140 total properties
Did you mean the neighborhood Windermere?
View 12530 CLIMBING VINE COURT Windermere, FL MLS# O6364745
$999,000
5

Beds

3.1

Baths

3,407

Sq.Ft.

12530 CLIMBING VINE COURT

Windermere, FL

Courtesy of THE AGENCY ORLANDO
View 12661 CALDERDALE AVENUE Windermere, FL MLS# O6364859
$495,000
3

Beds

2.0

Baths

1,696

Sq.Ft.

12661 CALDERDALE AVENUE

Windermere, FL

Courtesy of THE AGENCY ORLANDO
View 7028 VENTNOR DRIVE Windermere, FL MLS# O6363663
$515,000
4

Beds

3.0

Baths

1,980

Sq.Ft.

7028 VENTNOR DRIVE

Windermere, FL

Courtesy of UPSIDE REAL ESTATE INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1209 MAIN STREET Windermere, FL MLS# O6363588
  • Virtual Tour
1 of 44
$945,000
3

Beds

2.0

Baths

2,095

Sq.Ft.

1209 MAIN STREET

Windermere, FL

Courtesy of UPSIDE REAL ESTATE INC
View 2046 WESTOVER RESERVE BOULEVARD Windermere, FL MLS# O6364090
$999,000
5

Beds

4.0

Baths

3,516

Sq.Ft.

2046 WESTOVER RESERVE BOULEVARD

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 7625 SUTHERTON LANE Windermere, FL MLS# O6363486
$439,000
3

Beds

2.1

Baths

1,565

Sq.Ft.

7625 SUTHERTON LANE

Windermere, FL

Courtesy of SOLD BY SIX REALTY, LLC
View 12333 VIA DERNA PLACE Windermere, FL MLS# O6362685
$459,000
3

Beds

2.1

Baths

1,919

Sq.Ft.

12333 VIA DERNA PLACE

Windermere, FL

Courtesy of YELLOW ROCK REALTY CORP
View 416 MAGNOLIA STREET Windermere, FL MLS# O6362356
$885,000
2

Beds

1.1

Baths

2,115

Sq.Ft.

416 MAGNOLIA STREET

Windermere, FL

Courtesy of UPSIDE REAL ESTATE INC
View 12142 CANYON SUN TRAIL Windermere, FL MLS# S5138705
$520,000
3

Beds

2.1

Baths

2,032

Sq.Ft.

12142 CANYON SUN TRAIL

Windermere, FL

Courtesy of SIX STAR REALTY GROUP LLC
View 14551 YELLOW BUTTERFLY ROAD Windermere, FL MLS# O6361922
$814,888
5

Beds

3.1

Baths

3,546

Sq.Ft.

14551 YELLOW BUTTERFLY ROAD

Windermere, FL

Courtesy of ICON REALTY ASSOCIATES INC
View 6799 HELMSLEY CIRCLE Windermere, FL MLS# O6361417
$699,000
4

Beds

3.1

Baths

2,615

Sq.Ft.

6799 HELMSLEY CIRCLE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 6947 CUCAMELON COURT Windermere, FL MLS# O6361206
$999,000
5

Beds

5.1

Baths

3,680

Sq.Ft.

6947 CUCAMELON COURT

Windermere, FL

Courtesy of DALTON WADE INC
View 12060 VIA CASELLI LANE Windermere, FL MLS# O6360255
$499,999
4

Beds

3.0

Baths

1,786

Sq.Ft.

12060 VIA CASELLI LANE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 4818 BREEZY PALMS COURT Windermere, FL MLS# O6360779
$535,000
3

Beds

2.0

Baths

1,492

Sq.Ft.

4818 BREEZY PALMS COURT

Windermere, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 8726 GREENBANK BOULEVARD Windermere, FL MLS# O6362458
$500,000
3

Beds

2.0

Baths

1,745

Sq.Ft.

8726 GREENBANK BOULEVARD

Windermere, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 9237 MCDAVID COURT Windermere, FL MLS# O6360886
$849,999
4

Beds

2.1

Baths

2,269

Sq.Ft.

9237 MCDAVID COURT

Windermere, FL

Courtesy of GENESYS REALTY LLC
View 8638 BROOKVALE DRIVE Windermere, FL MLS# O6360958
  • Recently Listed
1 of 4
$395,000
3

Beds

2.1

Baths

1,520

Sq.Ft.

8638 BROOKVALE DRIVE

Windermere, FL

Courtesy of AK GLOBAL REALTY LLC
View 7411 RIPPLEPOINTE WAY Windermere, FL MLS# O6360114
$440,000
3

Beds

2.1

Baths

1,948

Sq.Ft.

7411 RIPPLEPOINTE WAY

Windermere, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 4415 BLUE MAJOR DRIVE Windermere, FL MLS# O6359496
$815,000
5

Beds

3.0

Baths

3,211

Sq.Ft.

4415 BLUE MAJOR DRIVE

Windermere, FL

Courtesy of M2M REALTY
View 12676 SALOMON COVE DRIVE Windermere, FL MLS# O6357657
$890,000
6

Beds

4.0

Baths

3,667

Sq.Ft.

12676 SALOMON COVE DRIVE

Windermere, FL

Courtesy of LPT REALTY, 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

290

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

PriceCount
$0 - 100K0
$100K - 200K0
$200K - 300K0
$300K - 400K25
$400K - 500K25
$500K - 600K15
$600K - 700K21
$700K - 800K17
$800K - 900K20
$900K - 1M17
$1M - Max150

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family230
Townhouse38
Condo9
Commercial1
Rental111
Lots and Land12
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 12/25/2025)

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 12/27/2025.