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2 Bedroom Homes in Osprey, FL
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13 listings
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2 Bedroom Homes in Osprey, FL

2 Bedroom Homes in Osprey, FL

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13 Listings
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2 Bedroom Homes in Osprey, FL

13 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 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

  2. 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.

  3. 109 Woodland Pl — photo44Active

    $255,000

    2 bd · 2 ba · 1,223 sqft

    109 Woodland Pl, Osprey, FL

    Monica DeSomma · PREFERRED SHORE LLC

  4. 1819 Highland Rd — photo57Active

    $319,000

    2 bd · 3 ba · 1,240 sqft

    1819 Highland Rd, Osprey, FL

    Jennifer Linehan · MICHAEL SAUNDERS & COMPANY

  5. 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

  6. 108 Villa Dr #108 — photoPrice Reduced16Active

    $299,950

    2 bd · 2 ba · 1,593 sqft

    108 Villa Dr #108, Osprey, FL

    Richard Gaspar · LOKATION

  7. 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

  8. 116 Woodland Pl #116 — photoPrice Reduced45Active

    $249,900

    2 bd · 2 ba · 1,325 sqft

    116 Woodland Pl #116, Osprey, FL

    Pat Williams · PAT WILLIAMS REALTY, LLC

  9. 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

  10. 320 Tropic Dr — photoPrice Reduced37Active

    $185,000

    2 bd · 2 ba · 1,199 sqft

    320 Tropic Dr, Osprey, FL

    Susan Retzke · RE/MAX PALM

  11. 242 Hidden Bay Dr #602 — photoPrice Reduced36Active

    $700,000

    2 bd · 2 ba · 1,932 sqft

    242 Hidden Bay Dr #602, Osprey, FL

    Cathy Rustin · FIRST LIGHT REAL ESTATE

  12. 1811 Highland Rd — photoPrice Reduced19Active

    $409,900

    2 bd · 2 ba · 1,725 sqft

    1811 Highland Rd, Osprey, FL

    Stephen Hachey · REALTY OF RIVERVIEW LLC

  13. 348 Tropic Dr — photoPrice Reduced34Active

    $104,900

    2 bd · 2 ba · 864 sqft

    348 Tropic Dr, Osprey, FL

    John Alexander · FINE PROPERTIES

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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.
  • 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

    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.