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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 7 of 10.

INCREDIBLE Pool Home in INCREDIBLE Community!...You Will Be Impressed by this Well-Appointed FURNISHED Lee Wetherington residence with NEW Barrel Tile ROOF (Nov 2025) in Sought After Willowbend----ideally located near the Community Fitness Center, Pool, Pickleball Courts & Playground.....Generous-Sized Living Spaces with Bright/Spacious Open Floor Plan affording ease of INDOOR/OUTDOOR LIVING where you will Enjoy Morning Coffees and Twilight Sunsets lounging in Expansive Screened Lanai.....Elegantly Updated Throughout, including: Cabinets, Countertops, Flooring, Crown Molding and Ceiling Fixtures---other recent improvements include Garage Door, Pool Heater & Retractable Solar Shade. Abundance of Storage, Built-ins and Closets.......Willowbend is a HIGHLY DESIRED boutique community with Great Proximity to Top Rated Pineview School; Shopping; Dining; Sarasota Memorial Hospital; the Legacy Bike Trail; Marina's and your choice of Multiple Beaches---including Top Rated Siesta Key!

OSPREY

1303 THORNAPPLE DRIVE

3 Beds

2 Baths

1,929 Sq.Ft.

$699,000

MLS#: A4675439

Come and enjoy the perfect maintenance free lifestyle in this exquisite townhouse located in one of the finest country
clubs on the gulf coast, The Oaks Golf and Country Club. Previously redesigned, this tuscan style home in the quaint
and charming Bishops Court in the Oaks Preserve features 2 large en suite bedrooms on the second floor, 2 1/2 baths, a spacious kitchen, and a great room overlooking a lovely lake view surrounded by canopied oaks and palm trees. The European designed kitchen has
top of the line appliances (SubZero and Bosch), contemporary wood cabinetry, sleek granite countertops and
ceramic tile flooring. Hand plastered walls adorn the home with art niches, plantation shutters, rounded archways,
and Sisal carpeting. A separate laundry room and powder bath are off the entry foyer, and the private bricked balcony
has space for a large outdoor table and chairs to dine al fresco.The primary and guest bedrooms are both ensuite. The
main bedroom has windows overlooking the lake, two walk in closets, and a spacious bathroom with luxurious fixtures.
The guest suite has built in shelving and closets for storage. Bishops Court Townhomes is part of the Oaks Country
Club, where you can play two championship18 hole golf courses, tennis, pickleball, bocce, croquet and work-out in the
fitness and wellness center. If you aren't into sports there are numerous social activities throughout the year to keep
busy.

OSPREY

33 BISHOPS COURT ROAD 118

2 Beds

2 Baths

1,890 Sq.Ft.

$695,000

MLS#: A4669237

TURN-KEY FURNISHED 5TH FLOOR RESIDENCE WITH LOVELY VIEWS! Experience luxury coastal living in this stunning 5th floor condo in Meridian at The Oaks Preserve. With water and Preserve views that rival those of higher floors, this residence offers 3 bedrooms, 3 full baths, and a dining room, all enhanced with NEW FURNISHINGS. OFFERED TURNKEY, ALL YOU NEED TO DO IS MOVE IN AND START ENJOYING A CAREFREE LIFESTYLE ON FLORIDA’S GORGEOUS GULF COAST. Enter through the secure lobby and take your private elevator to this lovely unit. The light-filled interior features crown molding, high ceilings, tile, and engineered hardwood floors. The open kitchen boasts a breakfast bar, pantry, white cabinets, and granite countertops. Washing up after cooking a gourmet meal is a pleasure with the view over the great room. The master suite, like most rooms in the unit, offers beautiful views and features a walk-in closet and a luxurious master bathroom with a soaking tub, separate walk-in shower, dual sinks, a built-in vanity, and ample cabinets and counter space. The two additional bedrooms are generously sized, with one featuring a custom-built Murphy bed for flexible use. Put it up for day-to-day living and take it down to accommodate visiting guests. When evening comes, there is no better place to toast the end of another picture-perfect day than the screened balcony, where you can witness some of the most spectacular sunsets you will ever see. Meridian residents can enjoy the nearby residents-only pool, spa, and gym, as well as all the offerings of The Oaks Club, including two championship golf courses, an incredible tennis program, pickle ball courts, a state-of-the-art WellFit center, a variety of dining options, and a celebrated social calendar. Membership is required with homeownership.

OSPREY

385 N POINT ROAD 503

3 Beds

3 Baths

2,203 Sq.Ft.

$690,000

MLS#: A4672342

One of the largest homes in Bay Oaks Estates, this 5-bed, 2.5-bath single-story pool retreat delivers the best of indoor-outdoor Florida living with flexible spaces for guests, work, and play. Curb appeal pops with a brick paver circular drive, lush landscaping, and a covered, columned entry with French double doors and an arched transom.

Inside, high ceilings and an abundance of natural light set a welcoming tone. The formal living and dining rooms flow to the heart of the home – a well-appointed kitchen designed for everyday living and entertaining, featuring granite counters, tile backsplash, stainless appliances, a center island with raised breakfast bar, closet pantry, built-in desk and wine rack, recessed & pendant lighting, and a picturesque breakfast nook with wraparound windows. The kitchen opens to the spacious family room with a tray ceiling and mirrored media niche. A pocketing three-panel slider seamlessly extends the living space to the covered lanai and screened pool; additional sliders from the formal living room, the primary suite, and a secondary bedroom maintain the indoor–outdoor connection.

Out back, the lanai enjoys a private, tranquil, tree-lined backdrop, overlooking a curved, free-form pool with twin arc fountain jets, a raised sun terrace for lounging, and generous space to relax or gather. A screen door leads to the lawn and a separate pergola patio with power – perfect for morning coffee or an evening grill. From the backyard you have direct access to the Legacy Trail, the popular paved, multi-use path linking Sarasota and Venice, for miles of biking and walking through nature.

The private primary retreat offers lanai access, two closets (one walk-in), and a spa-like en-suite bath with a Jacuzzi jetted soaking tub framed by an arched window with plantation shutters, separate walk-in shower with wall body sprays, a long double vanity, and a private water closet. Thoughtful split-bedroom design places three secondary bedrooms and a full bath together in their own wing (one is oversized with lanai access that can flex as a game/media space), while a full 5th bedroom – currently used as an office – sits near the primary suite. An interior laundry room adds storage shelves, cabinets, and a utility sink. Major updates for peace of mind include: replumbed water lines, roof (2015), A/C (2019), new water heater (2024), new pool pump (2024), kitchen appliances (2021), washer and dryer (2023), polycarbonate storm panels, and irrigation.

All in a well-kept, low-fee, pet-friendly Osprey community conveniently located just minutes from top-rated schools, including the prestigious Pine View School, and close to the Gulf beaches of world-renowned Siesta Key, Nokomis, and Venice, as well as Oscar Scherer State Park, and a variety of shopping, dining, entertainment, and everyday conveniences; the Gulf Coast lifestyle at its finest. Schedule your private showing today and fall in love with the lifestyle that 571 Pine Ranch East Rd has to offer.

OSPREY

571 PINE RANCH EAST ROAD

5 Beds

2 Baths

2,746 Sq.Ft.

$685,000

MLS#: A4665938

This meticulously maintained, waterfront residence is in an amenity-rich, gated community. Offering over 2,000 square feet of casual luxury, the well-designed living space includes two bedrooms, two baths and features a welcoming foyer, a breakfast area, and a separate room ideal for a den or home office. The upgraded appointments throughout are numerous and include top-of-the-line KitchenAid appliances, custom cabinet pullouts and the kitchen’s showstopper is the exquisite stone counter surfaces, which wow and make everyday cooking, or your gourmet meal preparation, a joy. Plantation shutters and remote-controlled blinds grace many of the windows. The views from your primary retreat vie for your attention thanks to the shimmering intracoastal front and center. Generous in size, the main retreat delights with a walk-in shower, large soaking tub, double vanities, a separate makeup area, private water closet and dual walk-in closets. The second bath features a recently installed walk-in tub, designed for enhanced comfort, ease and safety. Enjoy expansive water views from your fourth-floor balcony, where nesting birds, jumping fish and dazzling sunsets create a stunning backdrop for your daily pleasure. The inside laundry room and your two assigned parking spaces are under the building and out of the elements, adding to the opportunity. The lifestyle amenities in this friendly community include recently resurfaced tennis and pickleball courts, a heated swimming pool, a clubhouse with fitness area, kayak storage and launch, and fishing. Boat slips are available on a first-come basis for an additional fee. Enjoy a waterfront picnic under the gazebo, complete with grills, a walking path and pretty greenspace areas. Ideally close to shopping, dining, the crystal sand beaches and famed Oscar Scherer State Park, which offers biking, birdwatching, geocaching and over 15 miles of scenic hiking trails, and a natural lake for swimming, and the best part is the proximity, just across the street. Come be enchanted, as this slice of Florida paradise is one you won’t want to miss.

OSPREY

5100 JESSIE HARBOR DRIVE 403

2 Beds

2 Baths

2,143 Sq.Ft.

$679,900

MLS#: A4676382

BEAUTIFUL FULL WATER VIEWS OF NORTH CREEK, SARASOTA BAY, AND THE GULF! Watch the eagles and osprey fish and enjoy truly stunning sunsets from the balcony of this condo with 3 bedrooms, 3 full baths and a formal dining room/den. With this condo you have found a best-priced gem in Meridian at The Oaks Preserve to enjoy all the Gulf Coast has to offer. Take the private elevator to the sixth floor and explore this spacious unit with stunning maple wood floors throughout. The great room has high ceilings and sliding doors to the large, screened balcony that offers gorgeous water views in the day, and breath-taking sunsets in the evening. The open kitchen features a pantry, and a breakfast bar. The adjoining dining room gives you room to host formal meals or could be used as a den. The master suite has a door that opens to the balcony, two walk-in closets and an en-suite master bath with soaking tub, a walk-in shower, a good number of cabinets, mirrors and counter space. The 2nd bedroom is en-suite, and the third is spacious with beautiful preserve views. A nice option for those who want to work at home. Want to get outside and enjoy the Florida sunshine? You can walk to the Meridian residents-only pool and spa. Here you will also find an outdoor kitchen and workout room. As members of The Oaks Club, you also can take advantage of all it offers, two 18-hole championship golf courses, 12 HAR-TRU tennis courts maintained to tournament standards, 4 of which are lighted, bocce and pickle ball courts, a junior Olympic community pool, and a wide variety of dining, recreational and social offerings. GOLF or SOCIAL Membership is required and available immediately with homeownership.

OSPREY

409 N POINT ROAD 603

3 Beds

3 Baths

2,203 Sq.Ft.

$679,000

MLS#: A4601891

**BEAUTIFULLY UPDATED CONDO with MARVELOUS VIEW** features 3-BEDS and 3-FULL BATH, Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Impressively Renovated interior which boasts Engineered Hardwood and designer Wood Plank Tile flooring, Plantation Shutters, a well-equipped Kitchen with granite counter seating area, white cabinetry and Stainless-Steel appliances including Bosch etc. The Owner’s Bedroom Suite features a Walk-in Closet, Dual Vanities, Soaking Tub and Stunning, Custom Tiled Shower. The Spacious, Screened Balcony features lovely new tile flooring and automated Hurricane Shutters, offering a PRIVATE and serene setting where you can view wonderful wildlife and Gorgeous Sunsets! This residence offers a single, covered parking space and a climate-controlled storage unit. Meridian Condo residents enjoy private amenities including Heated Pool & Spa, Fitness and Outdoor Grill in addition to The Oaks Club’s main campus of amenities. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership.

OSPREY

385 N POINT ROAD 402

3 Beds

3 Baths

2,055 Sq.Ft.

$660,000

MLS#: A4635708

Welcome to this elegant and spacious luxury pool home offering over 2,500 square feet of refined living in one of the most desirable communities along the Gulf Coast. With a freshly painted exterior, stunning hardwood floors throughout, and an exceptional layout designed for both comfort and style, this residence is move-in ready and perfectly suited for modern living. Boasting four bedrooms, including a private guest suite area, and three beautifully appointed baths, the home offers flexible space ideal for hosting family and friends. Expansive living areas flow seamlessly to the outdoor oasis, where a sparkling pool creates the perfect backdrop for relaxing or entertaining in the Florida sunshine. Just 10 miles south of downtown Sarasota and 6 miles north of Venice, Park Trace Estates provides the best of both worlds: tranquil suburban living with unbeatable convenience. Outdoor enthusiasts will love being only one block from the Legacy Trail, offering miles of scenic pathways for biking, running, and recreation. Nature and waterfront activities abound with Oscar Scherer State Park, Bay Street Park, Nokomis Beach, Siesta Key Beach, Gulf Harbor Marina, and Blackburn Point Park all within close reach. Families will appreciate access to top-rated schools, including the prestigious Pine View School, known for its exceptional academic programs. Offering a rare blend of luxury, comfort, and prime location, this Park Trace Estates home is a true Sarasota-area gem, ready to welcome you to the lifestyle you’ve been dreaming of.

OSPREY

104 PARK TRACE BOULEVARD

4 Beds

3 Baths

2,557 Sq.Ft.

$650,000

MLS#: A4674221

Price reduced

**GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The coveted lifestyle of The Oaks Country Club with the convenience and amenities of maintenance-free condominium living come together at this Gorgeous Meridian 5th floor residence. Upon exiting the elevator into the private foyer, step inside and enjoy the breathtaking panoramic preserve, bay and Gulf of Mexico views! The dramatic step ceiling defines the foyer space while leading into the expansive dining room, living room and open kitchen featuring Granite countertops and Stainless Steel appliances. Both the primary bedroom suite and living room open to the balcony extending the sweeping views and providing ample outdoor living space. Premium features include Crown Moldings, High Ceilings, Luxury Vinyl Plank flooring, recently Painted Interior, etc. Owner’s Bedroom Suite features Walk-in Closet, Custom Tiled Shower, Soaking Tub and Dual Vanities, a 2nd En Suite Bedroom with walk-in closet, etc. NEW HVAC (Sept., 2024); Hurricane Impact Windows & Doors PLUS Hurricane Shutters across Balcony. This residence also offers a single covered parking space directly outside of lobby door and a climate-controlled storage unit. Meridian Condo residents enjoy private amenities including Heated Pool & Spa, Fitness and Outdoor Grill in addition to The Oaks Club’s main campus of amenities. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership.

OSPREY

409 N POINT ROAD 502

3 Beds

3 Baths

2,055 Sq.Ft.

$635,000

MLS#: A4621353

Stunning residence crafted by renowned builder Lee Wetherington. Nestled on a southern exposure, maintenance-free landscaped lot, this home offers the perfect blend of style, comfort, and functionality.
Interior Highlights-
Architectural Elegance: High tray ceilings, extensive crown molding, and built-in shelving throughout.
Gourmet Kitchen: Stainless steel appliances, natural gas cooking, and glass block accents that flood the space with natural light.
Spacious Great Room: Open floor plan ideal for entertaining, with seamless flow to dining and breakfast areas.
Owner’s Retreat: Expansive 14x28 suite with a private sitting area and dual walk-in closets.
Outdoor Living-
Striking Entry: Double doors welcome you into a light-filled, airy interior.
Covered Patio & Heated Pool: Extended lanai overlooks a tranquil pond, perfect for indoor/outdoor living.
Upgrades for Peace of Mind: Hurricane shutters, property is well maintained .
Community Perks-
Resort-Style Amenities: Heated pool, spa, pickleball courts, fitness center, and playground just steps away.
Low HOA Fees: Include high-speed internet, cable, yard maintenance, and irrigation.
Location & Lifestyle
Nature & Recreation: Hike Oscar Scherer State Park, bike Casey Key or the Legacy Trail, or enjoy the Intracoastal Waterway just 3 minutes away.
Convenience: Minutes to white sand beaches, Pine View School, downtown Sarasota and Venice, with Publix grocery nearby.

OSPREY

510 LATITUDE LANE

3 Beds

2 Baths

2,298 Sq.Ft.

$630,000

MLS#: A4667607

Condition, Condition, Condition – AND Location, Location, Location!! This house is a real gem! Immaculate and beautifully updated, it features 4 bedrooms (or 3 plus a den with a closet) in a split plan that provides privacy for owners and guests. When you sit on the front porch of this contemporary style home, you’ll enjoy an uninterrupted front yard, since the garage opens to the rear of the lot. The inviting front porch and foyer lead you into an open floor plan with high ceilings and special decor touches. The dining room has space for an expanding table for large gatherings. You’ll immediately see the lanai PLUS a large screened patio so you can enjoy being outside any time of the day or evening. The kitchen has been updated with granite counters, as well as new appliances and fixtures. You'll enjoy all the new details and porcelain tile and wood floors, making this house move-in ready. There's storage space in the attic and a storage rack and cabinets in the garage, for your convenience. The community offers a play area for children, places for anyone to sit and relax, and a heated community pool for fun gatherings. Pine View School for Gifted Children (grades 2-12, a National Blue Ribbon School) is within walking distance, with a path leading directly from Rivendell to the school. There are shops, groceries, and multiple businesses within a 5 minute drive. Oscar Sherer State Park abuts the neighborhood, an unexpected oasis and escape into Florida nature. Located between Sarasota and Venice, you'll enjoy all the music, theatre, dance, history, and arts venues of both! Come walk around the neighborhood and you'll want to stay!

OSPREY

711 SHADOW BAY WAY

4 Beds

2 Baths

2,133 Sq.Ft.

$600,000

MLS#: A4675020

Price reduced

Discover the perfect canvas for your dream home with this exceptional vacant lot located in the desirable Sorrento Shores community of Osprey, Florida. Spanning 0.34 acres, this spacious lot offers ample room for creative design and construction. With a generous front footage of 100 feet and dimensions that allow for multiple building possibilities, this property situated "WEST of Trail," is ideal for those looking to build a custom residence in a serene setting.Situated at the head of the saltwater canal, you’ll enjoy the best of both worlds—easy access to local amenities while still being surrounded by nature’s beauty. The RSF1 zoning permits residential single-family homes, making it a great opportunity for families or just looking to settle in a tranquil neighborhood.Embrace the lifestyle you’ve always wanted in Osprey, where you can enjoy outdoor activities, nearby beaches, and a welcoming community. With one of Sarasota Counties top rated schools just a mile away, don’t miss your opportunity to invest in this prime piece of real estate for you. Schedule a viewing today and start envisioning your future in Sorrento Shores! Owner Agent.

OSPREY

458 N SHORE DRIVE

None Beds

None Baths

0.34 acres

$600,000

MLS#: N6139405

#A4656074

OSPREY

4428 CONCHFISH LANE

4 Beds

2 Baths

1,861 Sq.Ft.

$599,000

MLS#: A4656074

Price reduced

Beautifully updated 4BR/2BA pool home in the sought-after Bay Oaks Estates community of Osprey. This single-story residence's backyard borders the Legacy Trail and includes a private gate for direct trail access. Inside, high ceilings and natural light complement luxury vinyl plank flooring, fresh paint, new doors, baseboards, and fixtures. The kitchen features quartz countertops, marble backsplash, recessed lighting, an undermount sink, and newer Whirlpool appliances. A split floor plan provides privacy with spacious bedrooms, including a primary suite with lanai access, two closets (one walk-in), and a spa-like bath with soaking tub, walk-in shower, and dual quartz vanities. The screened lanai overlooks an inviting pool and spa with a private, tree-lined backdrop. Other highlights include a dedicated laundry room, 2-car garage with new door and opener, newer roof, A/C, and water heater. All improvements and system updates completed in 2020. Last year, the pool was resurfaced and the waterline tile replaced. Additional upgrades include new pool equipment, a saltwater system, and a heater. Low HOA and no CDD. Conveniently located near top-rated schools, Oscar Scherer State Park, shopping, dining, and world-class beaches including Siesta Key, Nokomis, and Venice.

OSPREY

583 PINE RANCH EAST ROAD

4 Beds

2 Baths

2,203 Sq.Ft.

$599,000

MLS#: A4670669

This condominium has it all! Fantastic water views along the Intracoastal. Amazing sunsets from the large balcony. A private two-car garage. Three bedrooms, three full baths and 2,000 square feet of living area. The building has a new roof, the elevator was just replaced, and yet the condo dues were just reduced by $500 a quarter! The spacious screened-in balcony overlooks greenery and the Intracoastal Waterway and offers room for dining and relaxing. The gated resort-style community Hidden Bay offers a heated pool and spa, a grass-thatched tiki hut with grilling stations, a lighted tennis court plus two lighted pickleball courts. For water lovers, there is a kayak launch and a 500-yard elevated boardwalk that winds through lush mangroves. The beautifully renovated clubhouse features a catering kitchen with countertop seating, a fully stocked reading library and a fitness room. The location combines a peaceful, gated waterfront community with convenient access to nearby shopping, dining, recreation and only eight miles to Siesta Key, consistently ranked as one of the best beaches in the U.S. For cycling enthusiasts, the nearby Legacy Trail offers 20-plus miles of scenic, paved biking trails.

OSPREY

232 HIDDEN BAY DRIVE 504

3 Beds

3 Baths

2,000 Sq.Ft.

$599,000

MLS#: A4668602

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