311 total properties
Did you mean the neighborhood Windermere?
View 5421 GEMGOLD COURT Windermere, FL MLS# O6430765
$673,000
4

Beds

2.1

Baths

2,754

Sq.Ft.

5421 GEMGOLD COURT

Windermere, FL

Courtesy of IRM INVEST., REAL EST.& MGMT.
View 9600 AMBLESIDE DRIVE Windermere, FL MLS# O6433478
$975,000
3

Beds

3.0

Baths

2,700

Sq.Ft.

9600 AMBLESIDE DRIVE

Windermere, FL

Courtesy of NATIONAL REAL ESTATE
View 6102 S HAMPSHIRE CT Windermere, FL MLS# O6434011
$2,240,000
4

Beds

5.1

Baths

4,812

Sq.Ft.

6102 S HAMPSHIRE CT

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 17526 BLACK RAIL STREET Windermere, FL MLS# O6433513
$1,500,000
5

Beds

4.0

Baths

3,656

Sq.Ft.

17526 BLACK RAIL STREET

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 8701 IRON MOUNTAIN TRAIL Windermere, FL MLS# O6433721
$998,999
6

Beds

4.1

Baths

4,507

Sq.Ft.

8701 IRON MOUNTAIN TRAIL

Windermere, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 4282 MCKINNON ROAD Windermere, FL MLS# O6432910
$1,895,000
6

Beds

6.0

Baths

5,869

Sq.Ft.

4282 MCKINNON ROAD

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 7467 LAKE ALBERT DRIVE Windermere, FL MLS# O6432932
$1,870,000
6

Beds

6.1

Baths

5,140

Sq.Ft.

7467 LAKE ALBERT DRIVE

Windermere, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 8630 POWDER RIDGE TRAIL Windermere, FL MLS# C7529514
$528,000
3

Beds

2.1

Baths

1,853

Sq.Ft.

8630 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of SUNCOAST CHOICE REALTY
View 8241 TIBET BUTLER DRIVE Windermere, FL MLS# O6431500
$1,740,000
4

Beds

3.1

Baths

3,680

Sq.Ft.

8241 TIBET BUTLER DRIVE

Windermere, FL

Courtesy of GOLFPARK PROPERTIES
View 212 W 1ST AVENUE Windermere, FL MLS# S5155372
  • Virtual Tour
1 of 20
$1,499,000
4

Beds

2.0

Baths

2,627

Sq.Ft.

212 W 1ST AVENUE

Windermere, FL

Courtesy of HOME WISE REALTY GROUP, INC.
View 7668 FAIRGROVE AVENUE Windermere, FL MLS# O6432258
$485,000
4

Beds

2.1

Baths

1,866

Sq.Ft.

7668 FAIRGROVE AVENUE

Windermere, FL

Courtesy of VESTI LLC
View 1330 LAKE OLIVIA Windermere, FL MLS# S5155388
  • New Construction with Virtual Tour
1 of 13
$5,500,000
6

Beds

6.2

Baths

6,442

Sq.Ft.

1330 LAKE OLIVIA

Windermere, FL

Courtesy of EMPIRE NETWORK REALTY
View 6055 LOUISE COVE DRIVE Windermere, FL MLS# O6430931
$6,900,000
5

Beds

5.1

Baths

7,158

Sq.Ft.

6055 LOUISE COVE DRIVE

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 6679 DUNCASTER STREET Windermere, FL MLS# A4702367
$525,000
3

Beds

2.0

Baths

1,926

Sq.Ft.

6679 DUNCASTER STREET

Windermere, FL

Courtesy of FLATFEE.COM
View 4201 ISABELLA CIRCLE Windermere, FL MLS# O6430081
$3,990,000
6

Beds

7.0

Baths

6,896

Sq.Ft.

4201 ISABELLA CIRCLE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 14360 CREST PALM AVENUE Windermere, FL MLS# O6431854
$1,270,000
6

Beds

4.1

Baths

4,585

Sq.Ft.

14360 CREST PALM AVENUE

Windermere, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 12624 PARK AVENUE Windermere, FL MLS# O6429787
$3,100,000
0.0

Baths

12624 PARK AVENUE

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 12303 LANGSTAFF DRIVE Windermere, FL MLS# O6430630
$400,000
3

Beds

2.1

Baths

1,545

Sq.Ft.

12303 LANGSTAFF DRIVE

Windermere, FL

Courtesy of REAL BROKER, LLC
View 7236 PENKRIDGE LANE Windermere, FL MLS# O6429931
$675,000
5

Beds

4.1

Baths

2,963

Sq.Ft.

7236 PENKRIDGE LANE

Windermere, FL

Courtesy of ATLAS BLUE REALTY INC
View 11425 BROWNSTONE STREET Windermere, FL MLS# O6430411
$410,000
3

Beds

2.1

Baths

1,881

Sq.Ft.

11425 BROWNSTONE STREET

Windermere, FL

Courtesy of REDFIN CORPORATION

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

313

Estimated median home price

$1,000,000
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 - 200K1
$200K - 300K3
$300K - 400K27
$400K - 500K26
$500K - 600K25
$600K - 700K32
$700K - 800K20
$800K - 900K9
$900K - 1M14
$1M - Max156

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family240
Townhouse42
Condo10
Commercial1
Rental90
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 10/6/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

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 10/7/2026.