26 total properties
Did you mean the neighborhood Windermere?
View 5944 CAYMUS LOOP Windermere, FL MLS# O6448123
  • Recently Listed with Virtual Tour
1 of 45
$1,050,000
4

Beds

3.0

Baths

2,984

Sq.Ft.

5944 CAYMUS LOOP

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 11727 DELWICK DRIVE Windermere, FL MLS# O6445423
  • Recently Listed with Virtual Tour
1 of 37
$860,000
4

Beds

3.0

Baths

2,704

Sq.Ft.

11727 DELWICK DRIVE

Windermere, FL

Courtesy of BHHS FLORIDA REALTY
View 9010 REFLECTION POINTE DRIVE Windermere, FL MLS# G5117935
$945,000
4

Beds

3.1

Baths

3,264

Sq.Ft.

9010 REFLECTION POINTE DRIVE

Windermere, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 8524 VIVARO ISLE WAY Windermere, FL MLS# G5118124
  • Recently Listed with Virtual Tour
1 of 35
$950,000
4

Beds

3.0

Baths

2,680

Sq.Ft.

8524 VIVARO ISLE WAY

Windermere, FL

Courtesy of SERHANT
View 6309 EARTHGOLD DRIVE Windermere, FL MLS# O6436644
  • Virtual Tour
1 of 30
$880,000
4

Beds

2.1

Baths

2,648

Sq.Ft.

6309 EARTHGOLD DRIVE

Windermere, FL

Courtesy of REALTY HUB
View 9043 HORIZON POINTE TRAIL Windermere, FL MLS# O6436017
$870,000
4

Beds

3.0

Baths

3,746

Sq.Ft.

9043 HORIZON POINTE TRAIL

Windermere, FL

Courtesy of CENTURY 21 CARIOTI
View 1243 DINGENS AVENUE Windermere, FL MLS# O6435494
  • Virtual Tour
1 of 55
$950,000
4

Beds

3.0

Baths

2,728

Sq.Ft.

1243 DINGENS AVENUE

Windermere, FL

Courtesy of REALMULTIPROPERTY LLC
View 9609 WESTOVER CLUB CIRCLE Windermere, FL MLS# O6434228
$939,000
5

Beds

4.1

Baths

3,797

Sq.Ft.

9609 WESTOVER CLUB CIRCLE

Windermere, FL

Courtesy of ALPHA R.E. OF CENTRAL FL LLC
View 9600 AMBLESIDE DRIVE Windermere, FL MLS# O6433478
  • Virtual Tour
1 of 34
$975,000
3

Beds

3.0

Baths

2,700

Sq.Ft.

9600 AMBLESIDE DRIVE

Windermere, FL

Courtesy of NATIONAL REAL ESTATE
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 2512 TRYON PLACE Windermere, FL MLS# O6422154
  • Virtual Tour
1 of 65
$949,000
4

Beds

3.0

Baths

3,478

Sq.Ft.

2512 TRYON PLACE

Windermere, FL

Courtesy of CENTURY 21 CARIOTI
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 11544 WILLOW GARDENS DRIVE Windermere, FL MLS# O6412655
$1,000,000
0.0

Baths

11544 WILLOW GARDENS DRIVE

Windermere, FL

Courtesy of JC FLORIDA REALTY LLC
View 9117 OUTLOOK ROCK TRAIL Windermere, FL MLS# O6413948
$1,055,000
5

Beds

3.2

Baths

4,936

Sq.Ft.

9117 OUTLOOK ROCK TRAIL

Windermere, FL

Courtesy of REDFIN CORPORATION
View 11326 LEDGEMENT LANE Windermere, FL MLS# O6409714
  • Virtual Tour
1 of 63
$879,000
5

Beds

3.1

Baths

3,182

Sq.Ft.

11326 LEDGEMENT LANE

Windermere, FL

Courtesy of AAA GLOBAL VENTURES PA
View 14341 CREST PALM AVENUE Windermere, FL MLS# G5112469
  • New Construction with Virtual Tour
1 of 48
$1,070,990
4

Beds

4.0

Baths

3,153

Sq.Ft.

14341 CREST PALM AVENUE

Windermere, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 8525 BOWDEN WAY Windermere, FL MLS# O6405195
  • Virtual Tour
1 of 44
$940,000
4

Beds

3.0

Baths

2,357

Sq.Ft.

8525 BOWDEN WAY

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 14353 CREST PALM AVENUE Windermere, FL MLS# G5111542
  • New Construction with Virtual Tour
1 of 73
$959,990
4

Beds

3.0

Baths

2,740

Sq.Ft.

14353 CREST PALM AVENUE

Windermere, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 715 MAGNOLIA STREET Windermere, FL MLS# S5147648
  • Virtual Tour
1 of 44
$1,089,000
4

Beds

3.0

Baths

3,390

Sq.Ft.

715 MAGNOLIA STREET

Windermere, FL

Courtesy of IRIS INTERNATIONAL
View 14371 CREST PALM AVENUE Windermere, FL MLS# G5110664
  • New Construction with Virtual Tour
1 of 67
$949,990
4

Beds

4.0

Baths

3,153

Sq.Ft.

14371 CREST PALM AVENUE

Windermere, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC

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

298

Estimated median home price

$1,060,000
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 1
$100K - 200K 0
$200K - 300K 4
$300K - 400K 27
$400K - 500K 23
$500K - 600K 27
$600K - 700K 29
$700K - 800K 16
$800K - 900K 7
$900K - 1M 12
$1M - Max 152

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 226
Townhouse 39
Condo 13
Commercial 1
Rental 97
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 10/18/2026)

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 10/19/2026.