Osprey, FL Homes

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  /36

  $449,000

  Open Sat 11AM - 2PM

  • 2 Beds
  • 1 Bath
  • 1,211 Sq Ft

  811 Sarabay Rd, Osprey, FL 34229

  Nestled on a generous 0.74-acre lot, this 2-bedroom, 1-bath residence offers 1,211 square feet of living space in a peaceful, private setting just moments from Sarasota Bay. Set back on a semi-private driveway and surrounded by mature landscaping and fruit trees, this property provides a rare opportunity to enjoy the charm and character of Old Florida living while remaining close to all of

  Ariel Howell LPT REALTY, LLC

  811 Sarabay Rd, Osprey, FL 34229
• 

  

  /2

  $195,000

  Sold Jun 12, 2026

  252 Sun Air Cir, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1979

  Last Sold Summary

  • 17% Below List Price
  • $169/SF
  • 66 Days On Market

  Last Listing Agent Karen Geiger COLDWELL BANKER SARASOTA CENT.

  252 Sun Air Cir, Osprey, FL 34229
• 

  

  /2

  Est $1,597,739

  Not Listed For Sale

  738 N MacEwen Dr, Osprey, FL 34229

  • 5 Beds
  • 5.5 Baths
  • 4,614 Sq Ft
  • Built 2003

  738 N MacEwen Dr, Osprey, FL 34229

  Last Sold Summary

  • 193 Days On Market
• 

  

  

  /43

  $395,000

  • 2 Beds
  • 2 Baths
  • 1,255 Sq Ft

  7204 Jessie Harbor Dr, Osprey, FL 34229

  **BEAUTIFULLY UPDATED CONDO, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO** Featuring 2 Beds and 2 Full Baths, this FULLY RENOVATED, 2ND FLOOR unit features an Impressive Kitchen with quartz counters, stainless steel appliances, new solid wood cabinets while the Spacious Owner’s Suite boasts custom built-in cabinets/closets and an equally

  Mark Lyda GENEROUS PROPERTY

  7204 Jessie Harbor Dr, Osprey, FL 34229
• 

  

  /2

  $565,000

  Sold Jun 04, 2026

  102 Windward Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,134 Sq Ft
  • Built 1986

  Last Sold Summary

  • 29% Below List Price
  • $265/SF
  • 169 Days On Market

  Current Estimated Value $655,693

  Last Listing Agent Regina Putrino WILLIAM RAVEIS - FLORIDA LLC

  102 Windward Dr, Osprey, FL 34229
• 

  /2

  Est $1,197,895

  Not Listed For Sale

  110 N Creek Ln, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 4,071 Sq Ft
  • Built 2002

  110 N Creek Ln, Osprey, FL 34229

  Last Sold Summary

  • 8 Days On Market
• 

  

  /63

  $785,000

  $50K PRICE DROP Pending

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft

  393 N Point Rd Unit 401, Osprey, FL 34229

  Offered Turn-Key Furnished...This beautifully updated 3 bedroom, 3 bath residence with a den offers exceptional space, style, and privacy in Meridian at The Oaks Preserve. The home features a redesigned kitchen with new appliances and granite countertops, a newer A/C system, and rich wood flooring throughout. As an end unit, it enjoys abundant natural light, and the expansive screened

  Steve Abbe COLDWELL BANKER REALTY

  393 N Point Rd Unit 401, Osprey, FL 34229
• 

  /2

  $880,000

  Sold Jan 30, 2026

  392 Park Trace Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,802 Sq Ft
  • Built 2001

  Last Sold Summary

  • 6% Below List Price
  • $314/SF
  • 32 Days On Market

  Current Estimated Value $868,963

  Last Listing Agent Ryan Skrzypkowski COLDWELL BANKER REALTY

  392 Park Trace Blvd, Osprey, FL 34229
• 

  /2

  Est $963,336

  Not Listed For Sale

  146 Yacht Harbor Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,627 Sq Ft
  • Built 1986

  146 Yacht Harbor Dr, Osprey, FL 34229

  Last Sold Summary
• 

  

  /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

  $4,040,000

  Sold Jan 05, 2026

  1049 N Casey Key Rd, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,582 Sq Ft
  • Built 1990

  Last Sold Summary

  • 15% Below List Price
  • $1,565/SF
  • 212 Days On Market

  Current Estimated Value $3,711,429

  Last Listing Agent Courtney Green PREMIER SOTHEBYS INTL REALTY

  1049 N Casey Key Rd, Osprey, FL 34229
• 

  /2

  Est $1,897,664

  Not Listed For Sale

  916 MacEwen Dr, Osprey, FL 34229

  • 5 Beds
  • 7.5 Baths
  • 5,987 Sq Ft
  • Built 1991

  916 MacEwen Dr, Osprey, FL 34229

  Last Sold Summary

  • 1 Day On Market
• 

  

  /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
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  /2

  $925,000

  Sold Jun 08, 2026

  1016 Scherer Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,921 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $317/SF
  • 1 Day On Market

  Current Estimated Value $939,946

  Last Listing Agent Rachel Tritschler RE/MAX ALLIANCE GROUP

  1016 Scherer Way, Osprey, FL 34229
• 

  /2

  Est $1,859,274

  Not Listed For Sale

  676 Eagle Watch Ln, Osprey, FL 34229

  • 5 Beds
  • 5.5 Baths
  • 5,399 Sq Ft
  • Built 1992

  676 Eagle Watch Ln, Osprey, FL 34229

  Last Sold Summary

  • 12 Days On Market
• 

  

  /93

  $599,900

  $150K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 2,505 Sq Ft

  186 Windward Dr, Osprey, FL 34229

  Under contract-accepting backup offers. Price was dropped $50,000 on 5/7! Survey and pool quote are available! Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, and plenty of room for a private pool. As you enter the home, you will be greeted by the formal living room and dining

  Brittany Coleman KELLER WILLIAMS ON THE WATER S

  186 Windward Dr, Osprey, FL 34229
• 

  /2

  $625,000

  Sold Jul 26, 2025

  695 Rivendell Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,256 Sq Ft
  • Built 2001

  Last Sold Summary

  • 4% Below List Price
  • $277/SF
  • 1 Day On Market

  Current Estimated Value $626,267

  Last Listing Agent Dan Henson DALTON WADE INC

  695 Rivendell Blvd, Osprey, FL 34229
• 

  /2

  Est $246,161

  Not Listed For Sale

  104 Woodland Place, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1979

  104 Woodland Place, Osprey, FL 34229

  Last Sold Summary
• 

  

  /99

  $1,095,000

  Open Sat 11AM - 12:30PM $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 comfort,

  Edward Bieker DALTON WADE INC

  403 Longbow Trail, Osprey, FL 34229
• 

  /2

  $545,000

  Sold Mar 31, 2026

  711 Shadow Bay Way, Osprey, FL 34229

  • 4 Beds
  • 2 Baths
  • 2,133 Sq Ft
  • Built 2002

  Last Sold Summary

  • 9% Below List Price
  • $256/SF
  • 77 Days On Market

  Current Estimated Value $548,527

  Last Listing Agent Susan Keal MICHAEL SAUNDERS & COMPANY

  711 Shadow Bay Way, Osprey, FL 34229
• 

  

  /25

  Est $545,510

  Not Listed For Sale

  846 Oak Pond Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,126 Sq Ft
  • Built 1995

  846 Oak Pond Dr, Osprey, FL 34229

  Last Sold Summary

  • 113 Days On Market
• 

  /2

  $592,249

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  791 S Tamiami Trail Unit 201, Osprey, FL 34229

  Under Construction. UNDER CONSTRUCTION -STARTING FROM THE MID $500,000'S. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOW AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 3 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (2 BEDROOM AND 2 BATH UNITS ALSO

  Laurie Eshleman PRO GROUP REALTY & PROP MGT

  791 S Tamiami Trail Unit 201, Osprey, FL 34229
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  /2

  $520,000

  Sold Nov 14, 2025

  708 Anna Hope Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,133 Sq Ft
  • Built 2002

  Last Sold Summary

  • 5% Below List Price
  • $244/SF
  • 8 Days On Market

  Current Estimated Value $521,843

  Last Listing Agent Julien Collet PINEYWOODS REALTY LLC

  708 Anna Hope Ln, Osprey, FL 34229
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  /55

  Est $486,796

  Not Listed For Sale

  564 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,808 Sq Ft
  • Built 2003

  564 Meadow Sweet Cir, Osprey, FL 34229

  Last Sold Summary

  • 57 Days On Market
• 

  

  /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

  $631,000

  Sold Apr 23, 2026

  659 Rivendell Blvd, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,292 Sq Ft
  • Built 2001

  Last Sold Summary

  • 7% Below List Price
  • $275/SF
  • 22 Days On Market

  Current Estimated Value $642,871

  Last Listing Agent Stephanie Church COLDWELL BANKER REALTY

  659 Rivendell Blvd, Osprey, FL 34229
• 

  

  /79

  Est $562,181

  Not Listed For Sale

  587 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,217 Sq Ft
  • Built 1996

  587 Meadow Sweet Cir, Osprey, FL 34229

  Last Sold Summary

  • 16 Days On Market
• 

  

  /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

  $640,000

  Sold Jan 06, 2026

  5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,484 Sq Ft
  • Built 2004

  Last Sold Summary

  • 12% Below List Price
  • $258/SF
  • 130 Days On Market

  Current Estimated Value $639,293

  Last Listing Agent Robert Ruiz WILLIAM RAVEIS - FLORIDA LLC

  5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229
• 

  /2

  Est $487,880

  Not Listed For Sale

  230 Burney Rd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,219 Sq Ft
  • Built 1985

  230 Burney Rd, Osprey, FL 34229

  Last Sold Summary

  • 2 Days On Market
• 

  

  /47

  $259,900

  $10K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft

  232 Woodland Dr, Osprey, FL 34229

  Under contract-accepting backup offers. This condo has the 3 L's! Location Location Location! Located in the central area of Osprey making it an easy drive to area beaches, downtown Venice or Sarasota. Located about a half mile to the Inter Coastal, making for a great walking area on Casey Key. Located close to the well known Casey Key Fish House and Tiki Bar. Shopping and restaurants are all

  Pat Williams PAT WILLIAMS REALTY, LLC

  232 Woodland Dr, Osprey, FL 34229
• 

  /2

  $1,450,000

  Sold Jun 15, 2026

  76 Osprey Point Dr, Osprey, FL 34229

  • 3 Beds
  • 4.5 Baths
  • 4,364 Sq Ft
  • Built 1986

  Last Sold Summary

  • 17% Below List Price
  • $332/SF
  • 170 Days On Market

  Current Estimated Value $1,616,000

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  76 Osprey Point Dr, Osprey, FL 34229
• 

  

  /64

  Est $535,285

  Not Listed For Sale

  128 Villa Dr Unit 128, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1978

  128 Villa Dr Unit 128, Osprey, FL 34229

  Last Sold Summary

  • 67 Days On Market
• 

  

  /79

  $328,000

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft

  173 Navigation Cir Unit 107, Osprey, FL 34229

  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 backsplash, and stainless-steel appliances.

  Tim Weller EXIT KING REALTY

  173 Navigation Cir Unit 107, Osprey, FL 34229
• 

  /2

  $1,850,000

  Sold Apr 10, 2026

  140 N Casey Key Rd, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 2,473 Sq Ft
  • Built 1985

  Last Sold Summary

  • 26% Below List Price
  • $748/SF
  • 143 Days On Market

  Current Estimated Value $1,925,621

  Last Listing Agent Rhonda Carder EXP REALTY LLC

  140 N Casey Key Rd, Osprey, FL 34229
• 

  

  /70

  Est $615,244

  Not Listed For Sale

  433 S Shore Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,868 Sq Ft
  • Built 1984

  433 S Shore Dr, Osprey, FL 34229

  Last Sold Summary

  • 72 Days On Market
• 

  

  /64

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft

  764 Sarabay Rd Unit 8, Osprey, FL 34229

  One or more photo(s) has been virtually staged. 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 bayfront enclave of just 25 villas set across 10

  Michael Christo PREMIER SOTHEBYS INTL REALTY

  764 Sarabay Rd Unit 8, Osprey, FL 34229
• 

  /2

  $910,000

  Sold Nov 19, 2025

  766 Shadow Bay Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,438 Sq Ft
  • Built 1998

  Last Sold Summary

  • 9% Below List Price
  • $265/SF
  • 132 Days On Market

  Current Estimated Value $923,634

  Last Listing Agent Anne Pfitzenreiter COLDWELL BANKER SARASOTA CENT.

  766 Shadow Bay Way, Osprey, FL 34229
• 

  /2

  Est $745,025

  Not Listed For Sale

  242 Hidden Bay Dr Unit 304, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1999

  242 Hidden Bay Dr Unit 304, Osprey, FL 34229

  Last Sold Summary

  • 50 Days On Market
• 

  

  /10

  $269,000

  • Land
  • 13,939 Sq Ft
  • $840,625 per Acre

  0 Sarabay Rd, Osprey, FL 34229

  RARE OPPORTUNITY – WEST OF TRAIL -- OVERSIZED 0.32-ACRE CORNER HOMESITE in the sought-after Waterfront Community of Bay Acres in Osprey. Zoned RSF-2, the property offers the flexibility to build a custom home of approximately 4,500 square feet with a pool or design a smaller residence with a detached guest house or ADU. The lot is served by public water and sewer and includes a private well for a

  Mark Lyda GENEROUS PROPERTY

  0 Sarabay Rd, Osprey, FL 34229

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