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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

144

# of Listings

3

Avg # of Bedrooms

$532

Avg. $ / Sq.Ft.

$1,271,277

Med. List Price

Browse Osprey Real Estate Listings

All listings

$250,000 - $500,000

144 Properties Found. Page 4 of 10.

New listing alert in the highly sought-after community of Southbay Yacht & Racquet Club, where true resort-style living awaits. The community offers an impressive array of amenities, including a marina, a recently remodeled clubhouse, shuffleboard courts, three tennis courts, four pickleball courts, a bocce ball court, basketball courts, and kayak storage. Residents also enjoy a waterfront park and nearly 20 acres of common grounds with miles of walking trails. A true highlight is the gorgeous geothermal pool, which showcases stunning marina views and is a must-see when visiting Southbay! Now that you’ve fallen in love with the community, are you ready to explore this spectacular home that’s waiting to be yours? This spacious residence, spanning over 3,000 square feet, welcomes you with a brick-paver driveway and lush, mature landscaping along the front walkway. Continue through the gated entry to discover the tranquil sound of a soothing water feature before stepping inside. The interior boasts beautiful views of the pool and lush green landscape, hard flooring throughout, and a layout designed for both everyday living and effortless entertaining. The floor plan includes two distinct family rooms, one with a cozy fireplace, wet bar, and beverage refrigerator, and the other offering beautiful views of the pool. The primary bedroom includes an additional room with pool views, ideal for an office or exercise space...the choice is yours. A spacious laundry room, complete with a double desk and abundant storage, adds to the home’s functionality. Outside, the large lanai features a beautiful pool and provides generous covered areas, and plenty of open space for sunbathing under the clear blue sky. Recent updates include a new roof installed in 2023 and a recently refinished and resurfaced pool. The location is equally appealing, just minutes from a variety of restaurants and shopping, convenient highway access, and the soft, powdery sands of Southwest Florida's Gulf Beaches. I welcome you to visit this home... come see, come sigh, and make it your own!

OSPREY

1218 YACHT HARBOR DRIVE

3 Beds

3 Baths

3,297 Sq.Ft.

$1,150,000

MLS#: A4663579

Price reduced

FULLY UPDATED • WATER VIEWS • PRIVATE 2-CAR GARAGE • OFFICE/4TH BEDROOM OPTION • SELLER WILL PAY $80K TOWARD BUYER'S OAKS CLUB MEMBERSHIP CAPITAL CONTRIBUTION

From the moment the private elevator opens into your foyer, this residence reveals itself as a home crafted with intention, artistry, and a deep appreciation for its natural surroundings. Sunlight fills the space as water and preserve views stretch out beyond the generous lanai—an ever-changing backdrop that greets you at dawn and soothes you at day's end.
Inside, every detail has been thoughtfully reimagined. The custom kitchen is both beautiful and functional, featuring rich soapstone countertops, Bosch appliances, roll-out cabinet drawers, Everpure water filtration, and an elegant tray ceiling with crown molding. The Great Room flows effortlessly into the dining areas and lanai, creating an inviting environment for everyday living or effortless entertaining.
The serene Primary Suite is a retreat of its own, offering captivating views, a custom-designed walk-in closet, and a spa-inspired bathroom adorned with Italian tile, dual vanities, and stunning stone countertops. With an expansive split floor plan offering 3 Bedrooms, 3 Full Baths, and an Office/Study that can easily serve as a 4th Bedroom, the home provides both privacy and flexibility. Custom built-ins, upgraded closets, and a well-appointed laundry room enhance everyday comfort. A rare luxury in the Meridian—your own private 2-car garage—completes the offering.
The Meridian at The Oaks Preserve is surrounded by lush landscaping and winding pathways, with amenities including a pool, spa, fitness center, and outdoor grill. =>SELLER TO PAY $80,000 TOWARD BUYER'S OAK'S CLUB MEMBERSHIP (CAPITAL CONTRIBUTION FEE)<= Membership to The Oaks Club is mandatory, granting access to two championship golf courses, 12 Har-Tru tennis courts, croquet, wellness and fitness facilities, a resort-style pool, multiple dining venues, social events, and a distinguished clubhouse.
Ideally located less than 1 mile from Historic Spanish Point, approx. 6 miles from Siesta Key’s world-famous beaches, 10 miles from downtown Sarasota, and within 3 miles of the renowned Pine View School, this residence offers not just a home—but an elevated lifestyle.
Be sure to view the Video Virtual Tour for interior, exterior, and aerial perspectives. This is a home that must be experienced in person—schedule your private showing today!

OSPREY

401 N POINT ROAD 504

3 Beds

3 Baths

2,778 Sq.Ft.

$1,100,000

MLS#: A4653470

RARE OPPORTUNITY to own this stunning former John Cannon model home PLUS the adjacent buildable lot on peaceful Tranquility Circle. This pristine 4BR/3.5BA pool home is a kayaker and nature lover’s paradise, with direct access to North Creek, which leads to Little Sarasota Bay, offering abundant wildlife and serene water views.

Enjoy an open, spacious split-plan layout with Four bedrooms, formal and casual living spaces, and an open kitchen with granite countertops, island, and gas range—perfect for entertaining. The great room and lanai seamlessly connect to the sparkling pool, creating a private retreat with creek views.

The luxurious Primary suite is a true getaway, featuring bay windows, his-and-hers closets, Expansive Primary Bath with dual water closets, soaking tub, separate shower and dual vanities. Interior upgrades include tile flooring, crown molding, 8-foot doors, designer lighting, and ceiling fans.

Recent and notable upgrades: pool resurfaced (2023), pool cage replaced/rescreened (2018), A/C units (2020 & 2024), water heaters (2022/2023), new gutters & guards, paver driveway and pool deck, rimless shower doors, new front door, new refrigerator, new flooring in all bedrooms and closets, upgraded drainage system, and more.

Prime location near the Legacy Bike Trail, YMCA, Oscar Scherer Park, The Oaks, Palmer Ranch, Sarasota Square Mall, and minutes to Sarasota, Venice, and Gulf Coast beaches. A-rated schools, including top-ranked Pine View School, make this property ideal for families.

A rare, meticulously maintained home with exceptional upgrades and a double-lot offering—this property must be seen to fully appreciate its value and beauty. * Please be sure to watch Virtual Tours also. The Matterport will immerse you within the property as if you were doing a walk through*

OSPREY

919 TRANQUILITY CIRCLE

4 Beds

3 Baths

2,854 Sq.Ft.

$1,099,000

MLS#: A4674201

#A4670043

OSPREY

3936 WAYPOINT AVENUE

3 Beds

3 Baths

2,323 Sq.Ft.

$1,089,000

MLS#: A4670043

Price reduced

Premier restaurant ready or any other retail concept flagship space in Bay Street Village and Towncenter located at 3983 Destination Drive, Osprey in Sarasota County. This turnkey 2,030 SF ground-floor anchor space along US-41 is ideal for a restaurant, sushi bar, deli, or specialty dining concept. Fully built out with seating for approximately 150 guests, including indoor and outdoor dining areas. The interior offers a spacious dining room and a central bar designed for efficient, high-volume service.
Second-floor space is available separately (elevator accessible) for $700,000 and includes a balcony, additional kitchen and prep areas, storage, a walk-in cooler, and an extra dining or coffee bar area, ideal for private events, memberships, or overflow seating.
Both units are easy to be split, providing flexible space options depending on the operator's needs.
CG zoning provides flexible commercial use options and strong ROI potential. Restaurant equipment conveys; furniture is available and can be updated to match your concept. The property offers excellent exposure and signage visibility with a prominent entrance tower facing US-41.
Located in a thriving, walkable destination surrounded by complementary businesses such as a breakfast and lunch bistro, art galleries, jewelry shops, a spa, a florist, a dentist and coworking spaces. More than 270 new luxury residential units have recently been completed next to the property, bringing strong foot traffic and demand.
A rare opportunity to secure a highly visible, revenue-ready space in a growing, high-traffic corridor. Matterport virtual tour, equipment inventory, and floor plans available upon request.

OSPREY

3983 DESTINATION DRIVE 102

None Beds

None Baths

2,030 Sq.Ft.

$1,050,000

MLS#: TB8455523

Price reduced

Motivated Seller!!!Newly Built-Out Move-In Ready Retail / Office (GC) Zoned Space at Bay street Village!
Located in the heart of Osprey, this beautifully designed space at 3976 Destination Drive, Unit A-411, Osprey, FL 34229 is the perfect opportunity for your business to thrive. Bay street Village is a premier commercial enclave offering a mix of retail/medical and office spaces, just minutes away from The Oaks, Casey Key, and Pine view School, providing easy access to a thriving community.
This move-in ready office features modern finishes, full furnishings, and a layout designed for efficiency, allowing you to set up and start working immediately. Whether you're expanding your business or starting fresh, this space offers the perfect combination of convenience and professionalism.

Key Highlights:Newly built-out, fully furnished office space,Prime location in Baystreet Village, Osprey’s most sought-after commercial enclave. Close proximity to The Oaks Golf & Country Club, Casey Key Beach, and Pineview School
Easy access to major roads, offering quick connections to Sarasota and surrounding areas
Don’t miss this rare opportunity to position your business in one of Osprey’s best commercial locations. Schedule a tour today!

OSPREY

3976 DESTINATION DRIVE A411

None Beds

None Baths

2,314 Sq.Ft.

$1,045,000

MLS#: A4643099

#A4665288

OSPREY

1602 SOUTHBAY DRIVE

4 Beds

3 Baths

2,980 Sq.Ft.

$999,995

MLS#: A4665288

Welcome to your Boater's Paradise! This well-maintained South Bay home is your key to enjoy one of the best neighborhoods in the area. This three-bedroom pool home has the perfect layout with the primary bedroom and en suite on one side of the home and the two additional bedrooms on the other. A major renovation in 2017 included new flooring thought the entire home, totally gutted and installed new bathrooms with custom vanities and all new interior shaker doors throughout the house. This home was re-piped for both water and sewer. Every ceiling was updated with a new surface and new recessed lighting. The shiplap living room is bright and airy and flows onto the lanai where you will find the resurfaced pool, a new cage and new marble pavers. The lanai has plenty of covered space for a sitting area , TV and a dining area. There are 3 rooms with slider access to the lanai, master, living, and family room. All the closets have built-in shelfing and are well designed. The garage has new built-in storage with doors and epoxy floors. The landscaping creates a very private back yard with fence like privacy using 6-foot-high pitch apple plants. The magnificent big palm tree in the front yard along with 8 others palms on the property really makes you feel the Florida vibe. Southbay's active community has a newly renovated waterfront clubhouse featuring a grand ballroom, catering kitchen, and state-of-the-art fitness center overlooking the marina. Enjoy the heated pool, youth pool, tennis courts, pickleball courts, shuffleboard, bocce, playground, basketball, walking trails and an intercoastal waterfront park. Boating enthusiasts will appreciate the community-owned deep-water marina with direct access to the Intercoastal Waterway with no fixed bridges to the Gulf. The marina’s low-fee boat slips are exclusive to Southbay owners and can accommodate anything from personal watercraft to 55’ yachts. Southbay has a calendar full of social events, there's always something to connect over. The community is golf cart-friendly--just hop in your cart to go to one of the events or head out to local shopping, tiki bars, or the beach. Families will love the proximity to Pine View School, renowned as Florida's #1 charter school and one of the nation's few standalone gifted programs. Don't miss your chance to own in Southbay!

OSPREY

1486 LANDVIEW LANE

3 Beds

2 Baths

1,869 Sq.Ft.

$995,000

MLS#: D6144630

**TURNKEY FURNISHED, ELEGANT and TRADITIONAL ESTATE by Famed Architect, Bo MacEwen, on the Single Largest 0.32 Acre Cul De Sac Lot in the Popular SAINT JAMES PARK neighborhood in The Oaks Country Club. NEW ROOF (2024), HURRICANE IMPACT WINDOWS and SLIDING DOORS, FLOOD ZONE “X500”. Overlooking the Eagle Golf Course and Ideally Located near the Clubhouse and Campus of World Class Amenities, this Distinctive LIGHT AND BRIGHT floorplan offers 2-BEDS, 2 FULL BATHS, 2-Car Oversized Garage with EV Charging and features unique architectural details throughout including beautiful crown moldings, wainscoting, cozy fireplace, engineered hardwood and tile floors, built-in sound system, and More! A nicely equipped kitchen features hardwood cabinets and stainless steel appliances while the Spacious bedrooms include a primary bedroom suite with walk-in closet, dual vanities, soaking tub and custom-tiled shower. In addition to its wonderful curb appeal and beautifully manicured landscape, a Spacious and screened lanai offers Gorgeous Sunset Views with its ideal Western Exposure. 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

227 SAINT JAMES PARK

2 Beds

2 Baths

2,071 Sq.Ft.

$995,000

MLS#: A4635743

One or more photo(s) has been virtually staged. Waterfront Elegance at Blackburn Harbor! Experience the comfort of a home with the convenience of condo living in this spacious 3-bedroom, 3.5-bath plus den residence offering 3,771 sq. ft. of beautifully designed space and 10-foot tray ceilings throughout and a new roof. Enjoy panoramic water views from the gourmet kitchen, featuring wood cabinetry, granite countertops, stainless steel appliances, a cook’s island, and a cozy dinette — perfect for morning coffee with a view. All bedrooms are large with ensuite baths and walk in closets.
Set within Blackburn Harbor, a gated and pet-friendly waterfront community on 11 scenic acres, across the street has walking and bike trails including the Legacy Trail that runs from Sarasota to Venice. Residents can enjoy a lifestyle surrounded by nature and resort-style amenities with social gathering in the club house. It’s a boater’s paradise with protected deep-water dockage (up to 44 feet) complete with power, water, and no bridges to the Intracoastal Waterway.
Community highlights include kayak storage and launch, tennis and pickleball courts, a heated pool, fitness center, clubhouse, and a gazebo with grills. Outdoor enthusiasts will love the nature trails across the street at Oscar Scherer State Park, abundant birdlife, dolphins, manatees, and kayaking adventures to Casey Key Tiki Bar & Restaurant.
Perfectly located between Sarasota and Venice, Blackburn Harbor offers the best of both worlds — just minutes from beaches, cultural attractions, parks, shopping, and dining.

OSPREY

6100 JESSIE HARBOR DRIVE 202

3 Beds

3 Baths

3,771 Sq.Ft.

$970,000

MLS#: A4670353

This spacious residence offers over 3,500 square feet of thoughtfully designed living space that blends comfort, flexibility, and refined Florida style. From the moment you step inside, elevated and vaulted ceilings, architectural details, and abundant natural light create an inviting sense of openness. A flowing floor plan seamlessly connects the main living areas, anchored by a well-appointed kitchen featuring granite countertops, stainless steel appliances, generous cabinetry, and a large center island perfectly suited for both everyday living and entertaining.

Outdoor living takes center stage with a pool and expansive screened lanai, creating an ideal setting to relax, host guests, or enjoy the Florida sun while taking in tranquil water views framed by natural greenery. Conveniently located across from Oscar Scherer State Park, the home enjoys a permanent, no-build backyard setting with serene wetland views and frequent wildlife sightings, offering privacy and a true connection to nature. This outdoor space feels like a natural extension of the home and is designed for year-round enjoyment.

Luxury vinyl plank flooring throughout all bedrooms and the second-floor living area adds a modern touch while offering durability and ease of maintenance. Upstairs, a standout bonus area with a full bath and private balcony provides exceptional flexibility, making it ideal as a media room, guest suite, or home office. A three-car garage adds valuable storage and everyday convenience.

Ideally located near Downtown Venice, Sarasota, and the Gulf beaches, the home also offers easy access to golf, waterfront dining, and the area’s vibrant cultural scene. Designed for both relaxed living and effortless entertaining, this residence delivers space, privacy, and an exceptional Florida lifestyle.

Some photos have been virtually staged.

OSPREY

616 CRANE PRAIRIE WAY

3 Beds

4 Baths

3,561 Sq.Ft.

$960,000

MLS#: N6142165

Price reduced

**EXQUISITELY UPDATED, TURNKEY FURNISHED, POOL HOME** in Popular BAY OAKS ESTATES. This Stunning Residence is MOVE-IN READY (just Bring Your Suitcase!) and features a LIGHT and BRIGHT, OPEN FLOORPLAN including 3 BEDS plus STUDY/DEN and 2 FULL BATHS. The Gourmet Kitchen boasts a modern, European design with premium appliance package and counter sitting area while the primary bedroom suite offers an expansive, private retreat complete with walk-in closets, dual vanities, Jacuzzi tub, custom-tiled shower, Italian smart toilet-bidet, etc. A complete List of Recent Upgrades is attached and available upon request and includes but is not limited to NEW Kitchen & Baths, Interior and Exterior Paint, whole home LED lighting and smart fans, built-in Sound System, Flooring (tile, luxury vinyl, carpet), Washer & Dryer, water filtration, exterior LED lighting, pavered driveway, Irrigation system, privacy fence, storage shed and So Much MORE! Relish in the utmost Florida lifestyle with a Saltwater Pool in a large, screened lanai with covered seating area while overlooking the serene and private landscape. Enjoy peace of mind with NEW HURRICANE IMPACT WINDOWS and DOORS, MASONRY Wall Construction, and a structure situated in Flood Zone “X”. LOW HOA. Ideally Located close to Area Beaches including #1-Rated SIESTA BEACH, the Popular LEGACY BIKE TRAIL, #1-Rated PINE VIEW SCHOOL, Shopping, Downtown Sarasota and Venice cultural venues, and all that Florida’s Gulf Coast Living has to offer. **PLEASE ENJOY VIEWING THE 3D VIRTUAL TOUR**

OSPREY

599 PINE RANCH EAST ROAD

3 Beds

2 Baths

2,188 Sq.Ft.

$949,000

MLS#: A4660895

Price reduced

Private Key West–style retreat on 2.53 wooded acres in Osprey. Rarely does a property of this size become available in such a convenient location—just minutes from Pine View School, shopping, restaurants, and the Intracoastal Waterway—yet offering the privacy and space of a true country setting. This combination of acreage and accessibility makes the home exceptionally unique for the area. A generous 37x60 paver-brick patio surrounds the screened lap-style pool, now protected by a freshly updated pool cage. Multiple French doors open to wide second-floor decks overlooking the peaceful wooded backdrop. A recently added metal roof enhances durability, longevity, and value. Inside, the home features oak hardwood floors, vaulted tongue-and-groove cypress ceilings, and a striking wood-burning fireplace that add warmth and character throughout. The kitchen and baths retain their classic charm and present an excellent opportunity for updating to suit modern preferences. The flexible layout includes two potential primary suites and a first-floor bonus room with full bath that works well for guests or creative uses. The lower level remains plumbed for a second kitchen and laundry, offering an easy path for future installation or multigenerational living. With no deed restrictions and an expansive amount of usable land, this country estate in town offers endless potential—whether for hobbies, animals, enhancements, or simply enjoying the quiet beauty of its natural surroundings.

OSPREY

678 FAITH AVENUE

3 Beds

3 Baths

2,583 Sq.Ft.

$949,000

MLS#: A4674865

At last- the home you've been looking for! This updated 3-bedroom 3 bath retreat is tucked inside a lively marina community where every day feels like vacation. This home features modern updates throughout, saltwater pool, den, in home gym, new tile roof, new AC, hurricane impact windows and doors as well as an easy low maintenance open floorplan. Enjoy boating, fishing, biking, pickleball and evenings by the community pool looking out over the marina watching amazing sunsets. Walk, bike our take a golf cart to nearby shopping, restaurants and tiki bars. A definite value in an amazing community!

OSPREY

172 SEA ANCHOR DRIVE

3 Beds

3 Baths

2,283 Sq.Ft.

$936,000

MLS#: A4671745

**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

2,271 Sq.Ft.

$910,000

MLS#: A4633961

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