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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
Buy before you sell

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What's worth fixing first
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3 beds With a pool

Homes Under $2.25M in Windermere, FL — Page 4

153 listings

Homes Under $2.25M in Windermere, FL

Homes Under $2.25M in Windermere, FL

24 of 153 Listings

Homes Under $2.25M in Windermere, FL

24 of 153 Listings

Price Reduced40

Your Windermere agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLC

Active

$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

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 Reduced48Active

$1,250,000

4 bd · 3 ba · 2,887 sqft

6124 Foxfield Ct, Windermere, FL

Bo Julian · JULIAN PROPERTIES, INC.

Price Reduced31Active

$380,000

3 bd · 3 ba · 1,680 sqft

7723 Fairgrove Ave, Windermere, FL

Larry Bautista · CHARLES RUTENBERG REALTY ORLANDO

Price Reduced48Active

$397,500

3 bd · 3 ba · 1,840 sqft

8218 Mystic View Way #2801, Windermere, FL

Deb Obert · WEICHERT REALTORS HALLMARK PRO

Price Reduced37Active

$1,055,000

5 bd · 5 ba · 4,936 sqft

9117 Outlook Rock Trl, Windermere, FL

Rosanna Rivera · REDFIN CORPORATION

$430,000

3 bd · 3 ba · 1,919 sqft

12357 Via Derna Pl, Windermere, FL

Isabel Sirizzotti · SUNNY 365 REALTY GROUP

Price Reduced56Active

$799,900

4 bd · 5 ba · 2,450 sqft

11994 McKinnon Rd, Windermere, FL

Gloria Alvarez · CENTURY 21 CARIOTI

Price Reduced30Active

$635,000

3 bd · 2 ba · 1,819 sqft

9110 Palm Tree Dr, Windermere, FL

Tony Vicari · VICARI REALTY CORP

Price Reduced47Active

$1,350,000

5 bd · 4 ba · 3,929 sqft

1700 Lake Roberts Ct, Windermere, FL

David Johnston · CREEGAN GROUP

$625,000

4 bd · 3 ba · 2,236 sqft

13786 Summer Harbor Ct, Windermere, FL

Deborah Garson · DEBORAH E GARSON PA

Price Reduced19Active

$751,400

4 bd · 2 ba · 2,987 sqft

2128 Lake Crescent Ct, Windermere, FL

Jamarr Zellner · REALHOME SERVICE & SOLUTIONS INC

$1,318,000

6 bd · 4 ba · 3,900 sqft

11768 Hampstead St, Windermere, FL

Caroline De Castro Marcellini · COMPASS FLORIDA, LLC

1…3 4 5…7

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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.