29 total properties
Did you mean the neighborhood Windermere?
View 5061 SAWYER COVE WAY Windermere, FL MLS# O6403804
$2,590,000
5

Beds

4.1

Baths

3,888

Sq.Ft.

5061 SAWYER COVE WAY

Windermere, FL

View 5624 W LAKE BUTLER ROAD Windermere, FL MLS# O6411407
$2,550,000
4

Beds

3.1

Baths

3,736

Sq.Ft.

5624 W LAKE BUTLER ROAD

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 4205 CLARICE ESTATES DRIVE Windermere, FL MLS# O6419164
  • Recently Listed with Virtual Tour
1 of 88
$2,550,000
4

Beds

5.0

Baths

4,136

Sq.Ft.

4205 CLARICE ESTATES DRIVE

Windermere, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 6606 SAWYER SHORES LANE Windermere, FL MLS# O6386058
  • New Construction with Virtual Tour
1 of 19
$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 9648 WEATHERSTONE COURT Windermere, FL MLS# O6400680
$2,500,000
6

Beds

4.0

Baths

4,482

Sq.Ft.

9648 WEATHERSTONE COURT

Windermere, FL

View 6288 BLAKEFORD DRIVE Windermere, FL MLS# S5151608
$2,474,000
5

Beds

4.3

Baths

5,366

Sq.Ft.

6288 BLAKEFORD DRIVE

Windermere, FL

View 325 MAGNOLIA STREET Windermere, FL MLS# O6391047
$2,450,000
4

Beds

3.0

Baths

3,975

Sq.Ft.

325 MAGNOLIA STREET

Windermere, FL

Courtesy of REVEL REALTY LLC
View 10532 PARK RIDGE GOTHA ROAD Windermere, FL MLS# O6409569
$2,400,000
Studio

Beds

0.0

Baths

10532 PARK RIDGE GOTHA ROAD

Windermere, FL

Courtesy of DAVID WEAVER, REALTOR
View 10520 PARK RIDGE GOTHA ROAD Windermere, FL MLS# O6409659
$2,400,000
4

Beds

3.1

Baths

3,101

Sq.Ft.

10520 PARK RIDGE GOTHA ROAD

Windermere, FL

Courtesy of DAVID WEAVER, REALTOR
View 6102 S HAMPSHIRE COURT Windermere, FL MLS# O6344907
$2,399,000
4

Beds

5.1

Baths

4,810

Sq.Ft.

6102 S HAMPSHIRE COURT

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 4224 CLARICE ESTATES DRIVE Windermere, FL MLS# S5128974
$2,375,000
5

Beds

4.0

Baths

4,793

Sq.Ft.

4224 CLARICE ESTATES DRIVE

Windermere, FL

View 9620 MAYWOOD DRIVE Windermere, FL MLS# O6399315
$2,349,000
4

Beds

3.0

Baths

3,004

Sq.Ft.

9620 MAYWOOD DRIVE

Windermere, FL

View 81 OAKDALE STREET Windermere, FL MLS# S5138567
  • Virtual Tour
1 of 87
$2,300,000
5

Beds

4.1

Baths

4,284

Sq.Ft.

81 OAKDALE STREET

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 1316 ESTANCIA WOODS LOOP Windermere, FL MLS# S5146178
$2,290,000
5

Beds

6.1

Baths

5,448

Sq.Ft.

1316 ESTANCIA WOODS LOOP

Windermere, FL

Courtesy of EXP REALTY LLC
View 2068 ROBERTS POINT DRIVE Windermere, FL MLS# O6397543
$2,250,000
5

Beds

4.0

Baths

4,876

Sq.Ft.

2068 ROBERTS POINT DRIVE

Windermere, FL

Courtesy of CENTURY 21 CARIOTI
View 9011 PINNACLE CIRCLE Windermere, FL MLS# O6400872
$2,250,000
5

Beds

5.0

Baths

6,546

Sq.Ft.

9011 PINNACLE CIRCLE

Windermere, FL

View 1136 LAKE WHITNEY DRIVE Windermere, FL MLS# O6405536
$2,225,000
4

Beds

5.1

Baths

5,722

Sq.Ft.

1136 LAKE WHITNEY DRIVE

Windermere, FL

View 2 CHASE ROAD Windermere, FL MLS# O6345197
  • New Construction
1 of 3
$2,200,000
4

Beds

4.1

Baths

3,889

Sq.Ft.

2 CHASE ROAD

Windermere, FL

View 11545 BRICKYARD POND LANE Windermere, FL MLS# O6378961
$2,200,000
8

Beds

8.1

Baths

4,735

Sq.Ft.

11545 BRICKYARD POND LANE

Windermere, FL

View 1118 ESTANCIA WOODS LOOP Windermere, FL MLS# O6390567
$2,200,000
5

Beds

5.0

Baths

4,228

Sq.Ft.

1118 ESTANCIA WOODS LOOP

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

364

Estimated median home price

$1,110,000
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 - 300K3
$300K - 400K20
$400K - 500K36
$500K - 600K32
$600K - 700K27
$700K - 800K19
$800K - 900K21
$900K - 1M15
$1M - Max191

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family288
Townhouse51
Condo7
Commercial1
Rental99
Lots and Land17
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 7/1/2026)

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 7/2/2026.