324 total properties
Did you mean the neighborhood Windermere?
View PARK RIDGE GOTHA ROAD Windermere, FL MLS# S5156135
  • Recently Listed with Virtual Tour
1 of 6
$200,000
Studio

Beds

0.0

Baths

PARK RIDGE GOTHA ROAD

Windermere, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 12832 WESTSIDE VILLAGE LOOP Windermere, FL MLS# O6433322
$760,000
5

Beds

3.1

Baths

3,705

Sq.Ft.

12832 WESTSIDE VILLAGE LOOP

Windermere, FL

View 6828 HELMSLEY CIRCLE Windermere, FL MLS# O6435655
  • Recently Listed with Virtual Tour
1 of 21
$575,000
4

Beds

3.0

Baths

2,064

Sq.Ft.

6828 HELMSLEY CIRCLE

Windermere, FL

Courtesy of LPT REALTY, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1243 DINGENS AVENUE Windermere, FL MLS# O6435494
  • Recently Listed with Virtual Tour
1 of 55
$990,000
4

Beds

3.0

Baths

2,728

Sq.Ft.

1243 DINGENS AVENUE

Windermere, FL

View 3986 ISABELLA CIRCLE Windermere, FL MLS# O6432946
  • Recently Listed with Virtual Tour
1 of 29
$3,599,000
5

Beds

5.2

Baths

5,342

Sq.Ft.

3986 ISABELLA CIRCLE

Windermere, FL

View 1480 HEMPEL AVENUE Windermere, FL MLS# S5156040
  • Recently Listed with Virtual Tour
1 of 43
$1,755,000
5

Beds

4.1

Baths

4,219

Sq.Ft.

1480 HEMPEL AVENUE

Windermere, FL

View 8278 PROCIDA ISLE LANE Windermere, FL MLS# O6435099
  • Recently Listed with Virtual Tour
1 of 75
$890,000
6

Beds

4.0

Baths

4,176

Sq.Ft.

8278 PROCIDA ISLE LANE

Windermere, FL

View 11113 LAKE BUTLER BOULEVARD Windermere, FL MLS# O6434392
$2,395,000
5

Beds

5.1

Baths

4,094

Sq.Ft.

11113 LAKE BUTLER BOULEVARD

Windermere, FL

Courtesy of QUATTRO R E SOLUTIONS LLC
View 5125 SUN PALM DRIVE Windermere, FL MLS# O6435175
$560,000
3

Beds

2.0

Baths

1,723

Sq.Ft.

5125 SUN PALM DRIVE

Windermere, FL

Courtesy of THE SIMON SIMAAN GROUP
View 9609 WESTOVER CLUB CIRCLE Windermere, FL MLS# O6434228
$969,000
5

Beds

4.1

Baths

3,797

Sq.Ft.

9609 WESTOVER CLUB CIRCLE

Windermere, FL

View 2031 WILLOW LAUREN LANE L Windermere, FL MLS# O6429898
$1,179,000
5

Beds

4.1

Baths

3,664

Sq.Ft.

2031 WILLOW LAUREN LANE L

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 8860 HERENCIA ALLEY Windermere, FL MLS# O6433569
$409,900
3

Beds

2.1

Baths

1,547

Sq.Ft.

8860 HERENCIA ALLEY

Windermere, FL

View 5421 GEMGOLD COURT Windermere, FL MLS# O6430765
$682,000
4

Beds

2.1

Baths

2,754

Sq.Ft.

5421 GEMGOLD COURT

Windermere, FL

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 13831 FARELLA ALLEY Windermere, FL MLS# O6429767
$510,000
4

Beds

2.1

Baths

1,831

Sq.Ft.

13831 FARELLA ALLEY

Windermere, FL

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

View 9237 MCDAVID COURT Windermere, FL MLS# O6433234
$749,000
4

Beds

2.1

Baths

2,269

Sq.Ft.

9237 MCDAVID COURT

Windermere, FL

Courtesy of REALTY HUB
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
$999,000
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
  • Virtual Tour
1 of 73
OPEN HOUSE: Saturday 9/12 12:00 PM - 3:00 PM
$1,995,000
6

Beds

6.0

Baths

5,869

Sq.Ft.

4282 MCKINNON ROAD

Windermere, FL

Courtesy of COMPASS FLORIDA 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

328

Estimated median home price

$972,000
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 - 300K2
$300K - 400K25
$400K - 500K32
$500K - 600K32
$600K - 700K32
$700K - 800K22
$800K - 900K12
$900K - 1M12
$1M - Max158

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family247
Townhouse52
Condo10
Commercial1
Rental91
Lots and Land18
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 9/7/2026)

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 9/9/2026.