248 total properties
Did you mean the neighborhood Windermere?
View 8344 BOWDEN WAY Windermere, FL MLS# O6425171
$1,065,000
4

Beds

4.0

Baths

3,646

Sq.Ft.

8344 BOWDEN WAY

Windermere, FL

Courtesy of ALIGN REAL ESTATE LLC
View 5579 SOMERSBY ROAD Windermere, FL MLS# TB8517100
  • Virtual Tour
1 of 29
$375,000
3

Beds

2.1

Baths

1,579

Sq.Ft.

5579 SOMERSBY ROAD

Windermere, FL

Courtesy of HOMESMART
View 1629 HEMPEL AVENUE Windermere, FL MLS# O6418226
  • Virtual Tour
1 of 89
$2,500,000
6

Beds

4.0

Baths

4,858

Sq.Ft.

1629 HEMPEL AVENUE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 4642 RIVER GEM AVENUE Windermere, FL MLS# O6422241
  • Virtual Tour
1 of 53
$798,000
5

Beds

5.0

Baths

3,373

Sq.Ft.

4642 RIVER GEM AVENUE

Windermere, FL

Courtesy of JOHN SILVA REALTY & ASSOCIATES
View 14030 SPARKLING COVE LANE 603 Windermere, FL MLS# O6424774
$324,900
2

Beds

2.1

Baths

1,232

Sq.Ft.

14030 SPARKLING COVE LANE 603

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 6241 BLAKEFORD DRIVE Windermere, FL MLS# O6417788
  • Virtual Tour
1 of 57
$1,795,000
4

Beds

4.0

Baths

3,556

Sq.Ft.

6241 BLAKEFORD DRIVE

Windermere, FL

Courtesy of KEENE'S POINTE REALTY
View 9433 PALM TREE DRIVE Windermere, FL MLS# O6423262
  • Virtual Tour
1 of 37
$539,900
3

Beds

2.0

Baths

1,819

Sq.Ft.

9433 PALM TREE DRIVE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 2512 TRYON PLACE Windermere, FL MLS# O6422154
  • Virtual Tour
1 of 65
$980,000
4

Beds

3.0

Baths

3,478

Sq.Ft.

2512 TRYON PLACE

Windermere, FL

Courtesy of CENTURY 21 CARIOTI
View 2053 WOODY DRIVE Windermere, FL MLS# O6421738
  • Virtual Tour
1 of 49
$679,000
3

Beds

2.1

Baths

2,177

Sq.Ft.

2053 WOODY DRIVE

Windermere, FL

Courtesy of LPT REALTY, LLC
View 7060 VENTNOR DRIVE Windermere, FL MLS# S5153025
  • Virtual Tour
1 of 34
$444,900
3

Beds

2.1

Baths

1,642

Sq.Ft.

7060 VENTNOR DRIVE

Windermere, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 13219 CHARFIELD STREET Windermere, FL MLS# O6420991
$555,000
3

Beds

2.0

Baths

1,706

Sq.Ft.

13219 CHARFIELD STREET

Windermere, FL

Courtesy of DENIZ REALTY PARTNERS LLC
View 8168 BOAT HOOK LOOP 724 Windermere, FL MLS# O6421614
$325,000
3

Beds

2.0

Baths

1,455

Sq.Ft.

8168 BOAT HOOK LOOP 724

Windermere, FL

Courtesy of ROMAN REALTY GROUP, LLC
View 11446 JASPER KAY TERRACE 103 Windermere, FL MLS# O6420653
$325,000
3

Beds

2.0

Baths

1,442

Sq.Ft.

11446 JASPER KAY TERRACE 103

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 2009 WOODY DRIVE Windermere, FL MLS# O6422132
  • Virtual Tour
1 of 43
$1,150,000
4

Beds

3.0

Baths

3,540

Sq.Ft.

2009 WOODY DRIVE

Windermere, FL

Courtesy of REVEL REALTY LLC
View 13137 PENSHURST LANE Windermere, FL MLS# O6421270
  • Virtual Tour
1 of 48
$550,000
3

Beds

2.0

Baths

1,948

Sq.Ft.

13137 PENSHURST LANE

Windermere, FL

Courtesy of MORRIS WILLIAMS REALTY
View 7409 FAIRGROVE AVENUE Windermere, FL MLS# O6420597
  • Virtual Tour
1 of 29
$745,990
5

Beds

3.0

Baths

3,285

Sq.Ft.

7409 FAIRGROVE AVENUE

Windermere, FL

Courtesy of SUNSTAR REALTY FL INC
View 8180 BOAT HOOK LOOP 102 Windermere, FL MLS# O6420460
$295,000
2

Beds

2.0

Baths

1,161

Sq.Ft.

8180 BOAT HOOK LOOP 102

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 11217 WILLOW GARDENS DRIVE Windermere, FL MLS# O6417903
$1,075,000
4

Beds

3.0

Baths

2,824

Sq.Ft.

11217 WILLOW GARDENS DRIVE

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 11429 BROWNSTONE STREET Windermere, FL MLS# O6421245
$439,000
4

Beds

2.1

Baths

1,910

Sq.Ft.

11429 BROWNSTONE STREET

Windermere, FL

Courtesy of WEMERT GROUP REALTY LLC
View 2617 BUTLER BAY DRIVE N Windermere, FL MLS# O6420023
$1,649,000
4

Beds

4.0

Baths

3,086

Sq.Ft.

2617 BUTLER BAY DRIVE N

Windermere, FL

Courtesy of COLDWELL BANKER REALTY

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

313

Estimated median home price

$1,000,000
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

Price Count
$0 - 100K 0
$100K - 200K 1
$200K - 300K 3
$300K - 400K 27
$400K - 500K 26
$500K - 600K 25
$600K - 700K 32
$700K - 800K 20
$800K - 900K 9
$900K - 1M 14
$1M - Max 156

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 240
Townhouse 42
Condo 10
Commercial 1
Rental 90
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 10/6/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

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 10/7/2026.