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Start here

Homes for sale by state
Home buying tips
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
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

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What's my home worth?
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Get an instant cash offer
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3 beds With a pool

Homes with a Pool in Windermere, FL — Page 7

235 listings

Homes with a Pool in Windermere, FL

Homes with a Pool in Windermere, FL

24 of 235 Listings

Homes with a Pool in Windermere, FL

24 of 235 Listings

Price Reduced98

Your Windermere agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLC

Active

$1,750,000

4 bd · 3 ba · 3,297 sqft

2503 Butler Bay Drive N, Windermere, FL

Simon Simaan · THE SIMON SIMAAN GROUP

Price Reduced98Active

$1,750,000

4 bd · 3 ba · 3,297 sqft

2503 Butler Bay Dr N, Windermere, FL

Simon Simaan · THE SIMON SIMAAN GROUP

$1,090,000

4 bd · 3 ba · 2,842 sqft

1407 Hempel Ave, Windermere, FL

Lina Abi Hanna De El Bonney · MY REALTY GROUP, LLC.

$1,090,000

4 bd · 3 ba · 2,842 sqft

1407 Hempel Avenue, Windermere, FL

Lina Abi Hanna De El Bonney · MY REALTY GROUP, LLC.

$3,750,000

5 bd · 6 ba · 6,182 sqft

9960 6th St, Windermere, FL

Fernanda Negromonte · NOVA REAL ESTATE SERVICES INC

$3,750,000

5 bd · 6 ba · 6,182 sqft

9960 6th Street, Windermere, FL

Fernanda Negromonte · NOVA REAL ESTATE SERVICES INC

$5,300,000

6 bd · 7 ba · 4,665 sqft

5199 Latrobe Dr, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

$5,300,000

6 bd · 7 ba · 4,665 sqft

5199 Latrobe Dr, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

$2,899,000

7 bd · 6 ba · 5,122 sqft

4303 Isabella Cir, Windermere, FL

Gaby Sadler · SERHANT

$2,899,000

7 bd · 6 ba · 5,122 sqft

4303 Isabella Circle, Windermere, FL

Gaby Sadler · SERHANT

Price Reduced48Active

$1,169,900

5 bd · 4 ba · 3,064 sqft

2230 Ridgewind Way, Windermere, FL

Tim Frush · COLDWELL BANKER REALTY

Price Reduced48Active

$1,169,900

5 bd · 4 ba · 3,064 sqft

2230 Ridgewind Way, Windermere, FL

Tim Frush · COLDWELL BANKER REALTY

Price Reduced42Active

$1,450,000

5 bd · 5 ba · 3,868 sqft

11015 Hawkshead Court, Windermere, FL

Julie Davis, LLC · COLDWELL BANKER REALTY

Price Reduced44Active

$1,375,000

5 bd · 6 ba · 5,378 sqft

9527 Queensbury Ct, Windermere, FL

Tamar Hill · THE PROPERTY PROS REAL ESTATE, INC

Price Reduced44Active

$1,375,000

5 bd · 6 ba · 5,378 sqft

9527 Queensbury Court, Windermere, FL

Tamar Hill · THE PROPERTY PROS REAL ESTATE, INC

Price Reduced41Active

$1,395,000

4 bd · 4 ba · 3,997 sqft

9548 Crown Prince Lane, Windermere, FL

Dianna Desboyaux · DOUGLAS ELLIMAN

Price Reduced41Active

$1,395,000

4 bd · 4 ba · 3,997 sqft

9548 Crown Prince Ln, Windermere, FL

Dianna Desboyaux · DOUGLAS ELLIMAN

Price Reduced46Active

$6,595,000

5 bd · 6 ba · 7,178 sqft

6462 Deacon Cir, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

Price Reduced46Active

$6,595,000

5 bd · 6 ba · 7,178 sqft

6462 Deacon Cir, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

$27,000,000

7 bd · 10 ba · 22,108 sqft

5603 Marleon Drive, Windermere, FL

Llin Lu, PA · PREMIER SOTHEBYS INT'L REALTY

$27,000,000

7 bd · 10 ba · 22,108 sqft

5603 Marleon Dr, Windermere, FL

Llin Lu, PA · PREMIER SOTHEBYS INT'L REALTY

Price Reduced57Active

$1,275,000

4 bd · 3 ba · 3,427 sqft

1554 Lake Rhea Drive, Windermere, FL

Adam Shuler, II · PREMIER SOTHEBYS INT'L REALTY

Price Reduced57Active

$1,275,000

4 bd · 3 ba · 3,427 sqft

1554 Lake Rhea Dr, Windermere, FL

Adam Shuler, II · PREMIER SOTHEBYS INT'L REALTY

Price Reduced44Active

$940,000

4 bd · 3 ba · 2,357 sqft

8525 Bowden Way, Windermere, FL

Teresa Stewart · SOUTHERN REALTY GROUP LLC

1…6 7 8…10

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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.

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Your Windermere agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLC

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.