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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

Homes Under $2.5M in Osprey, FL — Page 2

92 listings

Homes Under $2.5M in Osprey, FL

Hide Map

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

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$449,000

3 bd · 2 ba · 1,883 sqft

7303 Jessie Harbor Dr #7303, Osprey, FL

Mairead Smialek · COLDWELL BANKER REALTY

50Active

$629,400

3 bd · 3 ba · 3,147 sqft

3603 N Point Rd #202, Osprey, FL

Mark Lyda · GENEROUS PROPERTY

55Active

$540,000

3 bd · 2 ba · 2,248 sqft

1346 Thornapple Dr, Osprey, FL

Debra Robinson · RE/MAX ALLIANCE GROUP

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

69Active

$679,000

2 bd · 3 ba · 1,890 sqft

33 Bishops Court Rd #118, Osprey, FL

Mark Lyda · GENEROUS PROPERTY

59Active

$1,399,000

3 bd · 3 ba · 2,695 sqft

256 Sugar Mill, Osprey, FL

Ivan Bovkun · KIMBERLITE WEST REALTY LLC

59Active

$165,000

2 bd · 2 ba · 924 sqft

23 Siesta Cir W, Osprey, FL

Karen Geiger · COLDWELL BANKER SARASOTA CENT.

Price Reduced100Active

$1,245,000

3 bd · 2 ba · 2,850 sqft

17 Bayhead Ln, Osprey, FL

Steve Abbe · COLDWELL BANKER REALTY

Price Reduced82Active

$1,349,999

4 bd · 4 ba · 3,255 sqft

1417 Landview Ln, Osprey, FL

Pat Williams · PAT WILLIAMS REALTY, LLC

Price Reduced46Active

$719,900

3 bd · 2 ba · 2,174 sqft

1328 Thornapple Dr, Osprey, FL

Heather Claridge · RIVER HILLS PROPERTIES, LLC B

Price Reduced43Active

$565,000

3 bd · 2 ba · 1,705 sqft

2046 Cordes St, Osprey, FL

Sue Mondello · MICHAEL SAUNDERS & COMPANY

Price Reduced14Active

$850,000

3 bd · 2 ba · 2,084 sqft

210 Patterson Ave, Osprey, FL

Troy Funk · REALTY ONE GROUP MVP

Price Reduced89Active

$1,350,000

3 bd · 3 ba · 2,591 sqft

226 Saint James Park, Osprey, FL

Justin Brunswick · KELLER WILLIAMS ON THE WATER S

Price Reduced50Active

$2,095,000

4 bd · 4 ba · 4,578 sqft

154 Lookout Point Dr, Osprey, FL

Stephen Hachey · FLAT FEE MLS REALTY

100Active

$1,100,000

5 bd · 4 ba · 3,354 sqft

296 Pine Ranch Trl, Osprey, FL

Darren Dowling · BEYOND REALTY LLC

62Active

$599,000

2 bd · 2 ba · 2,143 sqft

5100 Jessie Harbor Dr #404, Osprey, FL

Stuart Lawrence · MICHAEL SAUNDERS & COMPANY

60Active

$985,000

3 bd · 3 ba · 2,203 sqft

409 N Point Rd #803, Osprey, FL

Mark Lyda · GENEROUS PROPERTY

Price Reduced79Active

$699,000

3 bd · 2 ba · 2,328 sqft

299 Turquoise Ln, Osprey, FL

Mickey Jordan · BRIGHT REALTY

58Active

$775,000

3 bd · 3 ba · 1,950 sqft

260 Hidden Bay Dr #402, Osprey, FL

Thomas Netzel · PREMIER SOTHEBY'S INTERNATIONAL REALTY

54Active

$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

4Active

$99,500

— bd · 0 ba · — sqft

570 Blackburn Point Rd #36, Osprey, FL

David Babel · BRIGHT REALTY

54Active

$425,000

2 bd · 2 ba · 1,574 sqft

780 Sarabay Rd #16, Osprey, FL

Mark Segreto · RMS ELITE PROPERTIES

Price Reduced85Active

$480,000

3 bd · 3 ba · 2,006 sqft

2309 Jessie Harbor Dr #2402, Osprey, FL

Christine Pope · MICHAEL SAUNDERS & COMPANY

Price Reduced3Active

$89,000

— bd · 0 ba · — sqft

570 Blackburn Point Rd #23, Osprey, FL

Daniel Treiman · MICHAEL SAUNDERS & COMPANY

43Active

$395,000

2 bd · 2 ba · 1,255 sqft

7204 Jessie Harbor Dr #7204, Osprey, FL

Mark Lyda · GENEROUS PROPERTY

1 2 3 4

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.