Osprey, FL Homes

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  $525,000 Sold Dec 04, 2025

  1313 Thornapple Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,082 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $252/SF
  • 8 Days On Market

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1313 Thornapple Dr, Osprey, FL 34229
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  /24

  Est $301,615 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft

  4224 Expedition Way Unit 105, Osprey, FL 34229

  4224 Expedition Way Unit 105, Osprey, FL 34229
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  $1,295,000

  • 5 Beds
  • 3.5 Baths
  • 3,481 Sq Ft

  296 Pine Ranch Trail, Osprey, FL 34229

  **THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** & SELLER IS OFFERING A $25,000.00 CREDIT toward rate buy down/closing cost with acceptable contract. Welcome to your private retreat nestled in one of Osprey’s most desirable enclaves. This beautifully situated home rests on a lush greenbelt lot that borders the fairways of a

  Deborah Frederick ASHTON LAKES REALTY INC

  296 Pine Ranch Trail, Osprey, FL 34229
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  $765,000 Sold Jan 30, 2026

  385 N Point Rd Unit 404, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft
  • Built 2000

  Last Sold Summary

  • 17% Below List Price
  • $275/SF
  • 142 Days On Market

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  385 N Point Rd Unit 404, Osprey, FL 34229
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  Est $53,327 Not Listed For Sale

  • Studio
  • 45,244 Sq Ft

  570 Blackburn Point Rd Unit 1-SIES, Osprey, FL 34229

  570 Blackburn Point Rd Unit 1-SIES, Osprey, FL 34229
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  $1,970,000

  • 4 Beds
  • 4 Baths
  • 3,286 Sq Ft

  140 Sugar Mill Dr, Osprey, FL 34229

  **BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE RESIDENCE with Lush Garden Landscape** is located behind the Secure Gates of The Oaks Bayside, Country Club neighborhood. Featuring 4 BEDROOMS (2 En Suite) and 4 FULL BATHS, this Open Floorplan with Soaring Ceilings, Custom Built-Ins, Crown Moldings and refined details throughout is ideal for entertaining both inside and out! The

  Mark Lyda GENEROUS PROPERTY

  140 Sugar Mill Dr, Osprey, FL 34229
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  $760,000 Sold Jul 16, 2025

  790 Shadow Bay Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,091 Sq Ft
  • Built 2002

  Last Sold Summary

  • 9% Below List Price
  • $246/SF
  • 158 Days On Market

  Current Estimated Value $765,355

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  790 Shadow Bay Way, Osprey, FL 34229
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  Est $24,132 Not Listed For Sale

  • Studio
  • 45,244 Sq Ft

  570 Blackburn Point Rd Unit 9-LIDO, Osprey, FL 34229

  570 Blackburn Point Rd Unit 9-LIDO, Osprey, FL 34229
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  $2,100,000

  • 4 Beds
  • 5.5 Baths
  • 4,346 Sq Ft

  538 Dove Pointe, Osprey, FL 34229

  **ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous .83-acre elevated lot, this beautifully landscaped property offers the perfect combination of privacy, sophistication, and modern comfort. Built in 2002, this newer home

  Mark Lyda GENEROUS PROPERTY

  538 Dove Pointe, Osprey, FL 34229
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  $227,000 Sold Dec 15, 2025

  111 Woodland Place, Osprey, FL 34229

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

  Last Sold Summary

  • 7% Below List Price
  • $172/SF
  • 81 Days On Market

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

  111 Woodland Place, Osprey, FL 34229
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  Est $561,474 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,004 Sq Ft

  2006 Preymore St, Osprey, FL 34229

  2006 Preymore St, Osprey, FL 34229
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  $5,000,000

  • 4 Beds
  • 5.5 Baths
  • 5,087 Sq Ft

  101 Osprey Point Dr, Osprey, FL 34229

  A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within the private gates of The Oaks Bayside. Designed by architect Bo MacEwen, this one-of-a-kind home spans more than 5,000 square feet, all cleverly positioned on nearly an acre with 150 feet of lakefront. Situated on two of the community’s most desirable lots, the residence balances

  Joel Schemmel DOUGLAS ELLIMAN

  101 Osprey Point Dr, Osprey, FL 34229
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  $835,000 Sold May 21, 2025

  14021 Bellagio Way Unit 410, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 2,214 Sq Ft
  • Built 2006

  Last Sold Summary

  • 12% Below List Price
  • $377/SF
  • 42 Days On Market

  Current Estimated Value $830,539

  Last Listing Agent Adam Waxler UKEEPCOMMISSION REAL ESTATE

  14021 Bellagio Way Unit 410, Osprey, FL 34229
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  /17

  Est $304,462 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,244 Sq Ft

  4247 Expedition Way Unit 103, Osprey, FL 34229

  4247 Expedition Way Unit 103, Osprey, FL 34229
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  $899,000

  • 3 Beds
  • 2.5 Baths
  • 2,168 Sq Ft

  260 Hidden Bay Dr Unit B 405, Osprey, FL 34229

  Built in 2019 and perfectly positioned on the fourth floor, this waterfront residence offers sweeping views across the Intracoastal Waterway, tranquil mangroves, and surrounding waterways from nearly every room. Designed with comfort and functionality in mind, the three-bedroom plus office layout spans nearly 2,200 square feet of interior living space and captures the essence of relaxed coastal

  Roger Pettingell COLDWELL BANKER REALTY

  260 Hidden Bay Dr Unit B 405, Osprey, FL 34229
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  $747,850 Sold Aug 08, 2025

  424 Cezanne Dr, Osprey, FL 34229

  • 4 Beds
  • 4 Baths
  • 2,945 Sq Ft
  • Built 1975

  Last Sold Summary

  • 16% Below List Price
  • $254/SF
  • 128 Days On Market

  Current Estimated Value $764,700

  Last Listing Agent Christine Pope MICHAEL SAUNDERS & COMPANY

  424 Cezanne Dr, Osprey, FL 34229
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  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft

  169 Edgewood Dr, Osprey, FL 34229

  169 Edgewood Dr, Osprey, FL 34229
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  $789,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,168 Sq Ft

  260 Hidden Bay Dr Unit B 305, Osprey, FL 34229

  Under contract-accepting backup offers. Move-in Ready | Turnkey Furnished | Gulf & Intracoastal Views + Glorious Sunsets3 Bed | 2.5 Bath | Den w/ Custom Queen Murphy Bed | 2,168 Sq Ft | End Unit Bright, breezy, and beautifully maintained, this move-in ready End Unit at Edgewater at Hidden Bay is offered fully Turnkey Furnished by the original owners and designed for effortless coastal living.

  Cathy Rustin FIRST LIGHT REAL ESTATE

  260 Hidden Bay Dr Unit B 305, Osprey, FL 34229
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  $2,300,000 Sold Nov 05, 2025

  264 Saratoga Ct, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,857 Sq Ft
  • Built 1992

  Last Sold Summary

  • $596/SF
  • 9 Days On Market

  Current Estimated Value $2,214,696

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  264 Saratoga Ct, Osprey, FL 34229
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  Est $348,950 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,581 Sq Ft

  4260 Expedition Way Unit 4260, Osprey, FL 34229

  4260 Expedition Way Unit 4260, Osprey, FL 34229
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  $699,000

  • 3 Beds
  • 2 Baths
  • 2,032 Sq Ft

  242 Hidden Bay Dr Unit 302, Osprey, FL 34229

  Enjoy breathtaking water views and unforgettable sunsets over Little Sarasota Bay from this spacious three-bedroom condominium with an office, on the third floor with convenient elevator access. This beautifully appointed residence is in the exclusive, gated Hidden Bay community, a waterfront gem. The open floor plan features soaring ceilings, PGT impact windows, sliding glass doors, new

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  242 Hidden Bay Dr Unit 302, Osprey, FL 34229
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  $358,000 Sold Nov 13, 2025

  115 Green St, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Built 1990

  Last Sold Summary

  • 4% Above List Price
  • $238/SF
  • 5 Days On Market

  Last Listing Agent Robin Leonardi MICHAEL SAUNDERS & COMPANY

  115 Green St, Osprey, FL 34229
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  Est $605,947 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,975 Sq Ft

  2001 Cordes St, Osprey, FL 34229

  2001 Cordes St, Osprey, FL 34229
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  $699,000

  • 3 Beds
  • 3 Baths
  • 3,147 Sq Ft

  3603 N Point Rd Unit 202, Osprey, FL 34229

  **ELEGANT and SPACIOUS CORNER CONDO UNIT – NEARLY 3200sf – With MULTIPLE BALCONIES** found behind the gates of the highly sought after Oaks-Preserve neighborhood. This Light and Bright Open Floorplan offers 3 En Suite Bedrooms, 3 Baths, 2 assigned Parking spaces including 1 under building, Climate-controlled storage and much more! Crown moldings, engineered hardwood floors, expansive kitchen with

  Mark Lyda GENEROUS PROPERTY

  3603 N Point Rd Unit 202, Osprey, FL 34229
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  $540,000 Sold Nov 24, 2025

  813 Oak Pond Dr, Osprey, FL 34229

  • 4 Beds
  • 2 Baths
  • 1,981 Sq Ft
  • Built 1996

  Last Sold Summary

  • 4% Below List Price
  • $273/SF
  • 121 Days On Market

  Last Listing Agent Jeremy Egglefield PREFERRED SHORE LLC

  813 Oak Pond Dr, Osprey, FL 34229
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  /48

  Est $356,181 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft

  123 Revolution Way Unit 101, Osprey, FL 34229

  123 Revolution Way Unit 101, Osprey, FL 34229
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  $1,175,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,698 Sq Ft

  1235 Yacht Harbor Dr, Osprey, FL 34229

  Under contract-accepting backup offers. Relax, you can move right in this one! This Southbay home has been updated beautifully with so many quality and custom features. A complete interior remodel was done in 2016 including all new underground PVC piping. A well thought out floor plan offers plenty of entertaining area including a living room with vaulted ceiling and open dining room. The new

  Pat Williams PAT WILLIAMS REALTY, LLC

  1235 Yacht Harbor Dr, Osprey, FL 34229
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  $335,000 Sold Mar 12, 2025

  738 Harms Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 1,700 Sq Ft
  • Built 1986

  Last Sold Summary

  • 15% Below List Price
  • $197/SF
  • 26 Days On Market

  Current Estimated Value $374,824

  Last Listing Agent Warren McGregor MCGREGOR INTERNATIONAL REAL ESTATE CO

  738 Harms Dr, Osprey, FL 34229
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  Est $382,869 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft

  4185 Frontier Ln Unit 102, Osprey, FL 34229

  4185 Frontier Ln Unit 102, Osprey, FL 34229
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  /99

  $699,000

  • 3 Beds
  • 3 Baths
  • 2,203 Sq Ft

  401 N Point Rd Unit 603, Osprey, FL 34229

  One or more photo(s) has been virtually staged. This incredible offering has everything you need to live a luxury condominium lifestyle in comfort and ease; 3 bedrooms, 3 full baths, a formal dining room and a 2ND FLOOR PRIVATE 2 CAR GARAGE! Add to this, gorgeous views from almost every room, and you have found a well-priced gem in Meridian at The Oaks Preserve to enjoy all the Gulf Coast has to

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 603, Osprey, FL 34229
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  $179,000 Sold Apr 28, 2025

  312 Tropic Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft
  • Built 1979

  Last Sold Summary

  • 10% Below List Price
  • $160/SF
  • 57 Days On Market

  Last Listing Agent Michelle Ward COMPASS FLORIDA LLC

  312 Tropic Dr, Osprey, FL 34229
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  Est $360,880 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft

  99 Explorer Dr Unit 102, Osprey, FL 34229

  99 Explorer Dr Unit 102, Osprey, FL 34229
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  $617,999 New Construction

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

  791 S Tamiami Trail Unit 101, 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 101, Osprey, FL 34229
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  $999,500 Sold Feb 14, 2025

  146 Yacht Harbor Dr, Osprey, FL 34229

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

  Last Sold Summary

  • $380/SF

  Current Estimated Value $984,348

  Last Listing Agent Susanne Losso COLDWELL BANKER REALTY

  146 Yacht Harbor Dr, Osprey, FL 34229
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  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 673 Sq Ft

  36 Siesta Cir W, Osprey, FL 34229

  36 Siesta Cir W, Osprey, FL 34229
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  $660,000

  • 3 Beds
  • 3 Baths
  • 2,055 Sq Ft

  385 N Point Rd Unit 402, Osprey, FL 34229

  **BEAUTIFULLY UPDATED CONDO with MARVELOUS VIEW** features 3-BEDS and 3-FULL BATH, Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Impressively Renovated interior which boasts Engineered Hardwood and designer Wood Plank Tile flooring, Plantation

  Mark Lyda GENEROUS PROPERTY

  385 N Point Rd Unit 402, Osprey, FL 34229
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  $35,000 Sold Jul 22, 2025

  570 Blackburn Point Rd Unit 17, Osprey, FL 34229

  • Built 2006

  Last Sold Summary

  • 29% Below List Price
  • 62 Days On Market

  Current Estimated Value $34,584

  Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 17, Osprey, FL 34229
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  Est $29,380 Not Listed For Sale

  • Studio
  • 45,244 Sq Ft

  570 Blackburn Point Rd Unit 28, Osprey, FL 34229

  570 Blackburn Point Rd Unit 28, Osprey, FL 34229
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  $875,000 Pending

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

  242 Hidden Bay Dr Unit 401, Osprey, FL 34229

  END UNIT with RARE THREE CAR GARAGE, IMPACT WINDOWS AND SLIDERS, and sweeping panoramic views. This beautifully appointed Baypointe Vista condo in Osprey blends comfort, style, and convenience, all set against the backdrop of the Intracoastal Waterway and Little Sarasota Bay. Natural light pours through wide water view windows, while plantation shutters throughout add timeless coastal charm and

  Bart Tracy LASBURY-TRACY REALTY INC.

  242 Hidden Bay Dr Unit 401, Osprey, FL 34229
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  $395,000 Sold Apr 30, 2025

  418 Sarabay Rd, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,767 Sq Ft
  • Built 1960

  Last Sold Summary

  • 15% Below List Price
  • $224/SF
  • 81 Days On Market

  Current Estimated Value $406,069

  Last Listing Agent Tracey Fiedler DALTON WADE INC

  418 Sarabay Rd, Osprey, FL 34229

Showing Results 121 - 160, Page 4 of 18