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Luxury Homes in Osprey, FL
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Luxury Homes in Osprey, FL

Luxury Homes in Osprey, FL

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22 of 39 Listings
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Luxury Homes in Osprey, FL

22 of 39 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 1474 Landview Ln — photoNew79Active

    $1,485,999

    4 bd · 3 ba · 3,246 sqft

    1474 Landview Ln, Osprey, FL

    Angela Fowler · ANGELA FOWLER REAL ESTATE, LLC

  2. 642 Trenton Way — photoNew95Active

    $2,150,000

    4 bd · 5 ba · 3,939 sqft

    642 Trenton Way, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  3. 102 Windward Dr — photo54Active

    $1,047,000

    3 bd · 3 ba · 2,134 sqft

    102 Windward Dr, Osprey, FL

    Adam Leinwand · FUTURE HOME REALTY INC

  4. 366 S Creek Ct — photoOpen house Sun, Oct 18 · 12:00 PM56Active

    $1,049,000

    4 bd · 3 ba · 2,775 sqft

    366 S Creek Ct, Osprey, FL

    EJ Stukenborg · KELLER WILLIAMS ON THE WATER S

  5. 401 N Point Rd #404 — photo100Active

    $1,025,000

    3 bd · 3 ba · 2,778 sqft

    401 N Point Rd #404, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  6. 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

  7. 401 N Point Rd #703 — photo56Active

    $1,200,000

    3 bd · 3 ba · 2,203 sqft

    401 N Point Rd #703, Osprey, FL

    Mark Lyda · GENEROUS PROPERTY

  8. 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

  9. 385 North Point Rd #701 — photo100Active

    $1,399,000

    3 bd · 3 ba · 2,594 sqft

    385 North Point Rd #701, Osprey, FL

    Judy Wright, PA · MICHAEL SAUNDERS & COMPANY

  10. 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

  11. 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

  12. 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

  13. 17 Bayhead Ln — photoPrice Reduced100Active

    $1,270,000

    3 bd · 2 ba · 2,850 sqft

    17 Bayhead Ln, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  14. 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

  15. 1417 Landview Ln — photoPrice ReducedOpen house Sun, Oct 18 · 1:00 PM82Active

    $1,349,999

    4 bd · 4 ba · 3,255 sqft

    1417 Landview Ln, Osprey, FL

    Pat Williams · PAT WILLIAMS REALTY, LLC

  16. 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

  17. 226 Saint James Park — photoPrice Reduced89Active

    $1,350,000

    3 bd · 3 ba · 2,591 sqft

    226 Saint James Park, Osprey, FL

    Justin Brunswick · KELLER WILLIAMS ON THE WATER S

  18. 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

  19. 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

  20. 206 Four Knot Ln — photoPrice ReducedOpen house Sun, Oct 18 · 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

  21. 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

  22. 360 N Point Rd — photo49Active

    $1,495,000

    3 bd · 4 ba · 2,913 sqft

    360 N Point Rd, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

12

About Luxury Homes in Osprey, FL

Luxury Homes in Osprey, FL: 39 active listings as of October 17, 2026, 06:12 UTC.

Property types among these 39 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property typeListingsShare
Single Family Residence3384.6%
Condominium615.4%

Explore Osprey homes

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The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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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: 2026-10-17 04:15:44 UTC
Stellar MLS
Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    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 24, 2026

    Median sale price
    $490,000$323,750–$1,027,500 typical range
    Price per sq. ft.
    $293
    Sales
    18
    Paid in cash
    55.6%

    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.