Osprey, FL Homes

/48
$335,000
- 3 Beds
- 2 Baths
- 1,889 Sq Ft
4256 Expedition Way Unit 107, Osprey, FL 34229

Welcome to Bay Street. Step into the Florida lifestyle you've been dreaming of with this beautifully designed second-floor condo featuring 3 bedrooms and 2 full baths at 4256 Exhibition Way #107, Osprey, FL. Built just eight years ago, this home blends modern comfort with timeless appeal, offering a setting that feels both inviting and refined. From the moment you walk in, your eyes are drawn to

Geri Scheckner Bright Realty

4256 Expedition Way Unit 107, Osprey, FL 34229
/2
$2,625,000 Sold Sep 16, 2025

478 Oriskany Ct, Osprey, FL 34229
- 4 Beds
- 7 Baths
- 5,778 Sq Ft
- Built 1999
Last Sold Summary
- 12% Below List Price
- $454/SF
- 10 Days On Market
Current Estimated Value $2,589,890

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

478 Oriskany Ct, Osprey, FL 34229

/55
Est $963,610 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,360 Sq Ft
792 Placid Lake Dr, Osprey, FL 34229

792 Placid Lake Dr, 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
$1,325,000 Sold Nov 07, 2025

402 Walls Way, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 3,464 Sq Ft
- Built 2014
Last Sold Summary
- 22% Below List Price
- $383/SF
- 187 Days On Market
Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

402 Walls Way, Osprey, FL 34229

/45
Est $656,693 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,284 Sq Ft
573 Crane Prairie Way, Osprey, FL 34229

573 Crane Prairie Way, Osprey, FL 34229

/61
$325,000
- 3 Beds
- 2 Baths
- 1,430 Sq Ft
116 Navigation Cir Unit 106, Osprey, FL 34229

Location, Lifestyle, and Peace of Mind — All in One!Welcome home to this beautifully appointed 3-bedroom, 2-bath end-unit condo in one of the area's most desirable pet-friendly gated communities. Built with lasting quality in mind, this home offers solid block stucco construction paired with hurricane-impact windows and doors — giving you the comfort of security and the ease of low

Pan Steele, GRI COLDWELL BANKER REALTY

116 Navigation Cir Unit 106, Osprey, FL 34229
/2
$625,000 Sold Oct 10, 2025

644 Rivendell Blvd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,298 Sq Ft
- Built 2001
Last Sold Summary
- 16% Below List Price
- $272/SF
- 260 Days On Market
Last Listing Agent Veronica Manes MICHAEL SAUNDERS & COMPANY

644 Rivendell Blvd, Osprey, FL 34229

/40
Est $734,952 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,323 Sq Ft
669 Crane Prairie Way, Osprey, FL 34229

669 Crane Prairie Way, Osprey, FL 34229

/60
$2,690,000
- 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
$1,400,000 Sold May 07, 2025

378 MacEwen Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 3,094 Sq Ft
- Built 1997
Last Sold Summary
- 7% Below List Price
- $452/SF
- 0 Days On Market
Current Estimated Value $1,394,188

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

378 MacEwen Dr, Osprey, FL 34229

/11
Est $320,912 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,402 Sq Ft
217 Glenwood Ave, Osprey, FL 34229

217 Glenwood Ave, Osprey, FL 34229

/28
$1,150,000
- 3 Beds
- 2 Baths
- 2,374 Sq Ft
14041 Bellagio Way Unit 218, Osprey, FL 34229

Experience exceptional waterfront living at Osprey Harbor Village. This 3-bedroom, 2-bath residence offers 2,374 sq ft of well-designed space with direct west-facing views of Little Sarasota Bay from every main room. Located in one of Osprey’s most desirable boutique waterfront communities, this condo is being sold turnkey furnished, and includes a deeded 40’ wet slip—providing immediate access

Kelli Eggen COLDWELL BANKER REALTY

14041 Bellagio Way Unit 218, Osprey, FL 34229
/2
$237,000 Sold Mar 31, 2025

14 Old Venice Rd, Osprey, FL 34229
- Land
- 0.97 Acre
- $244,330 per Acre
Last Sold Summary
- 12% Below List Price
- 34 Days On Market
Current Estimated Value $276,241

Last Listing Agent Glenn Davis COLDWELL BANKER SARASOTA CENT.

14 Old Venice Rd, Osprey, FL 34229

/33
Est $2,857,206 Not Listed For Sale
- 4 Beds
- 7 Baths
- 8,763 Sq Ft
692 Oaks Creek Ct, Osprey, FL 34229

692 Oaks Creek Ct, Osprey, FL 34229

/73
$2,395,000
- 5 Beds
- 7 Baths
- 6,001 Sq Ft
340 Osprey Point Dr, Osprey, FL 34229

Introducing The Grand Estate at The Oaks Bayside—a true masterpiece of refined living within one of Sarasota’s most prestigious gated communities. Surrounded by majestic oak trees and lush tropical landscaping, this extraordinary residence offers the perfect blend of elegance, comfort, and privacy. A brand-new roof (2024) crowns this sprawling estate, while a pavered circular driveway leads to a

Lee Brewer RE/MAX ALLIANCE GROUP

340 Osprey Point Dr, Osprey, FL 34229
/2
$744,800 Sold Apr 24, 2025

448 Park Trace Blvd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,060 Sq Ft
- Built 2002
Last Sold Summary
- 22% Below List Price
- $243/SF
- 145 Days On Market
Current Estimated Value $771,313

Last Listing Agent Toni Zarghami KW COASTAL LIVING III

448 Park Trace Blvd, Osprey, FL 34229

/2
Est $588,017 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,229 Sq Ft
825 Oak Pond Dr, Osprey, FL 34229

825 Oak Pond Dr, Osprey, FL 34229

/60
$11,750,000
- 5 Beds
- 8 Baths
- 8,050 Sq Ft
1216 N Casey Key Rd, Osprey, FL 34229

This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family

Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

1216 N Casey Key Rd, Osprey, FL 34229
/2
$3,525,000 Sold Jun 06, 2025

275 Lookout Point Dr, Osprey, FL 34229
- 5 Beds
- 5 Baths
- 5,279 Sq Ft
- Built 2007
Last Sold Summary
- 26% Below List Price
- $668/SF
- 124 Days On Market
Current Estimated Value $3,474,356

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

275 Lookout Point Dr, Osprey, FL 34229

/48
Est $618,587 Not Listed For Sale
- 2 Beds
- 2 Baths
- 2,424 Sq Ft
522 Meadow Sweet Cir, Osprey, FL 34229

522 Meadow Sweet Cir, Osprey, FL 34229

/32
$159,900
- 2 Beds
- 2 Baths
- 1,031 Sq Ft
300 Tropic Dr, Osprey, FL 34229

Welcome to this charming, TURNKEY FURNISHED home in the desirable 55+ cooperative community of The Arbors, where you own your lot and enjoy the benefits of no monthly lot rent! Friendly neighbors and a peaceful setting make this a truly welcoming place to live! Enjoy affordable Florida living in this quaint community, where your neighbors quickly become your friends! Inside, you’ll find an open

Heidi Lionetti WHITE SANDS REALTY GROUP FL

300 Tropic Dr, Osprey, FL 34229
/2
$630,000 Sold Feb 03, 2025

480 Faith Ave, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,920 Sq Ft
- Built 1985
Last Sold Summary
- 16% Below List Price
- $328/SF
- 0 Days On Market
Current Estimated Value $657,603

Last Listing Agent Robin Leonardi MICHAEL SAUNDERS & COMPANY

480 Faith Ave, Osprey, FL 34229

/38
Est $600,632 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,325 Sq Ft
574 Oak Bay Dr, Osprey, FL 34229

574 Oak Bay Dr, Osprey, FL 34229

/48
$225,000
- 2 Beds
- 2 Baths
- 1,325 Sq Ft
244 Woodland Dr Unit 244, Osprey, FL 34229

Tranquil Coastal Living in Pine Run244 Woodland Dr, Osprey, FL 34229 Tucked beneath a canopy of mature oaks and palms, this beautifully updated 2-bedroom, 2-bath condo captures the easy, natural rhythm of coastal Florida living. Nestled within the sought-after Pine Run community, it offers both peace and connection just minutes from the beaches of Casey Key, charming Venice, and downtown

Derek Edwards KELLER WILLIAMS ON THE WATER S

244 Woodland Dr Unit 244, Osprey, FL 34229
/2
$2,000,000 Sold Apr 21, 2025

1862 Island Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,598 Sq Ft
- Built 1982
Last Sold Summary
- 18% Below List Price
- $556/SF
- 76 Days On Market
Current Estimated Value $1,952,139

Last Listing Agent Nancy Endara PREMIER SOTHEBY'S INTERNATIONAL REALTY

1862 Island Way, Osprey, FL 34229

/48
Est $790,419 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,093 Sq Ft
763 Shadow Bay Way, Osprey, FL 34229

763 Shadow Bay Way, Osprey, FL 34229

/92
$1,975,000 Pre-Foreclosure
- 4 Beds
- 4 Baths
- 4,001 Sq Ft
75 Osprey Point Dr, Osprey, FL 34229

**STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Sarasota Bay waters... situated on TWO LOTS totaling over 3/4 acres, the Main House on Lot #1 features 3 Beds / 3 Baths while the separate Guest House on adjacent Lot #2 boasts 1 Bed / 1 Bath, kitchenette, laundry, etc. An oversized Pool adorns the private setting with lush landscape and water view. This

Mark Lyda GENEROUS PROPERTY

75 Osprey Point Dr, Osprey, FL 34229
/2
$1,350,000 Sold Mar 28, 2025

409 N Point Rd Unit 704, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,778 Sq Ft
- Built 2004
Last Sold Summary
- 7% Below List Price
- $486/SF
- 11 Days On Market
Current Estimated Value $1,302,983

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

409 N Point Rd Unit 704, Osprey, FL 34229

/39
Est $737,626 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,492 Sq Ft
1096 Mallard Marsh Dr, Osprey, FL 34229

1096 Mallard Marsh Dr, Osprey, FL 34229

/78
$800,000 Open Sun 1PM - 4PM
- 3 Beds
- 2.5 Baths
- 2,134 Sq Ft
102 Windward Dr, Osprey, FL 34229

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

David Cyr WILLIAM RAVEIS REAL ESTATE

102 Windward Dr, Osprey, FL 34229
/2
$318,000 Sold Apr 30, 2025

115 Villa Dr Unit 115, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,411 Sq Ft
- Built 1972
Last Sold Summary
- 16% Below List Price
- $225/SF
- 125 Days On Market
Current Estimated Value $311,843

Last Listing Agent EJ Stukenborg KELLER WILLIAMS ON THE WATER S

115 Villa Dr Unit 115, Osprey, FL 34229

/39
Est $650,167 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,303 Sq Ft
680 Shadow Bay Way, Osprey, FL 34229

680 Shadow Bay Way, Osprey, FL 34229

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

Under contract-accepting backup offers. 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

Ryan Skrzypkowski COLDWELL BANKER REALTY

392 Park Trace Blvd, Osprey, FL 34229
/2
$1,855,000 Sold Feb 26, 2025

533 N MacEwen Dr, Osprey, FL 34229
- 4 Beds
- 4.5 Baths
- 3,794 Sq Ft
- Built 1999
Last Sold Summary
- 4% Below List Price
- $489/SF
- 9 Days On Market
Current Estimated Value $1,808,001

Last Listing Agent Mark Lyda GENEROUS PROPERTY

533 N MacEwen Dr, Osprey, FL 34229

/2
Est $745,803 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,441 Sq Ft
1000 Scherer Way, Osprey, FL 34229

1000 Scherer Way, Osprey, FL 34229

/24
$624,700
- Land
- 0.34 Acre
- $1,837,353 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 of Osprey, Florida. Spanning 0.34 acres, this spacious lot offers ample room for creative design and construction. With a generous front footage of 100 feet and dimensions that allow for multiple building possibilities, this property situated "WEST of Trail," is

Matthew Charland LLC GULF SHORES REALTY

458 N Shore Dr, Osprey, FL 34229
/2
$999,000 Sold Mar 21, 2025

505 S Shore Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,301 Sq Ft
- Built 1980
Last Sold Summary
- 3% Below List Price
- $434/SF
- 16 Days On Market
Current Estimated Value $1,015,389

Last Listing Agent Nancy Jordan COLDWELL BANKER REALTY

505 S Shore Dr, Osprey, FL 34229

/40
Est $542,161 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,892 Sq Ft
590 Oak Bay Dr, Osprey, FL 34229

590 Oak Bay Dr, Osprey, FL 34229

/3
$89,000
570 Blackburn Point Rd Unit 35, 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 35, Osprey, FL 34229

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