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Waterfront Homes in Osprey, FL
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34 listings
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3 bedsWith a pool

Waterfront Homes in Osprey, FL

Waterfront Homes in Osprey, FL

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24 of 34 Listings
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Waterfront Homes in Osprey, FL

24 of 34 Listings

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Thomas O'Leary

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Lic. #BK3453168

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  1. 14041 Bellagio Way #315 — photoNew100Active

    $640,000

    3 bd · 2 ba · 1,736 sqft

    14041 Bellagio Way #315, Osprey, FL

    Dawn Bear · WILLIAM RAVEIS - FLORIDA LLC

  2. 335 Park Trace Blvd — photo70Active

    $739,000

    3 bd · 2 ba · 2,326 sqft

    335 Park Trace Blvd, Osprey, FL

    Kim Klee · COLDWELL BANKER REALTY

  3. 570 Blackburn Point Rd #Siesta 25 — photo7Active

    $149,900

    — bd · 0 ba · — sqft

    570 Blackburn Point Rd #Siesta 25, Osprey, FL

    David Babel · BRIGHT REALTY

  4. 120 Villa Dr #120 — photo36Active

    $465,000

    2 bd · 2 ba · 1,404 sqft

    120 Villa Dr #120, Osprey, FL

    Antonio Lopez · MANGROVE REALTY ASSOCIATES

  5. 250 Hidden Bay Dr #302 — photoOpen house Sun, Oct 18 · 1:00 PM88Active

    $625,000

    3 bd · 2 ba · 1,937 sqft

    250 Hidden Bay Dr #302, Osprey, FL

    Pan Steele · COLDWELL BANKER REALTY

  6. 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

  7. 3603 N Point Rd #202 — photo50Active

    $629,400

    3 bd · 3 ba · 3,147 sqft

    3603 N Point Rd #202, Osprey, FL

    Mark Lyda · GENEROUS PROPERTY

  8. 1346 Thornapple Dr — photoOpen house Sun, Oct 18 · 1:00 AM55Active

    $540,000

    3 bd · 2 ba · 2,248 sqft

    1346 Thornapple Dr, Osprey, FL

    Debra Robinson · RE/MAX ALLIANCE GROUP

  9. 33 Bishops Court Rd #118 — photo69Active

    $679,000

    2 bd · 3 ba · 1,890 sqft

    33 Bishops Court Rd #118, Osprey, FL

    Mark Lyda · GENEROUS PROPERTY

  10. 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

  11. 1328 Thornapple Dr — photoOpen house Sun, Oct 18 · 2:00 PM46Active

    $749,900

    3 bd · 2 ba · 2,174 sqft

    1328 Thornapple Dr, Osprey, FL

    Heather Claridge · RIVER HILLS PROPERTIES, LLC B

  12. 2046 Cordes St — photoPrice Reduced43Active

    $565,000

    3 bd · 2 ba · 1,705 sqft

    2046 Cordes St, Osprey, FL

    Sue Mondello · MICHAEL SAUNDERS & COMPANY

  13. 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

  14. 5100 Jessie Harbor Dr #404 — photo62Active

    $599,000

    2 bd · 2 ba · 2,143 sqft

    5100 Jessie Harbor Dr #404, Osprey, FL

    Stuart Lawrence · MICHAEL SAUNDERS & COMPANY

  15. 260 Hidden Bay Dr #402 — photo58Active

    $775,000

    3 bd · 3 ba · 1,950 sqft

    260 Hidden Bay Dr #402, Osprey, FL

    Thomas Netzel · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  16. 570 Blackburn Point Rd #36 — photo4Active

    $99,500

    — bd · 0 ba · — sqft

    570 Blackburn Point Rd #36, Osprey, FL

    David Babel · BRIGHT REALTY

  17. 780 Sarabay Rd #16 — photo54Active

    $425,000

    2 bd · 2 ba · 1,574 sqft

    780 Sarabay Rd #16, Osprey, FL

    Mark Segreto · RMS ELITE PROPERTIES

  18. 7204 Jessie Harbor Dr #7204 — photo43Active

    $395,000

    2 bd · 2 ba · 1,255 sqft

    7204 Jessie Harbor Dr #7204, Osprey, FL

    Mark Lyda · GENEROUS PROPERTY

  19. 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

  20. 51 Macewen Dr #12 — photo71Active

    $275,000

    1 bd · 1 ba · 623 sqft

    51 Macewen Dr #12, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  21. 135 Tina Island Dr — photo47Active

    $3,295,000

    3 bd · 5 ba · 2,572 sqft

    135 Tina Island Dr, Osprey, FL

    Mark Lyda · GENEROUS PROPERTY

  22. 6100 Jessie Harbor Dr #202 — photoPrice Reduced83Active

    $798,000

    3 bd · 4 ba · 3,771 sqft

    6100 Jessie Harbor Dr #202, Osprey, FL

    Angelic Tassos · CORCORAN DWELLINGS REALTY

  23. 14021 Bellagio Way #404 — photoPrice Reduced70Active

    $999,900

    3 bd · 3 ba · 2,187 sqft

    14021 Bellagio Way #404, Osprey, FL

    Megan E. George, PA · PREMIER SOTHEBYS INTL REALTY

  24. 51 Macewen Dr #5 — photoPrice Reduced44Active

    $235,000

    1 bd · 1 ba · 595 sqft

    51 Macewen Dr #5, Osprey, FL

    Sabine Spycher · 342 REAL ESTATE

12

About Waterfront Homes in Osprey, FL

Waterfront Homes in Osprey, FL: 34 active listings as of October 17, 2026, 14:34 UTC.

Property types among these 34 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
Condominium1544.1%
Single Family Residence1338.2%

Explore Osprey homes

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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

    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.