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Osprey

One of the most popular communities provided by Michael Graf

Osprey

About Osprey

<p>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.</p>

One of the most popular communities provided by Michael Graf

146

# of Listings

3

Avg # of Bedrooms

$404

Avg. $ / Sq.Ft.

$981,910

Med. List Price

Browse Osprey Real Estate Listings

All listings

$250,000 - $500,000

146 Properties Found. Page 3 of 10.

#A4638035

OSPREY

393 N POINT ROAD 604

3 Beds

3 Baths

3,106 Sq.Ft.

$1,300,000

MLS#: A4638035

Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet club featuring 10 foot ceilings. 2024 tile roof, 2023 driveway, cabinets, lighting, appliances, tile and carpet are just the beginning. 2023 pool and spa led lighting, Pentair controller, saltwater conversion, and owned 250 gallon propane. Dry bar with ice maker, wine fridge, and beverage fridge. Large covered outdoor living space overlooking the large lanai with tv, private tanning area, and room to entertain. A split bedroom design, game room with space for billiards table, and separate dining area, and great room surround the private courtyard layout designed to entertain. Ample storage throughout including an air conditioned, secure 12x7 storeroom.

Southbay Yacht and Racquet Club offers a clubhouse, tennis, pickleball, basketball, shuffleboard, playground, and low fee, exclusive dockage for residents in the deep water marina. Frequent community activities provide opportunities for an active social atmosphere from cruises to sports.

OSPREY

1527 BUOY LANE

3 Beds

2 Baths

3,685 Sq.Ft.

$1,279,000

MLS#: A4654172

Welcome to Southbay Yacht & Racquet Club, one of the Gulf Coast’s most coveted communities—where every day feels like a vacation! Southbay boasts a world-class private marina with 172 deep-water slips, accommodating yachts up to 55 feet, along with personal watercraft and kayaks. Slip rentals are available and offered at a highly competitive rate, making this an exceptional value for boating enthusiasts. This remarkable residence is one of the largest in the community and offers a rare 3-car, side-load garage with a dedicated workshop—perfect for collectors, creatives, or anyone in need of additional space. Step outside to your private oasis: a peaceful lanai overlooking a sparkling, heated pool and spa—ideal for both lavish entertaining and quiet moments of retreat. Inside, every detail has been meticulously curated. A recent, designer-led renovation has transformed the home into a sophisticated showplace. The interiors reflect a timeless elegance, with a high-contrast black and white palette that creates a dramatic yet harmonious flow throughout the home. Clean lines, thoughtful textures, and classic materials elevate each space with effortless style. A reimagined front entrance welcomes you into soaring ceilings and a stunning great room filled with natural light. The gourmet kitchen is equally impressive, featuring white solid wood cabinetry with soft-close drawers, stainless steel appliances, and gleaming granite countertops—all designed with both beauty and functionality in mind. With two expansive living areas, oversized bedrooms, two en-suites, and multiple storage options, this home provides ample space for elegant living and entertaining. Southbay also offers a newly renovated clubhouse, resort style heated community pool, tennis courts, pickleball courts, miles of walking trails & green space, and a full calendar of vibrant social events year-round. The community is warm, welcoming, and lively—perfect for families and those who enjoy an active, coastal lifestyle. Conveniently located next to Publix, shops & restaurants. Across the street from Oscar Scherer State Park, and only 5 minutes to the number 1 school in the state-Pine View. This is not just a home; it is a statement of style, comfort, and grace. Come and experience the elevated lifestyle that only Southbay Yacht & Racquet Club can offer.

OSPREY

1484 SEAFARER DRIVE

4 Beds

3 Baths

4,908 Sq.Ft.

$1,250,000

MLS#: A4655585

#A4643157

OSPREY

201 EAGLENOOK WAY

4 Beds

3 Baths

4,707 Sq.Ft.

$1,200,000

MLS#: A4643157

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

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.

$1,099,000

MLS#: A4643099

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

**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.

$1,045,000

MLS#: A4635743

**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

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

Welcome to this beautifully updated Rutenberg Homes residence in the sought-after Woodlands at Rivendell. Designed for both comfort and style, it offers expansive lake views, a sparkling heated saltwater pool and spa, and a spacious screened lanai—perfect for year-round enjoyment.
Spanning over 3,000 sq ft, the home features 4 bedrooms, 3 baths, and a versatile upstairs 500 Sq Fp bonus room. Extensive 2023 updates include elegant ceramic tile flooring throughout, a chef’s kitchen, modern bathrooms, fresh interior paint, and new light fixtures and fans. Three skylight-style tube lights brighten the main living areas with natural sunshine.
The heated saltwater pool, spa, and screened cage were all newly installed in 2024, creating a true backyard oasis. A generous 3-car garage, quality Rutenberg craftsmanship, and a prime location near beaches, parks, and top-rated Pine View School for the gifted make this home a rare find.

OSPREY

1085 MALLARD MARSH DRIVE

4 Beds

3 Baths

4,240 Sq.Ft.

$970,000

MLS#: A4647633

**IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve. Recent updates include a new kitchen, bathrooms, flooring, fans, a four-year-old roof, a newly pavered driveway, and hurricane-rated patio and bedroom doors. All living areas have wood floors or Italian porcelain tile. The kitchen features a gas stove, Waterworks faucet, quartz countertops, modern stainless appliances, and solid wood cabinetry. The breakfast nook adjacent to the kitchen has aquarium glass windows offering a view of the pool and foliage. The family room glass doors stack behind the wall, providing views of the pool and preserve, and they are hurricane-rated. The owner's suite includes two walk-in closets, a linen closet and space for a sitting area or office. Hurricane-rated glass doors overlook the pool. There is a separate study/office/bedroom with built-in wood cabinetry and space and wiring for a media room. The guest suite has an ensuite bath updated with Quartz counters and a vessel sink. Enjoy the utmost in outdoor living with a stunning, PebbleTec POOL with Travertine deck while there is ample space for a spa or additional seating within the spacious screened lanai. Connections for an outdoor kitchen are also available. A beautiful new pavered driveway adds that special curb appeal. In addition to the metal, roll down hurricane shutters, there is an electric hurricane protective screen spanning the lanai area to protect outdoor furniture. The extra deep two car garage affords additional storage options. A collection of unique bougainvillea and crepe myrtle rounds out the gardens. This lot is located outside the FEMA flood zone Bishops Court in The Oaks Preserve is a 24-hour guard-gated community with walking and biking paths. Additionally, there is a year-round heated community pool nearby. 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

13 BAYHEAD LANE

2 Beds

2 Baths

3,093 Sq.Ft.

$965,000

MLS#: A4645829

Nestled in the heart of Southbay Yacht & Racquet Club, this exquisitely renovated and impeccably maintained residence offers an enviable lifestyle for those who cherish the water. The journey begins at the inviting brick paver entry, guiding you into a gracious foyer that sets the tone for the home's elegant charm. Upon entering, you are welcomed by a spacious great room featuring new tile flooring and a wall of sliding glass doors that seamlessly connect to the expansive covered lanai. The open floor plan is perfect for entertaining, with a dining area adjacent to the sophisticated kitchen equipped with 42” cabinets, stone countertops, stainless steel appliances, a breakfast bar, and easy access to the grilling area. Relax in the enormous owner’s retreat, thoughtfully secluded for privacy. This luxurious space boasts an ensuite bathroom with dual sinks and a free-standing shower, offering a serene sanctuary for unwinding after a day on the water. The home's layout includes two additional guest suites, providing comfort and privacy for visitors. A separate den with a wood-burning fireplace adds a cozy touch, creating a perfect spot for relaxation or reading. The outdoors are effortlessly integrated with the interior, featuring a lavish 12x60 screened lanai that is ideal for alfresco dining or simply enjoying the serene surroundings. Recent improvements, including newer plumbing throughout, a 2021 roof, and new screened lanai cage, make this home truly maintenance-free. Southbay Yacht & Racquet Club offers a variety of amenities designed to enhance your active lifestyle. The community-owned deep-water marina provides boat slips that accommodate large vessels, ensuring easy access for your nautical adventures. The club features lighted tennis courts, a heated community pool, an exercise room, a playground, and numerous clubs and social activities, catering to diverse interests. While the community is beautifully balanced with nature and the Bayfront, you'll still be minutes away from a plethora of fantastic restaurants, shopping destinations, and the pristine Casey Key beach. This sought-after location ensures that you can enjoy the best of both worlds—tranquility and convenience. Southbay Yacht & Racquet Club embodies the perfect blend of luxury and natural beauty, offering a unique opportunity to live an active lifestyle centered around the water. Whether you're an avid boater, a tennis enthusiast, or someone who simply loves the charm of coastal living, this community has something extraordinary to offer.

OSPREY

238 LOOKOUT POINT DRIVE

3 Beds

2 Baths

3,660 Sq.Ft.

$959,000

MLS#: A4650720

One or more photo(s) has been virtually staged. Welcome to your dream home! This 3-bedroom, 3-Bath residence offers the perfect blend of comfort, style, and outdoor living. Step inside to an open floorplan featuring a spacious living area, modern kitchen with stainless steel appliances. The separate den allows the perfect place to work from home! The highlight of this home is the inviting saltwater pool and roomy screened lanai. New tile roof and hurricane impact windows will give you peace of mind and protection. Additional features include a community clubhouse, private marina, waterfront park with a view of the Intracoastal, tennis courts, playground, pickleball and a prime location close to shopping, dining, parks and top-rated schools. Southbay Yacht and Racquet Club provides recreational and social activities for all ages. Come live the true Florida lifestyle!

OSPREY

172 SEA ANCHOR DRIVE

3 Beds

3 Baths

2,993 Sq.Ft.

$950,000

MLS#: A4650577

#A4641653

OSPREY

14021 BELLAGIO WAY 309

3 Beds

2 Baths

2,430 Sq.Ft.

$950,000

MLS#: A4641653

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