Luxury Homes in Osprey, FL

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22 of 26 Listings

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22 of 26 Listings

New96

26 listings

Luxury Homes in Osprey, FL

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22 of 26 Listings

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Luxury Homes in Osprey, FL

22 of 26 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

New96

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$4,590,000

5 bd · 5 ba · 5,279 sqft

275 Lookout Point Dr, Osprey, FL

Natalie Gutwein · MICHAEL SAUNDERS & COMPANY

100Active

$3,700,000

4 bd · 4 ba · 4,314 sqft

650 Oaks Creek Ct, Osprey, FL

Steve Abbe · COLDWELL BANKER REALTY

59Active

$1,399,000

3 bd · 3 ba · 2,695 sqft

256 Sugar Mill, Osprey, FL

Ivan Bovkun · KIMBERLITE WEST REALTY LLC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

100Active

$3,700,000

5 bd · 5 ba · 6,234 sqft

324 Osprey Point Dr, Osprey, FL

Steve Abbe · COLDWELL BANKER REALTY

82Active

$1,590,000

3 bd · 4 ba · 3,565 sqft

402 Macewen Dr, Osprey, FL

Steve Abbe · COLDWELL BANKER REALTY

99Active

$2,175,000

4 bd · 4 ba · 4,117 sqft

362 Macewen Dr, Osprey, FL

Steve Abbe · COLDWELL BANKER REALTY

100Active

$1,700,000

3 bd · 3 ba · 3,118 sqft

141 Sugar Mill Dr, Osprey, FL

Steve Abbe · COLDWELL BANKER REALTY

82Active

$1,399,000

4 bd · 4 ba · 3,255 sqft

1417 Landview Ln, Osprey, FL

Pat Williams · PAT WILLIAMS REALTY, LLC

71Active

$9,750,000

5 bd · 8 ba · 8,050 sqft

1216 N Casey Key Rd, Osprey, FL

Valerie Dall'Acqua · PREMIER SOTHEBY'S INTERNATIONAL REALTY

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

85Active

$1,100,000

4 bd · 3 ba · 3,984 sqft

907 Eagle Isle Ct, Osprey, FL

Becky Culp · CENTURY 21 ROSEBAY

Price ReducedOpen house Sun, Oct 4 · 1:00 PM50Active

$1,690,000

3 bd · 2 ba · 2,411 sqft

206 Four Knot Ln, Osprey, FL

65Active

$4,790,000

4 bd · 6 ba · 5,087 sqft

101 Osprey Point Dr, Osprey, FL

Joel Schemmel · DOUGLAS ELLIMAN

81Active

$1,289,000

3 bd · 4 ba · 3,112 sqft

156 Bishops Court Rd, Osprey, FL

Joel Schemmel · DOUGLAS ELLIMAN

61Active

$1,950,000

5 bd · 6 ba · 4,885 sqft

97 Sugar Mill Dr, Osprey, FL

Maria Domenech · PALM PARADISE REALTY GROUP

Price Reduced52Active

$1,165,000

3 bd · 3 ba · 2,830 sqft

1527 Buoy Ln, Osprey, FL

Matthew Lewis · BRIGHT REALTY

100Active

$5,999,999

4 bd · 5 ba · 5,337 sqft

313 Lookout Point Dr, Osprey, FL

Natalie Gutwein · MICHAEL SAUNDERS & COMPANY

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

$6,475,000

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

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: 2026-10-02 21:13:52 UTC
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 · 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.

Osprey, FL community profile

Area: 7.9 sq. mi.

Source: HJN community data

Your local brokerage

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: 2026-10-02 21:13:52 UTC
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 · 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.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Osprey housing market

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Osprey, FL community profile

Your local brokerage

Listing data & MLS disclosures

Osprey, FL community profile

Osprey housing market

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026