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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 4 of 11.

**IMPRESSIVE, METICULOUSLY MAINTAINED, SINGLE-STORY, CUL DE SAC ESTATE in the Highly Sought-After SOUTHBAY Community** offers 3 BEDS, 2 FULL and 1 HALF BATHS plus STUDY/DEN – and is nearly 100% SOLAR-POWERED (details available)! This Custom and Updated home offers many premium features including elegant Bolivian woodwork, beautiful tile floors throughout, Expansive Kitchen with Hardwood Cabinets, Granite Counters and Stainless Steel Appliances. The Spacious primary bedroom suite offers multiple walk-in closets and even a BONUS ROOM (possible Gym, Nursery, etc.) while the primary bathroom includes dual sinks, spa tub and custom-tiled shower. Ultimate enjoyment of the outdoors is made possible with an expansive screened lanai featuring a Solar-Heated Pool (Resurfaced in 2021) and ample entertaining space in a private and serene setting. With its HIGH ELEVATION (and NO FLOODING concerns during recent hurricanes and NO storm Damage), this residence is situated on an Oversized, Cul De Sac Lot with Circular Driveway, has wonderful curb appeal and an Ideal SOUTHERN Rear Exposure! Recent UPDATES include NEW ROOF, NEW HURRICANE IMPACT WINDOWS & SLIDING DOORS, NEW LANAI CAGE and Much More! SOUTHBAY YACHT & RACQUET CLUB is a BOATING COMMUNITY with a 170 Boat MARINA, Clubhouse, Tennis and Pickleball Courts! SOUTHBAY is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**

OSPREY

219 KEEL WAY

3 Beds

2 Baths

3,908 Sq.Ft.

$1,175,000

MLS#: A4666970

FULLY UPDATED ~ WATER VIEWS ~ PRIVATE 2 CAR GARAGE ~ OFFICE/4TH BEDROOM OPTION ~ The eye of an artist and perfected skill of a craftsman created this spacious, expertly designed residence. From the moment the elevator doors open to the private foyer, you'll notice every fine detail in this home was carefully thought out and executed, while the splendor of nature and water creates the backdrop from the peaceful, spacious lanai, welcoming you to the dawn of a new day and inviting you to relax and unwind at day's end. High end finishes and elegance abounds in this fully updated unit featuring a custom kitchen with soap stone countertops, modern sink, roll out drawers in cabinets, Bosch appliances, Everpure water filtration, and tray ceiling with crown molding. The luxurious Primary Suite features stunning water and preserve views, a custom walk-in closet, and stunning en-suite bathroom with custom cabinetry, dual sink vanity, stunning stone countertops, and Italian tile. The unit's sprawling split bedroom floor plan offers 3 Bedrooms, 3 Full Baths, an Office/Study that could serve as a 4th Bedroom, Laundry Room, Custom Built-in Bookshelves, custom closet built-ins, a Formal Dining Room, Great Room with Casual Dinette Area off the Kitchen, and includes your own Private Two Car Garage and Storage. The Meridian at the Oaks Preserve, lushly landscaped with winding sidewalks, features a pool, hot tub/spa, outdoor grill, and fitness center. Membership to The Oaks Club is mandatory. The Oaks Club features two golf courses, 12 Har-Tru tennis courts, croquet, pool, fitness and wellness which includes massage and body treatments, three restaurants for a variety of dining atmospheres, social events, and a magnificent clubhouse to relax, enjoy, and entertain. The Oaks / Oaks Preserve is less than one mile to Historic Spanish Point, approximately 6 miles to white quartz sand beaches of Siesta Key, and just 10 miles to Downtown Sarasota for world class dining, theater, ballet, nightlife and entertainment. In addition to District Schools, The Meridian at Oaks Preserve is less than 3 miles to Pine View School in Osprey! Please view the Video Virtual Tour which offers interior and exterior views not easily captured by still photos, while also providing a bird's eye flyover of the stately Oaks Club property. This unit is a must-see in person! Schedule your exclusive showing today!

OSPREY

401 N POINT ROAD 504

3 Beds

3 Baths

3,106 Sq.Ft.

$1,150,000

MLS#: A4653470

#A4672639

OSPREY

14041 BELLAGIO WAY 218

3 Beds

2 Baths

2,374 Sq.Ft.

$1,150,000

MLS#: A4672639

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

4,247 Sq.Ft.

$1,150,000

MLS#: A4663579

Discover this expansive 5-bedroom, 4-bathroom home with an oversized bonus room and 3,938 sq. ft. of living space, perfectly situated on a 10,548 sq. ft. lakefront lot. Recent upgrades provide peace of mind and modern comfort, including a new tile roof (2024), new zoned HVAC units (2022), a new pool heater (2024), a new water heater (2025) with a 25-year whole-home water conditioner, fresh interior paint and updated door hardware throughout (2025), new ceiling fans, and a fully re-screened lanai and pool cage. Outside the property has been freshley landscaped and mulched. Inside, all bathrooms have been beautifully updated with travertine flooring, wall tiles, glass shower enclosures, and chrome fixtures. The oversized 3-car garage features epoxy flooring and a utility sink, combining durability with functionality. Designed for both comfort and elegance, the home boasts an open-concept floor plan with crown molding, granite countertops, custom solid wood cabinets, a glass tile backsplash, induction oven, and stainless steel appliances. The spacious kitchen also offers a large island, matching granite breakfast table, reverse osmosis water system, and a wine bar—perfect for casual meals or entertaining. A separate formal dining room adds sophistication for larger gatherings. The outdoor living space is equally inviting, featuring a heated saltwater pool and spa with a dedicated bathroom and shower, plus a generous screened lanai with travertine flooring. From the bench swing, enjoy panoramic views of nearly 5 acres of Eagle Lake and the surrounding nature preserve, complete with bald eagle nests and Florida’s natural wildlife. The lush landscaping is fed by a sprinkler system sourced directly from the lake, ensuring year-round beauty. Upstairs, the owner’s suite offers engineered wood flooring, a sitting area ideal for fitness, work, or relaxation, and serene lake views. The second floor also includes three additional bedrooms, a convenient laundry room, and a giant bonus room that can flex as an extra bedroom, gym, game room, or media space. For added privacy, a guest suite is located downstairs—perfect for visitors or multi-generational living. Located in the highly sought-after Woodlands at Rivendell, this property provides direct access to Pine View School, ranked among Florida’s top five. Outdoor lovers will enjoy the Legacy Trail, Bay Street Park, and Oscar Scherer State Park just minutes away. Shopping and dining, including two nearby Publix grocery stores, are within easy reach, while Nokomis Beach is only 10 minutes away and Siesta Key Beach just 15. With I-75 less than 10 minutes from your doorstep, commuting is effortless. This rarely available homesite combines serenity, privacy, and convenience—offering the ultimate Florida lifestyle in a premier location. Don’t miss your chance to own this stunning, fully updated lakefront retreat in Woodlands at Rivendell.

OSPREY

820 PLACID LAKE DRIVE

5 Beds

4 Baths

4,628 Sq.Ft.

$1,095,000

MLS#: A4640947

#A4670043

OSPREY

3936 WAYPOINT AVENUE

3 Beds

3 Baths

3,248 Sq.Ft.

$1,089,000

MLS#: A4670043

Newly Built-Out & Fully Furnished Move-In Ready Office Space at Baystreet Village!

Located in the vibrant heart of Osprey, this beautifully designed office space at 3976 Destination Drive, Unit A-411, Osprey, FL 34229 is the perfect opportunity for your business to thrive. Baystreet Village is a premier commercial enclave offering a mix of retail and office spaces, just minutes away from The Oaks, Casey Key, and Pineview 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.

$1,075,000

MLS#: A4643099

Price reduced

#A4638035

OSPREY

393 N POINT ROAD 604

3 Beds

3 Baths

3,106 Sq.Ft.

$1,000,000

MLS#: A4638035

**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

2,815 Sq.Ft.

$995,000

MLS#: A4660895

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

3,024 Sq.Ft.

$995,000

MLS#: D6144630

#A4665288

OSPREY

1602 SOUTHBAY DRIVE

4 Beds

3 Baths

4,160 Sq.Ft.

$995,000

MLS#: A4665288

Price reduced

**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

2,744 Sq.Ft.

$995,000

MLS#: A4635743

Welcome to Emerald Woods, a desired cul-de-sac within The Oaks Preserve, and this private Lee
Wetherington custom home that will check all the boxes, and more. Situated on one of the
largest lots and surrounded by preserve for privacy, you’ll find essence and elegance as the
color palette interplays with natural light, and the southern facing lanai and pool will be where
you can enjoy the maintenance free lifestyle, and the quality of life second to none. Enter the
foyer through 8’ insulated front doors with impact glass, and 12’ high ceilings with wide
decorative crown molding. Designer exceptional interior and exterior details and finishes are
completed and tastefully appointed. The kitchen offers custom 42” wood upper cabinetry with
over and under cabinet lighting, granite countertops, a decorative tile backsplash, center island
with base cabinetry, a pantry with rollout shelving, stainless appliances (2023), and a seamless
glass aquarium window in the breakfast nook. The great room has 17” stone tile flooring,
custom built-in cabinetry and a custom designed stone fireplace with electric logs. The open
floor plan dining room has a hand painted tray ceiling, and a built in buffet with a granite top
and 42” upper cabinets with glass inserts. A fantastic escape awaits when you walk out your
sliding glass doors to the outdoor oasis that includes a newly resurfaced custom designed pool and spa
with a waterfall feature and a new pool screen and cage with a panoramic view maximizing the
enjoyment of the outdoor space. A dry bar/buffet makes entertaining outdoors so easy. The
primary suite offers an extended office/owner’s retreat with a custom designed built in desk and
cabinetry, handsome bamboo wood floors, two large walk-in closets with built-ins, a primary bath with
new vanities, undermount sinks, and designer brass and chrome fixtures. The second light and
bright guest suite has wood floors, a bay window with plantation shutters and an ensuite
custom designed bath. Additional special features include a new roof (2023) new landscaping
and sod, a paver brick driveway, and an oversized 2 car garage with tandem parking for a 3rd car
and tons of storage and cabinetry. Experience the best in this move in ready home, and begin
your lifestyle at The Oaks Country Club, with the best location in Sarasota County. Centrally
located to all the beautiful beaches and offering two 18 hole championship golf courses, tennis,
pickleball, croquet, fitness center, dining, and a wide variety of social options. The Oaks is a
Platinum Club of America, an Elite Distinguished Club of The World, and best of all there is no
waitlist for a golf or social membership! Don't wait to begin your terrific and exceptional lifestyle!

OSPREY

105 TURQUOISE LANE

3 Beds

2 Baths

3,465 Sq.Ft.

$995,000

MLS#: A4662015

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

4,209 Sq.Ft.

$970,000

MLS#: A4670353

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

2,993 Sq.Ft.

$936,000

MLS#: A4671745

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