47 total properties
Did you mean the neighborhood Windermere?
View 4 CHASE ROAD Windermere, FL MLS# O6384257
  • Recently Listed with Virtual Tour
1 of 47
OPEN HOUSE: Saturday 2/28 11:00 AM - 2:00 PM
$900,000
3

Beds

2.0

Baths

2,386

Sq.Ft.

4 CHASE ROAD

Windermere, FL

Courtesy of REAL BROKER, LLC
View 13263 STRODE LANE Windermere, FL MLS# O6383141
  • Recently Listed with Virtual Tour
1 of 53
$824,900
4

Beds

3.1

Baths

2,559

Sq.Ft.

13263 STRODE LANE

Windermere, FL

Courtesy of HOME WISE REALTY GROUP, INC.
View 13226 JERVEY STREET Windermere, FL MLS# O6383000
$995,000
4

Beds

5.1

Baths

3,608

Sq.Ft.

13226 JERVEY STREET

Windermere, FL

Courtesy of SPRING REALTY ONE LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 8324 VIVARO ISLE WAY Windermere, FL MLS# O6382641
  • Recently Listed with Virtual Tour
1 of 61
$850,000
6

Beds

4.0

Baths

4,176

Sq.Ft.

8324 VIVARO ISLE WAY

Windermere, FL

Courtesy of AGENT GROUP REALTY
View 11835 GOLD CREEK TRAIL Windermere, FL MLS# O6382068
  • Recently Listed with Virtual Tour
1 of 11
$900,000
4

Beds

4.1

Baths

3,119

Sq.Ft.

11835 GOLD CREEK TRAIL

Windermere, FL

Courtesy of BB GROUP REALTY CORP
View 9237 MCDAVID COURT Windermere, FL MLS# O6382243
  • Recently Listed with Virtual Tour
1 of 25
$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
  • Recently Listed with Virtual Tour
1 of 55
$799,000
4

Beds

3.1

Baths

3,360

Sq.Ft.

13609 ANCILLA BOULEVARD

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 9257 OUTLOOK ROCK TRAIL Windermere, FL MLS# S5143447
  • Recently Listed with Virtual Tour
1 of 56
$899,990
5

Beds

4.1

Baths

3,619

Sq.Ft.

9257 OUTLOOK ROCK TRAIL

Windermere, FL

Courtesy of PRIMUS CRE GROUP
View 13302 ROSKIN LANE Windermere, FL MLS# O6380701
  • Recently Listed with Virtual Tour
1 of 46
$899,900
4

Beds

3.1

Baths

3,424

Sq.Ft.

13302 ROSKIN LANE

Windermere, FL

Courtesy of RATIO REAL ESTATE, LLC
View 7123 CALM COVE COURT Windermere, FL MLS# O6380782
  • Recently Listed with Virtual Tour
1 of 35
$814,000
4

Beds

3.1

Baths

3,044

Sq.Ft.

7123 CALM COVE COURT

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 8767 IRON MOUNTAIN TRAIL Windermere, FL MLS# O6379681
  • Recently Listed with Virtual Tour
1 of 38
$870,000
5

Beds

3.1

Baths

3,724

Sq.Ft.

8767 IRON MOUNTAIN TRAIL

Windermere, FL

Courtesy of KARDOSH REALTY
View 6840 HELMSLEY CIRCLE Windermere, FL MLS# S5142930
  • Recently Listed with Virtual Tour
1 of 76
$799,000
4

Beds

4.0

Baths

2,847

Sq.Ft.

6840 HELMSLEY CIRCLE

Windermere, FL

Courtesy of IAD FLORIDA LLC
View 5018 RIVER GEM AVENUE Windermere, FL MLS# TB8469061
$785,000
3

Beds

2.1

Baths

2,379

Sq.Ft.

5018 RIVER GEM AVENUE

Windermere, FL

Courtesy of KELLER WILLIAMS SOUTH TAMPA
View 9047 REFLECTION POINTE DRIVE Windermere, FL MLS# O6378672
$755,000
4

Beds

4.0

Baths

3,019

Sq.Ft.

9047 REFLECTION POINTE DRIVE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 9495 WESTOVER CLUB CIRCLE Windermere, FL MLS# O6375951
$849,000
4

Beds

3.0

Baths

2,773

Sq.Ft.

9495 WESTOVER CLUB CIRCLE

Windermere, FL

Courtesy of ALL FLORIDA PREMIER REALTY GROUP LLC
View 17514 BLACK RAIL STREET Windermere, FL MLS# O6376756
$799,000
4

Beds

2.0

Baths

2,373

Sq.Ft.

17514 BLACK RAIL STREET

Windermere, FL

Courtesy of U S GLORY REALTY
View 11994 MCKINNON ROAD Windermere, FL MLS# O6374410
$824,990
3

Beds

2.2

Baths

2,450

Sq.Ft.

11994 MCKINNON ROAD

Windermere, FL

Courtesy of CENTURY 21 CARIOTI
View 6331 LITTLE LAKE SAWYER DRIVE Windermere, FL MLS# O6372786
$950,000
Studio

Beds

0.0

Baths

6331 LITTLE LAKE SAWYER DRIVE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 4345 SALTMARSH SPARROW DRIVE Windermere, FL MLS# O6372774
$830,000
6

Beds

5.1

Baths

3,698

Sq.Ft.

4345 SALTMARSH SPARROW DRIVE

Windermere, FL

Courtesy of ICON REALTY ASSOCIATES INC
View 11550 DELWICK DRIVE Windermere, FL MLS# S5140749
$995,000
5

Beds

3.0

Baths

2,843

Sq.Ft.

11550 DELWICK DRIVE

Windermere, FL

Courtesy of TRIMARCHI REALTY CORP

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

299

Estimated median home price

$1,050,000
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 - 400K19
$400K - 500K22
$500K - 600K25
$600K - 700K26
$700K - 800K23
$800K - 900K20
$900K - 1M11
$1M - Max153

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family246
Townhouse32
Condo7
Commercial1
Rental105
Lots and Land13
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 2/23/2026)

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 2/23/2026.