18 total properties
Did you mean the neighborhood Windermere?
View 6606 SAWYER SHORES LANE Windermere, FL MLS# O6386058
  • Recently Listed with Virtual Tour
1 of 22
$2,500,000
5

Beds

4.0

Baths

5,516

Sq.Ft.

6606 SAWYER SHORES LANE

Windermere, FL

Courtesy of PREMIUM PROPERTIES R.E. SERVICE
View 19 MAIN STREET Windermere, FL MLS# O6383837
$3,000,000
4

Beds

3.0

Baths

2,331

Sq.Ft.

19 MAIN STREET

Windermere, FL

Courtesy of GOLDEN GROUP REALTY LLC
View 6248 LOUISE COVE DR Windermere, FL MLS# O6378223
$2,850,000
5

Beds

5.1

Baths

6,253

Sq.Ft.

6248 LOUISE COVE DR

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 11255 MACAW COURT Windermere, FL MLS# O6371007
  • Virtual Tour
1 of 49
$2,987,500
5

Beds

5.1

Baths

5,845

Sq.Ft.

11255 MACAW COURT

Windermere, FL

Courtesy of REAL BROKER, LLC
View 3103 SEIGNEURY DRIVE Windermere, FL MLS# O6364283
$2,700,000
8

Beds

5.1

Baths

5,607

Sq.Ft.

3103 SEIGNEURY DRIVE

Windermere, FL

Courtesy of NEW SOLUTIONS REALTY INC
View 81 OAKDALE STREET Windermere, FL MLS# S5138567
  • Virtual Tour
1 of 87
$2,500,000
5

Beds

4.1

Baths

4,284

Sq.Ft.

81 OAKDALE STREET

Windermere, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 6288 BLAKEFORD DRIVE Windermere, FL MLS# O6361679
$2,600,000
5

Beds

4.3

Baths

5,366

Sq.Ft.

6288 BLAKEFORD DRIVE

Windermere, FL

Courtesy of REAL BROKER, LLC
View 6252 BLAKEFORD DR Windermere, FL MLS# O6356056
  • Virtual Tour
1 of 52
$2,390,000
5

Beds

4.0

Baths

4,287

Sq.Ft.

6252 BLAKEFORD DR

Windermere, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 12213 PARK AVENUE Windermere, FL MLS# O6351906
  • Virtual Tour
1 of 19
$3,000,000
Studio

Beds

0.0

Baths

12213 PARK AVENUE

Windermere, FL

Courtesy of PREMIUM PROPERTIES R.E. SERVICE
View 12923 WATER POINT BOULEVARD Windermere, FL MLS# O6350408
$2,750,000
5

Beds

4.1

Baths

5,005

Sq.Ft.

12923 WATER POINT BOULEVARD

Windermere, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 9204 TIBET POINTE CIRCLE Windermere, FL MLS# O6347671
$2,450,000
5

Beds

4.2

Baths

5,291

Sq.Ft.

9204 TIBET POINTE CIRCLE

Windermere, FL

Courtesy of THE SIMON SIMAAN GROUP
View 6102 S HAMPSHIRE COURT Windermere, FL MLS# O6344907
$2,499,000
4

Beds

5.1

Baths

4,810

Sq.Ft.

6102 S HAMPSHIRE COURT

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 6134 KEENES POINTE DRIVE Windermere, FL MLS# O6345101
$2,248,000
4

Beds

3.1

Baths

4,440

Sq.Ft.

6134 KEENES POINTE DRIVE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 8402 LAKE BURDEN CIRCLE Windermere, FL MLS# O6345629
$2,650,000
5

Beds

6.1

Baths

6,248

Sq.Ft.

8402 LAKE BURDEN CIRCLE

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 11209 MACAW COURT Windermere, FL MLS# O6326947
  • Virtual Tour
1 of 56
$2,795,000
5

Beds

6.1

Baths

6,105

Sq.Ft.

11209 MACAW COURT

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 9648 WEATHERSTONE Windermere, FL MLS# G5096890
  • Virtual Tour
1 of 100
$2,715,000
6

Beds

4.0

Baths

4,482

Sq.Ft.

9648 WEATHERSTONE

Windermere, FL

Courtesy of ERA GRIZZARD REAL ESTATE
View 409 W 2ND AVENUE Windermere, FL MLS# O6290296
  • Virtual Tour
1 of 55
$2,375,000
5

Beds

4.1

Baths

4,688

Sq.Ft.

409 W 2ND AVENUE

Windermere, FL

Courtesy of UPSIDE REAL ESTATE INC
View 11113 LAKE BUTLER BOULEVARD Windermere, FL MLS# O6195201
$2,449,000
5

Beds

5.1

Baths

4,094

Sq.Ft.

11113 LAKE BUTLER BOULEVARD

Windermere, FL

Courtesy of QUATTRO R E SOLUTIONS LLC

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 - 600K27
$600K - 700K24
$700K - 800K25
$800K - 900K19
$900K - 1M10
$1M - Max153

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family246
Townhouse32
Condo7
Commercial1
Rental104
Lots and Land13
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 2/26/2026)

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 2/27/2026.