60 total properties
Did you mean the neighborhood Windermere?
View 11903 CAVE RUN AVENUE Windermere, FL MLS# O6392757
  • Recently Listed with Virtual Tour
1 of 39
$750,000
4

Beds

3.1

Baths

3,413

Sq.Ft.

11903 CAVE RUN AVENUE

Windermere, FL

Courtesy of LOKATION
View 6613 MERRICK LANDING BOULEVARD Windermere, FL MLS# O6391719
$675,000
3

Beds

3.1

Baths

2,641

Sq.Ft.

6613 MERRICK LANDING BOULEVARD

Windermere, FL

Courtesy of THE AGENCY FL
View 13622 DARCHANCE ROAD Windermere, FL MLS# S5146266
  • Recently Listed with Virtual Tour
1 of 30
$649,000
3

Beds

2.0

Baths

2,147

Sq.Ft.

13622 DARCHANCE ROAD

Windermere, FL

Courtesy of AVANTI WAY REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 7180 BEEK STREET Windermere, FL MLS# O6393213
  • Recently Listed
1 of 40
$780,000
6

Beds

4.0

Baths

3,648

Sq.Ft.

7180 BEEK STREET

Windermere, FL

Courtesy of FOLIO REALTY LLC
View 7924 BROFIELD AVENUE Windermere, FL MLS# S5146185
$650,000
3

Beds

2.1

Baths

1,709

Sq.Ft.

7924 BROFIELD AVENUE

Windermere, FL

Courtesy of ALTIS REALTY
View 12989 WESTSIDE VILLAGE LOOP Windermere, FL MLS# S5145903
$655,000
4

Beds

3.1

Baths

2,665

Sq.Ft.

12989 WESTSIDE VILLAGE LOOP

Windermere, FL

Courtesy of NUMBER 1 BROKER, LLC
View 7208 TATTANT BOULEVARD Windermere, FL MLS# O6389785
$599,000
4

Beds

2.0

Baths

2,215

Sq.Ft.

7208 TATTANT BOULEVARD

Windermere, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 13320 FERNOW STREET Windermere, FL MLS# O6388986
$730,000
4

Beds

3.1

Baths

2,745

Sq.Ft.

13320 FERNOW STREET

Windermere, FL

Courtesy of HOMEVEST REALTY
View 6573 HELMSLEY CIRCLE Windermere, FL MLS# S5145061
$639,900
4

Beds

3.1

Baths

2,664

Sq.Ft.

6573 HELMSLEY CIRCLE

Windermere, FL

Courtesy of WATSON REALTY CORP.
View 7264 BACKWOODS TRAIL Windermere, FL MLS# O6387913
$650,000
4

Beds

2.1

Baths

2,214

Sq.Ft.

7264 BACKWOODS TRAIL

Windermere, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 4773 BLUE MAJOR DRIVE Windermere, FL MLS# O6386132
$619,900
4

Beds

2.1

Baths

2,620

Sq.Ft.

4773 BLUE MAJOR DRIVE

Windermere, FL

Courtesy of LPT REALTY, LLC
View 13240 ROSKIN LANE Windermere, FL MLS# S5144759
  • Virtual Tour
1 of 35
$724,000
4

Beds

3.1

Baths

3,108

Sq.Ft.

13240 ROSKIN LANE

Windermere, FL

Courtesy of HOMESMART
View 13013 OVERSTREET ROAD Windermere, FL MLS# O6380917
$679,994
4

Beds

2.1

Baths

2,053

Sq.Ft.

13013 OVERSTREET ROAD

Windermere, FL

Courtesy of EXP REALTY LLC
View 8552 POWDER RIDGE TRAIL Windermere, FL MLS# S5144276
$690,000
4

Beds

2.1

Baths

2,612

Sq.Ft.

8552 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 13263 STRODE LANE Windermere, FL MLS# O6383141
  • Virtual Tour
1 of 53
$798,900
4

Beds

3.1

Baths

2,559

Sq.Ft.

13263 STRODE LANE

Windermere, FL

Courtesy of HOME WISE REALTY GROUP, INC.
View 13237 FOSSICK ROAD Windermere, FL MLS# O6382389
$625,000
4

Beds

2.0

Baths

2,516

Sq.Ft.

13237 FOSSICK ROAD

Windermere, FL

Courtesy of EXP REALTY LLC
View 17520 BLACK RAIL STREET Windermere, FL MLS# O6384223
$777,000
4

Beds

2.0

Baths

2,380

Sq.Ft.

17520 BLACK RAIL STREET

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 6990 SMITHSHIRE LANE Windermere, FL MLS# O6380372
$675,000
4

Beds

3.1

Baths

2,986

Sq.Ft.

6990 SMITHSHIRE LANE

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 9237 MCDAVID COURT Windermere, FL MLS# O6382243
$798,000
4

Beds

2.1

Baths

2,269

Sq.Ft.

9237 MCDAVID COURT

Windermere, FL

Courtesy of VINTAGE REALTY GROUP LLC
View 13609 ANCILLA BOULEVARD Windermere, FL MLS# O6381542
$789,000
4

Beds

3.1

Baths

3,360

Sq.Ft.

13609 ANCILLA BOULEVARD

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE

About Windermere

"Among the lakes" is the phrase that the town of Windermere has chosen for its description, and aptly so.  Almost completely surrounded by water, Windermere is a lovely small town that will always be limited in population growth by available land.  Lake Butler is the largest body of water in the region, which is often referred to as the "Butler chain of lakes."  Situated in southeast Orange County, the residential villages and homes throughout the lake area are as beautiful as the backdrop of scenery they enjoy.  Some multi-million dollar lakefront mansions combine with more modest but often luxurious homes in a variety of architectural styles.  The Islesworth Golf & Country Club in Windermere rivals the lush fairways of highly acclaimed Bay Hill for sheer bayside splendor.  Also located in this small town is a fully accredited independent school for students in pre-kindergarten through eighth grade called Buena Vista Academy.  While the residents of Windermere can enjoy the exclusive resort setting and serenity of their community, the first-rate cultural, educational, and healthcare advantages of Orlando remain close to home. 

Listings in Windermere, FL

330

Estimated median home price

$1,009,995
Windermere FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Windermere, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Windermere, FL.

Homes for Sale by Price in Windermere, FL

PriceCount
$0 - 100K0
$100K - 200K0
$200K - 300K0
$300K - 400K15
$400K - 500K25
$500K - 600K33
$600K - 700K30
$700K - 800K24
$800K - 900K23
$900K - 1M15
$1M - Max165

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family276
Townhouse34
Condo5
Commercial1
Rental91
Lots and Land14
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 3/24/2026)

Information deemed reliable but not guaranteed.

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 3/25/2026.