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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 2

234 listings

Homes with a Pool in Windermere, FL

Homes with a Pool in Windermere, FL

24 of 234 Listings

Homes with a Pool in Windermere, FL

24 of 234 Listings

51

Your Windermere agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLC

Active

$19,500,000

6 bd · 10 ba · 13,494 sqft

5192 Vardon Drive, Windermere, FL

Jill Irwin · IRWIN REALTY GROUP LLC

$19,500,000

6 bd · 10 ba · 13,494 sqft

5192 Vardon Dr, Windermere, FL

Jill Irwin · IRWIN REALTY GROUP LLC

$1,395,000

5 bd · 4 ba · 4,186 sqft

101 Lee Street, Windermere, FL

Julie Bettosini, PA · STOCKWORTH REALTY GROUP

$1,395,000

5 bd · 4 ba · 4,186 sqft

101 Lee St, Windermere, FL

Julie Bettosini, PA · STOCKWORTH REALTY GROUP

$18,750,000

6 bd · 9 ba · 15,337 sqft

5036 Latrobe Drive, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

$18,750,000

6 bd · 9 ba · 15,337 sqft

5036 Latrobe Dr, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

$3,290,000

5 bd · 7 ba · 5,502 sqft

4243 Isabella Circle, Windermere, FL

John Silva · JOHN SILVA REALTY & ASSOCIATES

$2,685,000

5 bd · 7 ba · 5,747 sqft

8142 Tibet Butler Drive, Windermere, FL

Rob Rahter · STOCKWORTH REALTY GROUP

$3,290,000

5 bd · 7 ba · 5,502 sqft

4243 Isabella Cir, Windermere, FL

John Silva · JOHN SILVA REALTY & ASSOCIATES

$2,685,000

5 bd · 7 ba · 5,747 sqft

8142 Tibet Butler Dr, Windermere, FL

Rob Rahter · STOCKWORTH REALTY GROUP

$7,200,000

5 bd · 6 ba · 5,993 sqft

5373 Isleworth Country Club Drive, Windermere, FL

Rob Rahter · STOCKWORTH REALTY GROUP

$7,200,000

5 bd · 6 ba · 5,993 sqft

5373 Isleworth Country Club Dr, Windermere, FL

Rob Rahter · STOCKWORTH REALTY GROUP

$2,950,000

5 bd · 4 ba · 7,153 sqft

4301 Down Point Lane, Windermere, FL

Yuliya Mariani · MARIANI REALTY GROUP

$2,950,000

5 bd · 4 ba · 7,153 sqft

4301 Down Point Ln, Windermere, FL

Yuliya Mariani · MARIANI REALTY GROUP

$720,000

4 bd · 2 ba · 2,516 sqft

6243 Andreozzi Lane, Windermere, FL

Steven Koleno · BEYCOME OF FLORIDA LLC

$3,300,000

4 bd · 6 ba · 3,966 sqft

515 W 2nd Ave, Windermere, FL

Darrell Nunnelley · VINTAGE REALTY GROUP LLC

$3,300,000

4 bd · 6 ba · 3,966 sqft

515 W 2nd Avenue, Windermere, FL

Darrell Nunnelley · VINTAGE REALTY GROUP LLC

$3,189,000

4 bd · 5 ba · 3,365 sqft

5050 Isleworth Country Club Drive, Windermere, FL

Toni Cafferty · COMPASS FLORIDA LLC

$3,189,000

4 bd · 5 ba · 3,365 sqft

5050 Isleworth Country Club Dr, Windermere, FL

Toni Cafferty · COMPASS FLORIDA LLC

$1,500,000

5 bd · 7 ba · 5,312 sqft

13503 Lake Cawood Dr, Windermere, FL

Nick Horton · BANNER INT'L REAL ESTATE

$2,500,000

5 bd · 5 ba · 4,661 sqft

5526 Marleon Drive, Windermere, FL

Benjamin Attwood · SERHANT

Price Reduced70Active

$1,349,900

5 bd · 3 ba · 3,356 sqft

2540 Hempel Cove Ct, Windermere, FL

Tiffany Pantozzi · ALIGN REAL ESTATE LLC

$1,500,000

5 bd · 7 ba · 5,312 sqft

13503 Lake Cawood Drive, Windermere, FL

Nick Horton · BANNER INT'L REAL ESTATE

$1,399,900

5 bd · 3 ba · 3,356 sqft

2540 Hempel Cove Ct, Windermere, FL

Tiffany Pantozzi · ALIGN REAL ESTATE LLC

1 2 3…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.