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Osprey

One of the most popular communities provided by Michael Graf

Osprey

About Osprey

Osprey is a tranquil coastal community tucked between Sarasota and Venice, offering a perfect blend of natural beauty and upscale living. Known for its peaceful vibe, top-rated schools, and access to the Intracoastal Waterway, Osprey is ideal for nature lovers and boaters. Residents enjoy quick access to parks like Oscar Scherer State Park, waterfront dining, and nearby beaches. With elegant neighborhoods, quiet streets, and a strong sense of community, Osprey is a hidden gem on Florida’s Gulf Coast.

One of the most popular communities provided by Michael Graf

163

# of Listings

3

Avg # of Bedrooms

$463

Avg. $ / Sq.Ft.

$1,122,489

Med. List Price

Browse Osprey Real Estate Listings

All listings

$250,000 - $500,000

163 Properties Found. Page 5 of 11.

Looking for a home you can fall in love with? The search is over! Once you see this thoughtfully updated, impeccably maintained 3 bedroom, 2 bath home in The Oaks Preserve you will know you have found your home-sweet-home. From the moment you pull up to the pavered driveway, the care taken to maintain this property is evident. Walk past the two-car garage to the pretty, double front doors with leaded glass and step into the light-filled interior. Here you will find everything you need for comfortable Florida living. There is a dedicated home office off the entryway, with plantation shutters and a ceiling fan. The formal dining area features a lovely decorative ceiling, and a beautiful built-in buffet with glass-fronted cabinetry. The great room features another gorgeous piece of built-in furniture; floor to ceiling sliding glass doors connect the screened lanai and this room, making it bright and airy. The open kitchen, with breakfast bar, features beautiful new granite counters, stainless appliances, a chef’s desk, built-in wine and beverage cooler. The adjoining breakfast nook is flooded with natural light that streams through the aquarium window and offers an amazing view over the pool and spa. The master suit is huge and has a sitting area with a built-in window seat and large walk-in closets with glass front storage. The spacious master bedroom has been updated with granite countertops, and features dual sinks, a tub and separate shower and has marble wall accents. The two guest bedrooms are good sized and offer ample closet space. The second bathroom has been tastefully updated with granite counter and marble accents. The 2 car garage, with epoxy floor, is air conditioned with plentiful storage. Situated in the Bishopscourt neighborhood, behind the secure gates of The Oaks Preserve, this beautiful home backs a lush, tropical preserve providing privacy for the sparkling pool and spa. The lanai has two separate areas surrounding the pool. A large, covered area with an outdoor kitchen and ceiling fan, the perfect place for al fresco dining in the shade, and pool and spa area, covered by a cage, allowing for frolicking in the sunshine. Or meet your neighbors for a dip in the Bishopscourt community pool. The Oaks Club amenities include two championship golf courses, an award-winning tennis program, pickle ball and croquet courts, and a state-of-the-art fitness center. With three outstanding restaurants, and a wide variety of social and recreational options, there is no need to look any further than here for the perfect place to enjoy the best of Florida country club living. Club membership is required with homeownership.

OSPREY

21 BAYHEAD LANE

3 Beds

2 Baths

3,119 Sq.Ft.

$925,000

MLS#: A4664085

**STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the Secure Gates of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank, Plantation Shutters, an Oversized, Owner’s Bedroom Suite with Multiple walk-in closets and sitting area and much more! Enjoy the expansive and private outdoor living area in a screened lanai with wet bar and southern exposure overlooking a Garden and Tranquil Preserve. Mostly NEW Hurricane Impact Windows/Door. 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.

OSPREY

293 TURQUOISE LANE

3 Beds

2 Baths

2,998 Sq.Ft.

$910,000

MLS#: A4633961

Give yourself the gift of refined living in this expansive 2,778 square foot residence—the largest non-penthouse floor plan available in Meridian at The Oaks Preserve. Every detail in this meticulously maintained, and beautifully updated condominium has been thoughtfully designed to offer comfort, sophistication, and versatility, making it the perfect sanctuary for luxury living every day! Step inside and discover a home where space abounds and possibilities flourish. With three generously sized bedrooms, plus a dedicated dining room (currently being used as a den) and a versatile office/den or 4th bedroom, this home provides all the room you need to work, relax, and entertain, with the flexibility to use the rooms as you see fit. The great room is bathed in natural light, its gleaming wood floors enhancing the clean, contemporary lines of the interior. The updated kitchen will delight any home chef, offering optimal space for cooking and storage, whether you are preparing a casual breakfast or hosting a formal dinner. Enjoy your meals in the dining room, at the breakfast bar, in the cozy nook, or take them outside to the large, screened balcony, where a ceiling fan and the serene backdrop of a lush tropical preserve provide the ideal setting for alfresco dining. The small dry bar with wine cooler and cabinets to store your drink supplies and display your glassware is the perfect addition for when you are entertaining guests. Retreat to a sumptuous master suite. The large, carpeted bedroom is filled with natural light, and outfitted with a ceiling fan, plantation shutters, and custom closets. The master bathroom has been beautifully redone. With a soaking tub, separate shower and water closet, this space is absolutely gorgeous. Every inch of this unit has been curated to deliver both style and functionality, ensuring you feel pampered at every turn. Additional features include a large laundry room, Kevlar roll down hurricane shutters, two premium parking spaces and high-quality upgrades throughout. Club membership is required with homeownership. Residents of Meridian enjoy exclusive access to a private pool, relaxing spa, and a fully equipped workout room. Beyond these, The Oaks offers an impressive array of amenities including 36 holes of championship golf across two courses, twelve HAR-TRU tennis courts (four lighted), a state-of-the-art Wellfit Center, three on-site restaurants with year-round dining, croquet, bocce and pickleball courts and an active social calendar.

OSPREY

401 N POINT ROAD 304

3 Beds

3 Baths

3,106 Sq.Ft.

$900,000

MLS#: A4659785

Price reduced

Live like you’re on vacation in this updated Key West–style home West of the Trail. Upgrades include a new standing seam metal roof, hurricane impact windows, electric tankless water heater, wraparound "Lifeproof" composite decking, and a custom heated pool. Interior features vaulted ceilings with a mix of travertine, LVP, and tile flooring, plus a kitchen with solid wood cabinets, stainless steel appliances, beadboard ceiling, and custom backsplash. The screened second-story porch has an electronic roll-up system for open-air or enclosed comfort. A unique “hidden” door design allows the home to function as one residence or two separate units, with the lower level offering its own entrance, bedroom, bath, family room, and laundry—perfect for in-laws, guests, or rental income. Outdoors, enjoy lush landscaping, a tropical pool setting, and unbeatable location just a block from the public dock and kayak launch. Minutes to Sarasota, Venice Island, beaches, Legacy Trail, and Spanish Pointe.

OSPREY

38 W BAY STREET

3 Beds

2 Baths

2,818 Sq.Ft.

$899,000

MLS#: A4667010

This is an outstanding Southbay residence and a fantastic opportunity to live in one of the best boating communities on the Southwest coast of Florida. This home has been updated with a gourmet custom kitchen, perfect for entertaining guests and hosting company. From the granite countertops to the gas cooktop, and custom cabinetry, it is a pleasure to cook in here! The dining room is spacious with plenty of room plus a built-in custom buffet. overlooking the expansive living room with a wood-burning fireplace. One special feature of this home is the designed media room, set up for a large screen TV, and sound specially wired throughout to achieve maximum viewing and listening pleasure. The primary bedroom is huge with 2 large walk-in closets, and the en suite bathroom is well suited for comfort and convenience. The other two bedrooms are well-sized and outside, the oversized lanai provides plenty of room for entertaining. Southbay Yacht & Racquet Club is a premier marina community with a newly renovated clubhouse offering numerous amenities, including a fitness room, card room, and two kitchens for preparing for events. The community has a geo-thermal pool overlooking the marina, a shuffleboard court, three tennis courts, four pickleball courts, a bocce ball court, and a basketball court. Plus, there is kayak storage, a waterfront park, and nearly 20 acres of common grounds with miles of walking trails and paths. This house is a unique treasure, perfect for someone wanting to live in an exceptional home within an exceptional community! Call for your showing today!

OSPREY

238 LOOKOUT POINT DRIVE

3 Beds

2 Baths

3,660 Sq.Ft.

$895,000

MLS#: A4671468

Price reduced

**STUNNINGLY UPDATED CONDO with Breathtaking Water & Preserve Views that rival those of higher floors!** This LARGE, CORNER UNIT of nearly 2800sf features 3-Beds & 3 Full Baths PLUS Study/Den (or possible 4th Bedroom with Walk-In Closet) and 2 side-by-side Covered Parking Spaces near elevator, Etc. and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator foyer entrance, you will be enthralled by the Stunning View of Little Sarasota Bay and the Gulf of Mexico. The brilliantly RENOVATED, Light and Bright interior boasts a spectacular Kitchen with large waterfall island with seating area, Quartz countertops and Newer Stainless-Steel appliances, while other premium features include Plantation and Hurricane Shutters, Luxury Vinyl Plank and tile flooring, Crown moldings, Updated bathrooms with Quartz counters, NEW HVAC (2025), etc. The Owner’s Bedroom Suite features a Walk-in Closet, Custom Tiled Shower, Soaking Tub and Dual Vanities. The Spacious Balcony offers an ideal western exposure for enjoying gorgeous sunsets! Includes Climate-controlled Storage unit. This MERIDIAN I Condo Tower boasts a New Roof (2024) and New Elevators (2025 – in progress). Meridian Condo residents enjoy private amenities including Heated Pool & Spa, Fitness and Outdoor Grill in addition to The Oaks Club’s main campus of amenities. 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**

OSPREY

385 N POINT ROAD 404

3 Beds

3 Baths

3,106 Sq.Ft.

$889,000

MLS#: A4659275

**IMPRESSIVE POOL/SPA HOME on a Desirable Corner Lot with Partial Water View** Custom-built by John Cannon and situated on an interior Cul De Sac in popular North Creek Estates, this 3-BED + Office/Den, 3 FULL BATH, 2-Car Garage residence affords wonderful privacy and features 2622sf of heated living area plus a spacious screened lanai with Heated Pool/Spa and ample covered seating area, for the utmost enjoyment of the Florida lifestyle. This Light and Bright, Open Floorplan entails premium features including crown moldings, tray ceilings, custom built-ins, gas fireplace, expansive kitchen with large island, hardwood cabinets, stainless steel appliances, etc. The spacious Owners’ Suite includes a Large, Walk-in Closet, and primary bath with dual vanities, soaking tub and custom-tiled shower. Recent Updated including NEW ROOF (2025), Appliances, Freshly Painted Interior, Carpet & Wood Flooring, etc. LOW HOA Fees. Residents enjoy a Prime Location with easy access to US41/Tamiami Trail -- close to area beaches including #1 rated Siesta Beach, shopping, dining, cultural attractions, and the highly rated Pine View School. **Please Enjoy Viewing the 3D VIRTUAL TOUR**

OSPREY

903 TRANQUILITY CIRCLE

3 Beds

3 Baths

3,500 Sq.Ft.

$879,000

MLS#: A4669102

END UNIT with RARE THREE CAR GARAGE, IMPACT WINDOWS AND SLIDERS, and sweeping panoramic views. This beautifully appointed Baypointe Vista condo in Osprey blends comfort, style, and convenience, all set against the backdrop of the Intracoastal Waterway and Little Sarasota Bay.

Natural light pours through wide water view windows, while plantation shutters throughout add timeless coastal charm and privacy. The gourmet kitchen offers white cabinetry, granite countertops, stainless steel appliances, and a spacious island perfect for entertaining with the bay as your backdrop.

The open floor plan flows into the living and dining areas and onto the enclosed porch, where 180 degree views of Casey Key and the sparkling bay create a breathtaking focal point. Both oversized bedrooms are en suite with generous walk in closets. The primary suite features dual closets, tranquil water views, and a spa inspired bath with jetted tub, double vanity, and makeup counter. The guest suite has its own private entrance, walk in closet, and full bath.

This residence is offered turnkey furnished and ready for immediate enjoyment. Additional highlights include luxury laminate floors, recessed lighting, a spacious laundry room with cabinetry and sink, impact windows and sliders, and the oversized three car garage which is a rare and valuable feature.

Baypointe Vista is a gated resort style community with a pool, fitness center, tennis and pickleball courts, fishing pier, kayak launch and storage, tiki bar, and an active social calendar. HOA fees cover cable, internet, water, and sewer. Ideally located between Sarasota and Venice, you are just minutes from Gulf beaches, shopping, dining, golf, medical facilities, and Pine View School.

Experience turnkey coastal living with panoramic water views, elegant plantation shutters, and the convenience of a rare three car garage and impact windows and sliders. Schedule your private showing today.

OSPREY

242 HIDDEN BAY DRIVE 401

3 Beds

3 Baths

2,100 Sq.Ft.

$875,000

MLS#: D6143964

This immaculate and meticulously maintained 3-bedroom, 2-bath home in the sought-after Southbay Yacht & Racquet community is move-in ready and packed with beautiful updates. The open-concept kitchen has been tastefully remodeled with stainless steel appliances, center isle and lighting, and both bathrooms have also been updated. Natural light fills the home through replaced windows and elegant French doors, all of which are provided with hurricane protection for peace of mind. Crown molding and plantation shutters on all windows add a refined touch throughout, and engineered wood flooring enhances the living room and bedrooms, while ceramic tile flooring is featured in the kitchen and cozy family room complete with a charming wood-burning fireplace. Additional highlights include: a spacious utility room with ample cabinet storage, a new roof and fresh exterior paint in 2024 and new A/C system, dishwasher and garbage disposal in 2025. Florida-friendly landscaping with an abundance of fruit trees and native vegetation surrounding the home are perfect for the gardening enthusiast.

Southbay Yacht & Racquet is a golf cart community that offers an array of community features and exceptional lifestyle with a recently remodeled 10,000 sq. ft. clubhouse featuring a well equipped fitness center, adjacent swimming pool, and expansive patio. The community-owned marina with residents only boat slips offers direct access to the Intracoastal Waterway with no fixed bridges to hinder your journey to the Gulf. Enjoy a wide range of amenities, including: pickleball and tennis courts, bocce and shuffleboard court, scenic walking and biking paths throughout the community and playground.

Ideal location conveniently nestled between downtown Sarasota and downtown Venice, this home is close to top-rated dining, shopping, and entertainment. You’re just a short drive from world-renowned Siesta Key and Nokomis Beach, the Legacy Trail, and the nationally ranked Pine View School.

Don’t miss this opportunity to own a beautiful home in one of the Gulf Coast’s most desirable boating communities

OSPREY

123 WINDWARD DRIVE

3 Beds

2 Baths

2,661 Sq.Ft.

$850,000

MLS#: A4656319

The Development Site is a lakefront parcel overlooking the community’s internal lake and clubhouse. The concept plan shows 24 2-3 bedroom units in 4 stories over parking, but the parcel has unprecedented zoning and entitlements for up to 42 units. All utilities and the roads are to the development site. The utilities, roads, and parking areas, the gated entrance and the resort-style amenities are completed. The amenities include a beautiful, heated pool/spa area with deck overlooking a tranquil lake with a “fountain island,” an upscale clubhouse with living room which also houses a library, catering kitchen, central salon and fitness center, plus a Tiki Hut and grilling area for entertaining, a kayak launch, and USTA style tennis court and pickleball courts, car wash area, pet park and an elevated boardwalk that meanders through lush mangrove fields out to a long fishing pier, where you can drop a line into the water or watch never-ending sunsets. The community consists of mid-rise and low-rise condominium buildings.

OSPREY

HIDDEN BAY DRIVE

None Beds

None Baths

0.55 acres

$800,000

MLS#: A4645997

Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2.5-bath pool home with mature landscaping offers a functional layout and excellent community amenities. The home features a double-door front entry, a spacious great room with cathedral ceiling, an oversized garage, and a large private lot. Interior highlights include double primary bedrooms, tiled walk-in showers in both full bathrooms, an outdoor shower, a generous laundry room with cabinetry, a practical kitchen with pantry and hurricane rated windows. The paver lanai with automated hurricane screen and expansive paver deck surrounding the swimming pool with solar heat provide substantial outdoor living space. A long driveway adds convenient additional parking.

Southbay Yacht & Racquet Club is a golf-cart-friendly community featuring a recently remodeled 10,000 sq. ft. clubhouse with a fitness center, pool, and large patio. The community-owned marina—with residents-only boat slips—provides direct Intracoastal Waterway access with no fixed bridges to the Gulf. Additional amenities include pickleball and tennis courts, bocce, shuffleboard, walking and biking paths, and a playground. The community is ideally situated between Sarasota and Venice, close to dining, shopping, entertainment, beaches, the Legacy Trail, and Pine View School.

OSPREY

102 WINDWARD DRIVE

3 Beds

2 Baths

3,000 Sq.Ft.

$800,000

MLS#: A4671793

Price reduced

This is your chance to own a true waterfront property in the highly desirable Osprey area and transform it into your dream coastal retreat. Situated on a canal with direct access to the Intracoastal Waterway, this home offers an unbeatable location for boating enthusiasts and anyone seeking the ultimate Florida lifestyle. The property itself needs some love, but that’s exactly what makes it such an incredible opportunity. Bring your vision, contractor, and creativity to design a space that’s entirely your own. Unlike many homes nearby, this property did not experience any flooding, offering peace of mind and a solid foundation for your renovation. Whether you’re an investor looking for your next project or a buyer eager to build sweat equity in a prime waterfront community, 120 Candyce Drive delivers both value and potential in one of Sarasota County’s most sought-after coastal neighborhoods. Ideally located just minutes from Nokomis Beach, Casey Key, and popular waterfront dining, this home combines location and opportunity with no HOA restrictions. Turn this waterfront fixer-upper into your stunning Florida escape.

OSPREY

120 CANDYCE DRIVE

3 Beds

2 Baths

3,457 Sq.Ft.

$799,000

MLS#: A4667108

LOCATION! LOCATION! Tucked away on a quiet cul-de-sac and resting on a corner lot, this METICULOUSLY MAINTAINED, Custom-built, JOHN CANNON home in exclusive North Creek Estates offers the perfect blend of privacy, luxury, and convenience. With a NEW ROOF (2020), low HOA fees, and 2,443 sq. ft. of thoughtfully designed living space, this 3-Bedroom + Office/Den, 2-Bath residence is MOVE-IN READY and packed with quality upgrades. The updated kitchen is a chef’s dream, featuring stainless steel appliances including a New refrigerator, granite countertops, a center island, breakfast bar, raised-panel wood cabinetry, pantry, and a charming eat-in nook with an aquarium glass window. The light-filled great room showcases elegant wood flooring, a built-in entertainment center, and a surround sound system—ideal for entertaining or relaxing.
Unwind in the spacious master suite with walk-in closet and a luxurious bath complete with granite counters, a tiled walk-in shower, and a garden tub. Step outside to the large screened lanai (re-screened in 2021), framed by lush tropical landscaping—perfect for enjoying the Florida lifestyle. Additional features include crown molding, custom closets, hurricane shutters, an oversized 2-car garage, irrigation well, hot water recirculating pump, hot water tank (2021), washer and dryer (2019), double front door (2022), etc. Residents enjoy a prime location close to area beaches including #1 rated Siesta Beach, shopping, dining, cultural attractions, and the highly rated Pine View School. Don’t miss the opportunity to own this exceptional home in one of the area's most desirable communities!

OSPREY

901 REFLECTION WAY

3 Beds

2 Baths

3,415 Sq.Ft.

$795,000

MLS#: A4647865

One or more photo(s) has been virtually staged. Experience luxury living at The Oaks Preserve. This stunning 3 bedroom, 3 bath corner unit, COMPLETE WITH AN OFFICE, offers the ultimate country club lifestyle. Arrive in style with your private elevator to the 5th floor, where you'll find a pristine residence ready to welcome you. The modern kitchen, featuring stainless steel appliances, a breakfast nook, a center island with a wine rack and cookbook shelf, and elegant cabinetry, seamlessly flows into the great room. This space, which includes the formal dining area and living room, is bathed in natural light and offers wide views over the Preserve. Enjoy the serene beauty of the setting sun from your screened balcony or start the day with a cup of coffee and take in the tranquil water views. For added peace of mind, this unit is equipped with impact windows, doors, and electric hurricane shutters. Additionally, it includes a 1 CAR GARAGE AND AN UNDER-BUILDING PARKING SPACE. Residents of The Meridian can take advantage of exclusive amenities, a pool, spa, and workout room, just a short walk from the building. Mandatory membership in The Oaks Club also grants access to two championship 18-hole golf courses, 12 HAR-TRU tennis courts, pickleball courts, a state-of-the-art Wellfit Center, a croquet lawn, bocce courts, and three onsite restaurants.

OSPREY

409 N POINT ROAD 501

3 Beds

3 Baths

2,837 Sq.Ft.

$795,000

MLS#: A4611618

Move-in Ready | Turnkey Furnished | Gulf & Intracoastal Views + Glorious Sunsets
3 Bed | 2.5 Bath | Den w/ Custom Queen Murphy Bed | 2,168 Sq Ft | End Unit

Bright, breezy, and beautifully maintained, this move-in ready End Unit at Edgewater at Hidden Bay is offered fully Turnkey Furnished by the original owners and designed for effortless coastal living. Plantation shutters throughout, impact-rated windows and sliders, and a spacious open layout create a calm, sunlit interior with both comfort and style.

At 2,168 square feet, it’s the largest floor plan currently available—featuring 3 bedrooms, 2.5 baths, and a versatile den/office with a custom Queen-sized Murphy bed for guests or workspace flexibility. The heart of the home opens to a screened lanai with tiled floors, a built-in privacy panel, and unobstructed views of the Intracoastal Waterway, perfect for enjoying brilliant Gulf sunsets.

An electric sunshade in the living room enhances indoor comfort, while the glare-resistant TV is ideal for daytime viewing. A large, private storage unit located directly in front of the assigned covered parking space adds practical convenience.

Enjoy a host of resort-style amenities including a heated pool and spa, fitness center, clubhouse, tennis and pickleball courts, bayside boardwalk, and a tiki hut gathering area with grills.

Recently adjusted to reflect market activity, this home offers exceptional value in a sought-after gated waterfront community—an ideal opportunity for seasonal or full-time residents. Schedule your private showing today.

OSPREY

260 HIDDEN BAY DRIVE 305

3 Beds

2 Baths

2,433 Sq.Ft.

$789,000

MLS#: A4650487

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