8

Osprey, FL Homes under $500,000

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  • /70

    $479,000

    • 3 Beds
    • 2 Baths
    • 1,904 Sq Ft

    26 Bay Acres Ave, Osprey, FL 34229

    Discover this hidden gem in the sought-after waterfront community in Bay Acres, positioned West of the Trail with direct access to the Intracoastal Waterway situated on .037 acres that is completely fenced in for privacy! This beautifully renovated home has 3 spacious bedrooms and 2 bathrooms across 1,904 sqft, offering a split bedroom floor plan for maximum privacy. The primary suite features

    Erica Giesler RE/MAX ALLIANCE GROUP

    26 Bay Acres Ave, Osprey, FL 34229
  • /59

    $474,900

    • 3 Beds
    • 2 Baths
    • 1,883 Sq Ft

    7303 Jessie Harbor Dr Unit 7303, Osprey, FL 34229

    PENTHOUSE CONDO IN WATERFRONT COMMUNITY!Experience luxury coastal living in this spacious 3-bedroom, 2-bath penthouse condo, perfectly situated on a tranquil canal with dockage and direct, bridge-free access to the Intracoastal Waterway and the Gulf. This impressive 3rd-floor residence features an open floor plan with expansive rooms, plantation shutters, and three private balconies—ideal for

    Toy Coxey KW COASTAL LIVING

    7303 Jessie Harbor Dr Unit 7303, Osprey, FL 34229
  • /53

    $499,900

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

    780 Sarabay Rd Unit 16, Osprey, FL 34229

    Welcome to Heron Bay Club, an exclusive enclave of just 25 uniquely designed villas situated on 11 acres along the Little Sarasota Bay. This spacious 2-bedroom, 2-bath villa features a versatile bonus room—perfect for a home office, den, or even a guest bedroom. Inside, you'll find a thoughtfully updated interior with a renovated kitchen featuring raised panel maple cabinetry and granite

    Mark Segreto RMS ELITE PROPERTIES

    780 Sarabay Rd Unit 16, Osprey, FL 34229
  • /70

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,541 Sq Ft

    321 Sorrento Dr, Osprey, FL 34229

    Welcome to this beautifully maintained Sorrento Shores pool home, exuding timeless Mediterranean charm. Built in 1988, this residence offers a warm, inviting atmosphere with classic architectural details such as a tile roof, stucco exterior, and arched entryways.Inside, you'll find a spacious and functional layout ideal for both everyday living and entertaining. The sunlit living areas

    Jim Comly EXIT KING REALTY

    321 Sorrento Dr, Osprey, FL 34229
  • /36

    $444,000

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    352 Glenwood Ave, Osprey, FL 34229

    Beautifully Maintained 3-Bedroom Home with No HOA or Deed RestrictionsWelcome to this immaculate 3-bedroom, 2-bath home, newly built in 2021 and perfectly located just minutes from top-rated beaches, shopping, dining, and entertainment. This move-in-ready home offers a clean, modern design with a spacious open floor plan that’s ideal for both relaxing and entertaining.Enjoy

    Kano Keller WHITE SANDS REALTY GROUP FL

    352 Glenwood Ave, Osprey, FL 34229
  • /54

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,885 Sq Ft

    519 Bayview Ave, Osprey, FL 34229

    Live the Sarasota Coastal Lifestyle in Bay Acres – Boating Community! Nestled in the desirable waterfront neighborhood of Bay Acres, this charming 3-bedroom, 2-bath with extra Bonus Florida room and 2 car garage home offers a rare combination of coastal convenience, spacious living, and modern updates. Perfect for boating and RV enthusiasts, the property includes a 42' x 16' parking pad with

    Michael Gray COLDWELL BANKER REALTY

    519 Bayview Ave, Osprey, FL 34229
  • /62

    $449,900

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft

    2251 Jessie Harbor Dr, Osprey, FL 34229

    **1ST FLOOR END UNIT CONDO with WATER VIEW and PRIVATE 1-CAR GARAGE, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO (No Bridges)** Featuring 2 BEDS and 2 FULL BATHS, this LIGHT AND BRIGHT, 1ST FLOOR END UNIT dwelling features an Impressive Kitchen with Granite counters, Stainless Steel appliances and solid wood cabinets while the Spacious

    Mark Lyda GENEROUS PROPERTY

    2251 Jessie Harbor Dr, Osprey, FL 34229
  • /70

    $485,000

    • 2 Beds
    • 3 Baths
    • 2,837 Sq Ft

    264 Woods Point Rd, Osprey, FL 34229

    One or more photo(s) has been virtually staged. SELLER WILL CONSIDER A LEASE PURCHASE. Try it before you buy it. Experience maintenance free Florida living, just a short walk, bike or drive to Casey Key in this large villa situated in the rarely available neighborhood of Blackburn Point Woods. The home greets visitors with a large welcoming paver patio providing a place to relax and greet your

    Mark Midyett KELLER WILLIAMS ON THE WATER S

    264 Woods Point Rd, Osprey, FL 34229

Home Trends in Osprey, FL

Housing Trends

Median Sale Price
$750,000
Median Single Family Sale Price
$788,000
Median Townhouse Sale Price
$487,000
Median 2 Bedroom Sale Price
$292,500
Median 1 Bedroom Sale Price
$265,000
Average Price Per Sq Ft
$380
Number of Homes for Sale
106
Last 12 months Home Sales
185
Months of Supply
6.90
Median List Price
$791,950
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
-7%
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