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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

Save search Advertise Sign In

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

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Registered offenders on the map

Show registered offenders

Selling Options

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

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
What's worth fixing first
Find a seller's agent

3 beds With a pool

Luxury Homes in Windermere, FL

104 listings

Luxury Homes in Windermere, FL

Luxury Homes in Windermere, FL

24 of 104 Listings

Luxury Homes in Windermere, FL

24 of 104 Listings

New97

Your Windermere agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLC

Active

$2,400,000

5 bd · 4 ba · 5,139 sqft

12722 S Lake Sawyer Ln, Windermere, FL

Padgett McCormick · KELLY PRICE & COMPANY LLC

$8,500,000

4 bd · 5 ba · 7,100 sqft

5092 Isleworth Country Club Dr, Windermere, FL

Michelle Corbin · ISLEWORTH REALTY LLC

$6,950,000

7 bd · 8 ba · 8,722 sqft

6113 Grosvenor Shore Dr, Windermere, FL

Gwen Flynn · COLDWELL BANKER REALTY

$3,850,000

4 bd · 6 ba · 6,605 sqft

4906 Aviva Garden Ct, Windermere, FL

Simon Simaan · THE SIMON SIMAAN GROUP

$2,350,000

4 bd · 6 ba · 4,169 sqft

11532 Waterstone Loop Dr, Windermere, FL

Andrew Kincaid · BHHS FLORIDA REALTY

$3,595,000

3 bd · 5 ba · 4,333 sqft

9310 Isleworth Gardens Dr, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

$3,999,000

5 bd · 6 ba · 5,580 sqft

6120 Greatwater Dr, Windermere, FL

Teresa Stewart · SOUTHERN REALTY GROUP LLC

$1,488,000

4 bd · 4 ba · 3,763 sqft

12721 Jacob Grace Ct, Windermere, FL

Cathy Williams · LAKE NONA REALTY LLC

$3,250,000

3 bd · 4 ba · 2,848 sqft

6126 Payne Stewart Dr, Windermere, FL

Jill Irwin · IRWIN REALTY GROUP LLC

$4,395,000

6 bd · 6 ba · 4,739 sqft

5186 Vardon Dr, Windermere, FL

Michelle Corbin · ISLEWORTH REALTY LLC

$7,450,000

7 bd · 10 ba · 8,362 sqft

9343 Tibet Pointe Cir, Windermere, FL

Juliana Jardini Da Cunha Igayara De So · NOVA REAL ESTATE SERVICES INC

$1,100,000

5 bd · 4 ba · 3,557 sqft

11021 Hawkshead Ct, Windermere, FL

Heather Unger, PA · ACME REAL ESTATE FLORIDA 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 St, Windermere, FL

Julie Bettosini, PA · STOCKWORTH REALTY GROUP

$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 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 Dr, Windermere, FL

Rob Rahter · STOCKWORTH REALTY GROUP

$2,950,000

5 bd · 4 ba · 7,153 sqft

4301 Down Point Ln, Windermere, FL

Yuliya Mariani · MARIANI REALTY GROUP

$3,300,000

4 bd · 6 ba · 3,966 sqft

515 W 2nd Ave, Windermere, FL

Darrell Nunnelley · VINTAGE REALTY GROUP 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

Price Reduced70Active

$1,349,900

5 bd · 3 ba · 3,356 sqft

2540 Hempel Cove Ct, Windermere, FL

Tiffany Pantozzi · ALIGN REAL ESTATE LLC

$2,500,000

5 bd · 5 ba · 4,661 sqft

5526 Marleon Dr, Windermere, FL

Benjamin Attwood · SERHANT

1 2…5

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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 97.2% of asking price

Buyers here are paying below asking. MLS · 42 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 15, 2026

Median sale price: $767,500$548,400–$995,000 typical range
Price per sq. ft.: $285
Sales: 30
Paid in cash: 36.7%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 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.