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Homes Under $2.5M in Osprey, FL

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24 of 92 Listings

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24 of 92 Listings

Price Reduced45

Homes Under $2.5M in Osprey, FL — Page 3

92 listings

Homes Under $2.5M in Osprey, FL

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24 of 92 Listings

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Homes Under $2.5M in Osprey, FL

24 of 92 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced45

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$242,900

2 bd · 2 ba · 1,325 sqft

116 Woodland Pl #116, Osprey, FL

Pat Williams · PAT WILLIAMS REALTY, LLC

Price Reduced70Active

$1,595,000

4 bd · 4 ba · 4,001 sqft

75 Osprey Point Dr, Osprey, FL

Steve Abbe · COLDWELL BANKER REALTY

Price Reduced49Active

$1,445,000

3 bd · 4 ba · 2,913 sqft

360 N Point Rd, Osprey, FL

Steve Abbe · COLDWELL BANKER REALTY

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced49Active

$289,000

2 bd · 2 ba · 1,135 sqft

4296 Expedition Way #104, Osprey, FL

Pamela Kurpiewski · EXP REALTY LLC

Price Reduced55Active

$699,000

3 bd · 2 ba · 2,034 sqft

103 Bishops Court Rd, Osprey, FL

Mark Lyda · GENEROUS PROPERTY

Price Reduced37Active

$165,000

2 bd · 2 ba · 1,199 sqft

320 Tropic Dr, Osprey, FL

Susan Retzke · RE/MAX PALM

Price Reduced39Active

$745,000

3 bd · 2 ba · 1,937 sqft

280 Hidden Bay Dr #302, Osprey, FL

Jim Xarras, Jr · BERKSHIRE HATHAWAY HOMESERVICE

81Active

$1,289,000

3 bd · 4 ba · 3,112 sqft

156 Bishops Court Rd, Osprey, FL

Joel Schemmel · DOUGLAS ELLIMAN

71Active

$275,000

1 bd · 1 ba · 623 sqft

51 Macewen Dr #12, Osprey, FL

Steve Abbe · COLDWELL BANKER REALTY

Price ReducedOpen house Sun, Nov 1 · 1:00 PM83Active

$798,000

3 bd · 4 ba · 3,771 sqft

6100 Jessie Harbor Dr #202, Osprey, FL

Angelic Tassos · CORCORAN DWELLINGS REALTY

61Active

$1,950,000

5 bd · 6 ba · 4,885 sqft

97 Sugar Mill Dr, Osprey, FL

Maria Domenech · PALM PARADISE REALTY GROUP

Price Reduced19Active

$499,999

3 bd · 2 ba · 2,004 sqft

4429 Conchfish Ln, Osprey, FL

Jennifer Kenna · EXP REALTY, LLC

Price Reduced70Active

$999,900

3 bd · 3 ba · 2,187 sqft

14021 Bellagio Way #404, Osprey, FL

Megan E. George, PA · PREMIER SOTHEBYS INTL REALTY

Price Reduced90Active

$560,000

3 bd · 3 ba · 2,594 sqft

409 North Point Rd #401, Osprey, FL

Steve Abbe · COLDWELL BANKER REALTY

Price Reduced44Active

$235,000

1 bd · 1 ba · 595 sqft

51 Macewen Dr #5, Osprey, FL

Sabine Spycher · 342 REAL ESTATE

19Active

$285,000

1 bd · 1 ba · 595 sqft

51 Mac Ewen Dr #14, Osprey, FL

Steve Abbe · COLDWELL BANKER REALTY

Price Reduced51Active

$700,000

4 bd · 4 ba · 2,950 sqft

759 Fordingbridge Way, Osprey, FL

Steven Koleno · BEYCOME OF FLORIDA LLC

Price Reduced100Active

$1,050,000

3 bd · 3 ba · 3,180 sqft

61 Bayhead Ln, Osprey, FL

Anne Thomas, PA · RE/MAX ALLIANCE GROUP

50Active

$700,000

3 bd · 2 ba · 1,799 sqft

14041 Bellagio Way #214, Osprey, FL

Veronica Lee · COLDWELL BANKER REALTY

Price Reduced52Active

$1,100,000

3 bd · 3 ba · 2,830 sqft

1527 Buoy Ln, Osprey, FL

Matthew Lewis · BRIGHT REALTY

4Active

$36,000

— bd · 0 ba · — sqft

570 Blackburn Point Rd #26, Osprey, FL

David Babel · BRIGHT REALTY

Price Reduced38Active

$879,000

3 bd · 3 ba · 2,199 sqft

14021 Bellagio Way #309, Osprey, FL

Tristin Hopler · COMPASS FLORIDA, LLC

Price Reduced95Active

$525,000

3 bd · 3 ba · 2,680 sqft

3621 N Point Rd #301, Osprey, FL

Steve Abbe · COLDWELL BANKER REALTY

60Active

$1,995,000

3 bd · 3 ba · 3,029 sqft

401 N Point Rd #1001, Osprey, FL

Mark Lyda · GENEROUS PROPERTY

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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.

Osprey housing market

September 2026

Selling at 96.2% of asking price

Buyers here are paying below asking. MLS · 16 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 30, 2026

Median sale price: $500,000$305,000–$1,075,000 typical range
Price per sq. ft.: $302
Sales: 21
Paid in cash: 61.9%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $797,000
Homes for sale: 83
Median days on market: 111 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

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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.

Osprey, FL community profile

Area: 7.9 sq. mi.

Source: HJN community data

Osprey housing market

September 2026

Selling at 96.2% of asking price

Buyers here are paying below asking. MLS · 16 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 30, 2026

Median sale price: $500,000$305,000–$1,075,000 typical range
Price per sq. ft.: $302
Sales: 21
Paid in cash: 61.9%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $797,000
Homes for sale: 83
Median days on market: 111 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.