40 total properties
Did you mean the neighborhood Windermere?
View 13328 OVERSTREET ROAD Windermere, FL MLS# O6423949
  • Recently Listed with Virtual Tour
1 of 43
$639,900
4

Beds

3.0

Baths

2,648

Sq.Ft.

13328 OVERSTREET ROAD

Windermere, FL

View 4642 RIVER GEM AVENUE Windermere, FL MLS# O6422241
  • Recently Listed with Virtual Tour
1 of 53
$825,000
5

Beds

5.0

Baths

3,373

Sq.Ft.

4642 RIVER GEM AVENUE

Windermere, FL

View 2053 WOODY DRIVE Windermere, FL MLS# O6421738
  • Recently Listed with Virtual Tour
1 of 49
OPEN HOUSE: Saturday 7/11 1:30 PM - 2:00 PM
$679,000
3

Beds

2.1

Baths

2,177

Sq.Ft.

2053 WOODY DRIVE

Windermere, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 12912 DROXFORD ROAD Windermere, FL MLS# O6422064
  • Recently Listed with Virtual Tour
1 of 52
$650,000
5

Beds

3.1

Baths

2,966

Sq.Ft.

12912 DROXFORD ROAD

Windermere, FL

View 11249 RAPALLO LANE Windermere, FL MLS# O6421056
  • Recently Listed with Virtual Tour
1 of 37
$750,000
5

Beds

2.1

Baths

2,366

Sq.Ft.

11249 RAPALLO LANE

Windermere, FL

View 7409 FAIRGROVE AVENUE Windermere, FL MLS# O6420597
  • Recently Listed with Virtual Tour
1 of 29
$765,990
5

Beds

3.0

Baths

3,285

Sq.Ft.

7409 FAIRGROVE AVENUE

Windermere, FL

Courtesy of SUNSTAR REALTY FL INC
View 7211 STILL POND LANE Windermere, FL MLS# O6418089
$765,000
4

Beds

3.1

Baths

3,161

Sq.Ft.

7211 STILL POND LANE

Windermere, FL

View 7906 JAILENE DRIVE Windermere, FL MLS# O6416776
$724,900
5

Beds

3.0

Baths

2,618

Sq.Ft.

7906 JAILENE DRIVE

Windermere, FL

View 13407 LEMON ORCHARD BEND Windermere, FL MLS# TB8519889
  • New Construction with Virtual Tour
1 of 18
$648,683
3

Beds

2.1

Baths

1,714

Sq.Ft.

13407 LEMON ORCHARD BEND

Windermere, FL

View 6648 HELSTON LANE Windermere, FL MLS# O6413354
  • Virtual Tour
1 of 47
$665,000
4

Beds

3.1

Baths

3,072

Sq.Ft.

6648 HELSTON LANE

Windermere, FL

View 6606 SAWYER SHORES LANE Windermere, FL MLS# O6408952
$800,000
Studio

Beds

0.0

Baths

6606 SAWYER SHORES LANE

Windermere, FL

View 9110 PALM TREE DRIVE Windermere, FL MLS# O6414631
$650,000
3

Beds

2.0

Baths

1,819

Sq.Ft.

9110 PALM TREE DRIVE

Windermere, FL

View 6558 HELMSLEY CIRCLE Windermere, FL MLS# S5151342
$630,000
4

Beds

3.0

Baths

2,575

Sq.Ft.

6558 HELMSLEY CIRCLE

Windermere, FL

View 6363 SEDONA LEAF COURT Windermere, FL MLS# O6416993
$749,900
4

Beds

3.0

Baths

2,665

Sq.Ft.

6363 SEDONA LEAF COURT

Windermere, FL

View 6601 DUNCASTER STREET Windermere, FL MLS# O6416272
$627,900
4

Beds

3.0

Baths

3,001

Sq.Ft.

6601 DUNCASTER STREET

Windermere, FL

View 13786 SUMMER HARBOR COURT Windermere, FL MLS# O6414239
$625,000
4

Beds

2.1

Baths

2,236

Sq.Ft.

13786 SUMMER HARBOR COURT

Windermere, FL

View 12826 WOODMERE CLOSE DR Windermere, FL MLS# O6412588
$665,000
4

Beds

3.0

Baths

2,214

Sq.Ft.

12826 WOODMERE CLOSE DR

Windermere, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 13936 EDEN ISLE BOULEVARD Windermere, FL MLS# S5150801
$645,000
4

Beds

3.1

Baths

2,675

Sq.Ft.

13936 EDEN ISLE BOULEVARD

Windermere, FL

View 12633 HADDON DRIVE Windermere, FL MLS# O6411199
$650,000
5

Beds

3.1

Baths

3,000

Sq.Ft.

12633 HADDON DRIVE

Windermere, FL

View 8715 QUIET MEADOWS TRAIL Windermere, FL MLS# O6410762
$825,000
4

Beds

3.1

Baths

3,388

Sq.Ft.

8715 QUIET MEADOWS TRAIL

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

273

Estimated median home price

$1,151,000
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 - 300K4
$300K - 400K11
$400K - 500K27
$500K - 600K24
$600K - 700K22
$700K - 800K14
$800K - 900K14
$900K - 1M10
$1M - Max147

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family218
Townhouse30
Condo9
Commercial1
Rental91
Lots and Land15
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 7/11/2026)

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 7/11/2026.