5,082

Osprey, FL Homes

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  • /63

    $875,000

    $22K PRICE DROP Pending
    • 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

    $1,500,000

    Sold Dec 12, 2025

    325 Osprey Point Dr, Osprey, FL 34229

    • 3 Beds
    • 4.5 Baths
    • 3,905 Sq Ft
    • Built 1986

    Last Sold Summary

    • 11% Below List Price
    • $384/SF
    • 12 Days On Market

    Current Estimated Value $1,493,672

    Last Listing Agent Mark Lyda GENEROUS PROPERTY

    325 Osprey Point Dr, Osprey, FL 34229
    • /2

      Est $1,030,840

      Not Listed For Sale

      247 Keel Way, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 2,871 Sq Ft
      • Built 1979
      247 Keel Way, Osprey, FL 34229

      Last Sold Summary

      • 70 Days On Market

  • /70

    $2,199,900

    $100K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,236 Sq Ft

    180 Lookout Point Dr, Osprey, FL 34229

    Virtually Staged. Welcome to 180 Lookout Point Drive in the sought-after Southbay Yacht & Racquet Club with deep water marina and available boat slips, the opportunity to walk to your boat in a deep water marina with your home resting safely in Flood Zone X (where flood insurance is not even required by lenders) doesn't come along often. This is an extraordinary residence taken fully down to the

    Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

    180 Lookout Point Dr, Osprey, FL 34229
  • /2

    $285,000

    Sold Mar 24, 2026

    2043 Cordes St, Osprey, FL 34229

    • 3 Beds
    • 2 Baths
    • 1,186 Sq Ft
    • Built 1957

    Last Sold Summary

    • 5% Below List Price
    • $240/SF
    • 44 Days On Market

    Current Estimated Value $282,655

    Last Listing Agent Travis Matthews PREFERRED SHORE LLC

    2043 Cordes St, Osprey, FL 34229
    • /2

      Est $3,590,967

      Not Listed For Sale

      275 Lookout Point Dr, Osprey, FL 34229

      • 5 Beds
      • 5 Baths
      • 5,279 Sq Ft
      • Built 2007
      275 Lookout Point Dr, Osprey, FL 34229

      Last Sold Summary

      • 124 Days On Market

  • /92

    $789,000

    $136K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,246 Sq Ft

    21 Bayhead Ln, Osprey, FL 34229

    Looking for a home you can truly fall in love with? Your search ends here. This thoughtfully updated, impeccably maintained 3 bedroom, 2 bath residence in The Oaks Preserve offers the perfect blend of comfort, style, and privacy. And you can BUY WITH CONFIDENCE — THE PROACTIVE SELLERS HAVE COMPLETED INSPECTIONS IN ADVANCE TO SHARE WITH BUYERS, GIVING YOU CLARITY FROM THE START. No guessing...what

    Steve Abbe COLDWELL BANKER REALTY

    21 Bayhead Ln, Osprey, FL 34229
  • /2

    $113,000

    Sold Feb 17, 2026

    26 Siesta Cir W, Osprey, FL 34229

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft
    • Built 1968

    Last Sold Summary

    • 13% Below List Price
    • $188/SF
    • 55 Days On Market

    Last Listing Agent Gary Hoskins COLDWELL BANKER REALTY

    26 Siesta Cir W, Osprey, FL 34229
    • /18

      Est $539,822

      Not Listed For Sale

      458 N Shore Dr, Osprey, FL 34229

      • 2 Beds
      • Built 1968
      458 N Shore Dr, Osprey, FL 34229

      Last Sold Summary

      • 83 Days On Market

  • /50

    $1,850,000

    Open Sun 1PM - 4PM
    • 3 Beds
    • 2 Baths
    • 2,411 Sq Ft

    206 Four Knot Ln, Osprey, FL 34229

    Offering 3 bedrooms, 2 baths, den/office, 2,411 square feet under air, a spacious living room, a 2-car garage, and a private 14' x 37' heated pool centrally positioned as the focal point of the home. This beautifully updated, move-in-ready residence blends luxury, comfort, and the ultimate coastal lifestyle in the highly sought-after waterfront Southbay Yacht & Racquet Club/Marina Community. The

    Leighton Allenby Realty One Group MVP

    206 Four Knot Ln, Osprey, FL 34229
  • /2

    $1,700,000

    Sold Jan 15, 2026

    409 N Point Rd Unit 1003, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,778 Sq Ft
    • Built 2004

    Last Sold Summary

    • 6% Below List Price
    • $612/SF
    • 0 Days On Market

    Current Estimated Value $1,657,474

    Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

    409 N Point Rd Unit 1003, Osprey, FL 34229
    • /40

      Est $489,932

      Not Listed For Sale

      510 Meadow Sweet Cir, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 1,788 Sq Ft
      • Built 2001
      510 Meadow Sweet Cir, Osprey, FL 34229

      Last Sold Summary

      • 19 Days On Market

  • /95

    $1,349,000

    $51K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,824 Sq Ft

    365 S Shore Dr, Osprey, FL 34229

    Wake up to ever-changing INTRACOASTAL VIEWS – SUNSETS dancing across the water, BOATS gliding by, and untouched wildlife. Set on an EXTRA-DEEP WATER FRONT LOT with GULF ACCESS, this exceptional residence offers a rare blend of privacy, sweeping WATERFRONT views, timeless COASTAL DESIGN, and a DOCK WITH A 10,000LB BOAT LIFT that places open water just minutes away. A BOATERS PARADISE, this refined

    Lisa Asaro EXIT KING REALTY

    365 S Shore Dr, Osprey, FL 34229
  • /2

    $525,000

    Sold May 21, 2026

    1348 Thornapple Dr, Osprey, FL 34229

    • 3 Beds
    • 2 Baths
    • 2,171 Sq Ft
    • Built 2003

    Last Sold Summary

    • 2% Below List Price
    • $242/SF
    • 9 Days On Market

    Current Estimated Value $535,610

    Last Listing Agent Margot Vigar (Leonard) COLDWELL BANKER REALTY

    1348 Thornapple Dr, Osprey, FL 34229
    • /41

      Est $554,087

      Not Listed For Sale

      506 Oak Bay Dr, Osprey, FL 34229

      • 4 Beds
      • 2.5 Baths
      • 1,944 Sq Ft
      • Built 1995
      506 Oak Bay Dr, Osprey, FL 34229

      Last Sold Summary

      • 10 Days On Market

  • /97

    $690,000

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

    385 N Point Rd Unit 503, Osprey, FL 34229

    TURN-KEY FURNISHED 5TH FLOOR RESIDENCE WITH LOVELY VIEWS! Experience luxury coastal living in this stunning 5th floor condo in Meridian at The Oaks Preserve. With water and Preserve views that rival those of higher floors, this residence offers 3 bedrooms, 3 full baths, and a dining room, all enhanced with NEW FURNISHINGS. OFFERED TURNKEY, ALL YOU NEED TO DO IS MOVE IN AND START ENJOYING A

    Steve Abbe COLDWELL BANKER REALTY

    385 N Point Rd Unit 503, Osprey, FL 34229
  • /2

    $730,000

    Sold Oct 24, 2025

    1728 S Creek Dr, Osprey, FL 34229

    • 3 Beds
    • 2 Baths
    • 2,320 Sq Ft
    • Built 1989

    Last Sold Summary

    • 6% Below List Price
    • $315/SF
    • 44 Days On Market

    Current Estimated Value $739,737

    Last Listing Agent Melanie Albaric MICHAEL SAUNDERS & COMPANY

    1728 S Creek Dr, Osprey, FL 34229
    • /50

      Est $342,366

      Not Listed For Sale

      1821 Highland Rd, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 1,184 Sq Ft
      • Built 1998
      1821 Highland Rd, Osprey, FL 34229

      Last Sold Summary

      • 53 Days On Market

  • /7

    $269,999

    $10K PRICE INCREASE
    • Land
    • 5,662 Sq Ft
    • $2,076,915 per Acre

    456 Washington Ave, Osprey, FL 34229

    Owner Financing is Available. Prime Land at 456 Washington Ave, Osprey, FL 34229 – A Rare Gem Near Historic Spanish Point & Selby Gardens. Don’t miss out on this incredible opportunity to own a prime piece of land at 456 Washington Ave, located in the heart of Osprey, FL. Surrounded by natural beauty and rich history, this property is just moments from the renowned Historic Spanish Point and the

    Mike Vo FLOTACAL

    456 Washington Ave, Osprey, FL 34229
  • /2

    $120,000

    Sold Aug 29, 2025

    0 Cordes St Unit MFRN6137674, Osprey, FL 34229

    • Land
    • 7,840 Sq Ft
    • $666,667 per Acre

    Last Sold Summary

    • 18% Below List Price
    • 153 Days On Market

    Last Listing Agent Zuzanna Kacprzak CENTURY 21 SCHMIDT REAL ESTATE

    0 Cordes St Unit MFRN6137674, Osprey, FL 34229
    • /86

      Est $1,708,026

      Not Listed For Sale

      435 E MacEwen Dr, Osprey, FL 34229

      • 4 Beds
      • 3.5 Baths
      • 4,087 Sq Ft
      • Built 1998
      435 E MacEwen Dr, Osprey, FL 34229

      Last Sold Summary

      • 268 Days On Market

  • /34

    $109,900

    $29K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    348 Tropic Dr, Osprey, FL 34229

    Perfect Home for a SNOW BIRD OR A "YEAR-ROUNDER "!! The Arbors is the BEST of the Florida sun belt communities. THE ROOF -- New in 2022 with 15-Year Transferable Waranty. THE CARPORT -- New 2023 No leaks. This lovingly maintained manufactured home is in a PET FRIENDLY zone. Your LOW $215/month HOA provides: YOUR Water. YOUR Sewer. YOUR Lawn care. YOUR Cable service. A lucky buyer could move in

    John Alexander FINE PROPERTIES

    348 Tropic Dr, Osprey, FL 34229
  • /2

    $975,000

    Sold Aug 08, 2025

    3904 Waypoint Ave, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,344 Sq Ft
    • Built 2016

    Last Sold Summary

    • 18% Below List Price
    • $416/SF
    • 161 Days On Market

    Current Estimated Value $997,110

    Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

    3904 Waypoint Ave, Osprey, FL 34229
    • /2

      Est $947,075

      Not Listed For Sale

      1321 Southbay Dr, Osprey, FL 34229

      • 3 Beds
      • 2.5 Baths
      • 2,968 Sq Ft
      • Built 1978
      1321 Southbay Dr, Osprey, FL 34229

      Last Sold Summary

      • 29 Days On Market

  • /20

    $530,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,004 Sq Ft

    4429 Conchfish Ln, Osprey, FL 34229

    Beautiful residence located in The Palms of Casey Key community, offering a thoughtfully designed layout ideal for everyday living and entertaining. The home spans approximately 2,000+ square feet and features updated flooring throughout all bedrooms and closets, along with tile in the main living areas for durability and easy upkeep. A spacious great room anchors the interior, creating a natural

    Jennifer Kenna EXP REALTY, LLC

    4429 Conchfish Ln, Osprey, FL 34229
  • /2

    $170,000

    Sold Apr 01, 2026

    911 Tranquility Cir, Osprey, FL 34229

    • Land
    • 18,295 Sq Ft
    • $404,762 per Acre

    Last Sold Summary

    • 7 Days On Market

    Last Listing Agent Mike Winger TIDELINE REAL ESTATE BROKERS

    911 Tranquility Cir, Osprey, FL 34229
    • /2

      Est $1,145,772

      Not Listed For Sale

      327 Sea Anchor Dr, Osprey, FL 34229

      • 2 Beds
      • 3 Baths
      • 2,521 Sq Ft
      • Built 1981
      327 Sea Anchor Dr, Osprey, FL 34229

      Last Sold Summary

      • 20 Days On Market

  • /49

    $1,750,000

    $600K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,977 Sq Ft

    18 N Casey Key Rd, Osprey, FL 34229

    Under contract-accepting backup offers. Elegantly renovated bayfront retreat on Casey Key and tastefully remodeled in 2012, this stunning bayfront home blends timeless coastal elegance with modern functionality, all in one of the desired locations on Casey Key. Designed for relaxing and entertaining, the open-concept living room, kitchen, and family room offer inviting spaces to gather, while the

    Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

    18 N Casey Key Rd, Osprey, FL 34229
  • /2

    $534,000

    Sold Dec 11, 2025

    757 Placid Lake Dr, Osprey, FL 34229

    • 2 Beds
    • 2 Baths
    • 1,845 Sq Ft
    • Built 2001

    Last Sold Summary

    • 1% Below List Price
    • $289/SF
    • 3 Days On Market

    Current Estimated Value $526,136

    Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

    757 Placid Lake Dr, Osprey, FL 34229
    • /2

      Est $519,895

      Not Listed For Sale

      629 Oak Bay Dr, Osprey, FL 34229

      • 4 Beds
      • 2 Baths
      • 1,867 Sq Ft
      • Built 1996
      629 Oak Bay Dr, Osprey, FL 34229

      Last Sold Summary

      • 250 Days On Market

  • /96

    $1,495,000

    $255K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,872 Sq Ft

    422 Blue Garden Ln, Osprey, FL 34229

    Discover incredible value and endless potential in this beautifully maintained 3 bedroom, 3.5 bath home, tucked into lush tropical landscaping, on a quiet cul-de-sac in The Oaks Bayside. A grand traditional residence, with generous sized rooms, flexible living areas, and a private outdoor setting, the possibilities here are limitless. Step into the marble entry through the double front doors, and

    Steve Abbe COLDWELL BANKER REALTY

    422 Blue Garden Ln, Osprey, FL 34229
  • /2

    $247,000

    Sold Aug 14, 2025

    121 Woodland Place Unit 121, Osprey, FL 34229

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft
    • Built 1979

    Last Sold Summary

    • 7% Below List Price
    • $186/SF
    • 3 Days On Market

    Current Estimated Value $236,822

    Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

    121 Woodland Place Unit 121, Osprey, FL 34229
    • /2

      Est $1,865,679

      Not Listed For Sale

      451 E MacEwen Dr, Osprey, FL 34229

      • 4 Beds
      • 3.5 Baths
      • 4,368 Sq Ft
      • Built 1998
      451 E MacEwen Dr, Osprey, FL 34229

      Last Sold Summary

      • 3 Days On Market

  • /19

    $417,000

    $26K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,725 Sq Ft

    1811 Highland Rd, Osprey, FL 34229

    PRIVATE NEIGHBORHOOD - Fully Furnished 2 Bedroom Townhouse in the Casey Key area, QUAINT, SPACIOUS 2-CAR Tandem GARAGE + Carport, modern, high ceilings, kitchen upgrades, screened balcony, 2 beds + den; 2 baths; living area and kitchen open plan; community pool Conveniently located between Sarasota, Siesta Key, Venice, and the Gulf Beaches.Walking distance to Casey Key Mainland (Chef Rolfs),

    Stephen Hachey REALTY OF RIVERVIEW LLC

    1811 Highland Rd, Osprey, FL 34229
  • /2

    $511,500

    Sold Jun 17, 2026

    562 Oak Bay Dr, Osprey, FL 34229

    • 3 Beds
    • 2.5 Baths
    • 2,414 Sq Ft
    • Built 1995

    Last Sold Summary

    • 9% Below List Price
    • $212/SF
    • 22 Days On Market

    Current Estimated Value $554,851

    Last Listing Agent Julianna Burns BERKSHIRE HATHAWAY HOMESERVICE

    562 Oak Bay Dr, Osprey, FL 34229
    • /11

      Est $903,144

      Not Listed For Sale

      226 Saint James Park, Osprey, FL 34229

      • 3 Beds
      • 2.5 Baths
      • 2,591 Sq Ft
      • Built 1988
      226 Saint James Park, Osprey, FL 34229

      Last Sold Summary

      • 0 Days On Market

  • /61

    $1,950,000

    • 5 Beds
    • 5.5 Baths
    • 4,885 Sq Ft

    97 Sugar Mill Dr, Osprey, FL 34229

    Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed

    Maria 'Indy' Domenech PALM PARADISE REALTY GROUP

    97 Sugar Mill Dr, Osprey, FL 34229
  • /2

    $1,600,000

    Sold May 14, 2026

    228 Saint James Park, Osprey, FL 34229

    • 3 Beds
    • 2.5 Baths
    • 2,425 Sq Ft
    • Built 1997

    Last Sold Summary

    • 6% Below List Price
    • $660/SF
    • 33 Days On Market

    Current Estimated Value $1,615,231

    Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

    228 Saint James Park, Osprey, FL 34229
    • /70

      Est $1,700,504

      Not Listed For Sale

      337 Passage Way, Osprey, FL 34229

      • 5 Beds
      • 5 Baths
      • 4,551 Sq Ft
      • Built 1984
      337 Passage Way, Osprey, FL 34229

      Last Sold Summary

      • 57 Days On Market

  • /89

    $1,050,000

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

    292 Turquoise Ln, Osprey, FL 34229

    This stunning, updated home sits on a corner lot; the largest in Emerald Woods. Located behind the gates of The Oaks Preserve, this maintenance free residence features 3 bedrooms, 2 baths and a 2-car air conditioned garage along with premium finishes throughout. The updated kitchen, equipped with high-end stainless steel appliances, will delight any home chef. The spacious master suite includes a

    Steve Abbe COLDWELL BANKER REALTY

    292 Turquoise Ln, Osprey, FL 34229

Showing Results 241 - 280, Page 7 of 18

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