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Homes Under $2M in Windermere, FL

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24 of 149 Listings

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24 of 149 Listings

98Active

Homes Under $2M in Windermere, FL — Page 5

149 listings

Homes Under $2M in Windermere, FL

Hide Map

24 of 149 Listings

Map

Homes Under $2M in Windermere, FL

24 of 149 Listings

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

98Active

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

$475,000

3 bd · 3 ba · 1,600 sqft

11861 Vermillion Ave, Windermere, FL

Frederico Hexsel · KARDOSH REALTY

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.

19Active

$359,900

3 bd · 3 ba · 1,534 sqft

14442 Desert Haven St #4305, Windermere, FL

Umberto Da Cunha Neto · WRA BUSINESS & REAL ESTATE

Your Windermere agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

Price Reduced39Active

$499,990

4 bd · 3 ba · 2,221 sqft

7867 Berkshire Oak Aly, Windermere, FL

James Song · MULTI CHOICE REALTY LLC

Price Reduced48Active

$1,169,900

5 bd · 4 ba · 3,064 sqft

2230 Ridgewind Way, Windermere, FL

Tim Frush · COLDWELL BANKER REALTY

Price Reduced63Active

$879,000

5 bd · 4 ba · 3,182 sqft

11326 Ledgement Ln, Windermere, FL

Jingjing Guan · AAA GLOBAL VENTURES PA

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 Sun, Oct 4 · 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 Reduced31Active

$415,000

3 bd · 3 ba · 1,577 sqft

8866 Herencia Aly, Windermere, FL

Priscila Lima · WRA BUSINESS & REAL ESTATE

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

33Active

$440,000

3 bd · 3 ba · 1,742 sqft

7612 Fairgrove Ave, Windermere, FL

Maribel Minarro · FLORIDA FANTASY REAL ESTATE INC

Price Reduced44Active

$940,000

4 bd · 3 ba · 2,357 sqft

8525 Bowden Way, Windermere, FL

Teresa Stewart · SOUTHERN REALTY GROUP LLC

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 Reduced66Active

$1,795,000

5 bd · 6 ba · 3,728 sqft

11051 Hawkshead Ct, Windermere, FL

Ken Pozek · REAL BROKER, LLC

Price ReducedOpen house Sun, Oct 4 · 1:00 PM73Active

$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 Reduced64Active

$1,365,000

5 bd · 4 ba · 3,487 sqft

12718 Windermere Isles Pl, Windermere, FL

Patricia Zimath, LLC · CHARLES RUTENBERG REALTY ORLANDO

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

76Active

$1,130,000

8 bd · 5 ba · 4,830 sqft

6152 Golden Dewdrop Trl, Windermere, FL

Vitor Silva · VESTI LLC

1…4 5 6 7

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

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

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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.

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.