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447 listings

Homes for Sale in Windermere, FL

Show Map

24 of 447 Listings

Map

24 of 447 Listings

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

Price Reduced53

Active

$798,000

5 bd · 5 ba · 3,373 sqft

4642 River Gem Ave, Windermere, FL

John Silva · JOHN SILVA REALTY & ASSOCIATES

93Active

$6,700,000

8 bd · 10 ba · 8,133 sqft

8342 Boyla Ct, Windermere, FL

Simon Simaan · THE SIMON SIMAAN GROUP

93Active

$6,700,000

8 bd · 10 ba · 8,133 sqft

8342 Boyla Court, Windermere, FL

Simon Simaan · THE SIMON SIMAAN GROUP

49Active

$679,000

3 bd · 3 ba · 2,177 sqft

2053 Woody Drive, Windermere, FL

Vivian Saavedra · LPT REALTY, LLC

Price Reduced43Active

$1,150,000

4 bd · 3 ba · 3,540 sqft

2009 Woody Drive, Windermere, FL

Rebekkah Boskovich · REVEL REALTY LLC

Price Reduced43Active

$1,150,000

4 bd · 3 ba · 3,540 sqft

2009 Woody Dr, Windermere, FL

Rebekkah Boskovich · REVEL REALTY LLC

34Active

$444,900

3 bd · 3 ba · 1,642 sqft

7060 Ventnor Drive, Windermere, FL

Lidia Barberini · AGENT TRUST REALTY CORPORATION

Price Reduced65Active

$980,000

4 bd · 3 ba · 3,478 sqft

2512 Tryon Pl, Windermere, FL

Jamie Stolinas Crame, LLC · CENTURY 21 CARIOTI

34Active

$444,900

3 bd · 3 ba · 1,642 sqft

7060 Ventnor Dr, Windermere, FL

Lidia Barberini · AGENT TRUST REALTY CORPORATION

Price Reduced65Active

$980,000

4 bd · 3 ba · 3,478 sqft

2512 Tryon Place, Windermere, FL

Jamie Stolinas Crame, LLC · CENTURY 21 CARIOTI

Price Reduced31Active

$555,000

3 bd · 2 ba · 1,706 sqft

13219 Charfield Street, Windermere, FL

Patricia Schraiber · DENIZ REALTY PARTNERS LLC

Price Reduced32Active

$325,000

3 bd · 2 ba · 1,442 sqft

11446 Jasper Kay Ter #103, Windermere, FL

Jay Stewart · SOUTHERN REALTY GROUP LLC

32Active

$330,000

3 bd · 2 ba · 1,442 sqft

11446 Jasper Kay Terrace 103, Windermere, FL

Jay Stewart · SOUTHERN REALTY GROUP LLC

Price Reduced31Active

$555,000

3 bd · 2 ba · 1,706 sqft

13219 Charfield St, Windermere, FL

Patricia Schraiber · DENIZ REALTY PARTNERS LLC

Price Reduced48Active

$550,000

3 bd · 2 ba · 1,948 sqft

13137 Penshurst Lane, Windermere, FL

Jauquese Knowles · MORRIS WILLIAMS REALTY

Price Reduced48Active

$550,000

3 bd · 2 ba · 1,948 sqft

13137 Penshurst Ln, Windermere, FL

Jauquese Knowles · MORRIS WILLIAMS REALTY

17Active

$325,000

3 bd · 2 ba · 1,455 sqft

8168 Boat Hook Loop 724, Windermere, FL

Brian LeMay · ROMAN REALTY GROUP, LLC

Price Reduced55Active

$1,900,000

4 bd · 6 ba · 5,515 sqft

1238 Lake Whitney Drive, Windermere, FL

Jason Crane · JASON CRANE REAL ESTATE LLC

Price Reduced55Active

$1,900,000

4 bd · 6 ba · 5,515 sqft

1238 Lake Whitney Dr, Windermere, FL

Jason Crane · JASON CRANE REAL ESTATE LLC

73Active

$6,500,000

5 bd · 7 ba · 5,471 sqft

9316 Gladys Garden Ct, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

73Active

$6,500,000

5 bd · 7 ba · 5,471 sqft

9316 Gladys Garden Ct, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

98Active

$13,995,000

6 bd · 11 ba · 12,067 sqft

3057 Porto Lago Court, Windermere, FL

Julie Bettosini, PA · STOCKWORTH REALTY GROUP

Price Reduced29Active

$745,990

5 bd · 3 ba · 3,285 sqft

7409 Fairgrove Ave, Windermere, FL

Zhe Wang · SUNSTAR REALTY FL INC

98Active

$13,995,000

6 bd · 11 ba · 12,067 sqft

3057 Porto Lago Ct, Windermere, FL

Julie Bettosini, PA · STOCKWORTH REALTY GROUP

1…9 10 11…19

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.

Windermere housing market

September 2026 · This period is still settling

Selling at 97.1% of asking price

Buyers here are paying below asking. MLS · 46 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 22, 2026

Median sale price: $780,000$532,450–$1,125,000 typical range
Price per sq. ft.: $285
Sales: 39
Paid in cash: 41.0%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $1,090,000

Windermere, FL community profile

Population: 3,301
Median income: $148,077
Housing units: 1,328
People per sq. mi.: 115
Area: 28.7 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 Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

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Nearby areas

ZIP codes

34747 (2,311)
34746 (1,657)
33837 (1,447)
34787 (1,383)
33896 (1,136)
34771 (948)
33897 (893)
34748 (843)

Cities

Orlando (7,348)
Kissimmee (5,463)
Davenport (3,432)
St. Cloud (2,004)
Clermont (1,407)

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

Nearby areas

ZIP codes

34747 (2,311)
34746 (1,657)
33837 (1,447)
34787 (1,383)
33896 (1,136)
34771 (948)
33897 (893)
34748 (843)

Cities

Orlando (7,348)
Kissimmee (5,463)
Davenport (3,432)
St. Cloud (2,004)
Clermont (1,407)

Winter Garden (1,334)

Apopka (994)

LEESBURG (865)

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.

Windermere, FL community profile

Population: 3,301
Median income: $148,077
Housing units: 1,328
People per sq. mi.: 115
Area: 28.7 sq. mi.

Source: HJN community data

Windermere housing market

September 2026 · This period is still settling

Selling at 97.1% of asking price

Buyers here are paying below asking. MLS · 46 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 22, 2026

Median sale price: $780,000$532,450–$1,125,000 typical range
Price per sq. ft.: $285
Sales: 39
Paid in cash: 41.0%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $1,090,000

Homes for sale

248

Median days on market

32 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: -20.4%

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

Median home size: 2,645 sq. ft.

Windermere, FL Homes for Sale — Page 10 | Realty.com