87 total properties
Did you mean the neighborhood Windermere?
View 17538 BLACK RAIL STREET Windermere, FL MLS# O6425511
  • Recently Listed with Virtual Tour
1 of 32
$5,500
6

Beds

4.1

Baths

4,522

Sq.Ft.

17538 BLACK RAIL STREET

Windermere, FL

View 8394 LOOKOUT POINTE DRIVE Windermere, FL MLS# O6427316
  • Recently Listed with Virtual Tour
1 of 66
$5,500
5

Beds

4.0

Baths

3,971

Sq.Ft.

8394 LOOKOUT POINTE DRIVE

Windermere, FL

View 7023 KIWANO WAY Windermere, FL MLS# O6423493
  • Recently Listed with Virtual Tour
1 of 45
$4,980
5

Beds

4.1

Baths

3,136

Sq.Ft.

7023 KIWANO WAY

Windermere, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 8764 POWDER RIDGE TRAIL Windermere, FL MLS# O6421604
  • Recently Listed with Virtual Tour
1 of 43
$4,750
4

Beds

3.1

Baths

3,144

Sq.Ft.

8764 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of KARDOSH REALTY
View 13272 PENSHURST LANE Windermere, FL MLS# S5150230
$4,000
5

Beds

3.1

Baths

3,472

Sq.Ft.

13272 PENSHURST LANE

Windermere, FL

View 1363 GLENWICK DRIVE Windermere, FL MLS# O6418231
$4,000
3

Beds

2.0

Baths

2,077

Sq.Ft.

1363 GLENWICK DRIVE

Windermere, FL

View 6354 SWANSON STREET Windermere, FL MLS# O6421332
$3,950
4

Beds

2.0

Baths

2,370

Sq.Ft.

6354 SWANSON STREET

Windermere, FL

Courtesy of KELLER WILLIAMS LEGACY REALTY
View 9088 OUTLOOK ROCK TRAIL Windermere, FL MLS# O6424365
  • Recently Listed with Virtual Tour
1 of 28
$3,950
5

Beds

4.0

Baths

2,800

Sq.Ft.

9088 OUTLOOK ROCK TRAIL

Windermere, FL

Courtesy of EPIQUE REALTY INC.
View 1243 DINGENS AVENUE Windermere, FL MLS# O6300024
$3,900
4

Beds

3.0

Baths

2,728

Sq.Ft.

1243 DINGENS AVENUE

Windermere, FL

View 13544 RIGGS WAY Windermere, FL MLS# O6404050
$3,900
4

Beds

3.1

Baths

2,696

Sq.Ft.

13544 RIGGS WAY

Windermere, FL

View 6728 BRIDGEWATER VILLAGE ROAD Windermere, FL MLS# O6412340
$3,850
5

Beds

3.0

Baths

2,983

Sq.Ft.

6728 BRIDGEWATER VILLAGE ROAD

Windermere, FL

View 8752 POWDER RIDGE TRAIL Windermere, FL MLS# O6367881
$3,700
4

Beds

3.1

Baths

2,931

Sq.Ft.

8752 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of MS LAND & BUILDING LLC
View 1125 LASCALA DRIVE Windermere, FL MLS# O6409403
$3,500
5

Beds

4.1

Baths

2,874

Sq.Ft.

1125 LASCALA DRIVE

Windermere, FL

View 6526 GOLDEN DEWDROP TRAIL Windermere, FL MLS# S5152663
$3,300
3

Beds

2.1

Baths

2,139

Sq.Ft.

6526 GOLDEN DEWDROP TRAIL

Windermere, FL

View 14205 BRIDGEWATER CROSSINGS BOULEVARD Windermere, FL MLS# O6426758
  • Recently Listed with Virtual Tour
1 of 22
$3,275
4

Beds

2.1

Baths

2,476

Sq.Ft.

14205 BRIDGEWATER CROSSINGS BOULEVARD

Windermere, FL

View 6719 ROMNEY LANE Windermere, FL MLS# G5114414
$3,200
4

Beds

2.0

Baths

2,151

Sq.Ft.

6719 ROMNEY LANE

Windermere, FL

Courtesy of WATSON REALTY CORP., REALTORS
View 5007 RIVER GEM AVENUE Windermere, FL MLS# O6424829
  • Recently Listed with Virtual Tour
1 of 16
$3,200
3

Beds

2.0

Baths

1,903

Sq.Ft.

5007 RIVER GEM AVENUE

Windermere, FL

View 12947 RUNSWICK AVENUE Windermere, FL MLS# O6425118
  • Recently Listed
1 of 44
$3,200
4

Beds

2.0

Baths

2,300

Sq.Ft.

12947 RUNSWICK AVENUE

Windermere, FL

View 11316 RAPALLO LANE Windermere, FL MLS# O6418822
$3,195
3

Beds

2.1

Baths

1,925

Sq.Ft.

11316 RAPALLO LANE

Windermere, FL

Courtesy of CITY CAPITAL GROUP INC
View 8625 GREENBANK BLVD Windermere, FL MLS# O6413262
$3,100
4

Beds

3.0

Baths

2,190

Sq.Ft.

8625 GREENBANK BLVD

Windermere, FL

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

292

Estimated median home price

$1,072,500
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 - 300K3
$300K - 400K15
$400K - 500K30
$500K - 600K28
$600K - 700K24
$700K - 800K15
$800K - 900K14
$900K - 1M11
$1M - Max152

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family232
Townhouse37
Condo9
Commercial1
Rental87
Lots and Land13
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 7/22/2026)

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 7/23/2026.