54 total properties
Did you mean the neighborhood Windermere?
View 4773 BLUE MAJOR DRIVE Windermere, FL MLS# O6386132
  • Recently Listed
1 of 29
$619,900
4

Beds

2.1

Baths

2,620

Sq.Ft.

4773 BLUE MAJOR DRIVE

Windermere, FL

Courtesy of LPT REALTY, LLC
View 13013 OVERSTREET ROAD Windermere, FL MLS# O6380917
  • Recently Listed with Virtual Tour
1 of 47
OPEN HOUSE: Saturday 2/28 11:00 AM - 3:00 PM
$679,994
4

Beds

2.1

Baths

2,053

Sq.Ft.

13013 OVERSTREET ROAD

Windermere, FL

Courtesy of EXP REALTY LLC
View 12980 HOLDENBURY LANE Windermere, FL MLS# O6385797
  • Recently Listed with Virtual Tour
1 of 60
$589,900
3

Beds

2.1

Baths

2,504

Sq.Ft.

12980 HOLDENBURY LANE

Windermere, FL

Courtesy of LIVE MVRK LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 9319 WOODBREEZE BOULEVARD Windermere, FL MLS# O6384930
  • Recently Listed
1 of 41
OPEN HOUSE: Saturday 2/28 12:00 PM - 3:00 PM
$574,995
4

Beds

2.0

Baths

1,798

Sq.Ft.

9319 WOODBREEZE BOULEVARD

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 8552 POWDER RIDGE TRAIL Windermere, FL MLS# S5144276
  • Recently Listed with Virtual Tour
1 of 30
$690,000
4

Beds

2.1

Baths

2,612

Sq.Ft.

8552 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 7125 BEEK STREET Windermere, FL MLS# O6382948
  • Virtual Tour
1 of 48
$559,000
3

Beds

2.0

Baths

1,753

Sq.Ft.

7125 BEEK STREET

Windermere, FL

Courtesy of SUNNY 365 REALTY GROUP
View 13237 FOSSICK ROAD Windermere, FL MLS# O6382389
  • Recently Listed
1 of 41
$625,000
4

Beds

2.0

Baths

2,516

Sq.Ft.

13237 FOSSICK ROAD

Windermere, FL

Courtesy of EXP REALTY LLC
View 6990 SMITHSHIRE LANE Windermere, FL MLS# O6380372
$675,000
4

Beds

3.1

Baths

2,986

Sq.Ft.

6990 SMITHSHIRE LANE

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 11355 ARBORSIDE BEND WAY Windermere, FL MLS# O6377273
  • Recently Listed with Virtual Tour
1 of 32
$600,000
4

Beds

2.0

Baths

2,044

Sq.Ft.

11355 ARBORSIDE BEND WAY

Windermere, FL

Courtesy of EXP REALTY LLC
View 6382 GOLDEN DEWDROP TRAIL Windermere, FL MLS# O6379533
  • Virtual Tour
1 of 56
OPEN HOUSE: Saturday 2/28 12:00 PM - 2:00 PM
$595,000
3

Beds

2.1

Baths

2,139

Sq.Ft.

6382 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 13912 DARCHANCE ROAD Windermere, FL MLS# O6377606
$709,999
4

Beds

3.1

Baths

2,699

Sq.Ft.

13912 DARCHANCE ROAD

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 12936 DROXFORD ROAD Windermere, FL MLS# O6376097
$649,000
5

Beds

3.1

Baths

2,960

Sq.Ft.

12936 DROXFORD ROAD

Windermere, FL

Courtesy of UNITED REAL ESTATE PREFERRED
View 5463 GEMGOLD COURT Windermere, FL MLS# O6375567
$599,000
4

Beds

3.0

Baths

2,246

Sq.Ft.

5463 GEMGOLD COURT

Windermere, FL

Courtesy of INFINITY REALTY GROUP LLC
View 8650 ABBOTSBURY DRIVE Windermere, FL MLS# O6376488
$575,000
4

Beds

3.1

Baths

2,628

Sq.Ft.

8650 ABBOTSBURY DRIVE

Windermere, FL

Courtesy of THE AGENCY FL
View 6876 MERRICK LANDING BOULEVARD Windermere, FL MLS# O6373037
$664,000
4

Beds

2.1

Baths

2,781

Sq.Ft.

6876 MERRICK LANDING BOULEVARD

Windermere, FL

Courtesy of INTERNATIONAL REAL ESTATE LLC
View 6638 BRIDGEWATER VILLAGE ROAD Windermere, FL MLS# O6374429
$664,900
4

Beds

2.1

Baths

2,908

Sq.Ft.

6638 BRIDGEWATER VILLAGE ROAD

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 7451 FAIRGROVE AVENUE Windermere, FL MLS# O6375170
$580,000
3

Beds

2.0

Baths

2,092

Sq.Ft.

7451 FAIRGROVE AVENUE

Windermere, FL

Courtesy of TALENT REALTY SOLUTIONS
View 7885 BERKSHIRE OAK ALLEY Windermere, FL MLS# O6374875
$579,000
4

Beds

2.1

Baths

2,214

Sq.Ft.

7885 BERKSHIRE OAK ALLEY

Windermere, FL

Courtesy of U S GLORY REALTY
View 6841 HELMSLEY CIRCLE Windermere, FL MLS# O6372635
$625,000
4

Beds

3.0

Baths

2,371

Sq.Ft.

6841 HELMSLEY CIRCLE

Windermere, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 11578 ASHLIN PARK BOULEVARD Windermere, FL MLS# O6373714
$634,900
5

Beds

3.1

Baths

2,396

Sq.Ft.

11578 ASHLIN PARK BOULEVARD

Windermere, FL

Courtesy of CENTURY 21 CARIOTI

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

302

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 - 700K25
$700K - 800K25
$800K - 900K19
$900K - 1M10
$1M - Max155

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family249
Townhouse32
Condo7
Commercial1
Rental105
Lots and Land13
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 2/27/2026)

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 2/28/2026.