Osprey, FL Homes

/74
$385,000
- 3 Beds
- 3 Baths
- 1,879 Sq Ft
1795 Highland Rd, Osprey, FL 34229

One or more photo(s) has been virtually staged. Perfectly positioned west of the Trail in the desirable coastal community of Towns-End Shores, this versatile property offers an exceptional opportunity to enjoy the Florida lifestyle while generating income. This home provides both peace of mind and outstanding value in one of Sarasota County’s most sought-after areas. Designed with flexibility in

Rachel Tritschler RE/MAX ALLIANCE GROUP

1795 Highland Rd, Osprey, FL 34229
/2
$1,200,000 Sold Oct 24, 2025

1484 Seafarer Dr, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 3,479 Sq Ft
- Built 1987
Last Sold Summary
- 7% Below List Price
- $345/SF
- 82 Days On Market
Current Estimated Value $1,183,606

Last Listing Agent Seth Westerberg EXP REALTY LLC

1484 Seafarer Dr, Osprey, FL 34229

/2
Est $1,785,470 Not Listed For Sale

165 Sugar Mill Dr, Osprey, FL 34229
- 4 Beds
- 4.5 Baths
- 3,912 Sq Ft
- Built 1989
165 Sugar Mill Dr, Osprey, FL 34229

Last Sold Summary
- 1% Above List Price
- $454/SF
- 152 Days On Market
Last Sold Price $1,775,000

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

/51
$449,000
- 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
$1,275,000 Sold Sep 30, 2025

364 Renoir Dr, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 3,241 Sq Ft
- Built 2003
Last Sold Summary
- 6% Below List Price
- $393/SF
- 7 Days On Market
Current Estimated Value $1,289,032

Last Listing Agent Lore Miller RESULTS REALTY GROUP LLC

364 Renoir Dr, Osprey, FL 34229

/24
Est $1,032,632 Not Listed For Sale

228 Windward Dr, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,850 Sq Ft
- Built 1981
228 Windward Dr, Osprey, FL 34229

Last Sold Summary
- 14% Below List Price
- $421/SF
- 1 Day On Market
Last Sold Price $1,200,000

Last Listing Agent Sharon Lewis GOLF & BAY PROPERTIES LLC

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

Under contract-accepting backup offers. 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

Renee Preininger SARASOTA TRUST REALTY COMPANY

691 Eagle Watch Ln, Osprey, FL 34229
/2
$945,000 Sold Apr 15, 2025

128 Sea Anchor Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,677 Sq Ft
- Built 1978
Last Sold Summary
- 3% Below List Price
- $353/SF
- 4 Days On Market
Current Estimated Value $928,717

Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

128 Sea Anchor Dr, Osprey, FL 34229

/78
Est $734,397 Not Listed For Sale

522 Habitat Blvd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,321 Sq Ft
- Built 2003
522 Habitat Blvd, Osprey, FL 34229

Last Sold Summary
- 11% Below List Price
- $355/SF
- 48 Days On Market
Last Sold Price $825,000

Last Listing Agent David Cyr WILLIAM RAVEIS FLORIDA LLC

/4
$32,500
570 Blackburn Point Rd Unit 38, 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. Plus, HOA is prepaid thru the end of 2025! 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

Daniel Treiman MICHAEL SAUNDERS & COMPANY

570 Blackburn Point Rd Unit 38, 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 $2,588,179

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

478 Oriskany Ct, Osprey, FL 34229

/2
Est $711,020 Not Listed For Sale

520 Habitat Blvd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,323 Sq Ft
- Built 2003
520 Habitat Blvd, Osprey, FL 34229

Last Sold Summary
- 8% Below List Price
- $333/SF
- 4 Days On Market
Last Sold Price $774,500

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

/39
$1,099,000 Open Sun 11AM - 1PM
- 3 Beds
- 2 Baths
- 2,374 Sq Ft
14041 Bellagio Way Unit 218, Osprey, FL 34229

Elevate your expectations with this elegant waterfront home! This 3-bedroom, 2-bath FULLY FURNISHED home offers 2,374 sq ft of well-appointed living space, with water views of Little Sarasota Bay from every main room. Located in one of Osprey’s most desirable boutique waterfront communities, this condo includes a DEEDED 40' wet slip—providing immediate access to boating, fishing, and the

Kelli Eggen COLDWELL BANKER REALTY

14041 Bellagio Way Unit 218, 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
Current Estimated Value $1,401,967

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

402 Walls Way, Osprey, FL 34229

/41
Est $690,466 Not Listed For Sale

675 Crane Prairie Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,320 Sq Ft
- Built 2003
675 Crane Prairie Way, Osprey, FL 34229

Last Sold Summary
- 12% Below List Price
- $338/SF
- 37 Days On Market
Last Sold Price $783,000

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

/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
$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
Current Estimated Value $629,871

Last Listing Agent Veronica Manes MICHAEL SAUNDERS & COMPANY

644 Rivendell Blvd, Osprey, FL 34229

/40
Est $1,147,299 Not Listed For Sale

109 Tina Island Dr, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,827 Sq Ft
- Built 1988
109 Tina Island Dr, Osprey, FL 34229

Last Sold Summary
- 6% Below List Price
- $433/SF
- 15 Days On Market
Last Sold Price $1,225,000

Last Listing Agent Sherri Mills Michael Saunders

/60
$10,750,000
- 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
$675,000 Sold Jan 21, 2026

409 N Point Rd Unit 501, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
- Built 2004
Last Sold Summary
- 36% Below List Price
- $260/SF
- 575 Days On Market
Current Estimated Value $693,761

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

409 N Point Rd Unit 501, Osprey, FL 34229

/2
Est $524,953 Not Listed For Sale

502 Oak Bay Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,116 Sq Ft
- Built 1995
502 Oak Bay Dr, Osprey, FL 34229

Last Sold Summary
- 6% Above List Price
- $234/SF
- 88 Days On Market
Last Sold Price $495,000

Last Listing Agent Carey Beychok RE/MAX

/47
$200,000
- 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
$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 $1,397,129

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

378 MacEwen Dr, Osprey, FL 34229

/65
Est $950,909 Not Listed For Sale

800 Eaglenook Way, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,632 Sq Ft
- Built 1978
800 Eaglenook Way, Osprey, FL 34229

Last Sold Summary
- $361/SF
- 2 Days On Market
Last Sold Price $950,000

Last Listing Agent Ashley Wallace COLDWELL BANKER REALTY

/60
$519,000
- 2 Beds
- 2 Baths
- 1,555 Sq Ft
786 Sarabay Rd Unit 19, Osprey, FL 34229

Boat Slips included, Insurance included, Ground maintenance included!!Secluded waterfront community on Little Sarasota Bay with access to the Intracoastal Waterway and the Gulf. Heron Bay Club has boat slips available! This small community on Little Sarasota Bay offers striking sunsets. Across from the northern section of Casey Key, the 10-acre property features 26 villas. This complex is

Michael Christo PREMIER SOTHEBYS INTL REALTY

786 Sarabay Rd Unit 19, 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 $770,063

Last Listing Agent Toni Zarghami KW COASTAL LIVING III

448 Park Trace Blvd, Osprey, FL 34229

/9
Est $179,824 Not Listed For Sale

242 Washington Ave, Osprey, FL 34229
- 2 Beds
- 1 Bath
- 630 Sq Ft
- Built 1950
242 Washington Ave, Osprey, FL 34229

Last Sold Summary
- 6% Above List Price
- $270/SF
- 162 Days On Market
Last Sold Price $170,000

Last Listing Agent Dan Miller PREFERRED SHORE LLC

/92
$1,775,000 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
$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 $3,560,611

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

275 Lookout Point Dr, Osprey, FL 34229

/2
Est $648,006 Not Listed For Sale

385 N Point Rd Unit 602, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,055 Sq Ft
- Built 2000
385 N Point Rd Unit 602, Osprey, FL 34229

Last Sold Summary
- $316/SF
- 174 Days On Market
Last Sold Price $650,000

Last Listing Agent Matt Buttner LIST NOW REALTY, LLC

/86
$225,000
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
252 Sun Air Cir, Osprey, FL 34229

Welcome to easy Florida living in The Arbors of Osprey! This beautifully updated 2-bedroom, 2-bath manufactured home offers modern finishes, thoughtful upgrades, and a spacious open layout designed for comfort and entertaining. Step inside to discover newer tile and laminate flooring flowing throughout the home. The remodeled kitchen is a true showstopper, featuring raised-panel cabinetry, quartz

Karen Geiger COLDWELL BANKER SARASOTA CENT.

252 Sun Air Cir, Osprey, FL 34229
/2
$318,000 Sold Mar 25, 2026

116 Navigation Cir Unit 106, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,430 Sq Ft
- Built 2016
Last Sold Summary
- 2% Below List Price
- $222/SF
- 220 Days On Market
Current Estimated Value $324,771

Last Listing Agent Pan Steele, GRI COLDWELL BANKER REALTY

116 Navigation Cir Unit 106, Osprey, FL 34229

/2
Est $514,158 Not Listed For Sale

515 Oak Bay Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,977 Sq Ft
- Built 1995
515 Oak Bay Dr, Osprey, FL 34229

Last Sold Summary
- $259/SF
- 116 Days On Market
Last Sold Price $512,500

Last Listing Agent Thomas Cail RE/MAX

/78
$690,000 Open Sun 1PM - 3PM
- 3 Beds
- 2.5 Baths
- 2,134 Sq Ft
102 Windward Dr, Osprey, FL 34229

NEW PRICE! 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

David Cyr WILLIAM RAVEIS FLORIDA LLC

102 Windward Dr, Osprey, FL 34229
/2
$1,900,000 Sold Feb 10, 2026

340 Osprey Point Dr, Osprey, FL 34229
- 5 Beds
- 7 Baths
- 6,001 Sq Ft
- Built 1998
Last Sold Summary
- 24% Below List Price
- $317/SF
- 273 Days On Market
Current Estimated Value $1,954,948

Last Listing Agent Lee Brewer RE/MAX ALLIANCE GROUP

340 Osprey Point Dr, Osprey, FL 34229

/34
Est $593,309 Not Listed For Sale

1358 Thornapple Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,163 Sq Ft
- Built 2003
1358 Thornapple Dr, Osprey, FL 34229

Last Sold Summary
- 2% Below List Price
- $280/SF
- 86 Days On Market
Last Sold Price $605,000

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

/24
$600,000
- Land
- 0.34 Acre
- $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 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 ERA POWERED

458 N Shore Dr, 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 $2,035,195

Last Listing Agent Nancy Endara PREMIER SOTHEBY'S INTERNATIONAL REALTY

1862 Island Way, Osprey, FL 34229

/42
Est $590,748 Not Listed For Sale

564 Crane Prairie Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,079 Sq Ft
- Built 2005
564 Crane Prairie Way, Osprey, FL 34229

Last Sold Summary
- $284/SF
- 69 Days On Market
Last Sold Price $590,000

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

/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

Showing Results 401 - 440, Page 11 of 18

Florida Sarasota County Osprey

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