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4 Bedroom Homes in Windermere, FL

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24 of 83 Listings

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24 of 83 Listings

Price Reduced98

4 Bedroom Homes in Windermere, FL — Page 3

83 listings

4 Bedroom Homes in Windermere, FL

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24 of 83 Listings

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4 Bedroom Homes in Windermere, FL

24 of 83 Listings

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

Price Reduced98

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

Active

$1,750,000

4 bd · 3 ba · 3,297 sqft

2503 Butler Bay Dr N, Windermere, FL

Simon Simaan · THE SIMON SIMAAN GROUP

95Active

$1,090,000

4 bd · 3 ba · 2,842 sqft

1407 Hempel Ave, Windermere, FL

Lina Abi Hanna De El Bonney · MY REALTY GROUP, LLC.

Price Reduced39Active

$499,990

4 bd · 3 ba · 2,221 sqft

7867 Berkshire Oak Aly, Windermere, FL

James Song · MULTI CHOICE REALTY LLC

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

Price Reduced48Active

$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 Reduced4Active

$1,572,000

4 bd · 2 ba · 2,130 sqft

33 Main St, Windermere, FL

Bruce Higgins · SAND DOLLAR REALTY GROUP INC

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 Reduced44Active

$940,000

4 bd · 3 ba · 2,357 sqft

8525 Bowden Way, Windermere, FL

Teresa Stewart · SOUTHERN REALTY GROUP LLC

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 Reduced51Active

$4,999,500

4 bd · 5 ba · 4,330 sqft

5138 Fairway Oaks Dr, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

Price Reduced73Active

$979,990

4 bd · 3 ba · 2,740 sqft

14353 Crest Palm Ave, Windermere, FL

Cindy Sapp · OLYMPUS EXECUTIVE REALTY INC

Price Reduced65Active

$1,395,000

4 bd · 5 ba · 3,399 sqft

12411 Montalcino Cir, Windermere, FL

Mauro Costa · WILLIAM RAVEIS FLORIDA, LLC

Price Reduced30Active

$584,900

4 bd · 2 ba · 2,050 sqft

9011 Chapman Oak Ct, Windermere, FL

Shiran Moyal · TOWNE CENTER REALTY

Price Reduced44Active

$1,089,000

4 bd · 3 ba · 3,390 sqft

715 Magnolia St, Windermere, FL

Robert Trien · IRIS INTERNATIONAL

Price Reduced55Active

$725,000

4 bd · 4 ba · 2,742 sqft

910 Lascala Dr, Windermere, FL

Petra Bukalo PA · FLORIDA REALTY INVESTMENTS

Price Reduced40Active

$549,000

4 bd · 3 ba · 2,411 sqft

4627 Blue Major Dr, Windermere, FL

Daniel DeLuca · DENIZ REALTY PARTNERS LLC

Price Reduced44Active

$989,990

4 bd · 4 ba · 3,153 sqft

14371 Crest Palm Ave, Windermere, FL

Cindy Sapp · OLYMPUS EXECUTIVE REALTY INC

Price Reduced31Active

$780,000

4 bd · 4 ba · 3,124 sqft

5413 Walsh Pond Ct, Windermere, FL

Brenda Jebailey · HAVEN PROPERTY GROUP LLC

Price Reduced57Active

$3,800,000

4 bd · 5 ba · 5,301 sqft

5151 Latrobe Dr, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

Price Reduced10Active

$850,000

4 bd · 3 ba · 2,224 sqft

13542 Gorgona Isle Dr, Windermere, FL

Thiago De Ataide · WRA BUSINESS & REAL ESTATE

27Active

$915,000

4 bd · 3 ba · 2,988 sqft

9150 Outlook Rock Trl, Windermere, FL

Andrea Munoz · MOSAIC PARTNERS GROUP

Price Reduced41Active

$554,555

4 bd · 2 ba · 1,798 sqft

9319 Woodbreeze Blvd, Windermere, FL

Steven Looper · CHARLES RUTENBERG REALTY ORLANDO

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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 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.

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

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.

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

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.