Osprey Homes with Association Recreation - Owned Community Features

Osprey Homes with Association Recreation - Owned Community Features

Welcome to Osprey, Florida, a hidden gem nestled in the heart of Sarasota County. This charming coastal community seamlessly blends the tranquility of nature with the vibrancy of coastal living. With its picturesque landscapes, Osprey offers a serene escape just minutes from the bustling beaches of Nokomis and Venice.

Osprey is celebrated for its lush greenery, scenic waterways, and close-knit atmosphere. Residents enjoy a variety of outdoor activities, from kayaking along the tranquil waters of the Intracoastal Waterway to exploring the nearby Oscar Scherer State Park, where nature trails and wildlife abound. The community is also known for its rich history, with landmarks like the historic Spanish Point offering a glimpse into the area’s past.

For those seeking a vibrant lifestyle, Osprey boasts homes within association recreation-owned communities, providing an array of amenities designed to enhance your living experience. These communities often feature resort-style pools, tennis courts, fitness centers, and clubhouses, perfect for social gatherings and recreational activities. Imagine waking up to the sound of birds chirping, taking a leisurely stroll along beautifully manicured pathways, and enjoying a sunset swim with neighbors who quickly become friends.

Whether you’re looking for a permanent residence or a seasonal retreat, Osprey’s blend of natural beauty and community spirit makes it an ideal place to call home. Discover the charm of Osprey, where every day feels like a vacation and a vibrant community awaits you!

Newest Osprey Homes with Association Recreation - Owned Community Features

3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Offering 3 bedrooms, 2 baths, den/office, 2,411 square feet under air, a spacious living room, a 2-car garage, and a private 14' x 37' heated pool centrally positioned as the focal point of the home. This beautifully updated, move-in-ready residence blends luxury, comfort, and the ultimate coastal lifestyle in the highly sought-after waterfront Southbay Yacht & Racquet Club - Marina Community. The thoughtfully designed split floor plan is ideal for indoor-outdoor living. Multiple rooms overlook and open directly onto the covered lanais and the private heated pool, which is framed on three sides by the home creating a stunning courtyard oasis. Dramatic floor-to-ceiling impact-rated windows and sliders (2020) frame beautiful pool views, while soaring ceilings and an abundance of natural light enhance the bright, open feel. The luxurious primary suite includes an adjoining office/den and an ensuite bath with soaking tub and custom cabinetry. Two guest bedrooms and an updated guest bath are located in a separate wing. A custom queen-size library-style Murphy bed adds flexibility for guests or workspace. Step inside to discover stunning 12” x 72” Ceramica Sant’Agostino Italian porcelain plank tile flooring (Barkwood Ash) throughout, soaring ceilings, custom millwork, new 8-inch baseboards, upgraded lighting and fans, and fresh interior and exterior paint (2025). The chef-inspired kitchen features all-new custom cabinetry, quartz countertops, a large center island with seating for 8-10, high-end 2025 GE Monogram appliances (including 48” refrigerator, induction cooktop, and wall oven/microwave), a built-in wine refrigerator, and excellent storage. The open dining area includes a beautifully integrated bar with custom cabinetry and a fireplace (ready for insert). Additional highlights include dual-zone A/C systems (new 2025), new Electrolux stackable washer and dryer (2025), spacious laundry room with utility sink and coffee/tea bar, new concrete tile roof (2020), re-plumbed (2007), oversized 2-car garage with epoxy floor and custom storage, mature tropical landscaping with irrigation, private outdoor shower, and room to add a 4th-bedroom with ensuite bath or additional garage storage. Located in the desirable Southbay Yacht & Racquet Club - Marina Community, this premier boating community features a private 172-slip deep-water marina that can handle vessels up to 58 feet for very reasonable fees. Residents enjoy low HOA fees and a wonderful social atmosphere with a clubhouse, fitness center, heated community pool, spa, tennis courts, pickleball, basketball, bocce, playground, kayak launch/storage, jet ski pads, and more. This golf cart-family friendly community offers easy access to Nokomis Beach, Casey Key, waterfront dining, shopping, Publix, Aldi, restaurants, and tiki bars. All interior and exterior furnishings, artwork, TVs, potted plants, and outdoor gas grill with pizza oven are available for purchase separately via bill of sale. This is a must-see, comprehensively updated home in Southbay.

206 Four Knot Lane, Osprey

2 Beds ⋅ 2 Baths ⋅ Heron House SubDv. ⋅ 34229 Zip Code

**BEAUTIFULLY UPDATED CONDO, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO** Featuring 2 Beds and 2 Full Baths, this FULLY RENOVATED, 2ND FLOOR unit features an Impressive Kitchen with quartz counters, stainless steel appliances, new solid wood cabinets while the Spacious Owner’s Suite boasts custom built-in cabinets/closets and an equally Elegant Bath. CoreTec Vinyl Flooring throughout (except guest bedroom). Enjoy the serene and natural surroundings from your elevated, sprawling and screened balcony which is accessible from multiple rooms via sliding doors. This Secure and Gated Community offers the ultimate Florida Lifestyle! Amenities include Community Pool, Tennis and Pickleball Courts, Clubhouse with Fitness Center, Boat Dock (subject to availability), Kayak launch and storage, Gazebo with BBQ, etc. Private covered parking and storage are located on the ground level within the building. Blackburn Harbor is ideally situated in Osprey between Sarasota and Venice and is just minutes minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer! **RECENTLY COMPLETED PROJECTS INCLUDE: ASPHALT PAVING, IRRIGATION, WALKWAYS, WALKWAY LIGHTING, LIGHTING at TENNIS AND PICKLEBALL COURTS, etc.

7204 Jessie Harbor Drive Unit 7204, Osprey

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

INCREDIBLE OPPORTUNITY AND A MUST SEE AT THE MERIDIAN AT THE OAKS - GREAT PRICE, BAY VIEW, UPDATED KITCHEN, PRIVATE 2 CAR GARAGE AND MORE! Beautifully updated and thoughtfully designed, this exceptional 5th floor residence in The Meridian at The Oaks Preserve offers tranquil water and preserve views, a fantastic floor plan, and the rare convenience of a private 2-car garage just steps to the elevator lobby. The expansive split-bedroom floor plan includes 3 bedrooms, 3 full baths, and a private den/study/office that can easily function as a 4th bedroom, providing exceptional flexibility for both everyday living and visiting guests. Filled with natural light, the spacious great room and dining areas flow seamlessly to the generous terrace with upgraded ceramic tile, where peaceful water and preserve views create a serene backdrop for relaxing or entertaining. The custom kitchen, redesigned in 2023, is both elegant and functional, featuring soapstone countertops, Bosch appliances, roll-out cabinetry, Everpure water filtration, a tray ceiling, and detailed crown molding. The primary suite is a private retreat, offering picturesque water views, a custom-designed walk-in closet, and a beautifully appointed bath with Italian tile, dual vanities, and stunning stone countertops. Custom built-ins, upgraded closet systems, and a thoughtfully designed laundry room further enhance the home's comfort and functionality. Residents of The Meridian enjoy lushly landscaped grounds, winding pathways, a community pool and spa, fitness center, and outdoor grilling area. Membership in The Oaks Club is required, providing access to one of Sarasota's most distinguished private club lifestyles, including two championship golf courses, 12 Har-Tru tennis courts, pickleball, croquet, a state-of-the-art wellness center, resort-style pool, multiple dining venues, a vibrant social calendar, and an elegant clubhouse. Ideally located near Historic Spanish Point, Pine View School, Siesta Key Beach, and downtown Sarasota, this exceptional residence offers a rare combination of luxury, privacy, natural beauty, and resort-inspired living.

401 N Point Road Unit 504, Osprey

3 Beds ⋅ 4 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Virtually Staged. A unique offering! This like-new, never lived in Spanish mission style home is a rare find. Move in ready and set on a private .63 acre lot in The Oaks Preserve, the open floor plan includes 3 en suite bedrooms and 3.5 baths. Thoughtfully designed, it welcomes you with a circular driveway, porte cochere, and a detached 2 car garage equipped with an electric vehicle charger. Inside, soaring ceilings, neutral tile and wood flooring, recessed lighting, and an electric fireplace create a warm, refined ambiance. Built to current codes with impact glass and a new roof, the home offers peace of mind and the efficiency of modern construction. The chef’s kitchen, with Bosch stainless appliances, a gas 5 burner cooktop, soft close cabinetry, a center island with wine storage, and stylish tile finishes, has a breakfast bar and opens to the dining room. The luxurious master suite features a vaulted ceiling, spacious walk-in closet, and a spa inspired bath complete with freestanding tub, glass enclosed shower, dual vanities, bidet, and exquisite tilework. A central brick paver courtyard provides a private tropical retreat with ample room to add a pool. Sarasota’s premier golf and country club, The Oaks Club’s unmatched amenities include two championship 18-holf golf courses, 12 tennis courts and 4 pickleball courts, the state-of-the-art WellFit Center, a junior Olympic pool, a celebrated social calendar, and a wide array of dining options and recreational activities. There is currently no waiting list for either Golf or Sports/Social membership

360 N Point Road, Osprey

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Don't miss this opportunity to own a home in a desirable private marina community. This spacious 3-bedroom, 3-bath home features high ceilings and a beautifully updated kitchen designed for both everyday living and entertaining. An amazing Value! A combination of comfort and style with light-filled living spaces. Enjoy Florida living at its best with a private pool and amazing lanai area with plenty of covered patio. The oversized two car garage provides plenty of space for a golf cart. Southbay Yacht & Racquet Club is a highly sought-after Marina community offering a clubhouse, resort-style amenities and recreational activities for all ages. Tennis, pickleball, bocce ball, playground, kayak launch and storage, jet ski pads, fishing & boating. Southbay Yacht & Racquet Club is a community like no other in that it has a private 172 boat slip Marina with deep water able to accommodate boats up to 58 feet. Walk, bike or take your golf cart to beaches, shopping, restaurants & tiki bars.

204 Windward Drive, Osprey

3 Beds ⋅ 2 Baths ⋅ Edgewater At Hidden Bay SubDv. ⋅ 34229 Zip Code

Move right in and enjoy refined coastal living in this brand-new condominium at Edgewater at Hidden Bay. Offering 1,937 square feet, this thoughtfully designed home features three spacious bedrooms, two stylish bathrooms, and a versatile office—perfect for work or creativity. The sleek kitchen is the heart of the home, complete with premium LG appliances, solid wood cabinetry, and elegant quartz countertops. Sun-filled living spaces are enhanced by large windows with partial views of Little Sarasota Bay, creating a calm and inviting atmosphere. Well-appointed bedrooms and beautifully finished bathrooms provide comfort and style throughout, with high-end details and a seamless, modern layout. Set in the desirable Edgewater community, this home combines upscale living with easy access to scenic waterways and green spaces—offering the perfect balance of luxury and relaxation.

280 Hidden Bay Drive Unit 302, Osprey

2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code

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

754 Pine Run Drive Unit 754, Osprey

3 Beds ⋅ 4 Baths ⋅ Blackburn Harbor SubDv. ⋅ 34229 Zip Code

Virtually Staged. Experience elevated coastal living in this beautifully appointed waterfront residence, ideally located within the sought-after Blackburn Harbor community in Sarasota County. Situated on the second floor (building with elevator), this elegant and spacious 3BR + den / 3BA condominium offers over 3,700 SF of a harmonious blend of style and comfort, complemented by serene water views. The open-concept layout features expansive living and dining spaces bathed in natural light, perfect for both everyday living and effortless entertaining. Sliding glass doors lead to a generous wrap-around lanai, creating a seamless indoor-outdoor setting to relax and enjoy tranquil water views, refreshing coastal breezes and spectacular sunsets. The gourmet kitchen is as functional as it is inviting, showcasing rich wood cabinetry, granite countertops, stainless steel appliances, a center island for culinary enthusiasts, and a cozy dinette. A convenient breakfast bar opens to the main living area, ideal for casual dining and social gatherings. The primary suite serves as a peaceful retreat, complete with ample closet space and a well-appointed en-suite bath. Each additional bedroom features its own en-suite bathroom and walk-in closets, offering comfort and privacy for guests or versatility for a home office. Residents of Blackburn Harbor enjoy an array of resort-style amenities, including a heated pool, fitness center, clubhouse, tennis and pickleball courts, kayak storage and launch, and a gazebo with grilling areas. Boating enthusiasts will appreciate the protected deep-water dockage with power and water, and direct access to the Intracoastal Waterway with no bridges. Surrounded by natural beauty, the community provides a front-row seat to Florida’s coastal wildlife, including dolphins and manatees. Just across the street, Oscar Scherer State Park offers scenic trails and outdoor recreation, while nearby waterways invite kayaking adventures to local favorites like Casey Key. Perfectly positioned between Venice (10 minutes) and Sarasota (25 minutes), this location offers convenient access to shopping, dining, and cultural attractions, as well as world-renowned Gulf beaches, including Siesta Key Beach just 15 minutes away. Whether you’re seeking a seasonal escape or a year-round residence, this exceptional property captures the essence of Florida waterfront living.

6100 Jessie Harbor Drive Unit 202, Osprey

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

Experience effortless coastal living in this stunning third-floor FURNISHED waterfront residence, perfectly positioned for boaters and kayakers in protected waters just off Blackburn Bay and minutes from the Intracoastal Waterway and Gulf. Watch dolphins, manatees, otters, and breathtaking sunsets from your private balcony. Your water views continue inside, flowing through the living room, dining area, kitchen, and primary suite. This spacious, designer-furnished home showcases quartz surfaces, tile and luxury vinyl flooring, a primary suite with balcony access, oversized shower, jacuzzi tub, and three closets. This unit includes a beautifully appointed second bedroom and a versatile den that is currently used as a 3rd bedroom. There is ample storage inside and out- including a first-floor storage unit ideal for all your water toys. Use the community kayak launch for access to Blackburn Harbor and Oscar Scherer State Park. Enjoy the rare opportunity to keep your boat in your backyard with dockage currently available. Your home is set within an 11-acre gated community featuring walking trails, tennis and pickleball courts, a resort-style pool, waterside grill, clubhouse, and fitness center, all just minutes from Nokomis Beach, the Legacy Trail, and vibrant dining and shopping—this is truly the ultimate Florida waterfront lifestyle you’ve been waiting for.

5100 Jessie Harbor Drive Unit 304, Osprey

1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area is complemented by a full bathroom with a walk-in shower. It has a beautiful foyer, luxury laminate flooring, and is clean and well-maintained. From your window, you can enjoy lovely views out over the pool, across to the lake. This is an incredible opportunity to own your personal sanctuary, perfect for weekend golfers, vacationing guests or weekend get-a-ways. And you will appreciate the flexible rental policy. Windsor Lodge Residents have their own private swimming pool and club house. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options.

51 Mac Ewen Drive Unit 14, Osprey

1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.

51 Macewen Drive Unit 5, Osprey

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet club featuring 10 foot ceilings. 2026 AC unit, 2024 tile roof, 2023 driveway, cabinets, lighting, appliances, tile and carpet are just the beginning. 2023 pool and spa led lighting, Pentair controller, saltwater conversion, and owned 250 gallon propane. Dry bar with ice maker, wine fridge, and beverage fridge. Large covered outdoor living space overlooking the large lanai with tv, private tanning area, and room to entertain. A split bedroom design, game room with space for billiards table, and separate dining area, and great room surround the private courtyard layout designed to entertain. Ample storage throughout including an air conditioned, secure 12x7 storeroom. Southbay Yacht and Racquet Club offers a clubhouse, tennis, pickleball, basketball, shuffleboard, playground, and low fee, exclusive dockage for residents in the deep water marina. Frequent community activities provide opportunities for an active social atmosphere from cruises to sports.

1527 Buoy Lane, Osprey

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