One of the most popular communities provided by {{page_data.agentName}}

Osprey

One of the most popular communities provided by The Graf Group of Coldwell Banker

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 The Graf Group of Coldwell Banker

157

# of Listings

3

Avg # of Bedrooms

$528

Avg. $ / Sq.Ft.

$1,241,103

Med. List Price

Browse Osprey Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

68 Properties Found. Page 1 of 5.

Price reduced

Waterfront with your own private dock with 10,000lb elevator lift. This home is being offered fully furnished from the inside out to the lanai and boat dock. The kitchen features raised wood cabinets and a large 10ft long breakfast bar. The kitchen has views of the canal and opens up to the dining room and living room. As you walk into the nicely appointed open floor plan, you immediately feel relaxed while enjoying the water views and fish jumping. There is nothing to do but move in and enjoy your new home. Taking the boat out is a breeze. Just lower it into the water and you are a short ride out to the intracoastal, the Venice Jetties and Midnight Pass. There are many great waterfront restaurants you can access by boat. If you happen to catch some fish while you are out enjoying the boat, there is a fish cleaning station on the dock. Located between Sarasota and Venice with easy access to I-75. Close to shopping, beaches, restaurants, Oscar Scherer Park and so much more.

OSPREY

120 VILLA DRIVE 120

2 Beds

2 Baths

1,404 Sq.Ft.

$515,000

MLS#: N6138441

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.

$1,000,000

MLS#: A4643099

Experience refined waterfront living in Southbay, one of the area’s most coveted boating communities. This impeccably maintained three-bedroom pool residence offers a thoughtful, split-bedroom design that balances privacy with seamless flow—ideal for both relaxed everyday living and sophisticated entertaining. A comprehensive renovation in 2017 elevated the home with cohesive flooring throughout, fully redesigned spa-inspired bathrooms with custom vanities, updated ceilings, recessed lighting, and interior shaker doors. The home was also re-piped for water and sewer, offering both modern comfort and long-term peace of mind. The light-filled living room, accented with elegant shiplap detail, opens effortlessly to the lanai, creating a graceful indoor-outdoor connection. Outside, a private retreat awaits with a resurfaced pool, new screen enclosure, and marble pavers. Generous covered space accommodates lounging, dining, and entertaining, while sliding doors from the primary suite, living room, and family room invite the outdoors in and enhance the home’s open, airy ambiance. The primary suite is a serene escape, thoughtfully positioned for privacy and direct access to the lanai. Custom closet systems throughout the home provide elevated functionality, while the epoxy-finished garage with built-in cabinetry delivers a polished, organized finish. Mature tropical landscaping and six-foot pitch apple plantings create a secluded backyard sanctuary, complemented by stately palms that frame the home with unmistakable Florida elegance. Southbay offers a distinguished, resort-style lifestyle with a newly renovated waterfront clubhouse featuring a grand ballroom, catering kitchen, and state-of-the-art fitness center overlooking the marina. Residents enjoy a heated pool, youth pool, tennis and pickleball courts, shuffleboard, bocce, basketball courts, walking trails, and an Intracoastal waterfront park. For boating connoisseurs, the community-owned deep-water marina provides direct Intracoastal access with no fixed bridges to the Gulf. Exclusive, low-fee boat slips accommodate vessels up to 55 feet and are available only to Southbay owners. A vibrant social calendar and golf-cart-friendly streets make it effortless to enjoy community events, nearby boutiques, waterfront dining, and local beaches. Ideally located near Pine View School—Florida’s #1 charter school and one of the nation’s premier gifted programs—this residence presents a rare opportunity to enjoy luxury living within an active, waterfront enclave. A sophisticated coastal retreat where lifestyle, privacy, and boating converge—welcome to Southbay.

OSPREY

1486 LANDVIEW LANE

3 Beds

2 Baths

1,869 Sq.Ft.

$995,000

MLS#: D6144630

Price reduced

FULLY UPDATED • WATER VIEWS • PRIVATE 2-CAR GARAGE • OFFICE/4TH BEDROOM OPTION

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. 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.

$990,000

MLS#: A4653470

Experience the charm and wonderful location of this golf course home on Saint James Park, the leafy and quiet cul-de-sac where you can walk to tennis, golf, pickleball, croquet, heated pool and state of the art fitness center all within The Oaks Country Club, where the luxury lifestyle awaits! This 2 bedroom, 2 bath traditional home overlooks the first hole of the Eagle Golf course, and is being offered completely furnished, easy to maintain, and is move in ready. The roof is new in 2024, and all windows and sliding doors are newer and hurricane impact. Custom designed by Bo MacEwen, the architect who designed the clubhouse, features include crown molding, wainscoting, built-ins throughout, a wood burning fireplace, split bedrooms, both ensuite with wood floors, and open views from most rooms. The kitchen has a light and bright breakfast area. The expansive screened lanai is 20 feet by 48 feet, and the oversized two car garage has a charging station for your electric car. Saint James Park is the residential area closest to the athletic facilities so residents can easily walk or bike to all facets of the club, including dining as well as a social atmosphere that encourages all to stay engaged in all The Oaks Club has to offer. For those electing golf, the ability to play the two courses is immediate, no waiting period. Also, The Oaks has been designated a Platinum Club of America, and an Emerald Club, signifying it’s standing among the finest in Florida, not to mention 20 minutes to the best beaches in Sarasota County! Membership is required, either Social or Golf. Be sure to see this special home and begin enjoying a well rounded lifestyle!

OSPREY

227 SAINT JAMES PARK

2 Beds

2 Baths

2,071 Sq.Ft.

$980,000

MLS#: A4679867

Price reduced

#A4665288

OSPREY

1602 SOUTHBAY DRIVE

4 Beds

3 Baths

2,980 Sq.Ft.

$974,900

MLS#: A4665288

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

Amazing home with many improvements ideally located in a sought-after marina community. This beautifully updated 3-bedroom 3 bath residence has been thoughtfully enhanced for comfort, style and easy living. It's tucked inside a lively marina community where every day feels like vacation. This home features modern updates throughout. Newly remodeled kitchen, new master bath, luxury vinyl flooring, saltwater pool and newer cage, 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, tennis, bocci ball, kayak storage, jet ski pads and boat slips. Spend evenings sitting 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

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.

$925,000

MLS#: A4660895

**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

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

2,216 Sq.Ft.

$900,000

MLS#: A4664085

Enjoy breathtaking sunset views overlooking the intercostal waterway in this boater's paradise, complete with an on-site marina. Discover coastal living in this beautifully updated 3-bedroom, 2.5-bath residence located in Bellagio Harbor Village. Ideally positioned between Sarasota Big Pass and the Venice Jetty, and just minutes from Midnight Pass and the Gulf of Mexico, this home offers easy access to pristine beaches, fine dining, and boutique shopping. Walkable to local restaurants and boat docks, the community is both conveniently located and peacefully serene. Offering 2,199 square feet of thoughtfully designed living space, this residence has been enhanced for comfort and style. Updates include new lighting throughout, featuring four coastal ceiling fans and elegant Caprice chandeliers. The spacious primary suite and two additional bedrooms feature new cordless blinds and window treatments, creating private and tranquil retreats. Bathrooms have been refreshed with new toilets, fresh paint, and an updated vanity in the powder room. The well-appointed kitchen showcases shaker-style cabinetry and enjoys stunning Intracoastal and sunset views. Step onto the private lanai and enjoy seamless indoor-outdoor living with direct access to the pool area. Newly installed retractable screens provide shade and privacy when desired while preserving expansive water views. Outdoor enthusiasts will appreciate the on-site kayak storage and launch area, perfect for exploring the surrounding waterways. Located in southwest Osprey, this exceptional residence offers both a beautiful home and a vibrant waterfront community. Residents enjoy access to a resort-style pool, hot tub, sauna, and open-concept gathering spaces—creating a lifestyle where every day feels like a vacation.

*Boat slip available for rent, not included in sale*

This premium 50-foot boat slip, offers prime Gulf access just minutes from the newly opened Midnight Pass. Designed to accommodate vessels up to 45 feet in length overall (LOA), the slip is equipped with electricity and fresh water for your convenience. Located in Sarasota's top-rated marina, it offers a serene location off Little Sarasota Bay, ensuring a peaceful and secure docking experience. Situated in the exclusive Casey Key Marina, the slip provides 24-hour access within a gated community, offering both privacy and peace of mind for boat owners

OSPREY

14021 BELLAGIO WAY 309

3 Beds

2 Baths

2,199 Sq.Ft.

$899,995

MLS#: A4681589

Built in 2019 and perfectly positioned on the fourth floor, this waterfront residence offers sweeping views across the Intracoastal Waterway, tranquil mangroves, and surrounding waterways from nearly every room. Designed with comfort and functionality in mind, the three-bedroom plus office layout spans nearly 2,200 square feet of interior living space and captures the essence of relaxed coastal living.
Inside, the open floor plan is finished with travertine and Brazilian cherry wood flooring, crown molding, and wood-encased impact windows that frame the water views. The granite chef’s kitchen features solid-wood cabinetry, an Italian Carrara marble backsplash, center island with pendant lighting and seating, and upgraded stainless-steel appliances including a beverage refrigerator. The kitchen flows seamlessly into the formal dining area—anchored by a custom metal-and-granite dining table (included)—and the living room, where walls of glass sliders open to an oversized, screen-protected terrace.
The terrace extends the living space outdoors with tile flooring, ceiling fan, and custom electronic shades—ideal for morning coffee, sunset gatherings, or quiet evenings overlooking the water. Additional interior highlights include custom shelving in all bedroom closets, automatic sunscreen in the living room, LED lighting throughout, and an oversized laundry room with premium appliances, generous granite counters, and abundant storage.
The secluded, west-facing primary suite offers peaceful water views, French-door access to the balcony, dual walk-in closets, and a granite-finished en-suite bath. Two guest bedrooms (one with a walk-in closet) are positioned on the east side of the residence for privacy and share a granite and glass bathroom, creating a comfortable retreat for visitors.
Residents enjoy the full suite of resort-style amenities at Edgewater at Hidden Bay, including a heated pool and spa, tiki-hut covered grilling and lounge areas, clubhouse with catering kitchen, library, fitness center, tennis and pickleball courts, kayak launch and storage, picturesque boardwalks through mangroves and lakes with fountains, and a private fishing pier currently undergoing improvements.
Ideally located near Siesta Key and Nokomis beaches, this residence is also minutes from Bay Street Park, the Legacy Trail, Oscar Scherer State Park, marinas, golf courses, shopping, dining, and premier medical facilities. Offering a blend of waterfront serenity and everyday convenience, this home delivers an exceptional coastal lifestyle with easy access to everything Sarasota has to offer.

OSPREY

260 HIDDEN BAY DRIVE 405

3 Beds

2 Baths

2,168 Sq.Ft.

$899,000

MLS#: A4679287

Enjoy sweeping Intercoastal water views with peek-a-boo Gulf glimpses from this beautifully upgraded top-floor, end-unit residence filled with natural light, privacy, and coastal elegance. The interior features Luxury vinyl plank flooring, plantation shutters, crown molding, and higher ceilings unique to the top floor. The chef’s kitchen offers Bosch and JennAir appliances, a Liebherr split refrigerator/freezer, granite countertops, soft-close cabinetry with pullouts, beautiful wood finishes, and a true warming drawer. The spacious primary suite includes water views, a built-in fireplace, custom closets, and a spa-style bath with a multi-head shower, soaking tub, and dual vanities. Impact-rated sliders open to a large screened balcony with water hookup, perfect for indoor-outdoor living.

Live the ultimate Florida waterfront lifestyle with deep-water boat slips available for rent, no bridge access to open water, a kayak launch with storage, and waterfront park access. Additional highlights include two garage spaces, private storage with EV charging capability, laundry room with sink and cabinetry, newer washer/dryer and hot water heater, a new 2025 roof, and no upcoming assessments. A rare opportunity to enjoy luxury, convenience, and effortless coastal living.

OSPREY

6100 JESSIE HARBOR DRIVE 603

3 Beds

3 Baths

2,630 Sq.Ft.

$884,000

MLS#: A4676824

**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

2,622 Sq.Ft.

$879,000

MLS#: A4669102

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