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Before you start looking
The buying timeline

Afford it

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How much can I afford?
Get pre-approved

Make the deal

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Closing costs, itemized
Find a buyer's agent

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3 beds With a pool

Luxury Homes in Windermere, FL — Page 4

118 listings

Luxury Homes in Windermere, FL

Luxury Homes in Windermere, FL

24 of 118 Listings

Luxury Homes in Windermere, FL

24 of 118 Listings

1Active

Your Windermere agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLC

$3,750,000

5 bd · 6 ba · 6,182 sqft

9960 6th St, Windermere, FL

Fernanda Negromonte · NOVA REAL ESTATE SERVICES INC

$5,300,000

6 bd · 7 ba · 4,665 sqft

5199 Latrobe Dr, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

$2,899,000

7 bd · 6 ba · 5,122 sqft

4303 Isabella Cir, Windermere, FL

Gaby Sadler · SERHANT

Price Reduced48Active

$1,169,900

5 bd · 4 ba · 3,064 sqft

2230 Ridgewind Way, Windermere, FL

Tim Frush · COLDWELL BANKER REALTY

Price Reduced44Active

$1,375,000

5 bd · 6 ba · 5,378 sqft

9527 Queensbury Ct, Windermere, FL

Tamar Hill · THE PROPERTY PROS REAL ESTATE, INC

Price ReducedOpen house Sat, Oct 10 · 1:00 PM48Active

$1,090,990

4 bd · 4 ba · 3,153 sqft

14341 Crest Palm Ave, Windermere, FL

Nancy Pruitt, PA · OLYMPUS EXECUTIVE REALTY INC

Price Reduced41Active

$1,395,000

4 bd · 4 ba · 3,997 sqft

9548 Crown Prince Ln, Windermere, FL

Dianna Desboyaux · DOUGLAS ELLIMAN

Price Reduced46Active

$6,595,000

5 bd · 6 ba · 7,178 sqft

6462 Deacon Cir, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

Price Reduced4Active

$1,572,000

4 bd · 2 ba · 2,130 sqft

33 Main St, Windermere, FL

Bruce Higgins · SAND DOLLAR REALTY GROUP INC

$27,000,000

7 bd · 10 ba · 22,108 sqft

5603 Marleon Dr, Windermere, FL

Llin Lu, PA · PREMIER SOTHEBYS INT'L REALTY

Price Reduced57Active

$1,275,000

4 bd · 3 ba · 3,427 sqft

1554 Lake Rhea Dr, Windermere, FL

Adam Shuler, II · PREMIER SOTHEBYS INT'L REALTY

Price Reduced90Active

$6,995,000

5 bd · 8 ba · 7,529 sqft

9349 Tibet Pointe Cir, Windermere, FL

Jay Martin · CORCORAN PREMIER REALTY

Price Reduced35Active

$5,390,000

4 bd · 7 ba · 7,872 sqft

12264 Montalcino Cir, Windermere, FL

Jennifer Olmeda · WRA BUSINESS & REAL ESTATE

Price Reduced65Active

$1,375,000

4 bd · 4 ba · 4,052 sqft

9119 Balmoral Mews Sq, Windermere, FL

Seana Abdelmajid · LA ROSA REALTY BEACHES LLC

Price Reduced43Active

$2,275,000

4 bd · 3 ba · 3,004 sqft

9620 Maywood Dr, Windermere, FL

Linda O'Grady · PREMIER SOTHEBYS INT'L REALTY

Price Reduced66Active

$1,795,000

5 bd · 6 ba · 3,728 sqft

11051 Hawkshead Ct, Windermere, FL

Ken Pozek · REAL BROKER, LLC

Price Reduced51Active

$4,999,500

4 bd · 5 ba · 4,330 sqft

5138 Fairway Oaks Dr, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

Price Reduced65Active

$2,290,000

6 bd · 4 ba · 4,482 sqft

9648 Weatherstone Ct, Windermere, FL

Andy Neal · THE AGENCY FL

Price Reduced65Active

$1,395,000

4 bd · 5 ba · 3,399 sqft

12411 Montalcino Cir, Windermere, FL

Mauro Costa · WILLIAM RAVEIS FLORIDA, LLC

Price Reduced64Active

$1,365,000

5 bd · 4 ba · 3,487 sqft

12718 Windermere Isles Pl, Windermere, FL

Patricia Zimath, LLC · CHARLES RUTENBERG REALTY ORLANDO

$15,500,000

10 bd · 17 ba · 13,425 sqft

12488 Park Ave, Windermere, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

Price Reduced44Active

$1,089,000

4 bd · 3 ba · 3,390 sqft

715 Magnolia St, Windermere, FL

Robert Trien · IRIS INTERNATIONAL

Price Reduced63Active

$4,100,000

3 bd · 5 ba · 5,004 sqft

9144 Isleworth Gardens Dr, Windermere, FL

Megan Dowdy · MEGAN DOWDY REALTY, LLC

$1,130,000

8 bd · 5 ba · 4,830 sqft

6152 Golden Dewdrop Trl, Windermere, FL

Vitor Silva · VESTI LLC

1…3 4 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 97.1% 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.