Osprey, FL Homes

/23
$849,900
- 3 Beds
- 2 Baths
- 2,103 Sq Ft
120 Candyce Dr, Osprey, FL 34229

This is your chance to own a true waterfront property in the highly desirable Osprey area and transform it into your dream coastal retreat. Situated on a canal with direct access to the Intracoastal Waterway, this home offers an unbeatable location for boating enthusiasts and anyone seeking the ultimate Florida lifestyle. The property itself needs some love, but that’s exactly what makes it such

Michelle Ward COMPASS FLORIDA LLC

120 Candyce Dr, Osprey, FL 34229
/2
$725,000 Sold Jun 13, 2025
- 2,678 Sq Ft
- $271/SF
- 75 Days On Market
- 4 Beds
- 3 Baths
- Built 2005
608 Crane Prairie Way, Osprey, FL 34229

One or more photo(s) has been virtually staged. Exceptional Opportunity on this Newly Priced Gem with stunning views and privacy! Discover your dream home in this stunning 2,678 square foot Wyndham model by Lee Wetherington, one of the largest in the maintenance-free community of Willowbend in Osprey. The owner has added improvements in excess of $150K since their purchase and has been lovingly

Linda Williams GULF SHORES REALTY

608 Crane Prairie Way, Osprey, FL 34229

/2
Est $927,494 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,258 Sq Ft
127 Turquoise Ln, Osprey, FL 34229

127 Turquoise Ln, Osprey, FL 34229

/100
$3,995,000
- 4 Beds
- 7 Baths
- 6,705 Sq Ft
691 Eagle Watch Ln, Osprey, FL 34229

Nestled within the exclusive gated community of the Oaks Club in Osprey, Florida. This singular estate represents a masterful confluence of architectural refinement and modern luxury, encompassing nearly 7000 ft.2 of conditioned living space, the residence has undergone an extraordinary transformation – reflecting an investment exceeding $1.5 million – to achieve a standard of craftsmanship

Renee Preininger SARASOTA TRUST REALTY COMPANY

691 Eagle Watch Ln, Osprey, FL 34229
/2
$235,000 Sold Jun 13, 2025
- 1,223 Sq Ft
- $192/SF
- 144 Days On Market
- 2 Beds
- 2 Baths
- Built 1979
109 Woodland Place, Osprey, FL 34229

Welcome to 109 Woodland Place, a serene retreat nestled within the lush, natural surroundings of the Pine Run community in Osprey, Florida. This charming 2-bedroom, 2-bathroom condominium offers 1,223 square feet of thoughtfully designed living space, seamlessly blending comfort with the beauty of its environment. As you enter, you’ll be greeted by soaring ceilings and an open floor plan that

Derek Edwards KELLER WILLIAMS ON THE WATER S

109 Woodland Place, Osprey, FL 34229

/64
Est $250,544 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,325 Sq Ft
224 Woodland Dr, Osprey, FL 34229

224 Woodland Dr, Osprey, FL 34229

/19
$443,000
- 2 Beds
- 2 Baths
- 1,725 Sq Ft
1811 Highland Rd, Osprey, FL 34229

PRIVATE NEIGHBORHOOD - Fully Furnished 2 Bedroom Townhouse in the Casey Key area, QUAINT, SPACIOUS 2-CAR Tandem GARAGE + Carport, modern, high ceilings, kitchen upgrades, screened balcony, 2 beds + den; 2 baths; living area and kitchen open plan; community pool Conveniently located between Sarasota, Siesta Key, Venice, and the Gulf Beaches.Walking distance to Casey Key Mainland (Chef Rolfs),

Stephen Hachey REALTY OF RIVERVIEW LLC

1811 Highland Rd, Osprey, FL 34229
/2
$685,000 Sold Jun 12, 2025
- 2,203 Sq Ft
- $311/SF
- 5 Days On Market
- 3 Beds
- 3 Baths
- Built 2000
385 N Point Rd Unit 503, Osprey, FL 34229

Experience luxury coastal living in this 5th-floor condo, offering breathtaking water and Preserve views that rival those of higher floors. This residence in Meridian at The Oaks Preserve features 3 bedrooms, 3 full baths, and a dining room, all enhanced with new furnishings. Offered turnkey, all it needs is for you to move in and start living a carefree lifestyle on Florida’s gorgeous Gulf

Steve Abbe COLDWELL BANKER REALTY

385 N Point Rd Unit 503, Osprey, FL 34229

/59
Est $933,143 Not Listed For Sale
- 3 Beds
- 3 Baths
- 3,811 Sq Ft
384 S Creek Ct, Osprey, FL 34229

384 S Creek Ct, Osprey, FL 34229

/36
$595,000
- 3 Beds
- 2 Baths
- 2,172 Sq Ft
1337 Copperwood Dr, Osprey, FL 34229

This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm with elegant living. The desirable Willow floor plan with a sparkling pool and lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases meticulous attention to detail with features such as high ceilings,

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

1337 Copperwood Dr, Osprey, FL 34229
/2
$1,700,000 Sold Jun 12, 2025
- 2,315 Sq Ft
- $734/SF
- 108 Days On Market
- 3 Beds
- 3 Baths
- Built 1972
525 S Shore Dr, Osprey, FL 34229

This redesigned mid-century styled 3-bedroom Bayfront home has been fully remastered with entertaining in mind. The stunning outdoor oasis says it all, with a panoramic view pool cage, a large, covered area, outdoor kitchen, and an amazing pool and spa featuring a stone waterfall and propane-fueled fire sconces. The pool cage was recently rescreened with no see um screen. Inside, the split

Andree Huffine COLDWELL BANKER REALTY

525 S Shore Dr, Osprey, FL 34229

/99
Est $701,196 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,330 Sq Ft
801 Oak Briar Ln, Osprey, FL 34229

801 Oak Briar Ln, Osprey, FL 34229

/3
$79,000
570 Blackburn Point Rd Unit 2, Osprey, FL 34229

Hurricane-protected dry storage with top-tier amenities! This slip offers hassle-free storage in one of Sarasota County's most convenient locations. Keep your boat safe from Florida's unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn Point Bridge), this slip fits boats up to

Daniel Treiman MICHAEL SAUNDERS & COMPANY

570 Blackburn Point Rd Unit 2, Osprey, FL 34229
/2
$3,525,000 Sold Jun 06, 2025
- 5,279 Sq Ft
- $668/SF
- 124 Days On Market
- 5 Beds
- 5 Baths
- Built 2007
275 Lookout Point Dr, Osprey, FL 34229

This stunning waterfront residence in Southbay Yacht and Racquet Club is a gem on Florida’s Gulf Coast where boats are accommodated in a deep-water marina for low fees. Boasting over 135 feet of water frontage and surrounded by lush tropical landscaping and majestic Royal Palms. Its refined curb appeal sets it apart as a one-of-a-kind property. The custom John Cannon home features a grand double

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

275 Lookout Point Dr, Osprey, FL 34229

/2
Est $553,044 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,151 Sq Ft
584 Meadow Sweet Cir, Osprey, FL 34229

584 Meadow Sweet Cir, Osprey, FL 34229

/13
$249,900
- 2 Beds
- 2 Baths
- 1,578 Sq Ft
106 Villa Dr Unit 106, Osprey, FL 34229

Located West of the Trail in Sorrento Shores, Osprey, this spacious 2BR/2BA villa with a den and oversized 1-car garage offers 1,578 sq. ft. of comfortable living space. A boating community with private dock access and a heated pool just steps away, it’s perfect for boaters, kayakers, or anyone seeking the coastal lifestyle. Features include hurricane-rated windows and doors, updated kitchen and

Dan Ivanov PREFERRED SHORE LLC

106 Villa Dr Unit 106, Osprey, FL 34229
/2
$640,000 Sold Jun 04, 2025
- 2,234 Sq Ft
- $286/SF
- 15 Days On Market
- 3 Beds
- 3 Baths
- Built 2003
519 Habitat Blvd, Osprey, FL 34229

This exquisite three-bedroom, three-bath-plus-den home by Lee Wetherington Homes exemplifies intelligent design and beauty in the community of Willowbend. The Savannah floor plan is a rare great room plan with one of the few natural gas fireplaces in the neighborhood. This is the focal point of the home with stacked flagstone and a beautiful mantel flanked in shelving. The residence features an

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

519 Habitat Blvd, Osprey, FL 34229

/57
Est $645,345 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,630 Sq Ft
6100 Jessie Harbor Dr Unit 201, Osprey, FL 34229

6100 Jessie Harbor Dr Unit 201, Osprey, FL 34229

/71
$599,000 Open Sun 1PM - 4PM
- 4 Beds
- 2 Baths
- 2,186 Sq Ft
1036 Oak Meadow Ln Unit 3A, Osprey, FL 34229

Welcome to this attractive St. Charles floor plan found in the desirable Woodlands at Rivendell community! This charming home sits on a large corner lot directly across from the heated community pool and is within easy reach of the highly ranked Pine View School for the Gifted (Grades:2-12). Built in 2001, this well-maintained home features four bedrooms, or three bedrooms plus den with closet,

Helena Nordstrom PREMIER SOTHEBY'S INTERNATIONAL REALTY

1036 Oak Meadow Ln Unit 3A, Osprey, FL 34229
/2
$1,197,000 Sold May 30, 2025
- 3,321 Sq Ft
- $360/SF
- 20 Days On Market
- 3 Beds
- 5 Baths
- Built 1991
223 Saint James Park, Osprey, FL 34229

Luxury Clubside Living at The Oaks – featuring Elegance and Comfort! Stunning Clubside residence in the upscale Oaks Club, offering the perfect blend of estate charm and modern luxury. Nestled among grand oak trees with partial lake and full golf course views, this beautifully upgraded home offers 3,321 sq ft of refined living space in one of Sarasota’s most exclusive communities. You’re

John Hockenberry RE/MAX ALLIANCE GROUP

223 Saint James Park, Osprey, FL 34229

/96
Est $1,057,278 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
385 N Point Rd Unit 501, Osprey, FL 34229

385 N Point Rd Unit 501, Osprey, FL 34229

/80
$695,000
- 2 Beds
- 2.5 Baths
- 1,890 Sq Ft
33 Bishops Court Rd Unit 118, Osprey, FL 34229

Come and enjoy the perfect maintenance free lifestyle in this exquisite townhouse located in one of the finest countryclubs on the gulf coast, The Oaks Golf and Country Club. Previously redesigned, this tuscan style home in the quaintand 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

Rosalie Phillips MICHAEL SAUNDERS & COMPANY

33 Bishops Court Rd Unit 118, Osprey, FL 34229
/2
$904,900 Sold May 30, 2025
- 2,705 Sq Ft
- $335/SF
- 5 Days On Market
- 4 Beds
- 3 Baths
- Built 1989
336 Pine Ranch Rd E, Osprey, FL 34229

Nestled on a rare one-acre private oasis, this stunning lakefront home in Osprey offers the perfect blend of tranquility and convenience. With mature landscaping, majestic pine trees, and abundant wildlife, this is a true sanctuary—yet you're just minutes from Pine View School (Ranked #18 in the nation), Siesta Key Beach, The Legacy Trail, and US-41. Near I-75, centrally located between Venice

Marco Guadagnini PREFERRED SHORE LLC

336 Pine Ranch Rd E, Osprey, FL 34229

/73
Est $430,679 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,599 Sq Ft
291 Hidden Bay Dr Unit 201, Osprey, FL 34229

291 Hidden Bay Dr Unit 201, Osprey, FL 34229

/91
$2,195,000
- 3 Beds
- 3 Baths
- 3,681 Sq Ft
600 Eagle Watch Ln, Osprey, FL 34229

One or more photo(s) has been virtually staged. **BRILLIANTLY UPDATED, MOVE-IN READY, GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** offers an Ideal Southern-Exposure and View across the 3rd Fairway of the Interior, HERON GOLF COURSE. Situated on an Oversized 0.71 Acre Lot with Circular Driveway and manicured landscape, this Extensively Renovated Home offers 3

Mark Lyda GENEROUS PROPERTY

600 Eagle Watch Ln, Osprey, FL 34229
/2
$285,000 Sold May 30, 2025
- 1,255 Sq Ft
- $227/SF
- 112 Days On Market
- 2 Beds
- 2 Baths
- Built 1985
7102 Jessie Harbor Dr, Osprey, FL 34229

Spectacular views in all directions at highly desired Blackburn Harbor in Osprey. Tucked back and surrounded by mature and well groomed grounds you’ll park in your private under building parking space near your own large secured storage unit. Elevators take you up to Unit 71 where you’ll immediately appreciate the opportunity to utilize the covered outdoor space at the condo entrance to enjoy

Chris Rankin RE/MAX PALM REALTY

7102 Jessie Harbor Dr, Osprey, FL 34229

/33
Est $401,236 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,599 Sq Ft
293 Hidden Bay Dr Unit 201, Osprey, FL 34229

293 Hidden Bay Dr Unit 201, Osprey, FL 34229

/49
$2,350,000
- 3 Beds
- 2 Baths
- 1,977 Sq Ft
18 N Casey Key Rd, Osprey, FL 34229

Elegantly renovated bayfront retreat on Casey Key and tastefully remodeled in 2012, this stunning bayfront home blends timeless coastal elegance with modern functionality, all in one of the desired locations on Casey Key. Designed for relaxing and entertaining, the open-concept living room, kitchen, and family room offer inviting spaces to gather, while the split floor plan ensures privacy, ideal

Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

18 N Casey Key Rd, Osprey, FL 34229
/2
$855,000 Sold May 30, 2025
- 2,235 Sq Ft
- $383/SF
- 211 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2006
14021 Bellagio Way Unit 311, Osprey, FL 34229

Immerse yourself in the incredible views of Little Sarasota Bay & the Intracoastal waterway from this 3rd floor beautiful & spacious condominium. This upgraded end unit features 3 ensuite bedrooms, plus den, half bath & interior laundry room. The kitchen is a cook's delight with premium granite, upgraded wood cabinets & stainless steel appliances. The Primary bedroom offers expansive bay views &

Kristin O'Connor GULF TO BAY SOTHEBY'S INTERNAT

14021 Bellagio Way Unit 311, Osprey, FL 34229

/40
Est $1,531,461 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,567 Sq Ft
1787 S Creek Dr, Osprey, FL 34229

1787 S Creek Dr, Osprey, FL 34229

/100
$1,200,000
- 3 Beds
- 3 Baths
- 2,778 Sq Ft
401 N Point Rd Unit 404, Osprey, FL 34229

Step into a residence that redefines elegance and sophistication. This stunning 2,778 sq ft condo has been completely reimagined. Every inch has been thoughtfully redesigned to create a truly exceptional living experience. Boasting 3 spacious bedrooms, 3 bathrooms and an expansive den, the open-concept layout flows effortlessly, offering both comfort and style. From the moment you exit your

Steve Abbe COLDWELL BANKER REALTY

401 N Point Rd Unit 404, Osprey, FL 34229
/62
$560,000 Sold May 29, 2025
- 1,935 Sq Ft
- $289/SF
- 68 Days On Market
- 3 Beds
- 2 Baths
- Built 1984
221 Sorrento Dr, Osprey, FL 34229

Discover your slice of paradise in the highly sought-after boating community of Sorrento Shores. This meticulously maintained and updated 3 bedroom, 2 bath home offers an unapparelled blend of comfort, convenience, and outdoor living, all west of Hwy 41.Key Features. *** Prime location: Nestled in Sorrento Shores, just minutes from Nokomis Beach, Oscar Scherer State Park, and an array of

Glenn Davis COLDWELL BANKER SARASOTA CENT.

221 Sorrento Dr, Osprey, FL 34229

/68
Est $933,472 Not Listed For Sale
- 3 Beds
- 4 Baths
- 3,028 Sq Ft
501 Velasquez Dr, Osprey, FL 34229

501 Velasquez Dr, Osprey, FL 34229

/79
$2,850,000
- 6 Beds
- 4 Baths
- 4,546 Sq Ft
225 Harbor House Dr, Osprey, FL 34229

Considered one of the finest community owned marinas on Florida’s west coast, Southbay Yacht & Racquet Club is a premier waterfront community featuring a seven acre deep water boat basin and a lifestyle centered around the water. This exceptional 4,560 sq ft residence captures the essence of refined coastal living, blending modern updates with resort style amenities in one of Sarasota County’s

William Kerswill PINEYWOODS REALTY LLC

225 Harbor House Dr, Osprey, FL 34229
/2
$1,150,000 Sold May 28, 2025
- 2,521 Sq Ft
- $456/SF
- 20 Days On Market
- 2 Beds
- 3 Baths
- Built 1981
327 Sea Anchor Dr, Osprey, FL 34229

In the sought-after Southbay Yacht & Racquet Club, one of the premier boating communities on the southwest coast of Florida, this stunning home offers the ultimate in luxury living. With a community-owned marina and an expansive open layout, this property creates an ideal setting for relaxation and entertaining. This updated residence boasts volume ceilings, two fireplaces, built-in cabinetry and

Lisa Napolitano DOUGLAS ELLIMAN

327 Sea Anchor Dr, Osprey, FL 34229

/40
Est $511,685 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,788 Sq Ft
510 Meadow Sweet Cir, Osprey, FL 34229

510 Meadow Sweet Cir, Osprey, FL 34229

/27
$635,000
- 3 Beds
- 2 Baths
- 2,298 Sq Ft
510 Latitude Ln, Osprey, FL 34229

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

Marisa Marino BRIGHT REALTY

510 Latitude Ln, Osprey, FL 34229
/2
$85,000 Sold May 23, 2025
- 959 Sq Ft
- $89/SF
- 87 Days On Market
- 2 Beds
- 2 Baths
- Built 1978
199 Palm Air Dr, Osprey, FL 34229

MOTIVATED SELLER, BRING ALL OFFERS!!! Handyman special in a great location, the recent hurricane damaged the carport, shed, and Florida room. Priced for plenty of equity after repairs are made. The highly sought-after Arbors Mobile Home Park in Osprey is where location truly matters! This mobile home offers a perfect blend of comfort and convenience. With 2 bedrooms, 2 baths, and an inviting

Allison Bollero KELLER WILLIAMS ISLAND LIFE REAL ESTATE

199 Palm Air Dr, Osprey, FL 34229

/52
Est $2,354,580 Not Listed For Sale
- 5 Beds
- 8 Baths
- 5,521 Sq Ft
134 Marys Chapel Ct, Osprey, FL 34229

134 Marys Chapel Ct, Osprey, FL 34229

/38
$939,000
- 4 Beds
- 3 Baths
- 2,802 Sq Ft
392 Park Trace Blvd, Osprey, FL 34229

Set on a premier lakefront lot in Osprey, 392 Park Trace offers serene water views, incredible privacy, and a lifestyle surrounded by nature. Backing to Oscar Scherer State Park and just 1.9 miles from the Gulf waters and waterfront tiki bars, this home embraces Florida living. The Legacy Trail trailhead is only a quarter-mile away, connecting you to miles of scenic paths for biking, running, and

Ryan Skrzypkowski COLDWELL BANKER REALTY

392 Park Trace Blvd, Osprey, FL 34229

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