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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 5

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

78

Your Windermere agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLC

Active

$5,999,000

5 bd · 5 ba · 5,511 sqft

800 W 2nd Ave, Windermere, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

$5,999,000

5 bd · 5 ba · 5,511 sqft

800 W 2nd Avenue, Windermere, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

$2,800,000

6 bd · 8 ba · 6,781 sqft

13250 Bellaria Cir, Windermere, FL

Scarllet Lettre · CHARLES RUTENBERG REALTY INC

$2,800,000

6 bd · 8 ba · 6,781 sqft

13250 Bellaria Circle, Windermere, FL

Scarllet Lettre · CHARLES RUTENBERG REALTY INC

$1,595,000

4 bd · 4 ba · 3,166 sqft

12417 Montalcino Cir, Windermere, FL

Aziz Elbrak · LA ROSA REALTY LLC

$1,595,000

4 bd · 4 ba · 3,166 sqft

12417 Montalcino Circle, Windermere, FL

Aziz Elbrak · LA ROSA REALTY LLC

$15,900,000

8 bd · 11 ba · 14,068 sqft

6119 Grosvenor Shore Dr, Windermere, FL

Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY

$15,900,000

8 bd · 11 ba · 14,068 sqft

6119 Grosvenor Shore Drive, Windermere, FL

Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY

$2,500,000

6 bd · 4 ba · 4,858 sqft

1629 Hempel Avenue, Windermere, FL

Mike Borah · COLDWELL BANKER REALTY

$2,500,000

6 bd · 4 ba · 4,858 sqft

1629 Hempel Ave, Windermere, FL

Mike Borah · COLDWELL BANKER REALTY

$6,700,000

8 bd · 10 ba · 8,133 sqft

8342 Boyla Ct, Windermere, FL

Simon Simaan · THE SIMON SIMAAN GROUP

$6,700,000

8 bd · 10 ba · 8,133 sqft

8342 Boyla Court, Windermere, FL

Simon Simaan · THE SIMON SIMAAN GROUP

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

Price Reduced65Active

$980,000

4 bd · 3 ba · 3,478 sqft

2512 Tryon Pl, Windermere, FL

Jamie Stolinas Crame, LLC · CENTURY 21 CARIOTI

Price Reduced65Active

$980,000

4 bd · 3 ba · 3,478 sqft

2512 Tryon Place, Windermere, FL

Jamie Stolinas Crame, LLC · CENTURY 21 CARIOTI

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

$6,500,000

5 bd · 7 ba · 5,471 sqft

9316 Gladys Garden Ct, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

$6,500,000

5 bd · 7 ba · 5,471 sqft

9316 Gladys Garden Ct, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

$13,995,000

6 bd · 11 ba · 12,067 sqft

3057 Porto Lago Court, Windermere, FL

Julie Bettosini, PA · STOCKWORTH REALTY GROUP

$13,995,000

6 bd · 11 ba · 12,067 sqft

3057 Porto Lago Ct, Windermere, FL

Julie Bettosini, PA · STOCKWORTH REALTY GROUP

Price Reduced77Active

$2,450,000

4 bd · 5 ba · 4,136 sqft

4205 Clarice Estates Drive, Windermere, FL

Cynthia Casola · DALTON WADE INC

Price Reduced77Active

$2,450,000

4 bd · 5 ba · 4,136 sqft

4205 Clarice Estates Dr, Windermere, FL

Cynthia Casola · DALTON WADE INC

1…4 5 6…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.