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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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What's worth fixing first
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3 beds With a pool

Homes Under $3M in Windermere, FL — Page 4

173 listings

Homes Under $3M in Windermere, FL

Homes Under $3M in Windermere, FL

24 of 173 Listings

Homes Under $3M in Windermere, FL

24 of 173 Listings

Price Reduced42

Your Windermere agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLC

Active

$579,000

3 bd · 2 ba · 1,706 sqft

13231 Roxboro Rd, Windermere, FL

Shannon Tichenor · LA ROSA REALTY KISSIMMEE

Price Reduced49Active

$438,000

4 bd · 3 ba · 1,631 sqft

8386 Iron Mountain Trl, Windermere, FL

Hilda Teran Nava · MY REALTY GROUP, LLC.

Price Reduced28Active

$740,000

5 bd · 4 ba · 2,989 sqft

8931 Lookout Pointe Dr, Windermere, FL

Lilly Vazquez · SPECIALIZED PROPERTY MANAGEMENT

$2,800,000

6 bd · 8 ba · 6,781 sqft

13250 Bellaria Cir, 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

Price Reduced37Active

$350,000

3 bd · 3 ba · 1,644 sqft

7712 Fordson Ln, Windermere, FL

Jorge Martinez, Jr · KELLER WILLIAMS CLASSIC

Price Reduced30Active

$659,000

4 bd · 4 ba · 2,610 sqft

7537 Brofield Ave, Windermere, FL

Ping Song · SUNSHINE GROUP USA, INC

Price Reduced44Active

$1,065,000

4 bd · 4 ba · 3,646 sqft

8344 Bowden Way, Windermere, FL

Immu Korvenmaa · ALIGN REAL ESTATE LLC

Price Reduced29Active

$375,000

3 bd · 3 ba · 1,579 sqft

5579 Somersby Rd, Windermere, FL

Cheryl Kypreos · HOMESMART

Price Reduced40Active

$439,000

4 bd · 3 ba · 1,910 sqft

11429 Brownstone St, Windermere, FL

Jenny Wemert · WEMERT GROUP REALTY LLC

Price Reduced35Active

$324,900

2 bd · 3 ba · 1,232 sqft

14030 Sparkling Cove Ln #603, Windermere, FL

Shane Jordan · COLDWELL BANKER REALTY

$2,500,000

6 bd · 4 ba · 4,858 sqft

1629 Hempel Ave, Windermere, FL

Mike Borah · COLDWELL BANKER REALTY

Price Reduced37Active

$539,900

3 bd · 2 ba · 1,819 sqft

9433 Palm Tree Dr, Windermere, FL

Kitty Mark · COLDWELL BANKER REALTY

Price Reduced53Active

$798,000

5 bd · 5 ba · 3,373 sqft

4642 River Gem Ave, Windermere, FL

John Silva · JOHN SILVA REALTY & ASSOCIATES

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

$444,900

3 bd · 3 ba · 1,642 sqft

7060 Ventnor Dr, Windermere, FL

Lidia Barberini · AGENT TRUST REALTY CORPORATION

Price Reduced32Active

$325,000

3 bd · 2 ba · 1,442 sqft

11446 Jasper Kay Ter #103, Windermere, FL

Jay Stewart · SOUTHERN REALTY GROUP LLC

Price Reduced31Active

$555,000

3 bd · 2 ba · 1,706 sqft

13219 Charfield St, Windermere, FL

Patricia Schraiber · DENIZ REALTY PARTNERS LLC

Price Reduced48Active

$550,000

3 bd · 2 ba · 1,948 sqft

13137 Penshurst Ln, Windermere, FL

Jauquese Knowles · MORRIS WILLIAMS REALTY

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

Price Reduced29Active

$745,990

5 bd · 3 ba · 3,285 sqft

7409 Fairgrove Ave, Windermere, FL

Zhe Wang · SUNSTAR REALTY FL INC

$295,000

2 bd · 2 ba · 1,161 sqft

8180 Boat Hook Loop #102, Windermere, FL

Robert Christiano · COLDWELL BANKER REALTY

Price Reduced77Active

$2,450,000

4 bd · 5 ba · 4,136 sqft

4205 Clarice Estates Dr, Windermere, FL

Cynthia Casola · DALTON WADE INC

1…3 4 5…8

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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.