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3 bedsWith a pool
Luxury Homes in Osprey, FL
27 listings

Luxury Homes in Osprey, FL

Luxury Homes in Osprey, FL

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22 of 27 Listings
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Luxury Homes in Osprey, FL

22 of 27 Listings

  1. 366 S Creek Ct — photoNew56

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$1,049,000

4 bd · 3 ba · 2,775 sqft

366 S Creek Ct, Osprey, FL

EJ Stukenborg · KELLER WILLIAMS ON THE WATER S

  • 422 Blue Garden Ln — photo95Active

    $1,445,000

    3 bd · 4 ba · 3,872 sqft

    422 Blue Garden Ln, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  • 275 Lookout Point Dr — photo96Active

    $4,590,000

    5 bd · 5 ba · 5,279 sqft

    275 Lookout Point Dr, Osprey, FL

    Natalie Gutwein · MICHAEL SAUNDERS & COMPANY

  • 650 Oaks Creek Ct — photo100Active

    $3,700,000

    4 bd · 4 ba · 4,314 sqft

    650 Oaks Creek Ct, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  • 256 Sugar Mill — photo59Active

    $1,399,000

    3 bd · 3 ba · 2,695 sqft

    256 Sugar Mill, Osprey, FL

    Ivan Bovkun · KIMBERLITE WEST REALTY LLC

  • 324 Osprey Point Dr — photo100Active

    $3,700,000

    5 bd · 5 ba · 6,234 sqft

    324 Osprey Point Dr, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  • 402 Macewen Dr — photo82Active

    $1,590,000

    3 bd · 4 ba · 3,565 sqft

    402 Macewen Dr, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  • 141 Sugar Mill Dr — photo100Active

    $1,700,000

    3 bd · 3 ba · 3,118 sqft

    141 Sugar Mill Dr, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  • 1417 Landview Ln — photo82Active

    $1,399,000

    4 bd · 4 ba · 3,255 sqft

    1417 Landview Ln, Osprey, FL

    Pat Williams · PAT WILLIAMS REALTY, LLC

  • 1216 N Casey Key Rd — photo71Active

    $9,750,000

    5 bd · 8 ba · 8,050 sqft

    1216 N Casey Key Rd, Osprey, FL

    Valerie Dall'Acqua · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • 154 Lookout Point Dr — photoPrice Reduced50Active

    $2,095,000

    4 bd · 4 ba · 4,578 sqft

    154 Lookout Point Dr, Osprey, FL

    Stephen Hachey · FLAT FEE MLS REALTY

  • 296 Pine Ranch Trl — photo100Active

    $1,100,000

    5 bd · 4 ba · 3,354 sqft

    296 Pine Ranch Trl, Osprey, FL

    Darren Dowling · BEYOND REALTY LLC

  • 206 Four Knot Ln — photoPrice ReducedOpen house Sun, Oct 11 · 1:00 PM50Active

    $1,690,000

    3 bd · 2 ba · 2,411 sqft

    206 Four Knot Ln, Osprey, FL

    Leighton Allenby · Realty One Group MVP

  • 75 Osprey Point Dr — photoPrice Reduced70Active

    $1,595,000

    4 bd · 4 ba · 4,001 sqft

    75 Osprey Point Dr, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  • 101 Osprey Point Dr — photo65Active

    $4,790,000

    4 bd · 6 ba · 5,087 sqft

    101 Osprey Point Dr, Osprey, FL

    Joel Schemmel · DOUGLAS ELLIMAN

  • 156 Bishops Court Rd — photo81Active

    $1,289,000

    3 bd · 4 ba · 3,112 sqft

    156 Bishops Court Rd, Osprey, FL

    Joel Schemmel · DOUGLAS ELLIMAN

  • 97 Sugar Mill Dr — photo61Active

    $1,950,000

    5 bd · 6 ba · 4,885 sqft

    97 Sugar Mill Dr, Osprey, FL

    Maria Domenech · PALM PARADISE REALTY GROUP

  • 1527 Buoy Ln — photoPrice Reduced52Active

    $1,100,000

    3 bd · 3 ba · 2,830 sqft

    1527 Buoy Ln, Osprey, FL

    Matthew Lewis · BRIGHT REALTY

  • 313 Lookout Point Dr — photoPrice Reduced100Active

    $5,299,999

    4 bd · 5 ba · 5,337 sqft

    313 Lookout Point Dr, Osprey, FL

    Natalie Gutwein · MICHAEL SAUNDERS & COMPANY

  • 49 Osprey Point Dr — photoPrice Reduced96Active

    $2,399,000

    4 bd · 4 ba · 3,953 sqft

    49 Osprey Point Dr, Osprey, FL

    Jonathan Abrams, PLLC · MICHAEL SAUNDERS & COMPANY

  • 18 N Casey Key Rd — photoPrice Reduced49Active

    $1,750,000

    3 bd · 2 ba · 1,977 sqft

    18 N Casey Key Rd, Osprey, FL

    Valerie Dall'Acqua · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • 121 N Casey Key Rd — photoPrice Reduced66Active

    $6,100,000

    4 bd · 6 ba · 4,096 sqft

    121 N Casey Key Rd, Osprey, FL

    Lisa Napolitano · DOUGLAS ELLIMAN

  • 12

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    Thomas O'Leary

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    Listing data & MLS disclosures

    Florida Gulf Coast MLS/Royal Palm Coast Realtor Association(SWFLMLS)
    IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
    Listing information ©2026 Florida Gulf Coast MLS®, Inc®. All Rights Reserved. Last Updated: 2026-10-09 19:01:14 UTC
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    Osprey, FL community profile

    Area
    7.9 sq. mi.

    Source: HJN community data

    Osprey housing market

    September 2026 · This period is still settling

    Osprey 12-month median sale price trend

    Selling at 96.2% of asking price

    Buyers here are paying below asking. MLS · 16 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 22, 2026

    Median sale price
    $635,000$380,000–$1,250,000 typical range
    Price per sq. ft.
    $363
    Sales
    13
    Paid in cash
    46.2%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $797,000
    Homes for sale
    83
    Median days on market
    111 days

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

    Median home size
    2,254 sq. ft.