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Luxury Homes in Osprey, FL
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3 bedsWith a pool

Luxury Homes in Osprey, FL

Luxury Homes in Osprey, FL

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24 of 40 Listings
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Luxury Homes in Osprey, FL

24 of 40 Listings

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TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 452 Blue Garden Ln — photoNew68Active

    $1,925,000

    3 bd · 4 ba · 3,910 sqft

    452 Blue Garden Ln, Osprey, FL

    Mark Lyda · GENEROUS PROPERTY

  2. 312 Yacht Harbor Dr — photoNew58Active

    $2,250,000

    3 bd · 4 ba · 2,572 sqft

    312 Yacht Harbor Dr, Osprey, FL

    Thomas Netzel · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3. 156 Bishopscourt Rd — photo100Active

    $1,289,000

    3 bd · 4 ba · 3,112 sqft

    156 Bishopscourt Rd, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  4. 3621 N Point Rd #603 — photo32Active

    $1,295,000

    3 bd · 3 ba · 2,680 sqft

    3621 N Point Rd #603, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  5. 871 Macewen Dr — photo67Active

    $3,190,000

    5 bd · 6 ba · 5,218 sqft

    871 Macewen Dr, Osprey, FL

    Katy McBrayer · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  6. 403 Longbow Trl — photo73Active

    $1,100,000

    4 bd · 3 ba · 2,770 sqft

    403 Longbow Trl, Osprey, FL

    Carlos Santos · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  7. 409 N Point Rd #601 — photo93Active

    $1,175,000

    3 bd · 3 ba · 2,594 sqft

    409 N Point Rd #601, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  8. 168 Coastal Hammock Ct — photo59Active

    $1,900,000

    3 bd · 4 ba · 3,924 sqft

    168 Coastal Hammock Ct, Osprey, FL

    Lenore Treiman · MICHAEL SAUNDERS & COMPANY

  9. 1474 Landview Ln — photoOpen house Sun, Nov 1 · 12:00 AM79Active

    $1,485,999

    4 bd · 3 ba · 3,246 sqft

    1474 Landview Ln, Osprey, FL

    Angela Fowler · ANGELA FOWLER REAL ESTATE, LLC

  10. 642 Trenton Way — photo95Active

    $2,150,000

    4 bd · 5 ba · 3,939 sqft

    642 Trenton Way, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  11. 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

  12. 366 S Creek Ct — photo45Active

    $1,049,000

    4 bd · 3 ba · 2,775 sqft

    366 S Creek Ct, Osprey, FL

    EJ Stukenborg · KELLER WILLIAMS ON THE WATER S

  13. 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

  14. 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

  15. 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

  16. 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

  17. 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

  18. 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

  19. 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

  20. 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

  21. 17 Bayhead Ln — photoPrice Reduced100Active

    $1,245,000

    3 bd · 2 ba · 2,850 sqft

    17 Bayhead Ln, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  22. 1417 Landview Ln — photoPrice Reduced82Active

    $1,349,999

    4 bd · 4 ba · 3,255 sqft

    1417 Landview Ln, Osprey, FL

    Pat Williams · PAT WILLIAMS REALTY, LLC

  23. 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

  24. 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

12

About Luxury Homes in Osprey, FL

Luxury Homes in Osprey, FL: 40 active listings as of November 1, 2026, 03:30 UTC.

Property types among these 40 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 Residence3280.0%
Condominium820.0%

Explore Osprey homes

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Listing data & MLS disclosures

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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

    October 2026 · This period is still settling

    Selling at 93.9% of asking price

    Buyers here are paying below asking. MLS · 19 sales · as of Oct 20, 2026

    Homes on the market · MLS, as of Oct 18, 2026–Oct 20, 2026

    Median list price
    $806,500
    Homes for sale
    88
    Median days on market
    54 days

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

    Median home size
    2,254 sq. ft.