Osprey Homes with Street Lights Community Features

Osprey Homes with Street Lights Community Features

Welcome to Osprey, Florida – a hidden gem nestled in the heart of Sarasota County, where coastal charm meets suburban tranquility. This picturesque community, seamlessly blending the relaxing essence of a beach town with the vibrancy of city life, is perfect for those seeking a serene lifestyle without sacrificing convenience.

Osprey is ideally situated just minutes from the stunning beaches of Nokomis and Siesta Key, offering residents easy access to sun-soaked shores and breathtaking sunsets. With a rich tapestry of history, Osprey boasts beautiful parks, nature trails, and a variety of local shops and restaurants that showcase the best of Florida’s culinary scene. Whether you’re strolling through the scenic grounds of the historic Spanish Point or exploring the vibrant local art scene, Osprey is brimming with opportunities for adventure and relaxation alike.

One of the standout features of the Osprey community is its well-planned neighborhoods, complete with street lights that enhance safety and accessibility. These thoughtfully designed communities foster a sense of togetherness, encouraging evening walks and friendly interactions among neighbors. Families and individuals alike will appreciate the welcoming atmosphere, where children can play freely and residents can enjoy evening strolls under the warm Florida sky.

With its combination of natural beauty, community spirit, and convenient amenities, Osprey is more than just a place to live; it’s a lifestyle waiting to be embraced. Discover your dream home in this charming community and experience all that Osprey has to offer!

Newest Osprey Homes with Street Lights Community Features

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

385 North Point Road Unit 701, Osprey
$1,399,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
Experience the refined country club lifestyle of The Oaks Club in this exceptional waterfront residence within Meridian I at The Oaks Preserve in Osprey. From the moment you step through your private elevator foyer, unobstructed, sweeping water views make an unforgettable first impression. These vistas are beautifully framed from the living and dining areas, kitchen, primary suite, and private study. Step onto the generous balcony, where gentle breezes and breathtaking sunsets set the stage for serene waterfront living. This spacious, maintenance-free residence offers three bedrooms and three baths, including two en-suites, plus a separate den/study and a full laundry room. A private two-car garage beneath the building adds convenience and extra storage. Luxury finishes elevate the interiors, including marble flooring and countertops, stainless steel appliances, crown molding, and custom built-ins. The primary suite is a true retreat, with a sitting area overlooking tranquil water views and a spa-inspired bath featuring dual vanities, a spa tub, and a separate shower. Lovingly maintained by its original owner, the home reflects thoughtful design and pride of ownership throughout. Meridian I residents enjoy a private community pool, fitness center, outdoor grilling area, and on-site maintenance manager, all within the security of The Oaks Preserve's 24-hour guarded gate. Membership in The Oaks Club is required, with a range of membership options and privileges. Renowned for its coastal sophistication, the Club offers refined and casual dining, 36 holes of championship golf, 12 Har-Tru tennis courts, four pickleball courts, a regulation croquet lawn, a state-of-the-art fitness center, a junior Olympic pool, bocce, basketball, a playground, and a vibrant calendar of social and recreational events. Residence 701 at Meridian I is an extraordinary opportunity to embrace Sarasota's premier country club lifestyle, where unmatched amenities meet captivating waterfront views.

385 North Point Road Unit 701, Osprey

3603 N Point Road Unit 202, Osprey
$629,400
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
Virtually Staged. EXCEPTIONALLY SPACIOUS CORNER CONDO – NEARLY 3,200 SF – NO WAITLIST FOR GOLF MEMBERSHIP! Ideally situated behind the gates of the highly sought-after Oaks Preserve, this elegant and beautifully appointed corner residence offers an impressive combination of space, privacy, and resort-style living. The nearly 3,200 SF open floorplan features 3 en-suite bedrooms and 3 baths, providing exceptional comfort and flexibility. Light and bright throughout, the residence showcases crown molding, engineered hardwood flooring, and an expansive kitchen with granite countertops and stainless-steel appliances. Enjoy the serene, private preserve setting from multiple screened balconies, enhanced by convenient remote-controlled automatic hurricane shutters. Additional features include 2 assigned parking spaces, including 1 under-building space, plus climate-controlled storage. A rare opportunity to enjoy substantial living space, privacy, and the exceptional lifestyle of The Oaks! This NEWEST Tower (built in 2007) in the Meridian Condo Complex features Hurricane Impact Windows and Doors and is conveniently located next door to the condo residents’ private Amenity Center featuring Heated Pool & Spa, Fitness Room and outdoor grill in addition to The Oaks Club’s main campus of amenities. THE OAKS is a distinguished country club community which boasts many accolades including: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World - where amenities include two, 18-hole championship GOLF courses, award-winning TENNIS 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. 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. **A MUST SEE**

3603 N Point Road Unit 202, Osprey

1346 Thornapple Drive, Osprey
$540,000
3 Beds ⋅ 2 Baths ⋅ Willow Bend SubDv. ⋅ 34229 Zip Code
Welcome to Willowbend, where quiet meandering streets of manicured lawns live, and so can you! Well respected Builder, Lee Wetheringon built sturdy homes and this one will not disappoint! Every bell and whistle upgrade! Open your double stained glass front door to the foyer. Views of a peaceful lake and enormous great room greet you! Double tray ceiling has optional lighting feature and adds layers to the already extra, high quality custom built-ins. Taller doors grace the rooms throughout... Dining room is spacious enough for a large dining table. Convenient custom built-in sideboard for seasonal storage or serving pieces! Great room is 'just that', it's big! Sliding doors open to caged lanai and lakeside views. Kitchen is expansive and has a broom closet and pantry! Southern exposure and extremely high ceilings keep this house light and bright. Breakfast area has 3 panels of aquarium glass windows. Take a peek! But wait, there's much more! The master suite is substantial! More than spacious, it offers a peaceful sitting area also overlooking the lake and lanai. There are two walk-in closets! Double sinks in the master bath, along with a garden tub and water closet. Once again, light and bright! The 3rd bedroom, (has a closet), has been turned into an office! Get a lot of work done here! State of art custom cabinetry! Lovely... Bedroom #2 has its own wing with a full bath. This home has gas in place for the water heater, laundry, etc. The laundry room features a gas Fisher-Paykel laundry set and deep sink! Garage also has lots of storage! Community pool and small clubhouse close by! HOA provides all lawn services, to include care of shrubbery. Conveniently located close to both Sarasota and Venice. Willowbend is a short distance to Nokomis Beach, the wonderful waterfront restaurants off Blackburn Point and Laurel Road, Legacy Bike Trail and Historic Marie Selby Spanish Point! Costco is close and so will be the Trader Joes and Whole Market, both of which are being built! This home is special...

1346 Thornapple Drive, Osprey

33 Bishops Court Road Unit 118, Osprey
$679,000
2 Beds ⋅ 3 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
**EXPERIENCE EFFORTLESS LIVING in this BEAUTIFULLY UPDATED TOWNHOUSE with SERENE WATER VIEWS** Located behind the Secure Gates of The Oaks Preserve, Golf & Country Club neighborhood, this delightful residence features 2 En Suite Bedrooms on the 2nd Floor, 2 Full and 1 Half Baths, and offers a refined yet relaxed lifestyle surrounded by mature oak canopies and tranquil lake views. The main living area entails an inviting great room that opens to serene water views framed by palms and natural greenery while the European-style kitchen is thoughtfully designed with premium SubZero, Wolf and Bosch appliances, modern wood cabinetry, polished granite countertops, and durable ceramic tile flooring—ideal for both everyday living and entertaining. Architectural details add warmth and character throughout, including hand-plastered walls with art niches, graceful archways, plantation shutters, and sisal carpeting. Just off the entry foyer, you’ll find a convenient powder room and a separate laundry room. A private brick balcony provides ample space for outdoor dining or relaxing while enjoying the peaceful surroundings. The primary suite overlooks the lake and includes two walk-in closets and a spacious bathroom featuring dual vanities, walk-in shower, jacuzzi tub and appointed with upscale finishes. The guest suite is equally comfortable, complete with built-in shelving and ample storage. 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 lighted), 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.

33 Bishops Court Road Unit 118, Osprey

154 Lookout Point Drive, Osprey
$2,095,000
4 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
Welcome to exceptional Florida living in the highly sought-after Southbay Yacht & Racquet Club. Offering approximately 4,578 square feet under roof, this spacious 4-bedroom, 3.5-bath residence combines beautifully updated interiors, exceptionally generous rooms and an extraordinary indoor-outdoor lifestyle. The heart of the home is a completely renovated kitchen featuring quartz countertops, soft-close cabinetry and drawers, built-in organizers, pull-out spice storage, a specialty appliance lift for a mixer or blender, a new refrigerator and dishwasher, and abundant functional storage. The main living area is anchored by a fully functioning wood-burning fireplace with an elegant travertine stone surround, adding warmth and character to the home. All four bedrooms are exceptionally spacious and feature large walk-in closets with custom organization systems. The primary suite and a guest bedroom are conveniently located on the first floor, providing an ideal layout for family and guests. Additional conveniences include a whole-home central vacuum system and a spacious two-car garage with an already-installed Tesla EV charging station. Major recent improvements provide additional peace of mind, including two brand-new air-conditioning systems and brand-new hurricane-rated windows installed in August 2026. The outdoor living space is truly a standout. More than 1,500 square feet of screened lanai and outdoor living area surrounds an exceptionally large residential pool ranging from approximately 3 to 8 feet deep. Two covered outdoor areas provide comfortable spaces for entertaining and relaxing, including an outdoor kitchen with a brand-new THOR grill and a separate covered TV lounge area. A pool bath is conveniently accessible directly from the lanai. Across the back of the pool enclosure, an impressive approximately 50-foot panoramic screen creates a virtually unobstructed view with no intermediate posts interrupting the sightline. Beyond the pool is an expansive green space, creating a wonderful sense of openness and privacy. The newly landscaped yard and more than 25 palm trees lining the backyard complete the lush, tropical setting. Living in Southbay Yacht & Racquet Club is about much more than the home itself. Residents enjoy an impressive collection of community amenities, including a clubhouse, heated community pool, fitness center, tennis courts, pickleball courts, basketball courts, bocce ball, library, card and game room, ballroom and banquet facilities, and the community’s highly desirable marina, where residents have opportunities to rent or lease boat slips, subject to availability. The location is equally exceptional. Pine View School is approximately one mile away, while the bay, Gulf beaches, Publix, restaurants, coffee shops, fitness and yoga studios, CVS and everyday conveniences are all close at hand. The golf-cart-friendly community makes enjoying the neighborhood and surrounding area even easier. From its oversized bedrooms and beautifully renovated kitchen to its remarkable pool, panoramic screened view and expansive outdoor entertaining areas, this home offers an uncommon combination of space, thoughtful upgrades and Florida lifestyle. Add the boating and recreational amenities of Southbay Yacht & Racquet Club, and this is a home designed to enjoy everything the Sarasota area has to provide.

154 Lookout Point Drive, Osprey

5100 Jessie Harbor Drive Unit 404, Osprey
$599,000
2 Beds ⋅ 2 Baths ⋅ Blackburn Harbor SubDv. ⋅ 34229 Zip Code
Sweeping water views, beautiful updates and an enviable waterfront lifestyle come together in this exceptional fourth-floor residence at Blackburn Harbor. Docking available on the premises for a very reasonable quarterly fee. Set along South Creek with direct access via canal to the Intracoastal Waterway and the Gulf, this spacious 2-bedroom, 2-bath home with a versatile den captures the essence of coastal Florida living, from spectacular sunsets and gentle sea breezes to easy access for kayaking and boating. Thoughtfully renovated, the residence offers a fresh, modern feel with laminate wood flooring throughout, plantation-style window shutters, updated lighting and new vertical drapery on the sliding doors. The open living and dining areas flow seamlessly to the spacious screened lanai, where expansive water views create a beautiful setting for morning coffee, afternoon relaxation or sunset entertaining. The updated kitchen features quartz countertops and backsplash, stainless-steel appliances replaced in 2022, a new faucet and disposal, and thoughtfully added cabinet drawers for enhanced storage and functionality. Both bathrooms were beautifully updated in 2022 with new cabinetry, sinks, granite countertops, backsplashes, faucets, mirrors and fresh paint. The spacious primary suite enjoys tranquil water views, three closets—including two walk-ins—and a generous ensuite bath. The guest bedroom features a walk-in closet and convenient access to the second bath, creating a comfortable private suite for guests. The den adds valuable flexibility as a home office, reading room or occasional third bedroom. Additional improvements include a new HVAC system in 2023, water heater, washer and dryer in 2022, and a new metal community roof installed in 2025. HOA fees include water, sewer, cable and Wi-Fi, leaving electric as the primary utility expense. Blackburn Harbor is an inviting gated waterfront community surrounded by lush tropical grounds and an active social atmosphere. Residents enjoy a heated pool, fitness center, tennis, pickleball, shuffleboard, clubhouse, walking paths, waterside gathering areas, grills and a kayak launch. Boat dockage is available for approximately $252 per month, offering the rare opportunity to keep your boat close to home and enjoy the waterways at your leisure. Located minutes from Nokomis Beach, the Legacy Trail, Oscar Scherer State Park, shopping and dining, this is a wonderful opportunity to enjoy the best of the Sarasota-area waterfront lifestyle—with the updates already done and nothing left to do but settle in and enjoy.

5100 Jessie Harbor Drive Unit 404, Osprey

409 N Point Road Unit 803, Osprey
$985,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
ENJOY BREATHTAKING SUNSET VIEWS ACROSS LITTLE SARASOTA BAY AND THE GULF FROM THIS STUNNING 8TH-FLOOR PENTHOUSE! This exceptional 2,203SF Condominium offers 3 Bedrooms, 3 Full Baths, a coveted Private 2-Car Garage, and the privacy of the highly sought-after, gated Oaks Preserve neighborhood. Arrive through your private elevator foyer and step into a home where panoramic, unobstructed views of Little Sarasota Bay and the Gulf immediately take center stage. Thoughtfully designed with an impressive array of upgrades, the residence features high ceilings, crown molding, hardwood and tile flooring, and a beautifully appointed kitchen with a large island and seating area, granite countertops, stainless steel appliances, solid-wood cabinetry, and ample storage. The spacious Owner’s Suite is a peaceful retreat, complete with a generous walk-in closet, custom-tiled shower, relaxing soaking tub, and dual vanities. Step outside onto the expansive balcony and enjoy a serene setting surrounded by spectacular water views, abundant wildlife, and unforgettable Gulf sunsets. Hurricane-impact windows and sliding doors provide added peace of mind. Climate-controlled storage is conveniently located on the second floor. Residents of Meridian enjoy an array of private amenities, including a heated pool and spa, fitness center, and outdoor grilling area, along with access to the exceptional amenities of The Oaks Club’s main campus. Experience elevated coastal living, spectacular views, privacy, and resort-style amenities—all from this remarkable penthouse at The Oaks. The Oaks Club is a member-owned private golf community with more than 40 years of excellence and is the only private residential golf club in the Sarasota, Bradenton, and Fort Myers region recognized by both Platinum Clubs of America and Distinguished Emerald Clubs of the World. Residents enjoy a magnificent 30,000-square-foot clubhouse, three exceptional dining venues, two championship 18-hole golf courses, outstanding golf instruction, a premier racquet program with 12 Har-Tru HydroGrid tennis courts and pickleball courts, croquet, bocce, basketball, a Junior Olympic swimming pool, and a newly expanded state-of-the-art wellness, fitness, and spa facility. Recognized as "The Healthiest Club" and an Audubon Society-certified community, The Oaks offers an unmatched lifestyle. Ideally located in one of Sarasota County's most sought-after communities, this exceptional residence is just minutes from world-renowned beaches, top-rated schools, fine dining, shopping, and Sarasota's vibrant arts and cultural attractions, making it a rare opportunity to enjoy luxury living in a truly prime location.

409 N Point Road Unit 803, Osprey

7204 Jessie Harbor Drive Unit 7204, Osprey
$395,000
2 Beds ⋅ 2 Baths ⋅ Heron House SubDv. ⋅ 34229 Zip Code
**BEAUTIFULLY UPDATED WATERFRONT CONDO WEST OF THE TRAIL! BRING YOUR BOAT & KAYAK FOR DIRECT ACCESS TO THE INTRACOASTAL WATERWAY AND GULF OF MEXICO.** Unlike many Blackburn Harbor residences, this thoughtfully renovated 2-bedroom, 2-bath, second-floor condo is move-in ready, allowing the next owner to immediately enjoy the coveted waterfront lifestyle without the time or expense of major updates. The fully renovated interior showcases an impressive kitchen with quartz countertops, solid wood cabinetry, stainless steel appliances, and CoreTec luxury vinyl flooring throughout (except the guest bedroom). The spacious owner's suite features custom built-in closets and cabinetry, complemented by an elegantly updated en-suite bath. Multiple sliding glass doors open to an expansive screened balcony, where peaceful Florida nature views create the perfect setting to relax and unwind. Located within the secure, gated community of Blackburn Harbor, residents enjoy an exceptional waterfront lifestyle with boat docks (subject to availability), kayak launch and storage, direct Intracoastal access, a community pool, tennis and pickleball courts, fitness center, clubhouse, gazebo with BBQ area, and abundant natural surroundings. Private covered parking and ground-level storage are also included. Ideally situated in Osprey between Sarasota and Venice, Blackburn Harbor is just minutes from nationally ranked Pine View School, the Legacy Trail, Gulf beaches, shopping, dining, and everything the Gulf Coast lifestyle has to offer. RECENT COMMUNITY IMPROVEMENTS INCLUDE: Asphalt paving, irrigation, walkways, walkway lighting, and upgraded lighting for the tennis and pickleball courts.

7204 Jessie Harbor Drive Unit 7204, Osprey

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