Osprey Homes with Fitness Center Community Features

Osprey Homes with Fitness Center Community Features

Welcome to Osprey, Florida—a hidden gem nestled in Sarasota County that beautifully blends coastal charm with vibrant community living. Just a stone's throw from the stunning Gulf of Mexico, Osprey offers residents a unique lifestyle characterized by its picturesque landscapes, rich history, and an array of outdoor activities. With its lush parks, serene beaches, and proximity to the renowned Oscar Scherer State Park, Osprey is a nature lover's paradise, perfect for hiking, biking, or simply soaking up the sun.

For those seeking an active lifestyle, Osprey's homes with fitness center community features are a highlight. These thoughtfully designed residences not only provide comfortable living spaces but also offer state-of-the-art fitness facilities right at your doorstep. Imagine starting your day with a refreshing workout without ever having to leave your community! Whether you prefer a morning jog on the treadmill, a yoga session, or strength training, these fitness centers cater to all levels of fitness enthusiasts.

Beyond fitness, the community atmosphere in Osprey is warm and welcoming. Residents enjoy a range of amenities, including swimming pools, tennis courts, and social gathering spaces, fostering a sense of belonging and camaraderie. With a variety of local shops, dining options, and cultural attractions nearby, Osprey is not just a place to live—it's a lifestyle.

Discover the perfect blend of relaxation and recreation in Osprey, where your dream home awaits in a community that prioritizes health and happiness. Come explore the possibilities and make Osprey your new home today!

Newest Osprey Homes with Fitness Center Community Features

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 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 goes out to the enclosed back patio, making 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. 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 the lovely home, combined with the quiet, private setting on 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 pickle ball courts, a state-of-the art fitness center, fine and casual dining options, and a wealth for 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
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
232 Hidden Bay Drive Unit 303, Osprey
$569,000
2 Beds ⋅ 2 Baths ⋅ Baypointe Vista SubDv. ⋅ 34229 Zip Code
Waterfront resort-style living is behind the gates of Hidden Bay, set along the shores of the Intracoastal Waterway, Little Sarasota Bay, and a tranquil preserve and park in the heart of Osprey. This third-floor residence, accessible by elevator, has been tastefully remodeled and offers two full bedrooms, each with en-suite baths, a spacious den and a three-car garage. The lanai’s exterior sliders open to an all-season, tiled living area where you can enjoy birdwatching and wildlife in the mangroves, observe passing boats, feel gentle bay breezes and take in spectacular sunsets. The wonderfully efficient kitchen features Corian countertops, a breakfast bar with seating for four, new (2025) LG stainless steel appliances and abundant pantry storage within newly outfitted cabinetry, complete with pullout drawers in the kitchen and baths. This beautifully appointed home showcases Acacia engineered flooring, high ceilings, a generous laundry room with newer GE appliances, a sink, tile flooring and ample storage, plus a den or office off the breakfast area. This condominium features a rare three-car garage which includes a private single garage, allowing this space to be used as art studio workshop, or the ever-elusive onsite storage unit along with a separate and spacious two-car garage on the first level. A new roof and updated elevator motor were added in 2025, along with completed Milestone and Reserve studies. Many of the attractive furnishings are available under a separate bill of sale. This exceptional gated waterfront community features a 1,500-foot elevated wooden boardwalk winding through lush landscaping and palm-lined grounds, leading to a private bay front fishing pier. Residents enjoy a renovated clubhouse offering a full kitchen, with granite bar and graciously appointed social area which can be used for private events. Owners also enjoy a fully stocked library, a professional fitness center, and an entertainment and media area. Outside the clubhouse, there is a heated pool, hot tub and tiki hut for additional social gatherings. Hidden Bay is conveniently near restaurants, shopping, Legacy Trail and Nokomis Beach. Osprey is a lovely area between Sarasota and Venice featuring old Florida vibes, peaceful surroundings, and an easy, quiet, lifestyle. Seller willing to lease back.

232 Hidden Bay Drive Unit 303, Osprey
409 N Point Road Unit 601, Osprey
$1,175,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
Experience luxury living in this spacious, light-filled corner residence offering nearly 2,600 square feet of elegant living space. Featuring three bedrooms, a den/office, and three full baths, this exceptional condo also includes access to two elevator banks, two assigned second-level parking spaces, and a climate-controlled storage unit. Located behind the secure gates of The Oaks Preserve, this unit has a thoughtfully designed open floor plan showcasing beautiful flooring throughout, crown molding, two wine reserve refrigerators, and a smart Nest thermostat. The updated kitchen features granite countertops and premium stainless-steel appliances, including Bosch and GE Monogram. The spacious master suite offers private balcony access, a walk-in closet, and an updated spa-inspired bath with dual vanities, a custom-tiled shower, and a soaking tub. When you step out onto the screened balcony, equipped with Kevlar hurricane shutters, you will be taken with the expansive views over the Preserve and out to the Bay. And, as another perfect Florida day ends, this is the perfect place to take in breathtaking sunsets, as the sky is drenched with gorgeous color. Residents of the Meridian enjoy exclusive amenities, including a heated pool and spa, workout room and outdoor grilling area. Additionally, with mandatory club membership, you can take advantage of all that The Oaks offers: two championship 18-hole golf courses, an award-winning racquets program with 12 Har-Tru courts, pickleball courts, a junior Olympic community pool, state-of-the-art WellFit center and casual-to- refined dining options. There is currently no waiting list for either Golf or Sports/Social membership.

409 N Point Road Unit 601, Osprey
250 Hidden Bay Drive Unit 301, Osprey
$695,000
3 Beds ⋅ 3 Baths ⋅ Edgewater At Hidden Bay SubDv. ⋅ 34229 Zip Code
Enjoy sweeping water views and stunning sunsets over Little Sarasota Bay from this spacious third-floor corner residence in the gated waterfront community of Edgewater at Hidden Bay. Built in 2017 and moved into in January 2018, this three-bedroom plus den, 2.5-bath condominium offers nearly 2,200 square feet of living space with easy elevator access and one assigned parking space in the building. The attractive open floor plan features soaring ceilings, impact-rated windows and sliding doors, easy-to-maintain tile plank flooring and abundant natural light throughout. The kitchen includes granite countertops, solid wood cabinetry, stainless steel appliances and custom storage with pullout drawers. The living area opens to a large, screened-in terrace with privacy screens and expansive bay views. The primary suite includes dual walk-in closets and a luxurious bath with dual quartz vanities, decorative tile flooring, a makeup vanity and a walk-in shower. Additional features include a private den/office, an in-unit laundry room, two full baths and a powder room, and air conditioner from 2023. Edgewater at Hidden Bay is a gated, resort-style community set on 14 acres along Little Sarasota Bay and the Intracoastal Waterway, directly across from Casey Key. Community amenities include a waterfront clubhouse with a kitchen and quartz bar, a heated pool and spa, a fitness center, a library, a tiki hut with grilling stations, pickleball and tennis courts, a kayak launch, a fishing pier, a dog play area, and an elevated boardwalk through mangroves and palm-lined grounds. Hidden Bay is conveniently in Osprey, just south of Sarasota, near area beaches, shopping and dining and only minutes from Venice.

250 Hidden Bay Drive Unit 301, Osprey
14041 Bellagio Way Unit 315, Osprey
$640,000
3 Beds ⋅ 2 Baths ⋅ The Villas At Bellagio Harbor Village SubDv. ⋅ 34229 Zip Code
There is something extraordinary about living on the water, where passing sailboats, coastal breezes, and the beauty of the marina become part of everyday life. Welcome to Osprey Harbor Village, an intimate waterfront community perfectly positioned between Sarasota and Venice, where timeless elegance meets the relaxed sophistication of Southwest Florida living. From the moment you enter, the welcoming foyer introduces a thoughtfully designed residence that balances comfort, elegance, and effortless entertaining. The spacious kitchen features rich upgraded wood cabinetry, granite countertops, stainless steel appliances, and a generous breakfast bar where family and friends naturally gather. An inviting dining area transitions into the comfortable living room, with access to the expansive terrace that truly sets this home apart. Whether entertaining guests, enjoying a quiet evening, or simply watching the activity along the waterfront, this outdoor living space is destined to become one of your favorite places. The generously sized primary suite offers a peaceful retreat with a spacious walk-in closet and an ensuite bath featuring dual vanities, a soaking tub, separate shower, and private water closet. Two additional bedrooms provide wonderful flexibility for visiting family and friends, a home office, or whatever suits your lifestyle. Beyond the residence, Osprey Harbor Village offers an exceptional waterfront experience. This boutique community of just 54 condominiums showcases distinctive Italian-inspired architecture and was constructed in 2006 to hurricane building standards. Boating enthusiasts will appreciate the marina setting and approximately 7-foot draft channel, providing access to the beautiful waterways that make Florida's Gulf Coast a boating paradise. Whether you enjoy sailing, cruising, fishing, kayaking, or simply admiring the boats from your terrace, life here revolves around the water. The community amenities create an atmosphere that feels more like a private waterfront resort. Enjoy a newly renovated, fully equipped fitness center, sparkling community pool, poolside grilling area, relaxing spa, sauna, steam room, fishing dock, and kayak launch. Spend your afternoons poolside, take a peaceful paddle along the waterways, or gather with friends after a day of exploring the coast. Additional conveniences include two assigned garage parking spaces, onsite management, and a pet-friendly environment welcoming up to two large dogs. And the location? It's one of the best parts. Imagine being able to stroll to waterfront dining at Deep Lagoon Seafood & Oyster House or the beloved Casey Key Fish House, enjoy the casual atmosphere of a nearby tiki bar, or explore the waterfront park just across the street. The beautiful beaches of Casey Key are only a short drive away, while Publix, shopping, restaurants, medical facilities, and the endless attractions of Sarasota and Venice are all conveniently nearby. From boating adventures and beach days to waterfront dining and peaceful evenings at home, the possibilities are endless. What makes Osprey Harbor Village truly special isn't simply the architecture, the amenities, or even the spectacular marina setting. It's the lifestyle that comes with it. Spend more time outdoors, entertain the people you love, and enjoy the beauty of coastal living in a community that feels both exclusive and welcoming. Discover the waterfront lifestyle waiting for you at Osprey Harbor Village today!

14041 Bellagio Way Unit 315, 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
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
717 Pine Run Dr. Unit 717, Osprey
$159,900
1 Beds ⋅ 1 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
Ready for your own slice of Florida paradise? This fully furnished, turnkey one-bedroom condo in Osprey’s Pine Run community is ready to welcome you home. Its second-floor setting offers a charming treehouse feel, surrounded by the community’s lush, natural landscape. Well cared for and thoughtfully updated, this condo features BRAND-NEW A/C (SEPTEMBER 2026), A NEW TANKLESS WATER HEATER (2025), AND A NEW HURRICANE-RATED SLIDING GLASS ENTRY DOOR (2022). Soaring ceilings and three sliding glass doors fill the open living and updated kitchen area with natural light, creating a bright, airy atmosphere. The screened balcony is an inviting spot for morning coffee or relaxing at the end of the day. A carport space directly below the condo provides convenient covered parking, along with an oversized storage closet. Whether you’re purchasing your first Florida home, downsizing, or looking for a winter retreat, this condo offers comfortable, easy living and includes a second sleeping area with a pull out sleeper sofa in the livingroom. Shopping and restaurants are within easy walking distance, with the local favorite Casey Key Fish House and Tiki Bar just down the street, along with the Intracoastal Waterway. Nearby Blackburn Point Park and its boat launch offer even more ways to enjoy the outdoors. Pine Runs’ amenities include pickleball and tennis courts, two pools, a community clubhouse, and a fitness area - all nestled within a lush, natural setting. Come take a look and picture yourself enjoying the Florida Lifestyle!

717 Pine Run Dr. Unit 717, Osprey
401 N Point Road Unit 703, Osprey
$1,200,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
Enjoy spectacular Gulf sunsets from this Move-In Ready, Fully Renovated 7th-floor condominium residence featuring 3-Bedrooms, 3-Full-Baths and over 2,200 square feet of beautifully designed living space with an open floor plan ideal for both everyday living and entertaining. The thoughtfully updated kitchen features quartz countertops, stainless steel appliances, Sub-Zero refrigeration, a wine refrigerator, and an Invisacook® invisible induction cooktop, creating a sleek and highly functional culinary space. The spacious private balcony offers tranquil preserve views and abundant opportunities for wildlife watching. Additional highlights include two assigned parking spaces and an exceptional combination of expansive views, privacy, modern finishes, and coastal living. A new HVAC system adds to the convenience and peace of mind. A must-see property! Residents enjoy private amenities including a heated pool and spa, fitness center, and outdoor grilling area, along with full access to The Oaks Club’s renowned lifestyle amenities. Meridian Tower #3 also features a new roof (2025). 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**

401 N Point Road Unit 703, 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
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