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Luxury Homes in Osprey, FL

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12 of 36 Listings

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12 of 36 Listings

61Active

Luxury Homes in Osprey, FL — Page 2

36 listings

Luxury Homes in Osprey, FL

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12 of 36 Listings

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Luxury Homes in Osprey, FL

12 of 36 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

61Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$1,950,000

5 bd · 6 ba · 4,885 sqft

97 Sugar Mill Dr, Osprey, FL

Maria Domenech · PALM PARADISE REALTY GROUP

Price Reduced52Active

$1,100,000

3 bd · 3 ba · 2,830 sqft

1527 Buoy Ln, Osprey, FL

Matthew Lewis · BRIGHT REALTY

Price Reduced100Active

$5,299,999

4 bd · 5 ba · 5,337 sqft

313 Lookout Point Dr, Osprey, FL

Natalie Gutwein · MICHAEL SAUNDERS & COMPANY

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

60Active

$1,995,000

3 bd · 3 ba · 3,029 sqft

401 N Point Rd #1001, Osprey, FL

Mark Lyda · GENEROUS PROPERTY

Price Reduced62Active

$1,100,000

3 bd · 3 ba · 2,778 sqft

385 N Point Rd #304, Osprey, FL

Mark Lyda · GENEROUS PROPERTY

Price Reduced96Active

$2,399,000

4 bd · 4 ba · 3,953 sqft

49 Osprey Point Dr, Osprey, FL

Jonathan Abrams, PLLC · MICHAEL SAUNDERS & COMPANY

Price Reduced49Active

$1,750,000

3 bd · 2 ba · 1,977 sqft

18 N Casey Key Rd, Osprey, FL

Valerie Dall'Acqua · PREMIER SOTHEBY'S INTERNATIONAL REALTY

Price Reduced66Active

$6,100,000

4 bd · 6 ba · 4,096 sqft

121 N Casey Key Rd, Osprey, FL

Lisa Napolitano · DOUGLAS ELLIMAN

Price Reduced73Active

$2,395,000

3 bd · 4 ba · 4,519 sqft

852 Macewen Dr, Osprey, FL

Mark Lyda · GENEROUS PROPERTY

Price Reduced88Active

$2,700,000

6 bd · 7 ba · 6,246 sqft

236 Saint James Park, Osprey, FL

Karin Watt · MICHAEL SAUNDERS & COMPANY

61Active

$1,395,000

3 bd · 3 ba · 2,545 sqft

3603 N Point Rd #702, Osprey, FL

Mark Lyda · GENEROUS PROPERTY

Price Reduced62Active

$1,595,000

3 bd · 4 ba · 4,241 sqft

909 Macewen Dr, Osprey, FL

Mark Lyda · GENEROUS PROPERTY

1 2

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 · This period is still settling

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 22, 2026

Median sale price: $635,000$380,000–$1,250,000 typical range
Price per sq. ft.: $363
Sales: 13
Paid in cash: 46.2%

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 · This period is still settling

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 22, 2026

Median sale price: $635,000$380,000–$1,250,000 typical range
Price per sq. ft.: $363
Sales: 13
Paid in cash: 46.2%

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.