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

Selling Options

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

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
What's worth fixing first
Find a seller's agent

Save search Advertise Sign In

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

Registered offenders on the map

Show registered offenders

Registered offenders on the map

Show registered offenders

Safety & registry resources

Review official public-safety information for any area from these government sources:

U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
FBI: state sex-offender registry directory

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

Commercial

Registered offenders on the map

Show registered offenders

Selling Options

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

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
What's worth fixing first
Find a seller's agent

3 beds With a pool

Homes with a Pool in Windermere, FL — Page 8

234 listings

Homes with a Pool in Windermere, FL

Homes with a Pool in Windermere, FL

24 of 234 Listings

Homes with a Pool in Windermere, FL

24 of 234 Listings

Price Reduced90

Your Windermere agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLC

Active

$6,995,000

5 bd · 8 ba · 7,529 sqft

9349 Tibet Pointe Circle, Windermere, FL

Jay Martin · CORCORAN PREMIER REALTY

Price Reduced90Active

$6,995,000

5 bd · 8 ba · 7,529 sqft

9349 Tibet Pointe Cir, Windermere, FL

Jay Martin · CORCORAN PREMIER REALTY

Price Reduced35Active

$5,390,000

4 bd · 7 ba · 7,872 sqft

12264 Montalcino Circle, Windermere, FL

Jennifer Olmeda · WRA BUSINESS & REAL ESTATE

Price Reduced35Active

$5,390,000

4 bd · 7 ba · 7,872 sqft

12264 Montalcino Cir, Windermere, FL

Jennifer Olmeda · WRA BUSINESS & REAL ESTATE

Price Reduced43Active

$2,275,000

4 bd · 3 ba · 3,004 sqft

9620 Maywood Drive, Windermere, FL

Linda O'Grady · PREMIER SOTHEBYS INT'L REALTY

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 Reduced65Active

$1,399,000

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 Reduced66Active

$1,795,000

5 bd · 6 ba · 3,728 sqft

11051 Hawkshead Ct, Windermere, FL

Ken Pozek · REAL BROKER, LLC

Price Reduced66Active

$1,795,000

5 bd · 6 ba · 3,728 sqft

11051 Hawkshead Court, Windermere, FL

Ken Pozek · REAL BROKER, LLC

Price Reduced51Active

$4,999,500

4 bd · 5 ba · 4,330 sqft

5138 Fairway Oaks Dr, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

Price Reduced51Active

$4,999,500

4 bd · 5 ba · 4,330 sqft

5138 Fairway Oaks Dr, Windermere, FL

Monica Lochmandy · ISLEWORTH REALTY LLC

Price Reduced65Active

$2,290,000

6 bd · 4 ba · 4,482 sqft

9648 Weatherstone Ct, Windermere, FL

Andy Neal · THE AGENCY FL

Price Reduced65Active

$2,290,000

6 bd · 4 ba · 4,482 sqft

9648 Weatherstone Court, Windermere, FL

Andy Neal · THE AGENCY FL

Price Reduced33Active

$3,990,000

3 bd · 5 ba · 6,236 sqft

4906 Aviva Garden Court, Windermere, FL

William Campbell · CAMPBELL CUSTOM HOMES 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 Reduced65Active

$1,395,000

4 bd · 5 ba · 3,399 sqft

12411 Montalcino Circle, Windermere, FL

Mauro Costa · WILLIAM RAVEIS FLORIDA, LLC

Price Reduced30Active

$584,900

4 bd · 2 ba · 2,050 sqft

9011 Chapman Oak Court, Windermere, FL

Shiran Moyal · TOWNE CENTER REALTY

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 Reduced56Active

$1,375,000

5 bd · 4 ba · 3,487 sqft

12718 Windermere Isles Place, 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

$15,500,000

10 bd · 17 ba · 13,425 sqft

12488 Park Ave, Windermere, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

$15,500,000

10 bd · 17 ba · 13,425 sqft

12488 Park Avenue, Windermere, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

Price Reduced63Active

$4,100,000

3 bd · 5 ba · 5,004 sqft

9144 Isleworth Gardens Dr, Windermere, FL

Megan Dowdy · MEGAN DOWDY REALTY, LLC

1…7 8 9 10

Explore Windermere homes

By price

Homes Under $500K
Homes Under $600K
Homes Under $700K
Homes Under $800K
Homes Under $900K
Homes Under $1M
Homes Under $1.25M
Homes Under $1.5M
Homes Under $1.75M
Homes Under $2M
Homes Under $2.25M
Homes Under $2.5M
Homes Under $2.75M
Homes Under $3M
Homes Over $3M
Luxury Homes

By bedrooms

3 Bedroom Homes
4 Bedroom Homes
5 Bedroom Homes

By type

Single-Family Homes
Townhomes

By feature

Homes with a Pool
Waterfront Homes

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.

© 2026 Realty.com. All rights reserved.PrivacyTermsCalifornia Privacy RightsAccessibilityLicensing

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.