206 total properties
Did you mean the neighborhood Windermere?
View 2512 TRYON PLACE Windermere, FL MLS# O6422154
  • Recently Listed with Virtual Tour
1 of 69
$1,230,000
4

Beds

3.0

Baths

3,478

Sq.Ft.

2512 TRYON PLACE

Windermere, FL

View 2053 WOODY DRIVE Windermere, FL MLS# O6421738
  • Recently Listed with Virtual Tour
1 of 49
$679,000
3

Beds

2.1

Baths

2,177

Sq.Ft.

2053 WOODY DRIVE

Windermere, FL

View 7060 VENTNOR DRIVE Windermere, FL MLS# S5153025
  • Recently Listed with Virtual Tour
1 of 34
$444,900
3

Beds

2.1

Baths

1,642

Sq.Ft.

7060 VENTNOR DRIVE

Windermere, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 13219 CHARFIELD STREET Windermere, FL MLS# O6420991
  • Recently Listed with Virtual Tour
1 of 31
$565,000
3

Beds

2.0

Baths

1,706

Sq.Ft.

13219 CHARFIELD STREET

Windermere, FL

View 8146 JAILENE DRIVE Windermere, FL MLS# O6420838
  • Recently Listed with Virtual Tour
1 of 49
$574,900
3

Beds

2.0

Baths

2,099

Sq.Ft.

8146 JAILENE DRIVE

Windermere, FL

View 8168 BOAT HOOK LOOP 724 Windermere, FL MLS# O6421614
  • Recently Listed with Virtual Tour
1 of 17
$325,000
3

Beds

2.0

Baths

1,455

Sq.Ft.

8168 BOAT HOOK LOOP 724

Windermere, FL

View 11446 JASPER KAY TERRACE 103 Windermere, FL MLS# O6420653
$330,000
3

Beds

2.0

Baths

1,442

Sq.Ft.

11446 JASPER KAY TERRACE 103

Windermere, FL

View 12912 DROXFORD ROAD Windermere, FL MLS# O6422064
  • Recently Listed with Virtual Tour
1 of 52
$650,000
5

Beds

3.1

Baths

2,966

Sq.Ft.

12912 DROXFORD ROAD

Windermere, FL

View 13845 BRIDGEWATER CROSSINGS BLVD Windermere, FL MLS# O6421552
  • Recently Listed with Virtual Tour
1 of 23
$489,000
3

Beds

2.1

Baths

1,636

Sq.Ft.

13845 BRIDGEWATER CROSSINGS BLVD

Windermere, FL

View 2009 WOODY DRIVE Windermere, FL MLS# O6422132
  • Recently Listed with Virtual Tour
1 of 43
$1,200,000
4

Beds

3.0

Baths

3,540

Sq.Ft.

2009 WOODY DRIVE

Windermere, FL

View 11249 RAPALLO LANE Windermere, FL MLS# O6421056
  • Recently Listed with Virtual Tour
1 of 37
$750,000
5

Beds

2.1

Baths

2,366

Sq.Ft.

11249 RAPALLO LANE

Windermere, FL

View 13137 PENSHURST LANE Windermere, FL MLS# O6421270
  • Recently Listed with Virtual Tour
1 of 46
$560,000
3

Beds

2.0

Baths

1,948

Sq.Ft.

13137 PENSHURST LANE

Windermere, FL

View 2630 STANTON HALL COURT Windermere, FL MLS# O6420386
  • Recently Listed with Virtual Tour
1 of 26
$899,999
3

Beds

2.0

Baths

2,258

Sq.Ft.

2630 STANTON HALL COURT

Windermere, FL

View 7409 FAIRGROVE AVENUE Windermere, FL MLS# O6420597
  • Recently Listed with Virtual Tour
1 of 29
$765,990
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
  • Recently Listed with Virtual Tour
1 of 26
$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
  • Recently Listed with Virtual Tour
1 of 51
$1,170,000
4

Beds

3.0

Baths

2,824

Sq.Ft.

11217 WILLOW GARDENS DRIVE

Windermere, FL

View 516 JENNIFER LANE Windermere, FL MLS# O6419731
  • Virtual Tour
1 of 71
$1,295,000
3

Beds

2.1

Baths

3,021

Sq.Ft.

516 JENNIFER LANE

Windermere, FL

View 12580 CRAGSIDE LANE Windermere, FL MLS# O6418877
  • Recently Listed with Virtual Tour
1 of 62
$624,000
4

Beds

2.1

Baths

2,776

Sq.Ft.

12580 CRAGSIDE LANE

Windermere, FL

View 14347 CREST PALM AVENUE Windermere, FL MLS# G5114311
  • New Construction with Virtual Tour
1 of 41
$1,058,989
4

Beds

3.0

Baths

3,100

Sq.Ft.

14347 CREST PALM AVENUE

Windermere, FL

View 2722 INGEBORG COURT Windermere, FL MLS# O6419770
  • Recently Listed with Virtual Tour
1 of 53
$850,000
4

Beds

2.1

Baths

2,619

Sq.Ft.

2722 INGEBORG COURT

Windermere, FL

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

350

Estimated median home price

$1,077,500
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 - 300K3
$300K - 400K19
$400K - 500K36
$500K - 600K31
$600K - 700K29
$700K - 800K20
$800K - 900K19
$900K - 1M14
$1M - Max179

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family276
Townhouse46
Condo9
Commercial1
Rental87
Lots and Land18
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 7/6/2026)

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 7/7/2026.