Osprey Homes with Private Pool type

Osprey Homes with Private Pool type

Welcome to Osprey, Florida, a hidden gem nestled in the heart of Sarasota County. This charming community, located just south of the bustling city of Sarasota, offers a perfect blend of serene coastal living and vibrant local culture. With its picturesque landscapes, tranquil waterways, and proximity to stunning beaches, Osprey is an ideal destination for those seeking a peaceful yet engaging lifestyle.

Osprey is renowned for its lush parks, scenic trails, and rich history. Visitors and residents alike can enjoy the breathtaking views at the nearby Oscar Scherer State Park, which offers miles of hiking trails and opportunities for birdwatching. The area's historic downtown boasts delightful shops, cozy cafes, and local art galleries, creating a warm and inviting atmosphere that reflects the community's character.

For those dreaming of a home with a private pool, Osprey is the perfect place to turn that dream into reality. Many properties in this area feature stunning pools, allowing you to bask in the Florida sunshine right in your own backyard. Imagine hosting summer barbecues, relaxing with a good book by the water, or enjoying a refreshing dip after a long day. Homes with private pools in Osprey not only provide a luxurious lifestyle but also offer a tranquil retreat for families and individuals alike.

Whether you're looking to settle down or invest in a vacation home, Osprey's real estate market is thriving. With its beautiful surroundings and community spirit, this charming region is waiting to welcome you home. Explore the possibilities and discover the joys of living in Osprey, where your dream home with a private pool awaits!

Newest Osprey Homes with Private Pool type

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
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