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Homes Under $2M in Osprey, FL
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3 bedsWith a pool

Homes Under $2M in Osprey, FL

Homes Under $2M in Osprey, FL

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24 of 83 Listings
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Homes Under $2M in Osprey, FL

24 of 83 Listings

Your local brokerage

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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. 717 Pine Run Dr. #717 — photo34Active

    $159,900

    1 bd · 1 ba · 586 sqft

    717 Pine Run Dr. #717, Osprey, FL

    Pat Williams · PAT WILLIAMS REALTY, LLC

  3. 250 Hidden Bay Dr #302 — photoOpen house Sun, Oct 11 · 1:00 PM87Active

    $625,000

    3 bd · 2 ba · 1,937 sqft

    250 Hidden Bay Dr #302, Osprey, FL

    Pan Steele · COLDWELL BANKER REALTY

  4. 1104 Mallard Marsh Dr — photoOpen house Sun, Oct 4 · 1:00 PM59Active

    $799,000

    3 bd · 3 ba · 2,678 sqft

    1104 Mallard Marsh Dr, Osprey, FL

    Todd Currey · PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5. 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

  6. 385 N Point Rd #401 — photo100Active

    $695,000

    3 bd · 3 ba · 2,594 sqft

    385 N Point Rd #401, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  7. 7303 Jessie Harbor Dr #7303 — photoOpen house Sun, Oct 4 · 1:00 PM35Active

    $449,000

    3 bd · 2 ba · 1,883 sqft

    7303 Jessie Harbor Dr #7303, Osprey, FL

    Mairead Smialek · COLDWELL BANKER REALTY

  8. 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

  9. 1346 Thornapple Dr — photo55Active

    $540,000

    3 bd · 2 ba · 2,248 sqft

    1346 Thornapple Dr, Osprey, FL

    Debra Robinson · RE/MAX ALLIANCE GROUP

  10. 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

  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. 23 Siesta Cir W — photo59Active

    $165,000

    2 bd · 2 ba · 924 sqft

    23 Siesta Cir W, Osprey, FL

    Karen Geiger · COLDWELL BANKER SARASOTA CENT.

  13. 17 Bayhead Ln — photo100Active

    $1,295,000

    3 bd · 2 ba · 2,850 sqft

    17 Bayhead Ln, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  14. 3621 N Point Rd #403 — photo100Active

    $700,000

    3 bd · 3 ba · 2,680 sqft

    3621 N Point Rd #403, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  15. 700 Shadow Bay Way — photo19Active

    $655,000

    3 bd · 3 ba · 2,792 sqft

    700 Shadow Bay Way, Osprey, FL

    Kara Money · KARA MONEY LLC

  16. 109 Woodland Pl — photoOpen house Sat, Oct 3 · 1:00 PM44Active

    $255,000

    2 bd · 2 ba · 1,223 sqft

    109 Woodland Pl, Osprey, FL

    Monica DeSomma · PREFERRED SHORE LLC

  17. 402 Macewen Dr — photo82Active

    $1,590,000

    3 bd · 4 ba · 3,565 sqft

    402 Macewen Dr, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  18. 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

  19. 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

  20. 1328 Thornapple Dr — photoOpen house Sat, Oct 3 · 1:00 PM46Active

    $749,900

    3 bd · 2 ba · 2,174 sqft

    1328 Thornapple Dr, Osprey, FL

    Heather Claridge · RIVER HILLS PROPERTIES, LLC B

  21. 2046 Cordes St — photoPrice Reduced43Active

    $565,000

    3 bd · 2 ba · 1,705 sqft

    2046 Cordes St, Osprey, FL

    Sue Mondello · MICHAEL SAUNDERS & COMPANY

  22. 210 Patterson Ave — photoPrice Reduced14Active

    $950,000

    3 bd · 2 ba · 2,084 sqft

    210 Patterson Ave, Osprey, FL

    Troy Funk · REALTY ONE GROUP MVP

  23. 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

  24. 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

12…4

About Homes Under $2M in Osprey, FL

Homes Under $2M in Osprey, FL: 83 active listings as of October 3, 2026, 10:08 UTC.

Property types among these 83 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 Residence3643.4%
Condominium3339.8%
Boat Slip67.2%

Explore Osprey homes

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Listing data & MLS disclosures

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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    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

    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.