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Start here

Homes for sale by state
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Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
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Closing costs, itemized
Find a buyer's agent

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Commercial

182 listings

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182 listings

Homes for Sale in Osprey, FL

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24 of 182 Listings

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24 of 182 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced37

Active

$185,000

2 bd · 2 ba · 1,199 sqft

320 Tropic Dr, Osprey, FL

Susan Retzke · RE/MAX PALM

Price Reduced39Active

$719,000

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 Road, 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

71Active

$275,000

1 bd · 1 ba · 623 sqft

51 Macewen Drive 12, Osprey, FL

Steve Abbe · COLDWELL BANKER REALTY

71Active

$275,000

1 bd · 1 ba · 623 sqft

51 Macewen Dr #12, Osprey, FL

Steve Abbe · COLDWELL BANKER REALTY

47Active

$3,295,000

3 bd · 5 ba · 2,572 sqft

135 Tina Island Drive, Osprey, FL

Mark Lyda · GENEROUS PROPERTY

47Active

$3,295,000

3 bd · 5 ba · 2,572 sqft

135 Tina Island Dr, Osprey, FL

Mark Lyda · GENEROUS PROPERTY

Price Reduced83Active

$798,000

3 bd · 4 ba · 3,771 sqft

6100 Jessie Harbor Drive 202, Osprey, FL

Angelic Tassos · CORCORAN DWELLINGS REALTY

Price Reduced83Active

$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 Drive, Osprey, FL

Maria Domenech · PALM PARADISE REALTY GROUP

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

$510,000

3 bd · 2 ba · 2,004 sqft

4429 Conchfish Lane, Osprey, FL

Jennifer Kenna · EXP REALTY, LLC

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 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 Road 401, Osprey, FL

Steve Abbe · COLDWELL BANKER REALTY

Price Reduced90Active

$560,000

3 bd · 3 ba · 2,594 sqft

409 North Point Rd #401, Osprey, FL

Steve Abbe · COLDWELL BANKER REALTY

19Active

$285,000

1 bd · 1 ba · 595 sqft

51 Mac Ewen Drive 14, 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

Price Reduced44Active

$235,000

1 bd · 1 ba · 595 sqft

51 Macewen Drive 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 Reduced51Active

$700,000

4 bd · 4 ba · 2,950 sqft

759 Fordingbridge Way, Osprey, FL

Steven Koleno · BEYCOME OF FLORIDA LLC

1…4 5 6…8

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

Osprey, FL community profile

Area: 7.9 sq. mi.

Source: HJN community data

Explore Osprey homes

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Homes Under $500K
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Homes Under $800K
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Single-Family Homes

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

Condos

By feature

Homes with a Pool
Waterfront Homes

Nearby areas

ZIP codes

34293 (884)
34211 (853)
33981 (774)
34236 (636)
34287 (599)
34209 (580)
34275 (555)
34210 (551)

Cities

Sarasota (4,603)
Bradenton (3,728)
Port Charlotte (2,183)
North Port (1,687)
Venice (1,570)
Englewood (890)
Nokomis (518)
Longboat Key (505)

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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

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 Homes for Sale — Page 5 | Realty.com

Nearby areas

ZIP codes

34293 (884)
34211 (853)
33981 (774)
34236 (636)
34287 (599)
34209 (580)
34275 (555)
34210 (551)

Cities

Sarasota (4,603)
Bradenton (3,728)
Port Charlotte (2,183)
North Port (1,687)
Venice (1,570)
Englewood (890)
Nokomis (518)
Longboat Key (505)