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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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Saved homes Saved searches Your tours Your inquiries Recently viewed Account settings

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What's my home worth?
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Get an instant cash offer
Buy before you sell

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What's worth fixing first
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3 beds With a pool

Homes with a Pool in Windermere, FL — Page 4

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

Price Reduced100

Your Windermere agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLC

Active

$3,990,000

6 bd · 7 ba · 6,896 sqft

4201 Isabella Circle, Windermere, FL

Any Alves · WRA BUSINESS & REAL ESTATE

Price Reduced100Active

$3,990,000

6 bd · 7 ba · 6,896 sqft

4201 Isabella Cir, Windermere, FL

Any Alves · WRA BUSINESS & REAL ESTATE

$3,100,000

4 bd · 5 ba · 4,296 sqft

12102 Montalcino Cir, Windermere, FL

Kristy Cook · EXP REALTY LLC

Price Reduced84Active

$1,740,000

4 bd · 4 ba · 3,680 sqft

8241 Tibet Butler Dr, Windermere, FL

Robert Guidice · GOLFPARK PROPERTIES

Price Reduced84Active

$1,740,000

4 bd · 4 ba · 3,680 sqft

8241 Tibet Butler Drive, Windermere, FL

Robert Guidice · GOLFPARK PROPERTIES

$3,100,000

4 bd · 5 ba · 4,296 sqft

12102 Montalcino Circle, Windermere, FL

Kristy Cook · EXP REALTY LLC

Price Reduced82Active

$6,900,000

5 bd · 6 ba · 7,158 sqft

6055 Louise Cove Dr, Windermere, FL

Rob Rahter · STOCKWORTH REALTY GROUP

Price Reduced82Active

$6,900,000

5 bd · 6 ba · 7,158 sqft

6055 Louise Cove Drive, Windermere, FL

Rob Rahter · STOCKWORTH REALTY GROUP

$3,400,000

6 bd · 7 ba · 5,666 sqft

9679 Westover Roberts Rd, Windermere, FL

Tony Davids · TONYDAVIDSHOMES.COM, LLC

Price Reduced69Active

$675,000

5 bd · 5 ba · 2,963 sqft

7236 Penkridge Ln, Windermere, FL

Amine Berrada · ATLAS BLUE REALTY INC

Price Reduced69Active

$675,000

5 bd · 5 ba · 2,963 sqft

7236 Penkridge Lane, Windermere, FL

Amine Berrada · ATLAS BLUE REALTY INC

$3,400,000

6 bd · 7 ba · 5,666 sqft

9679 Westover Roberts Rd, Windermere, FL

Tony Davids · TONYDAVIDSHOMES.COM, LLC

$3,500,000

4 bd · 6 ba · 7,669 sqft

5524 Worsham Court, Windermere, FL

Ayoub Aitelhaj · ATLIS REALTY GROUP LLC

$3,500,000

4 bd · 6 ba · 7,669 sqft

5524 Worsham Ct, Windermere, FL

Ayoub Aitelhaj · ATLIS REALTY GROUP LLC

$6,650,000

5 bd · 7 ba · 6,970 sqft

9921 Lake Louise Drive, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

$1,300,000

6 bd · 4 ba · 3,667 sqft

12676 Salomon Cove Drive, Windermere, FL

Ramon Brandao · WEBB FLORIDA REALTY LLC

$6,650,000

5 bd · 7 ba · 6,970 sqft

9921 Lake Louise Dr, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

$3,100,000

6 bd · 5 ba · 4,282 sqft

7720 Ficquette Road, Windermere, FL

Ruthanne Martin · REVEL REALTY LLC

$3,100,000

6 bd · 5 ba · 4,282 sqft

7720 Ficquette Rd, Windermere, FL

Ruthanne Martin · REVEL REALTY LLC

Price Reduced73Active

$2,250,000

5 bd · 5 ba · 4,504 sqft

9904 Brentford Court, Windermere, FL

Kevin Sullivan · LAKESIDE REALTY WINDERMERE INC

Price Reduced73Active

$2,250,000

5 bd · 5 ba · 4,504 sqft

9904 Brentford Ct, Windermere, FL

Kevin Sullivan · LAKESIDE REALTY WINDERMERE INC

$4,495,000

5 bd · 7 ba · 6,159 sqft

6719 Valhalla Way, Windermere, FL

Luis Martins · CELEBRITY GLOBAL REALTY LLC

$4,495,000

5 bd · 7 ba · 6,159 sqft

6719 Valhalla Way, Windermere, FL

Luis Martins · CELEBRITY GLOBAL REALTY LLC

$5,999,000

5 bd · 5 ba · 5,511 sqft

800 W 2nd Ave, Windermere, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

1…3 4 5…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.