103 total properties
Did you mean the neighborhood Windermere?
View 8533 GREENBANK BOULEVARD Windermere, FL MLS# O6354672
$640,000
4

Beds

3.1

Baths

2,551

Sq.Ft.

8533 GREENBANK BOULEVARD

Windermere, FL

Courtesy of CENTURY 21 CARIOTI
View 11450 ARBORSIDE BEND WAY Windermere, FL MLS# O6354816
$759,900
4

Beds

3.0

Baths

2,622

Sq.Ft.

11450 ARBORSIDE BEND WAY

Windermere, FL

Courtesy of LOKATION
View 12716 LANGSTAFF DRIVE Windermere, FL MLS# O6352910
$345,000
2

Beds

2.1

Baths

1,181

Sq.Ft.

12716 LANGSTAFF DRIVE

Windermere, FL

Courtesy of UPSIDE REAL ESTATE INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 6846 HELMSLEY CIRCLE Windermere, FL MLS# O6342692
$637,500
5

Beds

3.0

Baths

2,555

Sq.Ft.

6846 HELMSLEY CIRCLE

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 7711 FAIRGROVE AVENUE Windermere, FL MLS# O6352360
$389,900
3

Beds

2.1

Baths

1,680

Sq.Ft.

7711 FAIRGROVE AVENUE

Windermere, FL

Courtesy of VOSS REALTY INC
View 11818 WATER RUN ALLEY Windermere, FL MLS# O6353649
$410,000
3

Beds

2.1

Baths

1,588

Sq.Ft.

11818 WATER RUN ALLEY

Windermere, FL

Courtesy of LA ROSA REALTY LLC
View 8179 MARITIME FLAG STREET 202/108 Windermere, FL MLS# S5136502
$327,000
3

Beds

2.0

Baths

1,442

Sq.Ft.

8179 MARITIME FLAG STREET 202/108

Windermere, FL

Courtesy of THE FIRM RE
View 11636 WATER RUN ALLEY Windermere, FL MLS# S5136888
$428,000
3

Beds

2.1

Baths

1,584

Sq.Ft.

11636 WATER RUN ALLEY

Windermere, FL

Courtesy of EXP REALTY LLC
View 8180 BOAT HOOK LOOP 106/306 Windermere, FL MLS# O6353569
$324,000
3

Beds

2.0

Baths

1,455

Sq.Ft.

8180 BOAT HOOK LOOP 106/306

Windermere, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 6712 THORNHILL CIRCLE Windermere, FL MLS# O6351284
$695,000
5

Beds

3.1

Baths

2,976

Sq.Ft.

6712 THORNHILL CIRCLE

Windermere, FL

Courtesy of HOMEVEST REALTY
View 13327 FERNOW STREET Windermere, FL MLS# O6351495
$795,000
5

Beds

5.1

Baths

3,600

Sq.Ft.

13327 FERNOW STREET

Windermere, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 9802 6TH STREET Windermere, FL MLS# O6349678
$550,000
Studio

Beds

0.0

Baths

9802 6TH STREET

Windermere, FL

Courtesy of UPSIDE REAL ESTATE INC
View 6965 TETTENHALL LANE Windermere, FL MLS# O6340538
$739,000
5

Beds

3.0

Baths

2,972

Sq.Ft.

6965 TETTENHALL LANE

Windermere, FL

Courtesy of VISION HOME REAL ESTATE, LLC
View 6891 NORTHWICH DRIVE Windermere, FL MLS# S5135631
$624,500
5

Beds

2.1

Baths

2,759

Sq.Ft.

6891 NORTHWICH DRIVE

Windermere, FL

Courtesy of TITAN REALTY GROUP LLC
View QUAIL COVE COURT Windermere, FL MLS# O6349414
$785,000
Studio

Beds

0.0

Baths

QUAIL COVE COURT

Windermere, FL

Courtesy of REGENCY REAL ESTATE LLC
View 8937 MATRIARCA ALLEY Windermere, FL MLS# O6347945
  • New Construction with Virtual Tour
1 of 17
$459,000
3

Beds

2.1

Baths

1,730

Sq.Ft.

8937 MATRIARCA ALLEY

Windermere, FL

Courtesy of SANCTUM REALTY PROFESSIONALS LLC
View 13775 BRESSLER ALLEY Windermere, FL MLS# O6342957
$455,000
3

Beds

2.1

Baths

2,001

Sq.Ft.

13775 BRESSLER ALLEY

Windermere, FL

Courtesy of BAHIA INTERNATIONAL REALTY
View 13430 HOPKINTON COURT Windermere, FL MLS# O6346406
$585,000
3

Beds

2.0

Baths

1,732

Sq.Ft.

13430 HOPKINTON COURT

Windermere, FL

Courtesy of EXP REALTY LLC
View 13943 EDEN ISLE BOULEVARD Windermere, FL MLS# G5101372
$625,000
4

Beds

2.0

Baths

2,420

Sq.Ft.

13943 EDEN ISLE BOULEVARD

Windermere, FL

Courtesy of TOP WISDOM REALTY INC
View 7211 STILL POND LANE Windermere, FL MLS# S5134812
$788,000
4

Beds

3.1

Baths

3,091

Sq.Ft.

7211 STILL POND LANE

Windermere, FL

Courtesy of MBT REALTY 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

290

Estimated median home price

$1,060,000
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 - 400K25
$400K - 500K25
$500K - 600K15
$600K - 700K21
$700K - 800K17
$800K - 900K20
$900K - 1M17
$1M - Max150

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family230
Townhouse38
Condo9
Commercial1
Rental111
Lots and Land12
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 12/25/2025)

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 12/26/2025.