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Waterfront Homes in Osprey, FL — Page 2

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Waterfront Homes in Osprey, FL

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10 of 34 Listings

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Waterfront Homes in Osprey, FL

10 of 34 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

50Active
$700,000
3 bd · 2 ba · 1,799 sqft
14041 Bellagio Way #214, Osprey, FL
Veronica Lee · COLDWELL BANKER REALTY
Price ReducedOpen house Sun, Oct 18 · 1:00 AM100Active
$5,299,999
4 bd · 5 ba · 5,337 sqft
313 Lookout Point Dr, Osprey, FL
Natalie Gutwein · MICHAEL SAUNDERS & COMPANY
Price Reduced38Active
$879,000
3 bd · 3 ba · 2,199 sqft
14021 Bellagio Way #309, Osprey, FL
Tristin Hopler · COMPASS FLORIDA, LLC

Price Reduced36Active
$700,000
2 bd · 2 ba · 1,932 sqft
242 Hidden Bay Dr #602, Osprey, FL
Cathy Rustin · FIRST LIGHT REAL ESTATE
4Active
$115,000
— bd · 0 ba · — sqft
570 Blackburn Point Rd #43, Osprey, FL
David Babel · BRIGHT REALTY
4Active
$109,000
— bd · 0 ba · — sqft
570 Blackburn Point Rd #13, Osprey, FL
David Babel · BRIGHT REALTY
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
61Active
$1,395,000
3 bd · 3 ba · 2,545 sqft
3603 N Point Rd #702, 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 · 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 24, 2026

Median sale price: $490,000$323,750–$1,027,500 typical range
Price per sq. ft.: $293
Sales: 18
Paid in cash: 55.6%

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.

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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Condos

By feature

Homes with a Pool
Waterfront Homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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 24, 2026

Median sale price: $490,000$323,750–$1,027,500 typical range
Price per sq. ft.: $293
Sales: 18
Paid in cash: 55.6%

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.