Osprey, FL Homes

/60
Est $532,645 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
- 18% Above List Price
- $366/SF
- 89 Days On Market
Last Sold Price $450,000

Last Listing Agent Bo Fuller FULLER GROUP

/76
$167,000
- 2 Beds
- 2 Baths
- 959 Sq Ft
166 Edgewood Dr, Osprey, FL 34229

Welcome to easy Florida living in The Arbors of Osprey! This charming 2-bedroom, 2-bath manufactured home offers comfort, updates, and plenty of space to relax and entertain. Step inside to a spacious living room filled with natural light, perfect for gathering with family and friends. The updated kitchen features warm wood cabinetry and a brand-new refrigerator (2025), making meal prep both

Karen Geiger COLDWELL BANKER SARASOTA CENT.

166 Edgewood Dr, Osprey, FL 34229
/2
$245,000 Sold Apr 21, 2025

225 Woodland Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,316 Sq Ft
- Built 1980
Last Sold Summary
- 18% Below List Price
- $186/SF
- 103 Days On Market
Current Estimated Value $225,403

Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

225 Woodland Dr, Osprey, FL 34229

/2
Est $712,531 Not Listed For Sale

668 Clear Creek Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,388 Sq Ft
- Built 2002
668 Clear Creek Dr, Osprey, FL 34229

Last Sold Summary
- 8% Below List Price
- $325/SF
- 11 Days On Market
Last Sold Price $775,000

Last Listing Agent Cheryl Guentner RE/MAX PALM

/23
$525,000 Open Sat 11AM - 2PM
- 3 Beds
- 2 Baths
- 1,947 Sq Ft
437 S Shore Dr, Osprey, FL 34229

Bring your BOAT or RV and store ON YOUR LOT. West of the Trail! Welcome home to Sorrento Shores, nestled perfectly between the vibrant communities of Sarasota and Venice, yet tucked away from the hustle and bustle of city life in the charming town of Osprey. This sought-after neighborhood offers spacious lots, a relaxed atmosphere, and the added bonus of low HOA fees and no CDD to worry about.

Dawn Barnett EXIT KING REALTY

437 S Shore Dr, Osprey, FL 34229
/2
$832,750 Sold Apr 10, 2025

280 Hidden Bay Dr Unit 303, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
- Built 2025
Last Sold Summary
- $430/SF
- 27 Days On Market
Current Estimated Value $762,143

Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

280 Hidden Bay Dr Unit 303, Osprey, FL 34229

/72
Est $638,969 Not Listed For Sale

593 Crane Prairie Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,340 Sq Ft
- Built 2005
593 Crane Prairie Way, Osprey, FL 34229

Last Sold Summary
- 4% Above List Price
- $263/SF
- 194 Days On Market
Last Sold Price $615,000

Last Listing Agent Cynthia Bowers COLDWELL BANKER SARASOTA CENT.

/95
$850,000
- 3 Beds
- 3 Baths
- 2,778 Sq Ft
401 N Point Rd Unit 304, Osprey, FL 34229

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

Steve Abbe COLDWELL BANKER REALTY

401 N Point Rd Unit 304, 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 $589,440

Last Listing Agent Jack Keller JACK KELLER INC

584 Meadow Sweet Cir, Osprey, FL 34229

/100
Est $1,174,780 Not Listed For Sale

328 Pine Ranch Trail, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,215 Sq Ft
- Built 1991
328 Pine Ranch Trail, Osprey, FL 34229

Last Sold Summary
- 2% Above List Price
- $358/SF
- 0 Days On Market
Last Sold Price $1,150,000

Last Listing Agent Sally Green HOMESMART

/5
$99,500
570 Blackburn Point Rd Unit 35, Osprey, FL 34229

Welcome to this quality high end marine facility. Take confidence knowing that your boat is stored in this completely enclosed hurricane rated boat building. Your privately owned boat rack offers unlimited in and out splashes, outside work racks, ethanol free fuel, independent detailing contractors, a full-service shop including deli, drinks, ice, bait and other miscellaneous services. The docks

David Babel BRIGHT REALTY

570 Blackburn Point Rd Unit 35, 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 $257,630

Last Listing Agent Jeffrey Gaudette COLDWELL BANKER SARASOTA CENT.

761 Pine Run Dr, Osprey, FL 34229

/54
Not Listed For Sale

871 MacEwen Dr, Osprey, FL 34229
- 5 Beds
- 5.5 Baths
- 5,168 Sq Ft
- Built 1990
871 MacEwen Dr, Osprey, FL 34229

Last Sold Summary
- $386/SF
- 226 Days On Market
Last Sold Price $1,995,000

Last Listing Agent Joel Schemmel DOUGLAS ELLIMAN

/56
$735,000 Pending
- 4 Beds
- 3 Baths
- 2,498 Sq Ft
1019 Scherer Way, Osprey, FL 34229

Welcome to this beautiful 4 bedroom 3 full bath home situated in the desirable community of Rivendell. Minutes to the distinguished Pine View School, the #1 rated public gifted college-prep school in Florida. Open Floor plan boasts a 'Chef's Delight' kitchen with plenty of custom cabinets, quartz countertop, updated stainless steel appliance, under cabinet lighting and oversized aquarium window

Christine Appice CENTURY 21 SCHMIDT REAL ESTATE

1019 Scherer Way, Osprey, FL 34229
/2
$2,327,000 Sold Jun 18, 2025

654 Trenton Way, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 3,582 Sq Ft
- Built 1990
Last Sold Summary
- 5% Below List Price
- $650/SF
- 86 Days On Market
Current Estimated Value $2,125,040

Last Listing Agent Mark Lyda GENEROUS PROPERTY

654 Trenton Way, Osprey, FL 34229

/65
Est $1,862,457 Not Listed For Sale

482 E MacEwen Dr, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,327 Sq Ft
- Built 2001
482 E MacEwen Dr, Osprey, FL 34229

Last Sold Summary
- 15% Below List Price
- $661/SF
- 212 Days On Market
Last Sold Price $2,200,000

Last Listing Agent David Butler Jr RE/MAX

/42
$4,995,000
- 4 Beds
- 5.5 Baths
- 6,308 Sq Ft
730 Sarabay Rd, Osprey, FL 34229

One or more photo(s) has been virtually staged. PREMIER HIGH-ELEVATION BAYFRONT ESTATE ON 2 PRIVATE ACRES 4 Bedrooms | 5.5 Bathrooms | 6,308 Sq. Ft. | 730 Sarabay Road is a rare opportunity to own two acres of private waterfront property in Osprey. Situated at the end of a long gated drive by a private pond, this expansive estate offers privacy, luxury, and direct boating access to the Gulf

Debbie Baraona ROBERT SLACK LLC

730 Sarabay Rd, Osprey, FL 34229
/2
$2,925,000 Sold Sep 23, 2025

550 Dove Pointe, Osprey, FL 34229
- 4 Beds
- 5.5 Baths
- 7,842 Sq Ft
- Built 2006
Last Sold Summary
- 11% Below List Price
- $373/SF
- 63 Days On Market
Current Estimated Value $2,858,187

Last Listing Agent Jennifer Linehan MICHAEL SAUNDERS & COMPANY

550 Dove Pointe, Osprey, FL 34229

/64
Est $314,996 Not Listed For Sale

112 Woodland Place, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 1,839 Sq Ft
- Built 1979
112 Woodland Place, Osprey, FL 34229

Last Sold Summary
- 13% Below List Price
- $196/SF
- 109 Days On Market
Last Sold Price $361,000

Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

/8
$750,000
- Land
- 0.47 Acre
- $1,595,745 per Acre
147 Osprey Point Dr, Osprey, FL 34229

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

Mick Jordan BRIGHT REALTY

147 Osprey Point Dr, Osprey, FL 34229
/2
$280,000 Sold Feb 04, 2026

232 Explorer Dr Unit 15, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
- Built 2019
Last Sold Summary
- 15% Below List Price
- $247/SF
- 220 Days On Market
Current Estimated Value $280,007

Last Listing Agent Gary Hoskins COLDWELL BANKER REALTY

232 Explorer Dr Unit 15, Osprey, FL 34229

/2
Est $388,805 Not Listed For Sale

308 Kensey Ln, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,304 Sq Ft
- Built 1972
308 Kensey Ln, Osprey, FL 34229

Last Sold Summary
- 3% Below List Price
- $309/SF
- 109 Days On Market
Last Sold Price $402,500

Last Listing Agent Tracey Punzone UKEEPCOMMISSION REAL ESTATE

/63
$799,000
- 4 Beds
- 3.5 Baths
- 2,854 Sq Ft
919 Tranquility Cir, Osprey, FL 34229

*BRAND NEW TILE ROOF TO BE INSTALLED SECOND WEEK OF APRIL* 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

Ann Winger TIDELINE REAL ESTATE BROKERS

919 Tranquility Cir, Osprey, FL 34229
/2
$1,500,000 Sold Jul 08, 2025

269 Pine Ranch Trail, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 3,572 Sq Ft
- Built 1997
Last Sold Summary
- 16% Below List Price
- $420/SF
- 76 Days On Market
Current Estimated Value $1,486,245

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

269 Pine Ranch Trail, Osprey, FL 34229

/30
Est $124,869 Not Listed For Sale

751 Pine Run Dr Unit 751, Osprey, FL 34229
- 1 Bed
- 1 Bath
- 586 Sq Ft
- Built 1973
751 Pine Run Dr Unit 751, Osprey, FL 34229

Last Sold Summary
- 12% Below List Price
- $243/SF
- 54 Days On Market
Last Sold Price $142,500

Last Listing Agent Stephanie Ham PARADISE EXCLUSIVE INC

/11
$699,000
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
110 Pine Ave, Osprey, FL 34229

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

Marisa Marino BRIGHT REALTY

110 Pine Ave, Osprey, FL 34229
/2
$335,000 Sold Mar 27, 2026

172 Explorer Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,449 Sq Ft
- Built 2016
Last Sold Summary
- 4% Below List Price
- $231/SF
- 3 Days On Market
Current Estimated Value $346,751

Last Listing Agent Ashley Wallace COLDWELL BANKER REALTY

172 Explorer Dr, Osprey, FL 34229

/50
Est $529,723 Not Listed For Sale

529 Meadow Sweet Cir, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,789 Sq Ft
- Built 2002
529 Meadow Sweet Cir, Osprey, FL 34229

Last Sold Summary
- 12% Below List Price
- $335/SF
- 4 Days On Market
Last Sold Price $600,000

Last Listing Agent Barbara Gahry COLDWELL BANKER SARASOTA CENT.

/47
$595,000
- 4 Beds
- 3 Baths
- 2,557 Sq Ft
104 Park Trace Blvd, Osprey, FL 34229

Welcome to this elegant and spacious luxury pool home offering over 2,500 square feet of refined living in one of the most desirable communities along the Gulf Coast. With a freshly painted exterior, stunning hardwood floors throughout, and an exceptional layout designed for both comfort and style, this residence is move-in ready and perfectly suited for modern living. Boasting four bedrooms,

Lisa Morreale PREMIER SOTHEBY'S INTERNATIONAL REALTY

104 Park Trace Blvd, Osprey, FL 34229
/2
$995,000 Sold Mar 05, 2026

105 Turquoise Ln, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,606 Sq Ft
- Built 2001
Last Sold Summary
- $382/SF
- 162 Days On Market
Current Estimated Value $956,263

Last Listing Agent Rosalie Phillips MICHAEL SAUNDERS & COMPANY

105 Turquoise Ln, Osprey, FL 34229

/68
Est $847,838 Not Listed For Sale

1081 Scherer Way, Osprey, FL 34229
- 6 Beds
- 3 Baths
- 3,982 Sq Ft
- Built 2004
1081 Scherer Way, Osprey, FL 34229

Last Sold Summary
- $213/SF
- 76 Days On Market
Last Sold Price $850,000

Last Listing Agent Brie Bender INNOVATE REAL ESTATE

/64
$799,990
- 4 Beds
- 4 Baths
- 3,183 Sq Ft
650 Crane Prairie Way, Osprey, FL 34229

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

Cheri Castro MICHAEL SAUNDERS & COMPANY

650 Crane Prairie Way, Osprey, FL 34229
/2
$510,000 Sold Jan 13, 2026

12689 Promenade Estates Blvd, Osprey, FL 34238
- 4 Beds
- 2.5 Baths
- 2,045 Sq Ft
- Built 2021
Last Sold Summary
- 10% Below List Price
- $249/SF
- 38 Days On Market
Current Estimated Value $516,575

Last Listing Agent Lee Brewer RE/MAX ALLIANCE GROUP

12689 Promenade Estates Blvd, Osprey, FL 34238

/37
Est $858,735 Not Listed For Sale

192 Park Trace Blvd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,023 Sq Ft
- Built 2001
192 Park Trace Blvd, Osprey, FL 34229

Last Sold Summary
- 8% Below List Price
- $308/SF
- 66 Days On Market
Last Sold Price $932,500

Last Listing Agent Jalina Beck Michael Saunders

/100
$1,695,000
- 3 Beds
- 2.5 Baths
- 2,425 Sq Ft
228 Saint James Park, Osprey, FL 34229

Experience the charm of this original Bo MacEwen–designed home in The Oaks Clubside. Ideally located on a quiet cul-de-sac, in the Saint James Park enclave, this 3 bedroom residence with 2.5 baths, overlooks the opening hole of the Heron Course. Clean, bright and beautifully updated and maintained, this home has an open floor plan and features high, coffered ceilings, crown molding, French doors

Steve Abbe COLDWELL BANKER REALTY

228 Saint James Park, Osprey, FL 34229
/2
$3,050,000 Sold Aug 15, 2025

5 N Casey Key Rd, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 2,380 Sq Ft
- Built 1969
Last Sold Summary
- 27% Below List Price
- $1,282/SF
- 278 Days On Market
Current Estimated Value $2,989,261

Last Listing Agent Kelley Ann Ayers AYERS AND ASSOCIATES REAL ESTATE

5 N Casey Key Rd, Osprey, FL 34229

/2
Est $2,532,125 Not Listed For Sale

388 Bunker Hill, Osprey, FL 34229
- 5 Beds
- 5.5 Baths
- 4,937 Sq Ft
- Built 1999
388 Bunker Hill, Osprey, FL 34229

Last Sold Summary
- 13% Below List Price
- $587/SF
- 64 Days On Market
Last Sold Price $2,900,000

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

/69
$897,000 Open Sat 1PM - 3PM
- 3 Beds
- 3 Baths
- 2,870 Sq Ft
664 Crane Prairie Way, Osprey, FL 34229

It’s always about the view and the new tile roof December 2025. This stunning waterfront home in Willowbend, bordering community greenbelt with views to Oscar Scherer State Park, is a luxurious Lee Wetherington-built Paloma floorplan designed to the highest standards, offering spectacular views and seamless indoor-outdoor living. On one of the community’s most desirable lots, it features

Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

664 Crane Prairie Way, Osprey, FL 34229
/2
$660,000 Sold Aug 26, 2025

463 Park Trace Blvd, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,153 Sq Ft
- Built 2002
Last Sold Summary
- 12% Below List Price
- $307/SF
- 63 Days On Market
Current Estimated Value $666,463

Last Listing Agent Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

463 Park Trace Blvd, Osprey, FL 34229

/2
Est $2,342,668 Not Listed For Sale

425 E MacEwen Dr, Osprey, FL 34229
- 5 Beds
- 5.5 Baths
- 5,153 Sq Ft
- Built 1999
425 E MacEwen Dr, Osprey, FL 34229

Last Sold Summary
- 2% Below List Price
- $466/SF
- 62 Days On Market
Last Sold Price $2,400,000

Last Listing Agent Robert Anderson Jr RE/MAX

Showing Results 281 - 320, Page 8 of 18

Florida Sarasota County Osprey

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