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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
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Closing costs, itemized
Find a buyer's agent

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3 beds With a pool

Homes with a Pool in Windermere, FL — Page 10

235 listings

Homes with a Pool in Windermere, FL

Homes with a Pool in Windermere, FL

19 of 235 Listings

Homes with a Pool in Windermere, FL

19 of 235 Listings

Price Reduced70

Your Windermere agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLC

Active

$7,250,000

5 bd · 7 ba · 7,099 sqft

5074 Isleworth Country Club Drive, Windermere, FL

Armaan Memarpouri · MEM REALTY GROUP

Price Reduced70Active

$7,250,000

5 bd · 7 ba · 7,099 sqft

5074 Isleworth Country Club Dr, Windermere, FL

Armaan Memarpouri · MEM REALTY GROUP

Price Reduced54Active

$5,975,000

7 bd · 7 ba · 8,000 sqft

9725 Chestnut Ridge Drive, Windermere, FL

Dianna Desboyaux · DOUGLAS ELLIMAN

Price Reduced54Active

$5,975,000

7 bd · 7 ba · 8,000 sqft

9725 Chestnut Ridge Dr, Windermere, FL

Dianna Desboyaux · DOUGLAS ELLIMAN

Price Reduced52Active

$2,950,000

4 bd · 5 ba · 4,676 sqft

6130 Grosvenor Shore Drive, Windermere, FL

Dianna Desboyaux · DOUGLAS ELLIMAN

Price Reduced52Active

$2,950,000

4 bd · 5 ba · 4,676 sqft

6130 Grosvenor Shore Dr, Windermere, FL

Dianna Desboyaux · DOUGLAS ELLIMAN

Price Reduced95Active

$4,750,000

7 bd · 8 ba · 8,931 sqft

9575 Westover Roberts Rd, Windermere, FL

Rob Rahter · STOCKWORTH REALTY GROUP

Price Reduced95Active

$4,750,000

7 bd · 8 ba · 8,931 sqft

9575 Westover Roberts Road, Windermere, FL

Rob Rahter · STOCKWORTH REALTY GROUP

Price Reduced21Active

$9,750,000

5 bd · 3 ba · 5,316 sqft

4226 Downeast Ln, Windermere, FL

Thad Czapka · COLDWELL BANKER RESIDENTIAL RE

Price Reduced29Active

$9,750,000

5 bd · 3 ba · 5,316 sqft

4226 Downeast Lane, Windermere, FL

Thad Czapka · COLDWELL BANKER RESIDENTIAL RE

$1,775,000

3 bd · 3 ba · 3,135 sqft

12001 Lake Butler Blvd, Windermere, FL

Bo Julian · JULIAN PROPERTIES, INC.

$1,775,000

3 bd · 3 ba · 3,135 sqft

12001 Lake Butler Boulevard, Windermere, FL

Bo Julian · JULIAN PROPERTIES, INC.

$3,699,000

3 bd · 5 ba · 4,262 sqft

4812 Alexandra Garden Court, Windermere, FL

Rob Rahter · STOCKWORTH REALTY GROUP

Price Reduced81Active

$4,778,000

6 bd · 9 ba · 8,305 sqft

9721 Carillon Park Drive, Windermere, FL

Dianna Desboyaux · DOUGLAS ELLIMAN

Price Reduced81Active

$4,778,000

6 bd · 9 ba · 8,305 sqft

9721 Carillon Park Dr, Windermere, FL

Dianna Desboyaux · DOUGLAS ELLIMAN

$3,200,000

4 bd · 5 ba · 3,745 sqft

4819 Alexandra Garden Court, Windermere, FL

Michelle Corbin · ISLEWORTH REALTY LLC

$3,200,000

4 bd · 5 ba · 3,745 sqft

4819 Alexandra Garden Ct, Windermere, FL

Michelle Corbin · ISLEWORTH REALTY LLC

Price Reduced71Active

$3,950,000

5 bd · 8 ba · 6,248 sqft

11002 Lake Butler Boulevard, Windermere, FL

Sean Oakley · SERENDIPITY REALTY LLC

Price Reduced71Active

$3,950,000

5 bd · 8 ba · 6,248 sqft

11002 Lake Butler Blvd, Windermere, FL

Sean Oakley · SERENDIPITY REALTY LLC

1…9 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.