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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

154

# of Listings

3

Avg # of Bedrooms

$521

Avg. $ / Sq.Ft.

$1,239,814

Med. List Price

Browse Osprey Real Estate Listings

All listings

$250,000 - $500,000

154 Properties Found. Page 6 of 11.

The Development Site is a lakefront parcel overlooking the community’s internal lake and clubhouse. The concept plan shows 24 2-3 bedroom units in 4 stories over parking, but the parcel has unprecedented zoning and entitlements for up to 42 units. All utilities and the roads are to the development site. The utilities, roads, and parking areas, the gated entrance and the resort-style amenities are completed. The amenities include a beautiful, heated pool/spa area with deck overlooking a tranquil lake with a “fountain island,” an upscale clubhouse with living room which also houses a library, catering kitchen, central salon and fitness center, plus a Tiki Hut and grilling area for entertaining, a kayak launch, and USTA style tennis court and pickleball courts, car wash area, pet park and an elevated boardwalk that meanders through lush mangrove fields out to a long fishing pier, where you can drop a line into the water or watch never-ending sunsets. The community consists of mid-rise and low-rise condominium buildings.

OSPREY

HIDDEN BAY DRIVE

None Beds

None Baths

0.55 acres

$800,000

MLS#: A4645997

Opportunities like this are increasingly rare in Willowbend. Offering over 3,180 square feet, this Lee Wetherington-built residence delivers exceptional scale, thoughtful architecture, and a preserve setting backing directly to Oscar Scherer State Park. With no rear neighbors and expansive natural views, the home offers privacy and tranquility while remaining minutes from beaches, dining, and cultural destinations.
The interior lives large and light-filled, centered around a dramatic great room with a 12-foot double-tray vaulted ceiling that establishes an immediate sense of volume and architectural presence. The open floor plan allows spaces to flow comfortably for everyday living and entertaining, with generous room sizes, flexible living areas, and a second-floor bonus retreat that adds versatility while preserving the ease of main-level living.
Built by Lee Wetherington in 2005, the home reflects enduring construction quality, balanced proportions, and a layout designed for longevity. This home stands out not by excess size, but by proportion, preserve setting, and livability—offering a strong foundation for personalization and long-term value within one of Willowbend’s most private settings.
Located in the maintenance-free Willowbend community, the lifestyle is intentionally simplified. HOA services include landscaping, irrigation, cable, and internet, supporting a lock-and-leave approach without sacrificing space or privacy. Community amenities include a resort-style pool, fitness center, and recreational spaces within a well-established, deed-restricted neighborhood.
For buyers who value build quality, natural views, and compelling price/square foot positioning, this residence presents a rare opportunity in Willowbend—best experienced in person.

OSPREY

650 CRANE PRAIRIE WAY

4 Beds

2 Baths

3,183 Sq.Ft.

$799,990

MLS#: A4680121

Price reduced

WOW! TOTAL OF 50,000 PRICE ADJUSTMENT! RARE OPPORTUNITY to own this stunning former John Cannon model home on peaceful Tranquility Circle . This pristine 4BR/3.5BA pool home is a kayaker and nature lover’s paradise on North Creek with direct access to Little Sarasota Bay via Kayak or Canoe offering abundant wildlife and serene water views. Enjoy your own "Selby Garden" like setting .So hard to find such a private lot with this level of privacy so close to everything. Enjoy an open, spacious split-plan layout with Four bedrooms, formal and casual living spaces, and an open kitchen with granite countertops, island, and gas range—perfect for entertaining. The great room and lanai seamlessly connect to the sparkling pool, creating a private retreat with creek views. The luxurious Primary suite is a true getaway, featuring bay windows, his-and-hers closets, Expansive Primary Bath with dual water closets, soaking tub, separate shower and dual vanities. Interior upgrades include tile flooring, crown molding, 8-foot doors, designer lighting, and ceiling fans. Recent and notable upgrades: pool resurfaced (2023), pool cage replaced/rescreened (2018), A/C units (2020 & 2024), water heaters (2022/2023), new gutters & guards, paver driveway and pool deck, rimless shower doors, new front door, new refrigerator, new flooring in all bedrooms and closets, upgraded drainage system, and more. Prime location near the Legacy Bike Trail, YMCA, Oscar Scherer Park, The Oaks, Palmer Ranch, Sarasota Square Mall, and minutes to Sarasota, Venice, and Gulf Coast beaches. A-rated schools, including top-ranked Pine View School, make this property ideal for families. A rare, meticulously maintained home with exceptional upgrades, This property must be seen to fully appreciate its value and beauty. * Please be sure to watch Virtual Tours also. The Matterport will immerse you within the property as if you were doing a walk through*.

OSPREY

919 TRANQUILITY CIRCLE CIRCLE

4 Beds

3 Baths

2,854 Sq.Ft.

$799,000

MLS#: A4678841

Price reduced

#A4638035

OSPREY

393 N POINT ROAD 604

3 Beds

3 Baths

2,778 Sq.Ft.

$795,000

MLS#: A4638035

Your dream homesite awaits! This lot is located within the Oaks Bayside, one of Southwest Florida‘s most exclusive private, gated communities. This amazing property is near the community dock and fountain and is surrounded by some of the most grand and luxurious homes in the entire gulf coast region. The Oaks Club boasts 2 Championship Golf Courses, 12 Har-Tru Tennis Courts (4 lighted), State Of The Art Fitness Center, Junior Olympic Swimming Pool, Regulation Croquet Court, 4 Pickle Ball Courts, along with numerous dining, social and recreational options. Conveniently located near Florida's top rated Pine View School, the Legacy Bike Trail, and the world renowned beaches of Siesta Key, Casey Key, and so much more. Just a short distance from shops, restaurants, and the cultural offerings of downtown Sarasota. The owner is conveying with sale (Complete Set of Architectural Building Plans which are ready for permit submittal, Structural Building Plans, Landscape and Irrigation Plans, Geotechnical Report, and the Tree and Boundary Survey). Owner has already received approval to begin construction from ARC. Membership to the Oaks Club is required. Owner is a licensed real estate broker in the State of Florida and the listing agent for this property.

OSPREY

147 OSPREY POINT DRIVE

None Beds

None Baths

0.47 acres

$750,000

MLS#: A4667023

NEW PRICE! Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2.5-bath pool home with mature landscaping offers a functional layout and excellent community amenities. The home features a double-door front entry, a spacious great room with cathedral ceiling, an oversized garage, and a large private lot. Interior highlights include double primary bedrooms, tiled walk-in showers in both full bathrooms, an outdoor shower, a generous laundry room with cabinetry, a practical kitchen with pantry and hurricane rated windows. The paver lanai with automated hurricane screen and expansive paver deck surrounding the swimming pool with solar heat provide substantial outdoor living space. A long driveway adds convenient additional parking.

Southbay Yacht & Racquet Club is a golf-cart-friendly community featuring a recently remodeled 10,000 sq. ft. clubhouse with a fitness center, pool, and large patio. The community-owned marina—with residents-only boat slips—provides direct Intracoastal Waterway access with no fixed bridges to the Gulf. Additional amenities include pickleball and tennis courts, bocce, shuffleboard, walking and biking paths, and a playground. The community is ideally situated between Sarasota and Venice, close to dining, shopping, entertainment, beaches, the Legacy Trail, and Pine View School.

OSPREY

102 WINDWARD DRIVE

3 Beds

2 Baths

2,134 Sq.Ft.

$750,000

MLS#: A4671793

Enjoy sweeping water views and stunning sunsets over Little Sarasota Bay from this spacious third-floor corner residence in the gated waterfront community of Edgewater at Hidden Bay. Built in 2017 and moved into in Jan 2018, this three-bedroom plus den, 2.5-bath condominium offers nearly 2,200 square feet of living space with easy elevator access and one assigned parking space in the building. The attractive open floor plan features soaring ceilings, impact-rated windows and sliding doors, easy maintenance tile plank flooring and abundant natural light throughout. The kitchen includes granite countertops, solid wood cabinetry, stainless steel appliances and custom storage with pullout drawers. The living area offers a built-in dry bar with wine refrigerator and opens to a large, screened-in terrace with privacy-screens and expansive bay views. The primary suite includes dual walk-in closets and a luxurious bath with dual quartz vanities, decorative tile flooring, makeup vanity and walk-in shower. Additional features include a private den/office, in-unit laundry room, two full baths and a powder room. Edgewater at Hidden Bay is a gated, resort-style community set on 14 acres along Little Sarasota Bay and the Intracoastal Waterway, directly across from Casey Key. Community amenities include a waterfront clubhouse with kitchen and quartz bar, heated pool and spa, fitness center, library, tiki hut with grilling stations, pickleball and tennis courts, kayak launch, fishing pier, dog play area, and an elevated boardwalk through mangroves and palm-lined grounds. Hidden Bay is conveniently in Osprey just south of Sarasota, near area beaches, shopping and dining, and only minutes from Venice.

OSPREY

250 HIDDEN BAY DRIVE 301

3 Beds

2 Baths

2,168 Sq.Ft.

$725,000

MLS#: A4679278

Discover a blend of comfort and sophistication in this meticulously maintained home in the desirable Willowbend community. The striking architecture of the Ashley floor plan makes it a favorite. Go into a serene oasis featuring breathtaking wide lake views overlooking a sparkling pool, complemented by desired western exposure that invites an abundance of natural light and showcases vibrant sunsets. Gourmet kitchen with natural gas range, stainless dishwasher and refrigerator (new 2026). The interior boasts custom features, including crown molding and elegant tray ceilings. This spacious four-bedroom, three-bath home includes a chef's kitchen outfitted with natural gas cooking, as well as a cozy eat-in area with an aquarium window that beautifully frames the pool and lake views. The owner's suite serves as a sanctuary, offering two walk-in closets and a luxurious bath complete with dual sinks, a walk-in shower, a soaker tub and a separate toilet for added privacy. Thoughtfully designed with a split floor plan, the home ensures guests enjoy ample separation from the owner's suite for optimal comfort. A full-size laundry room adds to the home’s convenience. This exceptional residence is a blank canvas for an extraordinary lifestyle, conveniently near downtown Venice and Sarasota, beautiful beaches, Pine View School and the Legacy Trail. With no CDD fees and in a preferred X flood zone, the low community fees cover ground maintenance, irrigation and access to a community pool and spa, gym, pickleball courts, as well as high-speed internet and DirecTV streaming. Embrace the lifestyle you’ve always dreamed of in this stunning Willowbend home.

OSPREY

665 CRANE PRAIRIE WAY

4 Beds

3 Baths

2,306 Sq.Ft.

$719,000

MLS#: A4666718

Penthouse Waterfront Residence | Enclosed Sunroom | Private Two-Car Garage | Optional Furnishings | Gated Bayfront Community

This 6th-floor penthouse waterfront condominium at Hidden Bay offers unobstructed views of Little Sarasota Bay, the Intracoastal Waterway, and the Gulf beyond Casey Key. Designed to capture light and water views throughout the main living areas, the open floor plan features high ceilings, tall interior doors, and crown molding, creating a bright and welcoming coastal interior.

The great room accommodates both living and dining areas and opens to an enclosed waterfront sunroom, an ideal space for morning coffee, sunset views, or quiet time overlooking the bay. The kitchen includes a counter-height breakfast bar, pantry storage, and an adjacent dining nook, offering both function and ease for everyday living or entertaining. A den provides flexible space for a home office or guest use.

The primary suite features multiple closets and an en suite bath with dual vanities, a soaking tub, walk-in shower, water closet, and a dedicated makeup vanity area. A second bedroom includes an adjoining bath and walk-in closet. Luxury vinyl flooring has been added in the bedrooms and den. Laundry is located inside the residence.

The condominium includes a private, fully enclosed two-car garage. Furnishings are included and may remain or be removed at the buyer’s preference.

Hidden Bay is a gated waterfront community set along Little Sarasota Bay, offering a clubhouse with fitness center, heated pool and spa, tennis and pickleball courts, kayak storage and launch, and a boardwalk through mangroves leading to a fishing pier. Located west of US 41 in Osprey, Hidden Bay is conveniently positioned between Sarasota and Venice, with nearby access to shopping, dining, the Legacy Trail, and area beaches.

OSPREY

242 HIDDEN BAY DRIVE 602

2 Beds

2 Baths

1,932 Sq.Ft.

$719,000

MLS#: A4678883

Price reduced

#A4673797

OSPREY

597 OAK RIVER COURT

4 Beds

2 Baths

2,111 Sq.Ft.

$715,000

MLS#: A4673797

Heart of Osprey, this remodeled 3-bedroom, 2-bathroom pool home with huge yard, bring your RV and all your toys. Lots of room for storage. Enjoy sunsets, steps to fishing pier, kayak launch, Spanish Pointe, Oscar Scherer State Park, and Pine View School. No restrictions. Move-in ready enjoying the Florida lifestyle! For outdoor enthusiasts, this location is unbeatable. Launch your kayak or paddleboard from a few steps away into Sarasota Bay, explore Mid night pass, Siesta Beach, nearby Bay Preserve at Osprey and Historic Spanish Point, close to Oscar Scherer State Park, Casey Key, Nokomis Beach. The large backyard offers plenty of space for entertaining, playing, or simply soaking in Florida’s year-round sunshine. Whether you're looking for a family home, a. vacation retreat, or a profitable rental property

OSPREY

110 PINE AVENUE

3 Beds

2 Baths

2,058 Sq.Ft.

$699,000

MLS#: A4646339

Exceptional opportunity to build your dream estate in The Oaks, one of South Sarasota’s most prestigious gated golf and country club communities. Situated on a rare cul-de-sac lot, this generous parcel offers privacy, mature landscaping, and an ideal canvas for a custom residence. Enjoy convenient access to world-class amenities including championship golf, tennis and pickleball facilities, a WellFit fitness center, swimming, croquet, dining venues, and an active year-round social calendar (club membership required). The Oaks’ prime location places you minutes from the renowned beaches of Siesta Key, upscale shopping, fine dining, cultural venues, and the vibrant lifestyle of downtown Sarasota. Don’t miss this rare opportunity to build in one of the Gulf Coast’s most coveted addresses.

Lot size approximately 0.55 acres. Membership in The Oaks Club mandatory with homeownership. Buyer to verify all information.

OSPREY

410 BLUE GARDEN LANE

None Beds

None Baths

0.55 acres

$699,000

MLS#: A4679677

Enjoy breathtaking water views and unforgettable sunsets over Little Sarasota Bay from this spacious three-bedroom condominium with an office, on the third floor with convenient elevator access. This beautifully appointed residence is in the exclusive, gated Hidden Bay community, a waterfront gem. The open floor plan features soaring ceilings, PGT impact windows, sliding glass doors, new air-conditioning system and Cortex luxury plank-style flooring. The updated kitchen is designed for function and style, offering granite countertops, solid wood cabinetry, KitchenAid stainless steel dishwasher, stainless LG appliances and a wall of custom storage with pullout drawers. The living room is ideal for entertaining, complete with a built-in dry bar and wine refrigerator. The primary suite is a private retreat with one walk-in closet and three additional reach-in closets. The remodeled primary bath showcases dual vanity sinks with quartz countertops, decorative tile flooring, a dedicated makeup vanity and a spacious walk-in shower. Hidden Bay lives up to its name, offering privacy and tranquility while being directly across from Casey Key, with views of the barrier island and Siesta Key. Restaurants and shopping are just a short distance away. Community amenities are second to none and include a stunning clubhouse with kitchen and quartz bar, a wood-paneled and fully stocked library, a professional fitness center, heated pool and spa with expansive sundeck, kayak launch, fishing pier, and a 500-yard elevated boardwalk winding through lush mangroves and palm landscapes. Additional amenities include a tiki hut with grilling stations, three pickleball courts, a lit tennis court and a dog play area. An oversized two-car garage completes this exceptional offering. Experience the best of waterfront, resort-style living in one of Sarasota’s desirable hidden communities. Being offered semi-furnished.

OSPREY

242 HIDDEN BAY DRIVE 302

3 Beds

2 Baths

2,032 Sq.Ft.

$699,000

MLS#: A4678187

Price reduced

BETTER HURRY, LOOK AT THE PRICE! Waterfront living and a true boater’s lifestyle await in this meticulously maintained end-unit residence located in the gated, amenity-rich community of Blackburn Harbor in Osprey. This beautifully upgraded condo offers sweeping Intracoastal water views with Gulf glimpses, abundant natural light, and exceptional privacy within an exclusive boutique building of only 15 residences. BEING SOLD WITH FURNITURE except for a couple of personal items.

The spacious floor plan features over 2,600 square feet of well-designed living space with 3 bedrooms, 3 baths, and flexible areas ideal for a den, office, or entertaining. A welcoming foyer, breakfast area, and expansive living room all showcase stunning, eye-level water views, while the large lanai is perfectly positioned for sunsets, birdlife, dolphins, and passing boats along the Intracoastal Waterway.

The chef’s kitchen is both functional and elegant, featuring exquisite granite countertops, custom cabinetry with soft-close pullouts, and ample workspace for everyday living and entertaining. Interior upgrades include tile flooring, plantation shutters, remote-controlled blinds, higher ceilings, a built-in bar, and generous closet space throughout.

The primary suite serves as a private waterfront retreat with beautiful Intracoastal views, custom closets, and a spa-style bath with a walk-in shower, soaking tub, dual vanities, makeup area, and private water closet. Guest baths are thoughtfully designed for comfort and convenience.

Boating enthusiasts will appreciate water access and protected dockage, with boat slips available on a first-come, first-serve basis and currently no waiting list, accommodating vessels up to approximately 39 feet. With no bridge access and only minutes to open water and the Gulf, this location is ideal for cruisers and avid boaters seeking quick, easy Intracoastal and Gulf access.

Additional features include two assigned parking spaces, one in the under-building garage and one covered carport, private unit storage, EV charging capability, an interior laundry room with sink and cabinetry, newer washer and dryer, newer hot water heater, impact-rated sliders, and a new 2025 roof with no upcoming assessments.

Residents enjoy resort-style amenities including a heated pool, tennis and pickleball courts, clubhouse with fitness area, kayak storage and launch, fishing, waterfront gazebo with grills, walking paths, and lush greenspace. Located directly across from Oscar Scherer State Park and near the Legacy Trail, the community offers easy access to biking, hiking, kayaking, and outdoor recreation.

Perfectly positioned between Sarasota and Venice, this prime Osprey location is approximately 15 minutes to Downtown Sarasota, about 10 minutes to Historic Venice Island, and just minutes to Nokomis Beach, Venice Beach, Casey Key, and Siesta Key. Close to hospitals, medical facilities, marinas, golf, dining, and shopping, this residence offers the ideal blend of waterfront luxury, boating convenience, and low-maintenance coastal living.

OSPREY

6100 JESSIE HARBOR DRIVE 203

3 Beds

3 Baths

2,630 Sq.Ft.

$699,000

MLS#: N6142959

A boater's dream. Enjoy waterfront living in this luxury penthouse unit with breathtaking views of the Intracoastal Waterway located in the premier gated community of The Villas at Bellagio. Upon entering the home, you are greeted by the inviting foyer leading down the art gallery-like hallway to the open family room and kitchen area. This three-bedroom, two-bathroom unit has many wonderful features and updates including a recently painted interior, updated light fixtures and ceiling fans, high-end touches such as crown molding, a Sub-Zero refrigerator, solid wood cabinets, gorgeous granite countertops, Bosch dishwasher, storage unit, and two assigned parking spaces in the garage close to the elevator that is only a few steps away from your front door. The owner's suite provides a nice retreat at the end of the day with a garden tub to de-stress and unwind, a separate shower, dual vanities, and a walk-in closet. Watch the spectacular sunsets on your spacious private balcony. The Villas at Bellagio Harbor offers resort-style amenities including a clubhouse, sauna, hot tub, heated swimming pool, fitness center, kayak launch and a connected full-service marina. Wet and dry slips are available for boating enthusiasts. Centrally located to downtown Venice or Sarasota, world-class beaches, fine dining and shopping. Best priced unit in the complex. Walk to Restaurants.

OSPREY

14041 BELLAGIO WAY 415

3 Beds

2 Baths

1,736 Sq.Ft.

$699,000

MLS#: TB8470897

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