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Osprey, FL Homes for Sale | Realty.com
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35 listings
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3 bedsWith a pool

Homes for Sale in Osprey, FL

Homes for Sale in Osprey, FL

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22 of 35 Listings
Map

Homes for Sale in Osprey, FL

22 of 35 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 401 N Point Rd #703 — photoNew56Active

    $1,200,000

    3 bd · 3 ba · 2,203 sqft

    401 N Point Rd #703, Osprey, FL

    Mark Lyda · GENEROUS PROPERTY

  2. 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

  3. 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

  4. 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

  5. 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

  6. 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

  7. 17 Bayhead Ln — photo100Active

    $1,295,000

    3 bd · 2 ba · 2,850 sqft

    17 Bayhead Ln, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  8. 402 Macewen Dr — photo82Active

    $1,590,000

    3 bd · 4 ba · 3,565 sqft

    402 Macewen Dr, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  9. 362 Macewen Dr — photo99Active

    $2,175,000

    4 bd · 4 ba · 4,117 sqft

    362 Macewen Dr, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  10. 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

  11. 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

  12. 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

  13. 226 Saint James Park — photo89Active

    $1,495,000

    3 bd · 3 ba · 2,591 sqft

    226 Saint James Park, Osprey, FL

    Justin Brunswick · KELLER WILLIAMS ON THE WATER S

  14. 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

  15. 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

  16. 907 Eagle Isle Ct — photo85Active

    $1,100,000

    4 bd · 3 ba · 3,984 sqft

    907 Eagle Isle Ct, Osprey, FL

    Becky Culp · CENTURY 21 ROSEBAY

  17. 206 Four Knot Ln — photoPrice ReducedOpen house Sun, Oct 4 · 1:00 PM50Active

    $1,690,000

    3 bd · 2 ba · 2,411 sqft

    206 Four Knot Ln, Osprey, FL

  18. 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

  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. 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

  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. 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

12

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    Your local brokerage

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    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

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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

    Selling at 96.2% of asking price

    Buyers here are paying below asking. MLS · 13 sales · as of Sep 29, 2026

    Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

    Median list price
    $797,000
    Homes for sale
    83
    Median days on market
    129 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.

    Nearby areas

    ZIP codes

    • 34293 (886)
    • 34211 (856)
    • 33981 (777)
    • 34236 (635)
    • 34287 (603)
    • 34209 (574)
    • 34275 (559)
    • 34210 (550)

    Cities

    • Sarasota (2,322)
    • SARASOTA (2,279)
    • Bradenton (1,878)
    • BRADENTON (1,857)
    • Port Charlotte (1,194)
    • PORT CHARLOTTE (991)
    • North Port (859)
    • NORTH PORT (824)