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Homes Under $600K in Osprey, FL
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3 bedsWith a pool

Homes Under $600K in Osprey, FL

Homes Under $600K in Osprey, FL

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24 of 33 Listings
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Homes Under $600K in Osprey, FL

24 of 33 Listings

Your local brokerage

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Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 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

  2. 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

  3. 1346 Thornapple Dr — photo55Active

    $540,000

    3 bd · 2 ba · 2,248 sqft

    1346 Thornapple Dr, Osprey, FL

    Debra Robinson · RE/MAX ALLIANCE GROUP

  4. 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.

  5. 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

  6. 2046 Cordes St — photoPrice Reduced43Active

    $565,000

    3 bd · 2 ba · 1,705 sqft

    2046 Cordes St, Osprey, FL

    Sue Mondello · MICHAEL SAUNDERS & COMPANY

  7. 1819 Highland Rd — photo57Active

    $319,000

    2 bd · 3 ba · 1,240 sqft

    1819 Highland Rd, Osprey, FL

    Jennifer Linehan · MICHAEL SAUNDERS & COMPANY

  8. 1140 Beachcomber Ct #11 — photo11Active

    $540,000

    3 bd · 3 ba · 2,040 sqft

    1140 Beachcomber Ct #11, Osprey, FL

    Ralph Harvey · LISTWITHFREEDOM.COM

  9. 5100 Jessie Harbor Dr #404 — photoOpen house Sun, Oct 4 · 1:00 PM62Active

    $599,000

    2 bd · 2 ba · 2,143 sqft

    5100 Jessie Harbor Dr #404, Osprey, FL

    Stuart Lawrence · MICHAEL SAUNDERS & COMPANY

  10. 108 Villa Dr #108 — photoPrice Reduced16Active

    $299,950

    2 bd · 2 ba · 1,593 sqft

    108 Villa Dr #108, Osprey, FL

    Richard Gaspar · LOKATION

  11. 570 Blackburn Point Rd #36 — photo4Active

    $99,500

    — bd · 0 ba · — sqft

    570 Blackburn Point Rd #36, Osprey, FL

    David Babel · BRIGHT REALTY

  12. 2309 Jessie Harbor Dr #2402 — photoPrice Reduced85Active

    $480,000

    3 bd · 3 ba · 2,006 sqft

    2309 Jessie Harbor Dr #2402, Osprey, FL

    Christine Pope · MICHAEL SAUNDERS & COMPANY

  13. 570 Blackburn Point Rd #23 — photoPrice Reduced3Active

    $89,000

    — bd · 0 ba · — sqft

    570 Blackburn Point Rd #23, Osprey, FL

    Daniel Treiman · MICHAEL SAUNDERS & COMPANY

  14. 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

  15. 116 Woodland Pl #116 — photoPrice ReducedOpen house Sat, Oct 3 · 1:00 PM45Active

    $249,900

    2 bd · 2 ba · 1,325 sqft

    116 Woodland Pl #116, Osprey, FL

    Pat Williams · PAT WILLIAMS REALTY, LLC

  16. 4296 Expedition Way #104 — photoPrice Reduced49Active

    $289,000

    2 bd · 2 ba · 1,135 sqft

    4296 Expedition Way #104, Osprey, FL

    Pamela Kurpiewski · EXP REALTY LLC

  17. 320 Tropic Dr — photoPrice Reduced37Active

    $185,000

    2 bd · 2 ba · 1,199 sqft

    320 Tropic Dr, Osprey, FL

    Susan Retzke · RE/MAX PALM

  18. 51 Macewen Dr #12 — photo71Active

    $275,000

    1 bd · 1 ba · 623 sqft

    51 Macewen Dr #12, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  19. 4429 Conchfish Ln — photoPrice Reduced19Active

    $499,999

    3 bd · 2 ba · 2,004 sqft

    4429 Conchfish Ln, Osprey, FL

    Jennifer Kenna · EXP REALTY, LLC

  20. 409 North Point Rd #401 — photoPrice Reduced90Active

    $560,000

    3 bd · 3 ba · 2,594 sqft

    409 North Point Rd #401, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  21. 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

  22. 51 Mac Ewen Dr #14 — photo19Active

    $285,000

    1 bd · 1 ba · 595 sqft

    51 Mac Ewen Dr #14, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

  23. 570 Blackburn Point Rd #26 — photo4Active

    $36,000

    — bd · 0 ba · — sqft

    570 Blackburn Point Rd #26, Osprey, FL

    David Babel · BRIGHT REALTY

  24. 3621 N Point Rd #301 — photoPrice Reduced95Active

    $525,000

    3 bd · 3 ba · 2,680 sqft

    3621 N Point Rd #301, Osprey, FL

    Steve Abbe · COLDWELL BANKER REALTY

12

About Homes Under $600K in Osprey, FL

Homes Under $600K in Osprey, FL: 33 active listings as of October 3, 2026, 07:29 UTC.

Property types among these 33 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
Condominium1545.5%
Boat Slip618.2%
Single Family Residence515.2%

Explore Osprey homes

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  • Homes Under $500K
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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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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    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.

    Osprey, FL community profile

    Area
    7.9 sq. mi.

    Source: HJN community data