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

160

# of Listings

3

Avg # of Bedrooms

$532

Avg. $ / Sq.Ft.

$1,266,683

Med. List Price

Browse Osprey Real Estate Listings

All listings

$250,000 - $500,000

160 Properties Found. Page 6 of 11.

Price reduced

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.

$874,900

MLS#: A4676824

Give yourself the gift of refined living in this expansive 2,778 square foot residence—the largest non-penthouse floor plan available in Meridian at The Oaks Preserve. Every detail in this meticulously maintained, and beautifully updated condominium has been thoughtfully designed to offer comfort, sophistication, and versatility, making it the perfect sanctuary for luxury living every day! Step inside and discover a home where space abounds and possibilities flourish. With three generously sized bedrooms, plus a dedicated dining room (currently being used as a den) and a versatile office/den or 4th bedroom, this home provides all the room you need to work, relax, and entertain, with the flexibility to use the rooms as you see fit. The great room is bathed in natural light, its gleaming wood floors enhancing the clean, contemporary lines of the interior. The updated kitchen will delight any home chef, offering optimal space for cooking and storage, whether you are preparing a casual breakfast or hosting a formal dinner. Enjoy your meals in the dining room, at the breakfast bar, in the cozy nook, or take them outside to the large, screened balcony, where a ceiling fan and the serene backdrop of a lush tropical preserve provide the ideal setting for alfresco dining. The small dry bar with wine cooler and cabinets to store your drink supplies and display your glassware is the perfect addition for when you are entertaining guests. Retreat to a sumptuous master suite. The large, carpeted bedroom is filled with natural light, and outfitted with a ceiling fan, plantation shutters, and custom closets. The master bathroom has been beautifully redone. With a soaking tub, separate shower and water closet, this space is absolutely gorgeous. Every inch of this unit has been curated to deliver both style and functionality, ensuring you feel pampered at every turn. Additional features include a large laundry room, Kevlar roll down hurricane shutters, two premium parking spaces and high-quality upgrades throughout. Club membership is required with homeownership. Residents of Meridian enjoy exclusive access to a private pool, relaxing spa, and a fully equipped workout room. Beyond these, The Oaks offers an impressive array of amenities including 36 holes of championship golf across two courses, twelve HAR-TRU tennis courts (four lighted), a state-of-the-art Wellfit Center, three on-site restaurants with year-round dining, croquet, bocce and pickleball courts and an active social calendar.

OSPREY

401 N POINT ROAD 304

3 Beds

3 Baths

2,778 Sq.Ft.

$850,000

MLS#: A4659785

Price reduced

**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

2,310 Sq.Ft.

$850,000

MLS#: A4645829

New on site 3 days ago

#A4680671

OSPREY

1211 LOST CREEK COURT

4 Beds

3 Baths

2,876 Sq.Ft.

$829,000

MLS#: A4680671

PRICE IMPROVEMENT! This immaculate and meticulously maintained 3-bedroom, 2-bath home in the sought-after Southbay Yacht & Racquet community is move-in ready and packed with beautiful updates. The open-concept kitchen has been tastefully remodeled with stainless steel appliances, center isle and lighting, and both bathrooms have also been updated. Natural light fills the home through replaced windows and elegant French doors, all of which are provided with hurricane protection for peace of mind. Crown molding and plantation shutters on all windows add a refined touch throughout, and engineered wood flooring enhances the living room and bedrooms, while ceramic tile flooring is featured in the kitchen and cozy family room complete with a charming wood-burning fireplace. Additional highlights include: a spacious utility room with ample cabinet storage, a new roof and fresh exterior paint in 2024 and new A/C system, dishwasher and garbage disposal in 2025. Florida-friendly landscaping with an abundance of fruit trees and native vegetation surrounding the home are perfect for the gardening enthusiast.

Southbay Yacht & Racquet is a golf cart community that offers an array of community features and exceptional lifestyle with a recently remodeled 10,000 sq. ft. clubhouse featuring a well equipped fitness center, adjacent swimming pool, and expansive patio. The community-owned marina with residents only boat slips offers direct access to the Intracoastal Waterway with no fixed bridges to hinder your journey to the Gulf. Enjoy a wide range of amenities, including: pickleball and tennis courts, bocce and shuffleboard court, scenic walking and biking paths throughout the community and playground.

Ideal location conveniently nestled between downtown Sarasota and downtown Venice, this home is close to top-rated dining, shopping, and entertainment. You’re just a short drive from world-renowned Siesta Key and Nokomis Beach, the Legacy Trail, and the nationally ranked Pine View School.

Don’t miss this opportunity to own a beautiful home in one of the Gulf Coast’s most desirable boating communities

OSPREY

123 WINDWARD DRIVE

3 Beds

2 Baths

1,894 Sq.Ft.

$820,000

MLS#: A4656319

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

READY FOR IMMEDIATE OCCUPANCY!
Modern Elegance at Edgewater: A Luxurious Haven Overlooking Little Sarasota Bay

Step into a world of contemporary sophistication with this new construction condominium nestled in the eminent enclave of Edgewater at Hidden Bay. Boasting 1937 square feet, this meticulously crafted residence offers three bedrooms, two bathrooms, and an inviting office space for your creative pursuits.

The allure begins in the heart of the home – a sleek kitchen adorned with top-of-the-line LG appliances, complemented by solid wood cabinetry and exquisite quartz countertops that beckon culinary adventures. As natural light dances through expansive windows, partial views of tranquil Little Sarasota Bay create a serene backdrop to everyday living.

Indulge in comfort and style as you unwind in the spacious bedrooms or revel in the luxurious ambiance of beautifully appointed bathrooms. Every detail has been thoughtfully considered to elevate your lifestyle, from high-quality finishes to seamless design elements that exude modern charm.

Edgewater's coveted location offers more than just a place to call home; it provides a gateway to upscale living near waterways and green spaces. Embrace a life where convenience meets luxury – where every day is an opportunity for relaxation and rejuvenation amidst breathtaking surroundings.

Discover unparalleled tranquility and refinement at Edgewater

OSPREY

280 HIDDEN BAY DRIVE 202

3 Beds

2 Baths

1,937 Sq.Ft.

$780,250

MLS#: A4643409

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.

$769,000

MLS#: N6142959

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

Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, and plenty of room for a private pool. As you enter the home, you will be greeted by the formal living room and dining room to the left and hallway to the family room, kitchen, and dinette straight ahead. The entire interior has been professionally painted in 2025, and there is tons of natural light that flows through the many windows of this home. The kitchen is open to the family room and dinette for easy entertaining. There is also a HUGE bonus room toward the back of the home. Next to the family room is entrance to the hallway leading to the two guest bedrooms and guest bathroom. On the opposite side of the home, past the dining room is the spacious primary suite with generous walk-in closet and ensuite bath. The laundry room is located near the family room. Entrance to the attached 2 car garage is near the foyer. Roof was replaced in 2022 & AC was installed in 2016. The entire house has also been replumbed! Southbay Yacht & Racquet Club is an active lifestyle community with many social, boating, and sports activities. The clubhouse has recently been renovated and features a community pool, fitness center, ballroom, two kitchens, card room, game room, and an elevator! Additional amenities include 3 tennis courts, 4 pickle ball courts, basketball, playground, bocce, shuffleboard, and miles of walking trails and green space. The community-owned marina—with residents-only boat slips—provides direct Intracoastal Waterway access with no fixed bridges to the Gulf. The community is welcoming and lively—perfect for families and those who enjoy an active, coastal lifestyle. This community is in the perfect location with several warm gulf beaches, Downtown Venice & Downtown Sarasota close by. The famous Casey Key Fish House and Tiki Bar are just a golf cart ride away! Oscar Scherer State Park is across Tamiami Trail and Pine View (#1 school in the state) is about 5 minutes away. This home is ready for you to start living the elevated Southbay lifestyle! **The street behind this house (Blackburn Point Rd.) is a fairly quiet two lane Rd. That's the road you can take your golf cart to Casey Key Fish House & Tiki Bar!**There is marina space available and fees range between $169-$705 per quarter.**

OSPREY

186 WINDWARD DRIVE

3 Beds

2 Baths

2,505 Sq.Ft.

$749,900

MLS#: N6142087

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

Price reduced

#A4673797

OSPREY

597 OAK RIVER COURT

4 Beds

2 Baths

2,111 Sq.Ft.

$724,900

MLS#: A4673797

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