Realty.com
Buy

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
Sell

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
Home Loans
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Save search

Map layers

Safety

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
Homes with a Pool in Windermere, FL
Realty.com
Buy

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 searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Commercial

120 listings
Sell

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
Home Loans
Find an Agent
Save search
3 bedsWith a pool

Homes with a Pool in Windermere, FL

Homes with a Pool in Windermere, FL

Hide Map
24 of 120 Listings
Map

Homes with a Pool in Windermere, FL

24 of 120 Listings

Your Windermere agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLCCall Veronica
  1. 6518 Sawyer Shores Ln — photo19Active

    $2,190,000

    5 bd · 6 ba · 3,582 sqft

    6518 Sawyer Shores Ln, Windermere, FL

    Daniel Pavel · WRA BUSINESS & REAL ESTATE

  2. 9615 Windy Ridge Rd — photo41Active

    $5,300,000

    6 bd · 7 ba · 9,669 sqft

    9615 Windy Ridge Rd, Windermere, FL

    Traci Cleveland · KELLER WILLIAMS CLASSIC

  3. 7231 Sangalla Dr — photo65Active

    $1,348,000

    5 bd · 5 ba · 3,835 sqft

    7231 Sangalla Dr, Windermere, FL

    Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

  4. 6544 Cartmel Ln — photo66Active

    $2,390,000

    5 bd · 5 ba · 4,185 sqft

    6544 Cartmel Ln, Windermere, FL

    Debora Segnini · FLORIDA CONNEXION PROPERTIES

  5. 6533 Cartmel Ln — photo52Active

    $1,598,000

    4 bd · 4 ba · 3,751 sqft

    6533 Cartmel Ln, Windermere, FL

    Carolina Medeiros · PREMIER SOTHEBYS INT'L REALTY

  6. 8229 Tibet Butler Dr — photo56Active

    $1,999,000

    4 bd · 4 ba · 3,912 sqft

    8229 Tibet Butler Dr, Windermere, FL

    Teresa Stewart · SOUTHERN REALTY GROUP LLC

  7. 9602 Maywood Dr — photo93Active

    $4,350,000

    5 bd · 5 ba · 5,305 sqft

    9602 Maywood Dr, Windermere, FL

    Tiphany Weeks · DIAMOND REAL ESTATE GROUP

  8. 7030 Mapperton Dr — photo65Active

    $649,000

    4 bd · 3 ba · 2,455 sqft

    7030 Mapperton Dr, Windermere, FL

    Keith Conklin, LLC · FOLIO REALTY LLC

  9. 104 E 1st Ave — photoOpen house Sat, Oct 17 · 11:00 AM53Active

    $1,280,000

    4 bd · 3 ba · 2,441 sqft

    104 E 1st Ave, Windermere, FL

    Fernanda Negromonte · NOVA REAL ESTATE SERVICES INC

  10. 8524 Vivaro Isle Way — photo35Active

    $950,000

    4 bd · 3 ba · 2,680 sqft

    8524 Vivaro Isle Way, Windermere, FL

    Vincent Cordaro · SERHANT

  11. 5092 Isleworth Country Club Dr — photo63Active

    $8,500,000

    4 bd · 5 ba · 7,100 sqft

    5092 Isleworth Country Club Dr, Windermere, FL

    Michelle Corbin · ISLEWORTH REALTY LLC

  12. 11727 Delwick Dr — photoPrice Reduced37Active

    $860,000

    4 bd · 3 ba · 2,704 sqft

    11727 Delwick Dr, Windermere, FL

    Catherine Lambert PA · BHHS FLORIDA REALTY

  13. 6113 Grosvenor Shore Dr — photo100Active

    $6,950,000

    7 bd · 8 ba · 8,722 sqft

    6113 Grosvenor Shore Dr, Windermere, FL

    Gwen Flynn · COLDWELL BANKER REALTY

  14. 4906 Aviva Garden Ct — photo100Active

    $3,850,000

    4 bd · 6 ba · 6,605 sqft

    4906 Aviva Garden Ct, Windermere, FL

    Simon Simaan · THE SIMON SIMAAN GROUP

  15. 11532 Waterstone Loop Dr — photoPrice Reduced74Active

    $2,199,000

    4 bd · 6 ba · 4,169 sqft

    11532 Waterstone Loop Dr, Windermere, FL

    Andrew Kincaid · BHHS FLORIDA REALTY

  16. 9310 Isleworth Gardens Dr — photo51Active

    $3,595,000

    3 bd · 5 ba · 4,333 sqft

    9310 Isleworth Gardens Dr, Windermere, FL

    Monica Lochmandy · ISLEWORTH REALTY LLC

  17. 6120 Greatwater Dr — photo74Active

    $3,999,000

    5 bd · 6 ba · 5,580 sqft

    6120 Greatwater Dr, Windermere, FL

    Teresa Stewart · SOUTHERN REALTY GROUP LLC

  18. 12721 Jacob Grace Ct — photo51Active

    $1,488,000

    4 bd · 4 ba · 3,763 sqft

    12721 Jacob Grace Ct, Windermere, FL

    Cathy Williams · LAKE NONA REALTY LLC

  19. 6126 Payne Stewart Dr — photo38Active

    $3,250,000

    3 bd · 4 ba · 2,848 sqft

    6126 Payne Stewart Dr, Windermere, FL

    Jill Irwin · IRWIN REALTY GROUP LLC

  20. 13738 Eden Isle Blvd — photoPrice Reduced47Active

    $530,000

    4 bd · 2 ba · 2,020 sqft

    13738 Eden Isle Blvd, Windermere, FL

    Kathryn Shevlin · THE PROPERTY FIRM

  21. 5186 Vardon Dr — photo52Active

    $4,395,000

    6 bd · 6 ba · 4,739 sqft

    5186 Vardon Dr, Windermere, FL

    Michelle Corbin · ISLEWORTH REALTY LLC

  22. 9343 Tibet Pointe Cir — photo60Active

    $7,450,000

    7 bd · 10 ba · 8,362 sqft

    9343 Tibet Pointe Cir, Windermere, FL

    Juliana Jardini Da Cunha Igayara De So · NOVA REAL ESTATE SERVICES INC

  23. 9010 Reflection Pointe Dr — photo45Active

    $945,000

    4 bd · 4 ba · 3,264 sqft

    9010 Reflection Pointe Dr, Windermere, FL

    Dawn Giachetti · PREMIER SOTHEBYS INT'L REALTY

  24. 5192 Vardon Dr — photo51Active

    $19,500,000

    6 bd · 10 ba · 13,494 sqft

    5192 Vardon Dr, Windermere, FL

    Jill Irwin · IRWIN REALTY GROUP LLC

12…5

About Homes with a Pool in Windermere, FL

Homes with a Pool in Windermere, FL: 120 active listings as of October 17, 2026, 01:38 UTC.

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
Realty.com

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

Equal Housing OpportunityEqual Housing Lender

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.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

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.
  • 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

    Your Windermere agent

    VF

    Veronica Figueroa

    The Figueroa Team LLC. eXp Realty, LLC

    The Figueroa Team LLC. eXp Realty, LLCCall Veronica

    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

    Windermere 12-month median sale price trend

    Selling at 97.1% of asking price

    Buyers here are paying below asking. MLS · 44 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 29, 2026

    Median sale price
    $780,000$532,450–$1,219,535 typical range
    Price per sq. ft.
    $303
    Sales
    51
    Paid in cash
    47.1%

    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
    31 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.