44 total properties
Did you mean the neighborhood Windermere?
View 11537 CLAYMONT CIR Windermere, FL MLS# O6395210
$1,400,000
5

Beds

4.0

Baths

3,164

Sq.Ft.

11537 CLAYMONT CIR

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 1554 LAKE RHEA DRIVE Windermere, FL MLS# O6406297
  • Recently Listed
1 of 59
$1,400,000
4

Beds

3.0

Baths

3,427

Sq.Ft.

1554 LAKE RHEA DRIVE

Windermere, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 106 PALM STREET Windermere, FL MLS# O6391350
  • Virtual Tour
1 of 35
$1,399,000
5

Beds

4.1

Baths

3,082

Sq.Ft.

106 PALM STREET

Windermere, FL

Courtesy of KELLER WILLIAMS WINTER PARK
The time to sell is now! THE TIME TO SELL IS NOW!
View 7231 SANGALLA DRIVE Windermere, FL MLS# O6390817
  • Adult Community with Virtual Tour
1 of 53
$1,398,000
5

Beds

4.1

Baths

3,835

Sq.Ft.

7231 SANGALLA DRIVE

Windermere, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 13596 GORGONA ISLE DRIVE Windermere, FL MLS# O6374555
$1,396,000
6

Beds

4.1

Baths

3,794

Sq.Ft.

13596 GORGONA ISLE DRIVE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 17538 BLACK RAIL STREET Windermere, FL MLS# O6349325
$1,390,000
6

Beds

4.1

Baths

4,522

Sq.Ft.

17538 BLACK RAIL STREET

Windermere, FL

Courtesy of GARCIA REALTY GROUP
View 13734 LAKE CAWOOD DRIVE Windermere, FL MLS# G5107723
$1,390,000
4

Beds

3.1

Baths

4,437

Sq.Ft.

13734 LAKE CAWOOD DRIVE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 8375 BOWDEN WAY Windermere, FL MLS# S5137385
  • Virtual Tour
1 of 68
$1,369,000
4

Beds

3.1

Baths

3,809

Sq.Ft.

8375 BOWDEN WAY

Windermere, FL

Courtesy of B LIVE COMMERCIAL AND RESIDENT
View 3138 SEIGNEURY DRIVE Windermere, FL MLS# O6387397
  • Virtual Tour
1 of 28
$1,350,000
4

Beds

4.1

Baths

3,831

Sq.Ft.

3138 SEIGNEURY DRIVE

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 1515 LAKE WHITNEY DRIVE Windermere, FL MLS# O6405903
$1,350,000
5

Beds

5.0

Baths

3,931

Sq.Ft.

1515 LAKE WHITNEY DRIVE

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 5837 CAYMUS LOOP Windermere, FL MLS# O6380732
  • Virtual Tour
1 of 36
$1,349,000
4

Beds

3.0

Baths

2,937

Sq.Ft.

5837 CAYMUS LOOP

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 2206 Ridgewind WAY Windermere, FL MLS# O6189162
$1,347,000
5

Beds

4.0

Baths

3,443

Sq.Ft.

2206 Ridgewind WAY

Windermere, FL

Courtesy of LPT REALTY
View 9663 GOTHA ROAD Windermere, FL MLS# O6399130
  • Virtual Tour
1 of 100
$1,299,900
5

Beds

3.1

Baths

3,731

Sq.Ft.

9663 GOTHA ROAD

Windermere, FL

Courtesy of ANNE ROGERS REALTY GROUP INC
View 1849 WATERMERE LANE Windermere, FL MLS# O6389840
  • Virtual Tour
1 of 31
$1,299,000
5

Beds

3.1

Baths

3,934

Sq.Ft.

1849 WATERMERE LANE

Windermere, FL

Courtesy of SUSANA JORDAN STUTSMAN
View 2219 RIDGEWIND WAY Windermere, FL MLS# O6400508
$1,299,000
6

Beds

3.1

Baths

3,364

Sq.Ft.

2219 RIDGEWIND WAY

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 6533 CARTMEL LANE Windermere, FL MLS# O6381498
  • Virtual Tour
1 of 37
$1,298,000
4

Beds

3.1

Baths

3,751

Sq.Ft.

6533 CARTMEL LANE

Windermere, FL

Courtesy of THE AGENCY FL
View 12640 SALOMON COVE DRIVE Windermere, FL MLS# O6388605
$1,295,000
5

Beds

3.1

Baths

3,694

Sq.Ft.

12640 SALOMON COVE DRIVE

Windermere, FL

Courtesy of WEBB FLORIDA REALTY LLC
View 11419 CAMDEN PARK DRIVE Windermere, FL MLS# O6392667
$1,295,000
5

Beds

4.1

Baths

3,686

Sq.Ft.

11419 CAMDEN PARK DRIVE

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 11334 CAMDEN LOOP WAY Windermere, FL MLS# O6367433
  • Virtual Tour
1 of 70
$1,250,000
4

Beds

3.0

Baths

3,021

Sq.Ft.

11334 CAMDEN LOOP WAY

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 11536 CLAYMONT CIRCLE Windermere, FL MLS# O6392958
  • Virtual Tour
1 of 68
OPEN HOUSE: Saturday 5/23 11:00 AM - 1:00 PM
$1,250,000
4

Beds

3.0

Baths

2,882

Sq.Ft.

11536 CLAYMONT CIRCLE

Windermere, FL

Courtesy of MATT ALLEN REAL ESTATE 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

341

Estimated median home price

$1,196,000
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 0
$200K - 300K 2
$300K - 400K 17
$400K - 500K 23
$500K - 600K 31
$600K - 700K 19
$700K - 800K 25
$800K - 900K 19
$900K - 1M 16
$1M - Max 189

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 287
Townhouse 35
Condo 6
Commercial 1
Rental 90
Lots and Land 12
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 5/21/2026)

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 5/22/2026.