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3 bedsWith a pool
Homes Under $2M in Osprey, FL — Page 2
83 listings

Homes Under $2M in Osprey, FL

Homes Under $2M in Osprey, FL

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

22 of 83 Listings

  1. 1819 Highland Rd — photo57Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$319,000

2 bd · 3 ba · 1,240 sqft

1819 Highland Rd, Osprey, FL

Jennifer Linehan · MICHAEL SAUNDERS & COMPANY

  • 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

  • 1140 Beachcomber Ct #11 — photo11Active

    $540,000

    3 bd · 3 ba · 2,040 sqft

    1140 Beachcomber Ct #11, Osprey, FL

    Ralph Harvey · LISTWITHFREEDOM.COM

  • 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

  • 409 N Point Rd #803 — photo60Active

    $985,000

    3 bd · 3 ba · 2,203 sqft

    409 N Point Rd #803, Osprey, FL

    Mark Lyda · GENEROUS PROPERTY

  • 108 Villa Dr #108 — photoPrice Reduced16Active

    $299,950

    2 bd · 2 ba · 1,593 sqft

    108 Villa Dr #108, Osprey, FL

    Richard Gaspar · LOKATION

  • 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

  • 299 Turquoise Ln — photoPrice Reduced79Active

    $719,000

    3 bd · 2 ba · 2,328 sqft

    299 Turquoise Ln, Osprey, FL

    Mickey Jordan · BRIGHT REALTY

  • 1036 Oak Meadow Ln — photo54Active

    $630,000

    4 bd · 2 ba · 2,186 sqft

    1036 Oak Meadow Ln, Osprey, FL

    Curtis Andrews · BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

  • 570 Blackburn Point Rd #36 — photo4Active

    $99,500

    — bd · 0 ba · — sqft

    570 Blackburn Point Rd #36, Osprey, FL

    David Babel · BRIGHT REALTY

  • listing photo45Active

    $824,900

    4 bd · 3 ba · 2,607 sqft

    Address withheld · Osprey, FL

    Claudia Dybala · DALTON WADE INC

  • 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

  • 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

  • 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

  • 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

  • 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

  • 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

  • 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

  • 103 Bishops Court Rd — photo55Active

    $749,000

    3 bd · 2 ba · 2,034 sqft

    103 Bishops Court Rd, Osprey, FL

    Mark Lyda · GENEROUS PROPERTY

  • 320 Tropic Dr — photoPrice Reduced37Active

    $185,000

    2 bd · 2 ba · 1,199 sqft

    320 Tropic Dr, Osprey, FL

    Susan Retzke · RE/MAX PALM

  • 280 Hidden Bay Dr #302 — photoPrice Reduced39Active

    $719,000

    3 bd · 2 ba · 1,937 sqft

    280 Hidden Bay Dr #302, Osprey, FL

    Jim Xarras, Jr · BERKSHIRE HATHAWAY HOMESERVICE

  • 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

  • 1234

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Listing data & MLS disclosures

    Florida Gulf Coast MLS/Royal Palm Coast Realtor Association(SWFLMLS)
    IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
    Listing information ©2026 Florida Gulf Coast MLS®, Inc®. All Rights Reserved. Last Updated: 2026-10-03 00:26:56 UTC
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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.

    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.