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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

Save search Advertise Sign In

Saved homes Saved searches Your tours Your inquiries Recently viewed Account settings

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What's my home worth?
Compare selling options
Get an instant cash offer
Buy before you sell

Resources

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When should I sell?
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What's worth fixing first
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3 beds With a pool

Homes Under $2.75M in Windermere, FL — Page 2

164 listings

Homes Under $2.75M in Windermere, FL

Homes Under $2.75M in Windermere, FL

24 of 164 Listings

Homes Under $2.75M in Windermere, FL

24 of 164 Listings

38Active

Your Windermere agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLC

$639,500

4 bd · 3 ba · 2,460 sqft

12909 Cragside Ln, Windermere, FL

Ashlee Hawk · FLORIDA IN MOTION REALTY INC

Open house Sat, Oct 3 · 12:00 PM54Active

$1,270,000

6 bd · 5 ba · 4,585 sqft

14360 Crest Palm Ave, Windermere, FL

Jonathan Cole · KELLER WILLIAMS WINTER PARK

$327,000

3 bd · 2 ba · 1,455 sqft

8156 Boat Hook Loop #623, Windermere, FL

Walter Taylor, III · KELLER WILLIAMS REALTY AT THE PARKS

$2,685,000

5 bd · 7 ba · 5,747 sqft

8142 Tibet Butler Dr, Windermere, FL

Rob Rahter · STOCKWORTH REALTY GROUP

$360,000

2 bd · 3 ba · 1,311 sqft

12417 Cruxbury Dr, Windermere, FL

Christopher Govatos · CHARLES RUTENBERG REALTY ORLANDO

$450,000

2 bd · 1 ba · 1,216 sqft

9764 Gotha Rd, Windermere, FL

Erica Diaz · HOMEVEST REALTY

$645,178

3 bd · 3 ba · 1,714 sqft

13325 Lush Lime Aly, Windermere, FL

Reed Williams · ASHTON WOODS FLORIDA REALTY LLC

$1,500,000

5 bd · 7 ba · 5,312 sqft

13503 Lake Cawood Dr, Windermere, FL

Nick Horton · BANNER INT'L REAL ESTATE

Price Reduced70Active

$1,349,900

5 bd · 3 ba · 3,356 sqft

2540 Hempel Cove Ct, Windermere, FL

Tiffany Pantozzi · ALIGN REAL ESTATE LLC

$445,000

3 bd · 3 ba · 1,748 sqft

13048 Garridan Ave, Windermere, FL

Isabel Sirizzotti · SUNNY 365 REALTY GROUP

$2,500,000

5 bd · 5 ba · 4,661 sqft

5526 Marleon Dr, Windermere, FL

Benjamin Attwood · SERHANT

Price Reduced56Active

$699,990

4 bd · 4 ba · 2,745 sqft

13239 Jervey St, Windermere, FL

Jay Winston · LPT REALTY, LLC

Price Reduced33Active

$1,159,000

4 bd · 4 ba · 2,665 sqft

12989 Westside Village Loop, Windermere, FL

Ramon Brandao · WEBB FLORIDA REALTY LLC

$320,000

3 bd · 2 ba · 1,442 sqft

8168 Boat Hook Loop #303, Windermere, FL

Jay Stewart · SOUTHERN REALTY GROUP LLC

$880,000

4 bd · 3 ba · 2,648 sqft

6309 Earthgold Dr, Windermere, FL

Vanessa Bruno Juca · REALTY HUB

Open house Sat, Oct 3 · 12:00 PM59Active

$354,900

2 bd · 3 ba · 1,412 sqft

7430 Bentonshire Ave, Windermere, FL

Chris Bunnell · EXP REALTY LLC

$445,000

3 bd · 3 ba · 1,727 sqft

11734 Water Run Aly, Windermere, FL

Blanca Armada · REMAX PREMIER PROPERTIES

$870,000

4 bd · 3 ba · 3,746 sqft

9043 Horizon Pointe Trl, Windermere, FL

Matine Pawlicki · CENTURY 21 CARIOTI

Price Reduced67Active

$998,999

6 bd · 5 ba · 4,507 sqft

8701 Iron Mountain Trl, Windermere, FL

Jorge Martinez, Jr · KELLER WILLIAMS CLASSIC

$775,000

4 bd · 3 ba · 2,224 sqft

8291 Procida Isle Ln, Windermere, FL

Anastasiia Zbihla · KELLER WILLIAMS REALTY AT THE LAKES

$990,000

4 bd · 3 ba · 2,728 sqft

1243 Dingens Ave, Windermere, FL

Peter Useche · REALMULTIPROPERTY LLC

$575,000

4 bd · 3 ba · 2,064 sqft

6828 Helmsley Cir, Windermere, FL

Abdallah Fawaz · LPT REALTY, LLC

Price Reduced43Active

$1,695,000

5 bd · 5 ba · 4,219 sqft

1480 Hempel Ave, Windermere, FL

Adriana Sanchez · AROD PARTNERS REALTY

$969,000

5 bd · 5 ba · 3,797 sqft

9609 Westover Club Cir, Windermere, FL

John Petit · ALPHA R.E. OF CENTRAL FL LLC

1 2 3…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 97.2% 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.