slips remain highly affordable, with water and electric included. With the marina quite literally in your front yard and the charming Southbay neighborhood stretching behind you, this fully renovated residence sits on one of only two waterfront streets in the community. It features three bedrooms, four full baths and a versatile flex space that can serve as an office or fourth bedroom, with beautiful water views from many rooms. Inside, an elegant tray-ceiling entry opens to porcelain plank tile flooring and expansive living spaces filled with natural light from abundant impact-rated windows and sliding glass doors. The beautifully designed entertainment kitchen and breakfast area flow seamlessly into the spacious family and dining rooms, creating a refined yet relaxed setting for everyday living and entertaining. The outdoor living space is equally impressive, with a custom-built pool and spa framed by a panoramic clear-span pool cage, an expansive stone-tile sun deck and generous covered areas for outdoor dining and entertaining. The private primary suite offers double-door access to the pool and spa, plus a luxurious bath with a deep soaking tub, frameless glass shower, dual vanities, large-format tile and two custom walk-in closets with built-in organization systems. Two guest suites each feature a private en-suite bath and custom closets; one enjoys marina views, while the other opens directly to the pool terrace. Additional features include a three-car garage, brick-paver driveway and mature tropical landscaping. Just a short distance away, the recently renovated Southbay Yacht and Racquet Club clubhouse overlooks the marina and offers a 99-person ballroom with a catering kitchen and dance floor, a community gathering room with piano and entertainment area, a fitness center, a card room, a library and a meeting room. Residents also enjoy a geothermal-heated pool, youth pool, covered waterfront patios, three tennis courts, four pickleball courts, bocce ball, shuffleboard, basketball court, kayak storage, waterfront park, 20 acres of common grounds and five miles of scenic sidewalks. Southbay is golf-cart friendly, with an active social calendar featuring weekly gatherings, seasonal events and a vibrant Power and Sail Club. This is a rare opportunity to enjoy marina views, waterfront living and one of the Gulf Coast’s most beloved boating communities.

312 Yacht Harbor Drive, Osprey
242 Lookout Point Drive, Osprey
$995,000
4 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
Meticulously maintained, furnished four-bedroom residence in Southbay Yacht and Racquet Club, a sought-after waterfront community in Osprey. The community-owned marina features 172 boat slips accommodating vessels up to 55 feet within a protected, deep-water basin. HOA fees are just $218 per month. Enjoy the remodeled clubhouse overlooking the marina, offering an impressive array of amenities, including two kitchens, an elegant ballroom, a fitness center, a card room and an inviting living room complete with a grand piano. Outdoor enthusiasts will appreciate the pickleball and tennis courts, bocce ball, swimming pool, playground and convenient kayak launch and storage. The spacious great room and dining area are highlighted by a charming wood-burning fireplace, creating a warm and inviting atmosphere for entertaining family and friends. The thoughtfully designed split-bedroom floor plan provides added privacy for family and guests. Recent improvements include a new metal roof, hurricane-rated windows, newer A/C units and beautiful brick pavers enhancing both the driveway and pool area. Conveniently located between Sarasota and Venice, approximately 20 minutes from Siesta Key Beach and just a quarter mile from the Legacy Trail, offering miles of scenic paths and easy access to Oscar Scherer State Park. Enjoy nearby waterfront dining, shopping and local amenities just a short distance away. Osprey is also home to Pine View School for the Gifted, a highly regarded public school.

242 Lookout Point Drive, Osprey
156 Bishopscourt Road, Osprey
$1,289,000
3 Beds ⋅ 4 Baths ⋅ Bishops Court At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
This stunning 3 bedroom, 3.5 bath home, designed by the renowned architect Frank Folsom Smith, stands out with its unique design. The charming Cape Cod style sets the stage for comfortable, graceful living. The home features a Sonos surround sound system throughout. The backyard, overlooking the preserve, is a quiet sanctuary, where you can enjoy the open-air freeform pool with spa in complete privacy. The whole-house stereo system extends to the enclosed back patio, making it a lovely place to sit and enjoy a peaceful, rare rainy afternoon with a good book and a cuppa. There is an additional 732 square feet of outdoor deck space off the second floor and rooftop. Recent renovations in 2023 include two main bathrooms with high-end decorator tile, premium glass enclosures, and premium plumbing fixtures, including an elegant standalone bathtub. The powder room has also been completely renovated. The kitchen boasts new ceramic tile floors, backsplashes, an induction cooktop, an LG smart refrigerator, a farmhouse sink, and a garburetor. The laundry room features new ceramic tile floors, a washer and dryer, extensive shiplap walls, and a sliding hanging barn door to the pantry. The second-floor bathroom has new tub fixtures, shiplap walls, and a decorator granite sink area. Additional updates include crown moldings throughout the ground floor, new ceiling fans in all bedrooms and the den/office, with a decorator oversized 52-inch windmill fan in the main bedroom. The home also has new LED ceiling can lights, new plantation shutters in the front hall/foyer, and new Levolor blinds in the kitchen and laundry room. **A new main-floor HVAC unit was installed in June 2026.** The pool area has been upgraded with a new heat pump pool heater, a new filtration system, and a new pool pump and motor. The lanai has new aluminum framing and screening with a screen door, installed in 2025. The second floor has a new flat roof by Curry Roofing with a warranty. The landscape has been renewed with new trees, bushes, sod, and flower plantings worth $20,000, completed in 2022. Premium decorator light fixtures have been added to the dining room, kitchen, and foyer. The entire house exterior was painted in August 2025, and a new second-floor deck was also completed in August 2025. The pristine condition of this lovely home, combined with the quiet, private setting on a double lot at the end of a cul-de-sac, makes it the perfect Florida retreat for you and your loved ones. Situated in the enclave of Bishopscourt, a maintenance-free neighborhood behind the gates of The Oaks Preserve, lawn and landscape maintenance, as well as irrigation, are included in the homeowner's association fees. You will delight in this graceful, inviting home. Membership in The Oaks, Sarasota's finest golf and country club, is required with homeownership. With two distinctly unique 18-hole championship golf courses, 12 HAR-TRU tennis courts (4 lighted), croquet and pickleball courts, a state-of-the-art fitness center, fine and casual dining options, and a wealth of social events, The Oaks is truly Sarasota's premier golf and country club. There is currently no waiting list for either Golf or Sports/Social membership.

156 Bishopscourt Road, Osprey
117 Bishops Court Road, Osprey
$850,000
3 Beds ⋅ 2 Baths ⋅ Bishops Court At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
Enjoy the benefits of living in a three bedroom, two bath, maintenance free home in the ever popular Bishops Court in the Oaks Preserve. This desirable floor plan with rear southern exposure allows for easy living with landscape maintenance and irrigation included. The interior features beautiful wood cabinetry, a gas range, complete house water filtration system, and granite countertops in the kitchen and baths. Attractive tile floors in most living areas are easy to maintain. The primary suite is spacious enough for a sitting area or a desk, and the guest suites are on the opposite side for privacy. The dining room has a custom built in buffet with abundant cabinetry for storage. The roof is 4 years new, and the lanai has a plunge pool to enjoy. Bishops Court is a quaint neighborhood, with canopied oak tress offering shade for strolling the neighborhood. Also, enjoy the community pool steps away for a quiet swim, or soaking up the sun. Being a member of The Oaks Country Club is an extraordinary experience offering the best of golf, dining, tennis, regulation croquet, and every social activity to keep you busy throughout the year. Choose either a social membership, or golf (two 18 hole courses) and begin your active and fun lifestyle in a beautiful community.

117 Bishops Court Road, Osprey
403 Longbow Trail, Osprey
$1,100,000
4 Beds ⋅ 3 Baths ⋅ Pine Ranch SubDv. ⋅ 34229 Zip Code
Rarely does a property offer this much flexibility in such a prime Osprey location. Set on two private acres in Pine Ranch, 403 Longbow Trail is more than just a home; it offers space to create a lifestyle most residential properties simply cannot accommodate. Bring the car collection, RV, boat, motorcycles or horses. The acreage offers the opportunity to explore a future RV or boat garage, collector-car garage, workshop or horse barn, subject to Pine Ranch and Sarasota County approvals. Pine Ranch restrictions permit horses and ponies at up to one per acre, allowing the possibility of up to two on this two-acre parcel, subject to applicable requirements. The approximately 2,770-square-foot residence features a bright, open interior and substantial updates. The remodeled kitchen offers extensive white cabinetry, sleek countertops, a farmhouse sink, stainless-steel appliances, gold-tone hardware and exceptional storage and workspace. Large windows and glass doors bring in natural light and connect the interior to the surrounding greenery. The flexible floor plan offers numerous possibilities. Upstairs, the primary retreat includes an en-suite bath, walk-in closet and private balcony overlooking the pool and grounds. On the first floor, adjoining rooms have been opened to create a larger bedroom area with access to a full bath and the pool area, offering excellent potential for a generous first-floor primary-style suite. Additional bedroom, bath and family room space near the garage creates excellent potential for an in-law or guest suite, office or multigenerational living. Car enthusiasts will appreciate the substantial three-car garage, while the acreage offers even greater possibilities for vehicle, RV, boat or recreational storage. A covered roof connection between the residence and garage area adds convenience, and the circular driveway provides generous access and parking. Outside, mature tropical landscaping surrounds the in-ground pool and patio. Beyond the pool, an expansive lawn, established trees and a peaceful pond with a waterside deck create a private setting for relaxing, gardening, pets or simply enjoying nature. The location is exceptional. Pine View School is approximately 0.6 mile away, with convenient access to the Legacy Trail via the nearby Osprey Junction Trailhead, Oscar Scherer State Park and Blackburn Point Park, where a public boat ramp provides access to Little Sarasota Bay and the Intracoastal Waterway. Nokomis Beach, Siesta Key, marinas, restaurants, shopping, US-41 and I-75 are all within easy reach. Whether your vision includes a collector-car garage, RV or boat storage, workshop, horses, multigenerational living or simply room to breathe, 403 Longbow Trail offers something increasingly difficult to find along Florida's Gulf Coast: space, privacy, flexibility, location and the opportunity to make the property your own. Certain listing photographs include virtually renovated or conceptual representations intended solely to illustrate possible future improvements. Those improvements are not existing features. Buyers should independently verify proposed uses, construction, permitting, zoning and association requirements.

403 Longbow Trail, Osprey
871 Macewen Drive, Osprey
$3,190,000
5 Beds ⋅ 6 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
A gracious columned front porch, classic dormers and a grand entry staircase introduce this distinctive residence in The Oaks. Set along the 13th hole, the home and separate guesthouse occupy more than half an acre framed by mature trees, with southern exposure, expansive greenspace to the east and no golf cart path bordering the property's side of the course. The setting feels remarkably private and spacious, with beautiful views from virtually every room. Timeless Southern character meets thoughtful updates, including a new tile roof, new hurricane-rated windows and skylights, freshly painted interiors and exterior, refinished wood floors, new upstairs flooring and updated lighting inside and out. Designer wallpaper and a new powder room vanity add fresh style, while the generous covered front porch offers an inviting place for morning coffee and relaxed gatherings. The kitchen features white cabinetry, quartz countertops, a waterfall-edge peninsula and a walk-in pantry. An oversized Viking six-burner gas range with a griddle, a Thermador refrigerator, a EuroCave wine cooler, a built-in Miele coffee maker and reverse osmosis system complement the space. Formal dining, a living room with a fireplace and a light-filled family room create inviting settings for entertaining and everyday living. The main-level primary suite overlooks the pool and grounds, spacious custom-organized closet, dual vanities, soaking tub and separate shower. A study and an exceptionally large laundry room with abundant storage complete the first floor. Upstairs, three bedrooms each feature an en suite bath and walk-in closet. A hidden playroom with skylights offers a magical retreat for imagination and creativity, with its area additional to the stated living square footage. With a full kitchen and bath, the separate guesthouse provides flexible accommodations for visitors, extended family or an au pair. Together, the main home and guesthouse frame an inviting outdoor retreat with an open-air pool and spa, palms and expansive golf course views. Generous entertaining areas, a fenced yard and a screened patio with a fireplace offer spaces to gather or unwind throughout the seasons. The home also includes a recently installed whole-house Generac generator with a 200-gallon buried propane tank. The Oaks lifestyle includes golf, tennis, pickleball, fitness and multiple dining venues, complemented by social gatherings and holiday traditions. Enjoy a casual meal at the Overlook or an evening celebration at the club, with the Legacy Trail, Pine View School and the beaches of Siesta Key and Casey Key nearby. Located in Flood Zone X with no reported history of flooding, this residence brings together architectural charm, substantial recent improvements and an exceptional golf course setting.

871 Macewen Drive, Osprey
455 Oak Point Road, Osprey
$600,000
4 Beds ⋅ 3 Baths ⋅ Blackburn Point Woods SubDv. ⋅ 34229 Zip Code
It’s always about the experience of living near Casey Key and the Intracoastal Waterway from this two-story town home in the maintenance-free community of Blackburn Point Woods. Nearby marina, waterfront park with boat ramp and trail for those seeking a lifestyle that celebrates the water, the wildlife, and the open spaces of Florida — nothing compares. A charming entry to the home leads to the inviting great room with soaring ceilings and a wood-burning fireplace. The first level features a private two-car garage and paver drive, French doors leading to a lanai and private pool area, and a secondary patio with an above-ground hot tub. With two bedrooms on the first level, one a generously sized primary with an en-suite bath, and two on the second, there is abundant space for everyone. Upper-level area for a den and a space for home fitness and an oversized closet. The chef's kitchen has solid wood cabinetry; topped in granite, there is kitchen dining as well as adjacent spacious formal dining. Thoughtful dry bar area for entertaining. Each floor/area of the residence has balconies for seamless indoor/outdoor living, the second-level 8-by-18 balcony has had wood replaced in 2026. Luxury Vinyl flooring throughout the living areas provides warmth and sophistication. Nearby are Publix, CVS, ice cream and coffee shops and numerous restaurants. This location is a short distance to Bayfront Park, tiki bar and two waterfront restaurants, a short scenic drive down Casey Key takes you to Nokomis Beach. The community amenities offer two heated pools, pickleball and tennis, a clubhouse and gym. This extraordinary home is the ideal frame for exceptional, easy living. Home is being offered turnkey furnished, excluding personal effects, some homeowner's decor, and staging decor.

455 Oak Point Road, Osprey
819 Golden Pond Court, Osprey
$799,000
4 Beds ⋅ 3 Baths ⋅ Rivendell The Woodlands SubDv. ⋅ 34229 Zip Code
Virtually Staged. Set on a private, preserve lot in Woodlands at Rivendell, this inviting home offers peaceful views and a desirable open floor plan. 4 bedrooms, 3 full bathrooms, 2-car garage with epoxy-coated flooring and roof replaced in June 2025. The grand covered entry and front porch lead into formal living and dining rooms, with neutral tile throughout the main living areas. The spacious family room features a built-in entertainment center and sliding glass doors opening to the lanai. The eat-in kitchen is appointed with maple wood cabinetry, granite countertops, tumbled marble backsplash, stainless steel appliances, farmhouse sink, under-cabinet lighting, ample pantry storage, and a breakfast bar. The primary suite features two walk-in closets and a separate bonus room overlooking the pool, ideal for a sitting area or home office. The ensuite bath offers separate vanities, soaking tub, and a walk-in shower. A split-bedroom layout provides three additional bedrooms and two full bathrooms on the opposite side of the home, offering privacy and flexibility. One bathroom serves as a convenient pool bath with direct access to the lanai. Enjoy the privacy of the secluded backyard, featuring an expanded screened lanai, heated pool and spa, and an expansive stone paver deck with plenty of room for entertaining. Additional stone paver space beyond the pool enclosure offers even more outdoor living options. Woodlands at Rivendell is a quiet, nature-filled community nestled among acres of lakes, preserves, and open spaces. Amenities include a heated community lap pool, playground, and scenic nature trails. Outdoor enthusiasts will appreciate the nearby Bay Street entrance to the Legacy Trail for biking and hiking, Oscar Scherer State Park for camping, hiking, kayaking, canoeing, and birding, and the boat and kayak launch on Blackburn Point for access to the Intracoastal Waterway. Conveniently located between Sarasota and Venice, the community is minutes from Gulf beaches, as well as shopping, dining, medical facilities, and cultural attractions. Experience the best of Florida living, surrounded by nature and close to everything you need.

819 Golden Pond Court, Osprey
1474 Landview Lane, Osprey
$1,485,999
4 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
Welcome to 1474 Landview Ln, a charming single-family home located in the desirable Southbay Yacht & Racquet Club in Osprey, FL. This spacious property features and exceptional layout with a total finished area of 3,246 sq.ft. As you step inside, you'll be greeted by a warm and inviting atmosphere with plenty of natural light flowing through the home. Quality, attention to detail, and fine finishes surround you in every room. The interior features 3 bathrooms, providing convenience and privacy for all residents and guests. Premium upgrades throughout include a built-in coffee system, custom cabinetry, multiple living rooms- including a 6' fireplace! The gourmet kitchen flows into the hearth room and simultaneously opens to the pool counter. The lot size is an impressive 10,560 sq.ft. offering ample outdoor space for entertaining, gardening, or simply relaxing in serene privacy. Whether you're looking to host a BBQ with friends or enjoy a quiet evening under the stars, this property has plenty of room to accommodate your lifestyle. Southbay Yacht & Racquet Club has it's own PRIVATE MARINA with well maintained boat slips up to 55ft. Easy access to the ICW and Gulf passes make Southbay one of Florida's most unique neighborhoods. Southbay is conveniently located near a variety of amenities and attractions, including the Heritage Bicycle and Recreational Trail. Finally, shopping, dining, a micro brewery, coffee shop, Pilates studio, fitness center, beauty salon and more are accessible with your golf cart via a designated entrance to the adjacent shopping center. Don't miss your chance to make this wonderful property your new home. With its ideal location, ample space, and charming features, boat slip, racquet courts, and more, 1474 Landview Ln is the perfect place to create lasting memories and enjoy the Florida lifestyle to the fullest. Contact us today to schedule a showing and see all that this property has to offer.

1474 Landview Lane, Osprey
642 Trenton Way, Osprey
$2,150,000
4 Beds ⋅ 5 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Beautifully updated and carefully maintained, this Rutenberg-designed home is idyllically situated on a half-acre corner lot surrounded by beautiful landscaping with views of the lake and the 14th Fairway of the Heron Course. This 4 bedroom residence has 4 full baths, 1 half bath, a formal living room with pool views, a separate formal dining room, and an open gourmet kitchen with gas cooktop, stainless appliances, two wallovens, a breakfast bar, an adjoining dining area and two pantries. The kitchen opens to an expansive family room overlooking the pool. The spacious master suite features a large luxury bath, two large his-and-hers closets and a lovely sitting area overlooking the pool. All three additional bedrooms are en suite. A dedicated office with built ins and a versatile bonus room/game room adds valuable flexibility for a wide variety of lifestyles. The large and lovely lanai includes an outdoor grill and bar, covered seating, awnings, and a freeform pool and spa overlooking the water and golf course. With a four-car garage, abundant storage and numerous updates, including a new roof installed in December 2024 (with warranty), a new pool heater installed in 2024, new central air conditioning (2 units, 2 zones) in 2022, freshly painted interior and exterior, this home is the perfect choice for those who want to live in comfort and luxury. A complete list of updates is available. The mandatory Membership to The Oaks Club will provide everything for living a country club lifestyle; two championship golf courses, tennis and pickleball courts, a regulation croquet lawn, state-of-the-art wellness center and a wide array of dining and social options. There is currently no waiting list for either Golf or Sports/Social membership.

642 Trenton Way, Osprey
335 Park Trace Boulevard, Osprey
$689,000
3 Beds ⋅ 2 Baths ⋅ Park Trace Estates SubDv. ⋅ 34229 Zip Code
Virtually Staged. Significant PRICE CORRECTION! Welcome to 335 Park Trace Blvd, an exceptional residence in the sought-after Park Trace Estates of Osprey, close to Pineview Education Center and The Legacy Trail where refined interiors, custom craftsmanship, and spectacular water views come together to create an elegant Florida retreat. From the moment you enter, the home makes a statement with its open living and dining spaces, dramatic triple tray ceilings, custom woodwork, and beautifully detailed wainscoting. A custom electric fireplace serves as a striking focal point, while the private den is enhanced by custom built-in shelving and handsome bookcases—an ideal setting for a home office, library, or quiet retreat. The kitchen features a Viking gas range, a Bosch dishwasher and refrigerator, offering both style and functionality for everyday living and entertaining. Designed for an exceptional indoor-outdoor lifestyle, the home opens to an extraordinary 44' x 39' screened lanai, featuring a gas-heated saltwater pool and approximately 32' x 24' of covered outdoor living space. Whether hosting an elegant gathering or enjoying a quiet evening at home, the expansive outdoor setting provides a front-row seat to the beautiful water views. The residence offers three generously proportioned bedrooms, each complemented by plantation shutters and an updated Jack & Jill Bath. The luxurious primary suite is a private sanctuary, featuring a spacious bath with a walk-in shower, soaking tub, and large walk-in closet. Important updates provide added peace of mind, including a new flat tile roof installed in 2026, plus an updated A/C system and hot water heater, both replaced in 2022. A large two-car garage adds valuable functionality, complete with a workbench and impact-rated garage door, providing ample space for vehicles, storage, and projects. With its remarkable water views, extensive custom millwork, designer-quality details, resort-style pool and lanai, updated systems, and exceptional outdoor living space, this home is waiting for you.

335 Park Trace Boulevard, Osprey
102 Windward Drive, Osprey
$1,047,000
3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
Experience refreshed coastal living in Southbay Yacht and Racquet Club. This beautifully updated pool home pairs inviting interiors with outdoor spaces made for relaxing and entertaining. Fresh exterior paint and refreshed landscaping with new sod and palm trees create a welcoming arrival. Inside, new vinyl flooring flows through the living spaces and bedrooms, complemented by large format tile in the bathrooms. High ceilings and a decorative beam add character to the open living area. The redesigned kitchen features new cabinetry, quartz countertops with a waterfall detail, stainless steel appliances, a range hood, pendant lighting, illuminated shelving and a walk in pantry. The home offers three bedrooms, two full bathrooms and one half bathroom. The primary retreat offers two newly built closets and a beautifully remodeled bathroom with a spacious double vanity, freestanding soaking tub, separate shower, new fixtures and mirrors. The remodeled guest bathroom features a large double vanity, coordinating tile and updated shower fixtures. The layout features dual primary bedrooms, with the second offering a generous walk in closet, an attached half bathroom and exterior access. Practical updates complement the refreshed interiors, with hurricane rated windows throughout the home and hurricane shutters for added storm protection. New ceiling fans in the bedrooms, an interior laundry room with a new washer and dryer combo, and an oversized garage with an epoxy painted finish add everyday convenience. Step outside to the screened pool and covered lanai, with a new outdoor shower for rinsing off after a swim. An expanded paver area beyond the lanai with a built in outdoor fireplace offers another inviting space to relax and entertain. Enjoy Southbay Yacht and Racquet Club’s waterfront lifestyle, featuring a community marina with Intracoastal access, a community pool, tennis, pickleball, a fitness center and clubhouse. From time on the water to relaxing evenings by your own pool, this home brings together beautifully updated spaces and an active coastal lifestyle. No CDD.

102 Windward Drive, Osprey
422 Blue Garden Lane, Osprey
$1,445,000
3 Beds ⋅ 4 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
Discover incredible value and endless potential in this beautifully maintained 3 bedroom, 3.5 bath home, tucked into lush tropical landscaping, on a quiet cul-de-sac in The Oaks Bayside. A grand traditional residence, with generous sized rooms, flexible living areas, and a private outdoor setting, the possibilities here are limitless. Step into the marble entry through the double front doors, and you will love what you find inside. Just off the entry, a cozy den with fireplace sits opposite a spacious guest suite. The heart of the home is the light-filled great room, with formal living and dining areas opening through French doors to the covered patio and resort-style pool. The kitchen combines beauty and function with granite countertops, center island cooktop, breakfast bar, and a sunny nook overlooking the pool. The elegant primary suite offers marble floors, soaring ceilings, plantation shutters, and private access to the pool for an early swim or late-night dip. A glamorous dressing area leads to the spa-like bath with soaking tub, walk-in shower, and marble finishes. Two additional oversized en suite bedrooms provide comfort and privacy for guests. A large laundry room with ample cabinetry and an adjacent private sauna completes the interior. Outdoors, the free-form pool with rock outcroppings and waterfall is a showstopper, surrounded by both shaded and open areas for dining and relaxing. With two adjoining lots preserved as gardens, this home offers rare seclusion in a natural setting. The Oaks Club features two 18-hole championship golf courses, an award-winning tennis program, pickleball courts, a state-of-the-art fitness center and a junior Olympic, community pool as well as a celebrated social calendar, and incredible dining options. There is currently no waiting list for either Golf or Sports/Social membership.

422 Blue Garden Lane, Osprey
168 Coastal Hammock Court, Osprey
$1,900,000
3 Beds ⋅ 4 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
Experience an extraordinary waterfront lifestyle in this distinctive 3-bedroom, 3.5-bath Mizner-inspired residence, ideally positioned along Little Sarasota Bay in the prestigious Oaks Bayside. Tucked away on an intimate cul-de-sac shared by just 3 homes, this exceptional property with close to 4,000 SF of living space, offers remarkable privacy, an enchanting Old Florida setting surrounded by mature oaks and lush tropical foliage, and captivating views and sunsets stretching across Little Sarasota Bay. Thoughtfully custom designed to embrace its spectacular surroundings, the home is filled with natural light and showcases beautiful architectural details throughout, including porcelain tile flooring, soaring 14-foot and tray ceilings, extensive custom millwork and built-ins, and walls of impact-rated windows and French doors framing the surrounding landscape and water views. Fresh interior paint and brand-new porcelain tile floors and carpeting in 2026 bring a crisp, refreshed feel to the residence while preserving its distinctive character. At the heart of the home, the kitchen features stone countertops, a Sub-Zero refrigerator, ASKO dishwasher, stainless steel appliances and generous workspace, opening comfortably to the home's main gathering areas. French doors create a seamless connection to the elevated pool and spa terrace, an inviting private retreat for entertaining, relaxing in the Florida sunshine or enjoying the bay breezes and spectacular evening skies. The expansive primary suite enjoys an entire level of its own, creating a true private retreat complete with a separate sitting room/office, custom built-ins, generous closet, dedicated laundry and an ensuite bath. The upper level provides exceptional privacy for family and guests with 2 additional bedrooms, a full bath, and flexible office/media space. The convenient 3+ car oversized garage with ample storage is on the ground floor. A brand new five-stop elevator will be installed to provide convenient access throughout the home, extending to the rooftop terrace where panoramic water views and unforgettable Florida sunsets take center stage. Enjoy ultimate peace of mind with a gas generator included on-site. Beyond the residence, ownership in The Oaks provides access to one of Sarasota's most established private country club lifestyles, with championship golf, racquet sports, state-of-the-art fitness, dining and an active social calendar. Community dock located on Little Sarasota Bay. Private, distinctive and surrounded by natural beauty, 168 Coastal Hammock Court presents a rare opportunity to enjoy gracious bayfront living in one of Sarasota's most coveted gated communities.

168 Coastal Hammock Court, Osprey
275 Lookout Point Drive, Osprey
$4,590,000
5 Beds ⋅ 5 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
Experience exceptional waterfront living in Southbay Yacht & Racquet Club at this expansive custom John Cannon residence offering more than 5,200 square feet, 5 bedrooms, 5 baths and sweeping panoramic water views from both levels. Set along more than 135 feet of waterfront, the home was thoughtfully designed to embrace its remarkable setting, with soaring ceilings, generous expanses of glass and beautifully proportioned indoor and outdoor living spaces overlooking the bay and Intracoastal Waterway. A completely reimagined front drive and all-new landscaping create a striking first impression and a fresh, refined coastal presence. Beyond the grand double-door entry, the home immediately opens to dramatic water views, drawing the eye through the interior and out toward the horizon. Ceilings rising to approximately 21 feet enhance the sense of scale, while a series of inviting living and entertaining spaces allow the home to feel equally suited for intimate evenings or larger gatherings. The kitchen serves as the heart of the residence, anchored by a substantial granite island and complemented by a gas cooktop with pot filler, while views stretch beyond the pool to the water. A full bar and dedicated wine room enhance the main level, with an additional wet bar upstairs for effortless entertaining throughout the home. Privately positioned on the main level, the primary suite is a serene waterfront retreat with a sitting area, two generous closets and an expansive bath. Additional downstairs bedrooms are thoughtfully located on the opposite side of the residence, creating privacy and separation for family and guests. Upstairs, either an office or a fifth bedroom offers an elevated and inspiring setting for work or quiet retreat, with access to the upper terrace and its sweeping water views. From both floors, the landscape of water and sky becomes part of the experience of the home. Outdoor living is equally memorable. A heated pool and spa, covered and screened entertaining areas, outdoor kitchen, fireplace, expansive terraces and private dock create a seamless connection between the residence and the waterfront. Mornings begin with peaceful views across the water, afternoons unfold poolside, and evenings are defined by the colors of sunset. Southbay Yacht & Racquet Club offers one of the area's most distinctive boating lifestyles. Its community-owned deep-water marina accommodates vessels up to 55 feet, allowing residents to walk or take a golf cart from home to their boat. Community amenities include a renovated clubhouse, geothermal pool, fitness center overlooking the marina, tennis and pickleball courts, bocce, shuffleboard, basketball, kayak storage, a waterfront park, approximately 20 acres of common grounds and miles of walking trails. Perfectly positioned between Sarasota and Venice and convenient to Siesta Key, Nokomis Beach, the Legacy Trail, Pine View School, waterfront dining, shopping and Oscar Scherer State Park, 275 Lookout Point is a compelling blend of scale, setting and lifestyle—a substantial waterfront residence with panoramic views, private outdoor living and direct access to the heart of Southbay’s boating community.

275 Lookout Point Drive, Osprey
650 Oaks Creek Court, Osprey
$3,700,000
4 Beds ⋅ 4 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
This custom-built 2024 masterpiece was thoughtfully designed to deliver the perfect balance of luxury, functionality, and effortless indoor-outdoor living. Positioned to capture sweeping views of the 6th and 7th holes of the Heron Course, the home showcases exceptional craftsmanship and attention to detail at every turn. From the moment you arrive, the impressive 10 foot hurricane-rated steel front door, circular driveway, and beautiful exterior create a lasting first impression. Inside, wood-look tile flooring flows throughout. The expansive open concept layout seamlessly connects the main living spaces while still offering dedicated rooms for privacy and everyday comfort. The designer kitchen is a true showpiece, featuring a custom range hood, pot filler, oversized refrigerator, and premium finishes that cater to both casual family meals and formal entertaining. The large master suite is a study in elegance. The luxurious master bath is the pinnacle of luxury, with dual sinks, a lighted stand alone make up table, claw foot tub, huge steam shower, expansive countertop and storage space along with custom lighting. The upstairs loft is a great addition for those who love to entertain and host guests. It has a bedroom, bathroom, and living area with a bar and a balcony providing lovely views over the pool. Step outside to a truly exceptional outdoor retreat where luxury and tranquility come together in a breathtaking setting. The resort-style pool and spa serve as the centerpiece of the home's outdoor living experience. Designed for both relaxation and entertaining, this private oasis features expansive lounging areas, an incredible outdoor kitchen, and seamless indoor-outdoor connectivity through hurricane-rated bifold sliders that open the home to the stunning golf course backdrop. Built not only for beauty, but also for convenience and peace of mind, the home is equipped with premium hurricane-rated windows and bifold sliders, spray foam insulation, central vacuum, automated lighting and climate control systems, and wiring for a generator. Everyday functionality is enhanced by a dedicated mudroom, spacious laundry room, climate-controlled storage, and a four-car garage complete with epoxy floors, custom storage solutions, and additional space for a gym or workout area. shaded dining, and a sun-splashed pool and spa area under a screened enclosure. With mandatory membership, this home offers access to all of the amenities being a member of The Oaks has to offer. There is currently no waiting list for either Golf or Sports/Social membership.

650 Oaks Creek Court, Osprey
256 Sugar Mill, Osprey
$1,349,000
3 Beds ⋅ 3 Baths ⋅ Oaks The SubDv. ⋅ 34229 Zip Code
This beautifully appointed residence sits on a private, well-maintained lot surrounded by grand, colossal oaks and palm trees, delivering the privacy and curb appeal today's buyers are searching for. Step through the front door and feel the difference - soaring tray ceilings, rich crown molding, and tons of natural sunlight set an elegant tone throughout. The gourmet kitchen is the true showstopper, with gleaming stone countertops, solid wood cabinetry, and an open flow into the living and dining areas — perfect for entertaining or unwinding after a day at the club. Retreat to the luxurious owner's suite complete with dual walk-in closets and a private sitting area, while two additional bedrooms offer guests or family their own well-appointed space. Move-in ready and meticulously maintained, this home features updated salt pool equipment, a refreshed kitchen area, and an updated 3-car garage with maintenance-free epoxy flooring. The compulsory membership in The Oaks Club unlocks an unbeatable lineup of amenities. Schedule a viewing today!

256 Sugar Mill, Osprey
324 Osprey Point Drive, Osprey
$3,700,000
5 Beds ⋅ 5 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
Welcome to extraordinary living! This completely private oasis is perfectly positioned along North Creek in The Oaks Bayside, one of the most sought-after communities in South Sarasota. Situated on a lot and a half, the view is peppered with lush foliage, creating total seclusion and the feel of a luxury retreat. One of the most desirable floor plans in the community, with open flow and complete separation from the master suite and guest accommodations, creates a comfortable and highly functional living space. The casita provides the perfect separate space for an office, a studio or long-term guest accommodations, with stunning views from the second floor. Fine finishes and quality craftsmanship are showcased throughout this home, custom built by renowned contractor Baron Construction. Features include French oak flooring, quartz countertops, premium appliances, central vac, wired Sono speakers throughout the house, ADT security and Ring camerias around the exterior, and numerous custom details. The combined living and dining area provides an ideal setting for entertaining, opening directly to the outdoor pool and spa. For more casual gatherings, the spacious kitchen and breakfast nook flow seamlessly into the family room and out to the covered outdoor living space. This screened area is beautifully designed with a pool and spa, and grill. The covered areas and ceiling fans provide comfort for al fresco dining. The lots’ site is spectacular, with great water views, and areas to launch your kayak or paddleboard. Add in the practical features like a newer roof, oversized three car garage and huge pantry and you have found a home of distinction with no peer. The Oaks Bayside is a gated bayfront community within The Oaks. The distinguished private club offers 2 championship golf courses, pickleball and tennis courts, a state-of-the-art WellFit Center, exquisite dining options and a celebrated social calendar. The location provides convenient access to downtown Sarasota, dining, nightlife, and the cultural amenities of the Gulf Coast. Club membership is required with home ownership. There is currently no waiting list for either Golf or Sports/Social membership.

324 Osprey Point Drive, Osprey
1417 Landview Lane, Osprey
$1,349,999
4 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
Looking for a home with room for everyone? This expansive 3255 square foot Southbay residence delivers! Located in the highly desirable Southbay Yacht & Racquet Club and close to the renowned Pine View School, this spacious home is just 12 years young. Built with 10-foot ceilings, generously sized rooms, beautiful architectural details and hurricane-rated windows and doors, it offers both style and peace of mind. Step inside the foyer to a welcoming dining room with an architectural wall opening to the living room featuring a shiplap accent wall and sliding glass doors leading to the covered lanai and pool area. The private primary suite is tucked away on its own and includes direct lanai access, two spacious walk-in closets, a large shower and two separate vanity areas. The kitchen is the heart of the home, with custom cabinetry, new KitchenAid black appliances, a center island, and a breakfast bar. It opens to both the dinette and family room, where an impressive wood-plank tray ceiling, decorative tile accent wall and electric fireplace create a warm and inviting gathering space. Toward the rear of the home are two Jack-and-Jill bedrooms with a shared bath. You’ll also find an office or den with built-ins, along with another full bath offering convenient access to the lanai. The staircase is discreetly tucked toward the back of the home and leads to an oversized bonus room,spacious bedroom, and additional full bath offering convenient- perfect for guests, extended family, a media room or private retreat. Thoughtful finishes continue throughout the home with attractive ceiling fans and light fixtures. Also located on the first floor is a dedicated laundry room tucked away off a hallway convenient to the kitchen. A two car oversized garage completes the first floor. Outdoor living is equally impressive. The lanai offers a large covered entertaining area, outdoor BBQ and easy access to the pool. The exterior features new sod and a circular paver driveway, adding to the home’s curb appeal. Other extra features include foam insulation in the roof, attic area and the exterior walls. Extra insulation added between master and living room and then shared wall for family room and bedroom. Southbay is a golf-cart-friendly community with something for all ages. Residents enjoy an active clubhouse with a fitness center, gathering rooms, two kitchens, ball room, card room, library, pickleball and tennis courts, bocce ball, basketball, kayak launch and storage, and a community pool overlook the marina. One of Southbay’s standout features is its resident-only marina, capable of accommodating a wide range of boat sizes at very reasonable slip rates, with direct access to the Intracoastal Waterway. The popular Casey Key Fish House and Tiki Bar is just an easy boat, golf-cart, or car ride away. Southbay is also conveniently located near restaurants, shopping, major roadways, and the Legacy Trail. Beautiful Gulf beaches are close by with Siesta Key less than 10 miles away and Nokomis Beach less than 5 miles away. Come see everything this special home - and the Southbay lifestyle - has to offer!

1417 Landview Lane, Osprey
1328 Thornapple Drive, Osprey
$719,900
3 Beds ⋅ 2 Baths ⋅ Willow Bend SubDv. ⋅ 34229 Zip Code
Virtually Staged. **PRICE IMPROVEMENT BY $30K!** Welcome to your ultimate lakeside maintenance free sanctuary! This home is nestled in a premier community renowned for its top-rated gifted school district & the renowned high quality builder Lee Wetherington. This expanded floor plan in the Willowbend Community offers 2,183 square feet of meticulously designed, sun-drenched living space with high ceilings, crown molding, ceiling fans and window treatments. Boasting 50 feet of lakefront views, the property features a North-facing orientation, allowing you to bask in the desirable southern rear exposure from your covered lanai with a retractable awning, sparkling pool, or soothing spa with a cascading waterfall—all without the harsh glare of direct sun. Through the glass paned front doors into an open-concept haven defined by a neutral color palette that acts as a blank canvas for your personal decor. Porcelain tile floors flow seamlessly through the common areas, while beautiful, warm hardwood floors bring comfort and sophistication to the bedrooms. Flooded with natural light, the main living areas feature large windows equipped with remote-controlled custom Hunter Douglas blinds for effortless light management. Just beyond the formal living and dining areas is the heart of the home in the inspired kitchen that serves as the perfect entertainment hub and a breakfast dinette area that overlooks the pool and spa. It features a counter top that flows into the main living room and the vibrant pool deck, sleek quartz countertops, and premium stainless steel appliances. Cooking appliances are electric, but you do have the option of installing gas if preferred. Pantry shelving is equipped with pull-outs. Working from home is a luxury in the oversized office/study, completely outfitted with a custom built-in desk and extensive shelving and drawers. The primary suite is a true homeowner's retreat, generously scaled to comfortably fit a king-sized bed, nightstands, and a dedicated sitting area. It offers two spacious walk-in closets and a spa-like ensuite bathroom complete with a water closet, a deep soaking tub, a glass-enclosed shower, and two separate vanities packed with storage. The two additional bedrooms are equally impressive, each featuring large windows and substantial closet space. Peace of mind and efficiency are built right into this structurally sound property. The majority of the windows and doors are hurricane-impacted, supplemented by heavy-duty accordion shutters for the lanai sliding doors. Living here means enjoying a low-maintenance, resort-style lifestyle. The comprehensive HOA fee conveniently covers lawn care maintenance, high-speed internet, basic cable TV, and irrigation water. Beyond your front door, the neighborhood provides access to fantastic family amenities, including tennis, pickleball and basketball courts, a fully equipped workout center, a community pool & spa, and a playground. Have a piece of mind with a HVAC installed in 2023, a gas water heater from 2018 and a washer and dryer from 2021, and a NEW pool heater installed September 2026, all well maintained and in perfect working order. The location of Willow Bend offers not only a top rated gifted school district, its proximity to shopping, top rated hospitals and medical care, you are also close to some of the most beautiful beaches of Osprey, Nokomis & Venice. This lakefront masterpiece perfectly combines luxury, safety, and community—that you can start enjoying today!

1328 Thornapple Drive, Osprey
1216 N Casey Key Road, Osprey
$9,750,000
5 Beds ⋅ 8 Baths ⋅ Casey Key SubDv. ⋅ 34229 Zip Code
At the northernmost point of Casey Key, where the Gulf meets the tranquil waters of Little Sarasota and Blackburn Bay, an extraordinary private estate unfolds between two worlds of water. Beyond a secluded entrance lies a residence of remarkable distinction, an Italianate architectural masterpiece spanning more than 8,000 square feet, with a private sandy beach on the Gulf and a rare, grandfathered covered boat lift on the bay. Designed by renowned architect Clifford A. Scholz and masterfully built by Delta Southern Construction, the estate was envisioned not simply as a home but as a setting for an exceptional life. Here, timeless architecture, impeccable craftsmanship and modern coastal luxury converge in a residence designed to bring family and guests together while preserving moments of treasured privacy. From the moment of arrival, the architecture reveals a quiet sense of grandeur. Cypress-beamed ceilings, graceful arches, French doors, handcrafted millwork, and luminous water views create a sequence of spaces that feel both magnificent and deeply welcoming. The living room commands a captivating panorama across the Bay, while walls of glass and elegantly framed openings blend the boundary between interior and landscape. The culinary spaces are equally impressive. A sophisticated kitchen is complemented by a dedicated wine cellar, butler’s pantry, and wet bar—an entertainer’s dream conceived for intimate dinners and spectacular gatherings alike. Beyond, a grand media room provides an elegant retreat for cinematic evenings, music, and cultural pursuits. The primary suite is a private sanctuary unto itself. A serene sitting room, sumptuous bath, dual closets, breakfast nook, and expansive water views create an atmosphere of effortless indulgence. Three additional bedroom suites offer luxurious accommodations for family and guests, while a fifth suite transforms into a private wellness retreat with a home gym, steam room, and sauna. A magnificent marble staircase leads to an office and library distinguished by leaded-glass doors, handcrafted built-in shelving, a coffered ceiling, and mesmerizing Gulf views. Throughout the residence, additional spaces for recreation, relaxation, and quiet spaces have been thoughtfully integrated, ensuring that every corner serves the extraordinary rhythm of life on the water. Outside, stone terraces cascade toward a shimmering infinity pool, where the architecture gives way to sky and water. Days unfold between the pool and the Gulf, afternoons drift toward the bay, and evenings become unforgettable beneath the coastal sky. For the boating enthusiast, the deep-water dock offers quick access with no bridges to the Gulf through Midnight Pass and features one of the area’s rare grandfathered covered boat lifts. For those drawn to the Gulf, a private sandy beach provides a front-row seat to spectacular sunsets and the timeless beauty of the sea. Yet perhaps the estate’s greatest luxury is its sense of place. North Casey Key remains one of Sarasota County’s most coveted enclaves—a sanctuary of quiet privacy and natural beauty, remarkably close to world-class golf, tennis, dining, shopping, and the cultural attractions of Sarasota. This is more than an exceptional residence. It is a private coastal world—an irreplaceable estate where architecture, water, nature, and the art of gracious living come together in extraordinary harmony.

1216 N Casey Key Road, Osprey
296 Pine Ranch Trail, Osprey
$1,000,000
5 Beds ⋅ 4 Baths ⋅ Pine Ranch East SubDv. ⋅ 34229 Zip Code
Welcome to this rare slice of coastal paradise tucked away in the boutique enclave of Pine Ranch East in Osprey, Florida. Situated on a sprawling 1.137-acre private lot, this magnificent residence offers an extraordinary blend of space, serenity, and convenience. The property boasts five spacious bedrooms and three-and-a-half baths, providing a flexible layout designed to accommodate large families, host overnight guests, or create dedicated home office spaces. Every detail of the interior reflects thoughtful maintenance and pride of ownership, offering a seamless flow between the primary living areas. Designed for quintessential Florida living, the expansive backyard functions as your own private resort. Step out onto the oversized covered lanai to entertain year-round, or cool off in the crystal-clear heated pool and integrated spa while taking in the tranquil scenery of your secluded acreage. Despite the incredible privacy, you are just minutes away from pristine Gulf beaches and iconic local dining hot spots like Pops Sunset Grill and the Casey Key Fish House. Adding to the unmatched value of this property is its setting within Pine Ranch East, an exclusive neighborhood comprised of only 26 homes. While the community maintains an established HOA structure, homeowners enjoy the astonishing benefit of paying no HOA fees thanks to a unique financial setup that leaves the neighborhood fully funded years into the future. Contact us today to learn more about this remarkable community story or to schedule your private tour.

296 Pine Ranch Trail, Osprey
299 Turquoise Lane, Osprey
$649,000
3 Beds ⋅ 2 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
Remarkable 3 bedroom 2 bathroom home in Emerald Woods now available for purchase. Nestled in the Oaks Preserve Neighborhood and offering a maintenance free lifestyle with 24 hour guarded gate. Features include; Beautiful Tray Ceilings, Crown Moldings, Plantation Shutters, Solid Surface Countertops, Tile flooring throughout living spaces, and an Spectacular Owner’s Suite with multiple walk-in closets and sitting area.The Oaks Club boasts 2 Championship Golf Courses, 12 Har-Tru Tennis Courts (4 lighted), State Of The Art Fitness Center, Junior Olympic Swimming Pool, Regulation Croquet Court, 4 Pickle Ball Courts, along with numerous dining, social and recreational options. Conveniently located near Florida's top rated Pine View School, the Legacy Bike Trail, and the world renowned beaches of Siesta Key, Casey Key, and so much more. Just a short distance from shops, restaurants, and the cultural offerings of downtown Sarasota. Membership to the club is mandatory. Some images may have been Virtually Staged/Edited...

299 Turquoise Lane, Osprey
75 Osprey Point Drive, Osprey
$1,595,000
4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks. Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting. A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fireplace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout. The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer. Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community. Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.

75 Osprey Point Drive, Osprey

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