Osprey, FL Homes

/41
$700,000

$19K PRICE DROP
- 2 Beds
- 2 Baths
- 1,932 Sq Ft
242 Hidden Bay Dr Unit 602, Osprey, FL 34229

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

Cathy Rustin FIRST LIGHT REAL ESTATE

242 Hidden Bay Dr Unit 602, Osprey, FL 34229
/2
$3,900,000

Sold Aug 27, 2025

426 N Casey Key Rd, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,876 Sq Ft
- Built 1992
Last Sold Summary
- 20% Below List Price
- $2,079/SF
- 657 Days On Market
Current Estimated Value $3,588,633

Last Listing Agent Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

426 N Casey Key Rd, Osprey, FL 34229

/2
Est $915,043

Not Listed For Sale

32 Bayhead Ln, Osprey, FL 34229
- 3 Beds
- 3.5 Baths
- 2,570 Sq Ft
- Built 1993
32 Bayhead Ln, Osprey, FL 34229

Last Sold Summary
- 82 Days On Market
Last Listing Agent Rosalie Phillips MICHAEL SAUNDERS & COMPANY

/71
$275,000
- 1 Bed
- 1 Bath
- 623 Sq Ft
51 MacEwen Dr Unit 12, Osprey, FL 34229

Situated in Windsor Lodge in The Oaks Clubside, this updated second floor condo has a kitchenette with quartz countertops, a modern bath, a bonus space set up as a small office area and in-unit laundry. An end unit, it has more windows than the typical interior location, filling the interior with wonderful natural light and offering sweeping views of Eagle #18 and lake. This immaculate condo is

Steve Abbe COLDWELL BANKER REALTY

51 MacEwen Dr Unit 12, Osprey, FL 34229
/2
$3,500,000

Sold Dec 17, 2025

431 Yacht Harbor Dr, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 3,006 Sq Ft
- Built 1979
Last Sold Summary
- 19% Below List Price
- $1,164/SF
- 11 Days On Market
Current Estimated Value $3,489,704

Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

431 Yacht Harbor Dr, Osprey, FL 34229

/48
Est $742,562

Not Listed For Sale

763 Shadow Bay Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,093 Sq Ft
- Built 1998
763 Shadow Bay Way, Osprey, FL 34229

Last Sold Summary
- 22 Days On Market
Last Listing Agent Barbara Gahry COLDWELL BANKER SARASOTA CENT.

/97
$1,900,000
- 5 Beds
- 7.5 Baths
- 5,986 Sq Ft
916 MacEwen Dr, Osprey, FL 34229

Virtually Staged. A rare canvas of luxury, positioned on a lush double lot within the sought-after, gated community of The Oaks, in Osprey, adjacent to stunning Sarasota, known for the arts. Bordering the Heron Course on the eighth fairway, this iconic two-story estate boasts incredible opportunity for limitless potential. The entire interior is freshly painted, to enhance vision of stateliness.

Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

916 MacEwen Dr, Osprey, FL 34229
/2
$535,000

Sold Jun 03, 2026

242 Hidden Bay Dr Unit 603, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,932 Sq Ft
- Built 1999
Last Sold Summary
- 9% Below List Price
- $277/SF
- 100 Days On Market
Current Estimated Value $539,177

Last Listing Agent Susan Retzke RE/MAX PALM

242 Hidden Bay Dr Unit 603, Osprey, FL 34229

/69
Est $244,040

Not Listed For Sale

360 Pine Run Dr Unit 360, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,379 Sq Ft
- Built 1973
360 Pine Run Dr Unit 360, Osprey, FL 34229

Last Sold Summary
- 74 Days On Market
Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

/52
$1,165,000

$34K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,830 Sq Ft
1527 Buoy Ln, Osprey, FL 34229

Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet club featuring 10 foot ceilings. 2026 AC unit, 2024 tile roof, 2023 driveway, cabinets, lighting, appliances, tile and carpet are just the beginning. 2023 pool and spa led lighting, Pentair controller, saltwater conversion, and owned 250 gallon propane. Dry bar with ice maker, wine fridge, and beverage

Matthew Lewis BRIGHT REALTY

1527 Buoy Ln, Osprey, FL 34229
/2
$1,105,000

Sold Jul 17, 2026

272 Four Knot Ln, Osprey, FL 34229
- 5 Beds
- 3 Baths
- 2,723 Sq Ft
- Built 1978
Last Sold Summary
- 1% Above List Price
- $406/SF
- 2 Days On Market
Current Estimated Value $1,085,870

Last Listing Agent Andrew Peterson EVOLVE REAL ESTATE

272 Four Knot Ln, Osprey, FL 34229

/39
Est $700,253

Not Listed For Sale

1096 Mallard Marsh Dr, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,492 Sq Ft
- Built 2000
1096 Mallard Marsh Dr, Osprey, FL 34229

Last Sold Summary
- 39 Days On Market
Last Listing Agent Barbara Gahry COLDWELL BANKER SARASOTA CENT.

/43
$395,000
- 2 Beds
- 2 Baths
- 1,255 Sq Ft
7204 Jessie Harbor Dr, Osprey, FL 34229

**BEAUTIFULLY UPDATED WATERFRONT CONDO WEST OF THE TRAIL! BRING YOUR BOAT & KAYAK FOR DIRECT ACCESS TO THE INTRACOASTAL WATERWAY AND GULF OF MEXICO.** Unlike many Blackburn Harbor residences, this thoughtfully renovated 2-bedroom, 2-bath, second-floor condo is move-in ready, allowing the next owner to immediately enjoy the coveted waterfront lifestyle without the time or expense of major updates.

Mark Lyda GENEROUS PROPERTY

7204 Jessie Harbor Dr, Osprey, FL 34229
/2
$530,000

Sold Jun 11, 2026

1116 Beachcomber Ct Unit 3, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,040 Sq Ft
- Built 2005
Last Sold Summary
- 3% Below List Price
- $260/SF
- 31 Days On Market
Current Estimated Value $527,441

Last Listing Agent Christine Green COLDWELL BANKER REALTY

1116 Beachcomber Ct Unit 3, Osprey, FL 34229

/2
Est $722,848

Not Listed For Sale

1000 Scherer Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,441 Sq Ft
- Built 2003
1000 Scherer Way, Osprey, FL 34229

Last Sold Summary
- 54 Days On Market
Last Listing Agent Jody Callan PREMIER SOTHEBYS INTL REALTY

/96
$2,399,000

$196K PRICE DROP
- 4 Beds
- 3.5 Baths
- 3,953 Sq Ft
49 Osprey Point Dr, Osprey, FL 34229

Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes,

Jonathan Abrams MICHAEL SAUNDERS & COMPANY

49 Osprey Point Dr, Osprey, FL 34229
/2
$1,265,000

Sold Jun 01, 2026

1471 Shoal Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,798 Sq Ft
- Built 1985
Last Sold Summary
- 16% Below List Price
- $452/SF
- 47 Days On Market
Current Estimated Value $1,270,728

Last Listing Agent Lauren Doyle DALTON WADE INC

1471 Shoal Way, Osprey, FL 34229

/2
Est $627,779

Not Listed For Sale

519 Habitat Blvd, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,234 Sq Ft
- Built 2003
519 Habitat Blvd, Osprey, FL 34229

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

/49
$299,990
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
4296 Expedition Way Unit 104, Osprey, FL 34229

Welcome to Bay Street Village in Osprey, gorgeous gated community where maintenance-free living awaits. This immaculate end-unit condo freshly painted with new LVP stairs and flooring features 2 bedrooms, 2 bathrooms, garage, located beneath the unit and offers a private interior stairway leading to your second-floor residence. Open-concept living and dining area are perfect for entertaining

Pamela Kurpiewski EXP REALTY LLC

4296 Expedition Way Unit 104, Osprey, FL 34229
/2
$1,325,000

Sold Aug 25, 2026

486 Yacht Harbor Dr, Osprey, FL 34229
- 3 Beds
- 3.5 Baths
- 2,939 Sq Ft
- Built 1981
Last Sold Summary
- 5% Below List Price
- $451/SF
- 3 Days On Market
Current Estimated Value $1,377,008

Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

486 Yacht Harbor Dr, Osprey, FL 34229

/55
Est $571,044

Not Listed For Sale

5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 2,143 Sq Ft
- Built 2004
5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229

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

/99
$1,095,000

$102K PRICE DROP
- 4 Beds
- 3 Baths
- 2,770 Sq Ft
403 Longbow Trail, Osprey, FL 34229

Welcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in one of Osprey's most desirable communities Pine Ranch. Located 15 minutes from Siesta Key and Nokomis Beach and is within a short distance from the nationally top-rated Pine View School, #1 High School in Florida and the natural beauty of the Legacy Trail.This charming home offers a perfect blend of

Edward Bieker DALTON WADE INC

403 Longbow Trail, Osprey, FL 34229
/2
$164,000

Sold May 14, 2026

200 Woodland Dr Unit 200, Osprey, FL 34229
- 1 Bed
- 1.5 Baths
- 865 Sq Ft
- Built 1980
Last Sold Summary
- 6% Below List Price
- $190/SF
- 45 Days On Market
Current Estimated Value $168,678

Last Listing Agent Kathleen Griffin MICHAEL SAUNDERS & COMPANY

200 Woodland Dr Unit 200, Osprey, FL 34229

/2
Est $532,444

Not Listed For Sale

590 Oak Bay Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,892 Sq Ft
- Built 1999
590 Oak Bay Dr, Osprey, FL 34229

Last Sold Summary
- 53 Days On Market
Last Listing Agent Kathy White PREFERRED SHORE LLC

/79
$739,000
- 3 Beds
- 2 Baths
- 2,328 Sq Ft
299 Turquoise Ln, Osprey, FL 34229

Remarkable 3 bedroom 2 bathroom home in Emerald Woods now available for purchase. Nestled in the Oaks Preserve Neighborhood and offering a maintenance free lifestyle with 24 hour guarded gate. Features include; Beautiful Tray Ceilings, Crown Moldings, Plantation Shutters, Solid Surface Countertops, Tile flooring throughout living spaces, and an Spectacular Owner’s Suite with multiple walk-in

Mick Jordan BRIGHT REALTY

299 Turquoise Ln, Osprey, FL 34229
/2
$2,400,000

Sold Jan 09, 2026

432 Sorrento Dr, Osprey, FL 34229
- 3 Beds
- 3.5 Baths
- 3,640 Sq Ft
- Built 2007
Last Sold Summary
- 6% Below List Price
- $659/SF
- 7 Days On Market
Current Estimated Value $2,343,909

Last Listing Agent Tanya Waxler UKEEPCOMMISSION REAL ESTATE

432 Sorrento Dr, Osprey, FL 34229

/2
Est $415,105

Not Listed For Sale

418 Sarabay Rd, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,767 Sq Ft
- Built 1960
418 Sarabay Rd, Osprey, FL 34229

Last Sold Summary
- 81 Days On Market
Last Listing Agent Tracey Fiedler DALTON WADE INC

/100
$5,999,999
- 4 Beds
- 4.5 Baths
- 5,337 Sq Ft
313 Lookout Point Dr, Osprey, FL 34229

Bring your yacht. This is Sarasota waterfront living at its most refined. First time on the market, this custom-built John Cannon estate is perfectly positioned within Southbay Yacht & Racquet Club—one of Sarasota’s most exclusive waterfront communities offering a true private yacht club lifestyle within the neighborhood. With a deep-water marina reserved for residents, accommodating vessels up

Natalie Gutwein MICHAEL SAUNDERS & COMPANY

313 Lookout Point Dr, Osprey, FL 34229
/2
$285,000

Sold May 22, 2026

4173 Frontier Ln, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
- Built 2019
Last Sold Summary
- 1% Below List Price
- $251/SF
- 3 Days On Market
Current Estimated Value $281,676

Last Listing Agent Michael A Martino KELLER WILLIAMS ON THE WATER S

4173 Frontier Ln, Osprey, FL 34229

/2
Est $751,924

Not Listed For Sale

356 S Creek Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,369 Sq Ft
- Built 1990
356 S Creek Dr, Osprey, FL 34229

Last Sold Summary
- 36 Days On Market
Last Listing Agent Christiana Kopetzky MICHAEL SAUNDERS & COMPANY

/41
$419,000

$5K PRICE DROP
- 3 Beds
- 2 Baths
- 1,760 Sq Ft
524 Sarabay Rd, Osprey, FL 34229

Location, Location. In the Heart of Osprey, centrally located in the highly sought-after well-established Bay Acres Community. Lowest priced home west of the Taril. These 3 bedrooms 2 bath ranch home is West of 41 within 10-minute commutes to downtown Sarasota and downtown Venice, Florida. Across the street from Walmart with bus transportation to Sarasota and Venice. You can walk to Walmart, the

Ibetta Giannone SUN N SAND REAL ESTATE LLC

524 Sarabay Rd, Osprey, FL 34229
/2
$470,000

Sold Feb 10, 2026

1363 New Forest Ln, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,738 Sq Ft
- Built 2002
Last Sold Summary
- 14% Below List Price
- $270/SF
- 260 Days On Market
Current Estimated Value $474,830

Last Listing Agent Pamela Strom RE/MAX PALM

1363 New Forest Ln, Osprey, FL 34229

/21
Est $1,043,174

Not Listed For Sale

1108 Bayhead Ln, Osprey, FL 34229
- 4 Beds
- 4 Baths
- 3,541 Sq Ft
- Built 1997
1108 Bayhead Ln, Osprey, FL 34229

Last Sold Summary
- 99 Days On Market
Last Listing Agent Rosalie Phillips MICHAEL SAUNDERS & COMPANY

/71
$319,500

$9K PRICE DROP Under Contract
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
173 Navigation Cir Unit 107, Osprey, FL 34229

Under contract-accepting backup offers. Immaculate and lightly lived-in 3BR/2BA condo in the gated community of Bay Street Village, offering beautiful water views with a fountain from the main living areas, the primary suite, and the screened lanai. The popular Ibis floor plan features an open-concept kitchen, dining, and great room with 42" upper cabinets, granite countertops, a custom tile

Tim Weller EXIT KING REALTY

173 Navigation Cir Unit 107, Osprey, FL 34229
/2
$43,000

Sold Nov 04, 2025

570 Blackburn Point Rd Unit 6, Osprey, FL 34229
Last Sold Summary
- 2% Below List Price
- 98 Days On Market
Last Listing Agent Rick Bumbaca NORTHGROUP REAL ESTATE, INC

570 Blackburn Point Rd Unit 6, Osprey, FL 34229

/2
Est $241,067

Not Listed For Sale

707 Pine Run Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,379 Sq Ft
- Built 1973
707 Pine Run Dr, Osprey, FL 34229

Last Sold Summary
- 134 Days On Market
Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

/64
$399,000

$51K PRICE DROP Under Contract
- 2 Beds
- 2 Baths
- 1,392 Sq Ft
764 Sarabay Rd Unit 8, Osprey, FL 34229

Under contract-accepting backup offers. Virtually Staged. BOAT SLIP-KAYAK LAUNCH-FISHING STATION!!! Live the Florida dream on the water! Wake up to shimmering bay views, spend your days boating and fishing, and end every evening with breathtaking sunsets over Little Sarasota Bay, all from this rarely available, maintenance-free waterfront villa. In the exclusive Heron Bay Club, an intimate

Michael Christo PREMIER SOTHEBYS INTL REALTY

764 Sarabay Rd Unit 8, Osprey, FL 34229
/2
$215,000

Sold May 01, 2026

362 Pine Run Dr Unit 362, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,224 Sq Ft
- Built 1973
Last Sold Summary
- $176/SF
Current Estimated Value $216,553

Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

362 Pine Run Dr Unit 362, Osprey, FL 34229

/22
Est $554,020

Not Listed For Sale

743 Anna Hope Ln, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,150 Sq Ft
- Built 2000
743 Anna Hope Ln, Osprey, FL 34229

Last Sold Summary
- 177 Days On Market
Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

/25
$600,000
- Land
- 14,810 Sq Ft
- $1,764,706 per Acre
458 N Shore Dr, Osprey, FL 34229

Discover the perfect canvas for your dream home with this exceptional vacant lot located in the desirable Sorrento Shores community in Osprey, Florida. Spanning 0.34 acres, this spacious lot offers ample room for creative design and construction. Featuring a generous 100-foot frontage and dimensions that allow for multiple building possibilities, this property is ideal for those looking to build

Matthew Charland LLC PREMIER SOTHEBYS INTL REALTY

458 N Shore Dr, Osprey, FL 34229

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