Osprey, FL Homes

/39
$719,000

New Construction $30K PRICE DROP
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
280 Hidden Bay Dr Unit 302, Osprey, FL 34229

Move right in and enjoy refined coastal living in this brand-new condominium at Edgewater at Hidden Bay. Offering 1,937 square feet, this thoughtfully designed home features three spacious bedrooms, two stylish bathrooms, and a versatile office—perfect for work or creativity.The sleek kitchen is the heart of the home, complete with premium LG appliances, solid wood cabinetry, and elegant

Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

280 Hidden Bay Dr Unit 302, Osprey, FL 34229
/2
$545,000

Sold Jul 10, 2026

104 Park Trace Blvd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,557 Sq Ft
- Built 2002
Last Sold Summary
- 16% Below List Price
- $213/SF
- 180 Days On Market
Current Estimated Value $562,335

Last Listing Agent Lisa Morreale PREMIER SOTHEBY'S INTERNATIONAL REALTY

104 Park Trace Blvd, Osprey, FL 34229

/41
Est $544,452

Not Listed For Sale

506 Oak Bay Dr, Osprey, FL 34229
- 4 Beds
- 2.5 Baths
- 1,944 Sq Ft
- Built 1995
506 Oak Bay Dr, Osprey, FL 34229

Last Sold Summary
- 10 Days On Market
Last Listing Agent Sharon Morea EXIT KING REALTY

/22
$139,900

Under Contract
- Land
- 8,712 Sq Ft
- $699,500 per Acre
0 Westview Dr, Osprey, FL 34229

Under contract-accepting backup offers. Perfectly positioned west of the Trail in the desirable coastal community of Towns-End Shores, this versatile lot offers an exceptional opportunity to enjoy the Florida lifestyle. A perfect opportunity to build a new home on a lot that totals 8,800 square feet (80-by-110-feet) along with the rare convenience of a private kayak launch, allowing you to

Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

0 Westview Dr, Osprey, FL 34229
/2
$249,000

Sold Aug 21, 2026

754 Pine Run Dr Unit 754, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,379 Sq Ft
- Built 1973
Last Sold Summary
- 7% Below List Price
- $181/SF
- 82 Days On Market
Current Estimated Value $261,254

Last Listing Agent Sasha Volosevych CALL IT CLOSED INTL REALTY

754 Pine Run Dr Unit 754, Osprey, FL 34229

/50
Est $346,204

Not Listed For Sale

1821 Highland Rd, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,184 Sq Ft
- Built 1998
1821 Highland Rd, Osprey, FL 34229

Last Sold Summary
- 53 Days On Market
Last Listing Agent Patrick Brogley KELLER WILLIAMS ON THE WATER S

/38
$172,000
- 1 Bed
- 1 Bath
- 586 Sq Ft
701 Pine Run Dr, Osprey, FL 34229

Rare “Treehouse” Condo Available in Pine Run! Thinking of making the move to Florida? This charming one-bedroom condominium is the perfect place to start. Or just want a tiny house for ease of living? This is it! Bright and airy, the home features soaring cathedral ceilings and abundant natural light from both the east and west. The spacious living room opens through sliding glass doors to a

Pat Williams PAT WILLIAMS REALTY, LLC

701 Pine Run Dr, Osprey, FL 34229
/2
$534,000

Sold Dec 11, 2025

757 Placid Lake Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,845 Sq Ft
- Built 2001
Last Sold Summary
- 1% Below List Price
- $289/SF
- 3 Days On Market
Current Estimated Value $533,631

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

757 Placid Lake Dr, Osprey, FL 34229

/86
Est $1,618,199

Not Listed For Sale

435 E MacEwen Dr, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 4,087 Sq Ft
- Built 1998
435 E MacEwen Dr, Osprey, FL 34229

Last Sold Summary
- 268 Days On Market
Last Listing Agent Candy Swick CANDY SWICK & COMPANY

/38
$550,000

$45K PRICE DROP
- 3 Beds
- 2 Baths
- 1,731 Sq Ft
547 Meadow Sweet Cir, Osprey, FL 34229

Discover one of Osprey's best-kept secrets-The Cottages of Rivendell. Tucked away within The Woodlands of Rivendell, offers a lifestyle that is becoming increasingly rare. Towering oak trees create a tranquil, park-like setting, while charming front porches, white picket fences, and classic Old Florida architecture give the neighborhood its unmistakable character. This beautifully maintained 3/2

Zita Bowers MICHAEL SAUNDERS & COMPANY

547 Meadow Sweet Cir, Osprey, FL 34229
/2
$511,500

Sold Jun 17, 2026

562 Oak Bay Dr, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,414 Sq Ft
- Built 1995
Last Sold Summary
- 9% Below List Price
- $212/SF
- 22 Days On Market
Current Estimated Value $518,893

Last Listing Agent Julianna Burns BERKSHIRE HATHAWAY HOMESERVICE

562 Oak Bay Dr, Osprey, FL 34229

/2
Est $940,399

Not Listed For Sale

1321 Southbay Dr, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,968 Sq Ft
- Built 1978
1321 Southbay Dr, Osprey, FL 34229

Last Sold Summary
- 29 Days On Market
Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

/51
$425,000

$24K PRICE DROP
- 2 Beds
- 2 Baths
- 1,284 Sq Ft
107 Sorrento Dr, Osprey, FL 34229

This beautifully updated, 1,284-square-foot, mid-century home sits on over one-third of an acre and has been thoughtfully renovated with distinctive Sarasota modern flair by HGTV Design team. Go through the vibrant turquoise door into a light-filled interior featuring gleaming terrazzo floors and clean mid-century lines. Sliding walls of glass create seamless indoor-outdoor living, opening from

Crystal Cosby, LLC PREMIER SOTHEBYS INTL REALTY

107 Sorrento Dr, Osprey, FL 34229
/2
$1,600,000

Sold May 14, 2026

228 Saint James Park, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,425 Sq Ft
- Built 1997
Last Sold Summary
- 6% Below List Price
- $660/SF
- 33 Days On Market
Current Estimated Value $1,537,623

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

228 Saint James Park, Osprey, FL 34229

/2
Est $1,131,332

Not Listed For Sale

327 Sea Anchor Dr, Osprey, FL 34229
- 2 Beds
- 3 Baths
- 2,521 Sq Ft
- Built 1981
327 Sea Anchor Dr, Osprey, FL 34229

Last Sold Summary
- 20 Days On Market
Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

/4
$99,500
570 Blackburn Point Rd Unit 36, Osprey, FL 34229

This high end, hurricane rated building sits ideally located between Sarasota and Venice. It is just minutes away from Midnight Pass. This slip holds a boat 32.5' in length, 9' in height and 10' in width. The marina is professionally staffed and is opened 7 days a week. Amenities include outside service racks, wash down stations, pump out, 90 octane rec fuel, water and electric on the docks,

David Babel BRIGHT REALTY

570 Blackburn Point Rd Unit 36, Osprey, FL 34229
/2
$685,000

Sold Jan 30, 2026

866 Oak Briar Ln, Osprey, FL 34229
- 4 Beds
- 2 Baths
- 2,434 Sq Ft
- Built 2001
Last Sold Summary
- 2% Below List Price
- $281/SF
- 182 Days On Market
Current Estimated Value $674,975

Last Listing Agent Brian Leakeas COLDWELL BANKER REALTY

866 Oak Briar Ln, Osprey, FL 34229

/2
Est $538,379

Not Listed For Sale

629 Oak Bay Dr, Osprey, FL 34229
- 4 Beds
- 2 Baths
- 1,867 Sq Ft
- Built 1996
629 Oak Bay Dr, Osprey, FL 34229

Last Sold Summary
- 250 Days On Market
Last Listing Agent Toni Zarghami KW COASTAL LIVING III

/42
$829,000

Pending
- 4 Beds
- 3 Baths
- 2,876 Sq Ft
1211 Lost Creek Ct, Osprey, FL 34229

Under contract-accepting backup offers. **BEAUTIFULLY UPDATED AND MOVE-IN READY, THIS SPACIOUS 4-BEDROOM + OFFICE/DEN HOME OFFERS NEARLY 2,900 SQUARE FEET** of thoughtfully designed living space with potential for a private in-law or multi-generational suite. Featuring 3 full baths and a coveted 3-car garage, this reconfigured floor plan provides flexibility, privacy, and comfort for today’s

Mark Lyda GENEROUS PROPERTY

1211 Lost Creek Ct, Osprey, FL 34229
/2
$845,000

Sold Jul 01, 2026

664 Crane Prairie Way, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,870 Sq Ft
- Built 2003
Last Sold Summary
- 6% Below List Price
- $294/SF
- 93 Days On Market
Current Estimated Value $871,205

Last Listing Agent Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

664 Crane Prairie Way, Osprey, FL 34229

/2
Est $1,862,604

Not Listed For Sale

451 E MacEwen Dr, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 4,368 Sq Ft
- Built 1998
451 E MacEwen Dr, Osprey, FL 34229

Last Sold Summary
- 3 Days On Market
Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

/30
$284,900

$10K PRICE DROP
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
184 Explorer Dr, Osprey, FL 34229

Luxury Corner Residence in Osprey | Top-Rated Pine View School District.Welcome to an exceptional opportunity in the heart of Osprey, one of Sarasota County’s most desirable and rapidly growing locations. This beautifully maintained corner-unit residence in Bay Street Village offers an elevated lifestyle just moments from world-class amenities.This FULLY FURNISHED 2-bedroom, 2-bathroom

Claudia Dybala DALTON WADE INC

184 Explorer Dr, Osprey, FL 34229
/2
$635,000

Sold Jan 29, 2026

178 Willow Bend Way, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,889 Sq Ft
- Built 2001
Last Sold Summary
- 1% Below List Price
- $336/SF
- 8 Days On Market
Current Estimated Value $624,073

Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

178 Willow Bend Way, Osprey, FL 34229

/11
Est $915,114

Not Listed For Sale

226 Saint James Park, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,591 Sq Ft
- Built 1988
226 Saint James Park, Osprey, FL 34229

Last Sold Summary
- 0 Days On Market
Last Listing Agent Mark Lyda GENEROUS PROPERTY

/70
$675,000

$64K PRICE DROP Under Contract
- 2 Beds
- 2.5 Baths
- 2,216 Sq Ft
347 Bayshore Dr, Osprey, FL 34229

Under contract-accepting backup offers. This custom built home is located in the Osprey subdivision Bay Acres, west of the trail, in an established neighborhood along Little Sarasota Bay between Sarasota and Venice. This location allows easy access to I-75, top rated schools to include the magnet school Pine View , and Nokomis and Siesta Key Beaches, and all amenities of both cities. This home

Sharon Sprow COLDWELL BANKER REALTY

347 Bayshore Dr, Osprey, FL 34229
/2
$335,000

Sold May 14, 2026

291 Hidden Bay Dr Unit 102, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,479 Sq Ft
- Built 2000
Last Sold Summary
- 16% Below List Price
- $227/SF
- 69 Days On Market
Current Estimated Value $343,436

Last Listing Agent Pat McMillan PREMIER SOTHEBY'S INTERNATIONAL REALTY

291 Hidden Bay Dr Unit 102, Osprey, FL 34229

/70
Est $1,627,386

Not Listed For Sale

337 Passage Way, Osprey, FL 34229
- 5 Beds
- 5 Baths
- 4,551 Sq Ft
- Built 1984
337 Passage Way, Osprey, FL 34229

Last Sold Summary
- 57 Days On Market
Last Listing Agent Benjamin Moricz KELLER WILLIAMS ON THE WATER S

/19
$285,000
- 1 Bed
- 1 Bath
- 595 Sq Ft
51 MacEwen Dr Unit 14, Osprey, FL 34229

This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area

Steve Abbe COLDWELL BANKER REALTY

51 MacEwen Dr Unit 14, Osprey, FL 34229
/2
$1,285,000

Sold Apr 08, 2026

137 Osprey Point Dr, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,303 Sq Ft
- Built 1996
Last Sold Summary
- 10% Below List Price
- $389/SF
- 118 Days On Market
Current Estimated Value $1,562,976

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

137 Osprey Point Dr, Osprey, FL 34229

/24
Est $807,695

Not Listed For Sale

130 N Creek Ln, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,448 Sq Ft
- Built 1997
130 N Creek Ln, Osprey, FL 34229

Last Sold Summary
- 140 Days On Market
Last Listing Agent Mariana Georgieva HORIZON REALTY INTERNATIONAL

/62
$599,000
- 2 Beds
- 2 Baths
- 2,143 Sq Ft
5100 Jessie Harbor Dr Unit 404, Osprey, FL 34229

Sweeping water views, beautiful updates and an enviable waterfront lifestyle come together in this exceptional fourth-floor residence at Blackburn Harbor. Docking available on the premises for a very reasonable quarterly fee. Set along South Creek with direct access via canal to the Intracoastal Waterway and the Gulf, this spacious 2-bedroom, 2-bath home with a versatile den captures the essence

Stuart Lawrence MICHAEL SAUNDERS & COMPANY

5100 Jessie Harbor Dr Unit 404, Osprey, FL 34229
/2
$700,000

Sold Oct 08, 2025

826 Oak Briar Ln, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,589 Sq Ft
- Built 2003
Last Sold Summary
- 10% Below List Price
- $270/SF
- 160 Days On Market
Current Estimated Value $705,265

Last Listing Agent Peter LaSalle PREFERRED SHORE LLC

826 Oak Briar Ln, Osprey, FL 34229

/2
Est $503,767

Not Listed For Sale

544 Meadow Sweet Cir, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,700 Sq Ft
- Built 2001
544 Meadow Sweet Cir, Osprey, FL 34229

Last Sold Summary
- 7 Days On Market
Last Listing Agent Zita Bowers MICHAEL SAUNDERS & COMPANY

/90
$560,000

$65K PRICE DROP
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
409 N Point Rd Unit 401, Osprey, FL 34229

Nestled at treetop level, in Meridian behind the gates of The Oaks Preserve, you will find this elegant residence waiting for you to make it your own. With a spacious master suite, two guest bedrooms (one en suite) and a den, this condo lives large, with room for comfortable, gracious living. Beautifully appointed, every special touch you would want can be found here, Italian ceramic tile, crown

Steve Abbe COLDWELL BANKER REALTY

409 N Point Rd Unit 401, Osprey, FL 34229
/2
$585,000

Sold Mar 27, 2026

584 Meadow Sweet Cir, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,151 Sq Ft
- Built 1996
Last Sold Summary
- 2% Below List Price
- $272/SF
- 18 Days On Market
Current Estimated Value $575,857

Last Listing Agent Jack Keller JACK KELLER INC

584 Meadow Sweet Cir, Osprey, FL 34229

/2
Est $1,953,216

Not Listed For Sale

703 N MacEwen Dr, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 4,641 Sq Ft
- Built 2007
703 N MacEwen Dr, Osprey, FL 34229

Last Sold Summary
- 95 Days On Market
Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

/50
$1,775,000

$75K PRICE DROP
- 3 Beds
- 2 Baths
- 2,411 Sq Ft
206 Four Knot Ln, Osprey, FL 34229

Offering 3 bedrooms, 2 baths, den/office, 2,411 square feet under air, a spacious living room, a 2-car garage, and a private 14' x 37' heated pool centrally positioned as the focal point of the home. This beautifully updated, move-in-ready residence blends luxury, comfort, and the ultimate coastal lifestyle in the highly sought-after waterfront Southbay Yacht & Racquet Club/Marina

Leighton Allenby Realty One Group MVP

206 Four Knot Ln, Osprey, FL 34229
/2
$260,000

Sold Jan 23, 2026

761 Pine Run Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,379 Sq Ft
- Built 1973
Last Sold Summary
- 7% Below List Price
- $189/SF
- 31 Days On Market
Current Estimated Value $251,707

Last Listing Agent Jeffrey Gaudette COLDWELL BANKER SARASOTA CENT.

761 Pine Run Dr, Osprey, FL 34229

/60
Est $498,583

Not Listed For Sale

455 N Shore Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,229 Sq Ft
- Built 1966
455 N Shore Dr, Osprey, FL 34229

Last Sold Summary
- 89 Days On Market
Last Listing Agent Bo Fuller FULLER GROUP

/4
$39,500

$3K PRICE DROP
570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229

Dry boat slip for sale at Osprey Harbor Village, hurricane-protected dry storage with top-tier amenities! Keep your boat safe from Floridas 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 33L x 9.5W x 6.5H. With valet boat service,

Daniel Treiman MICHAEL SAUNDERS & COMPANY

570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229

Showing Results 241 - 280, Page 7 of 18

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