100 total properties
Did you mean the neighborhood Windermere?
View 7249 SHADEVIEW ALLEY Windermere, FL MLS# S5143736
$2,800
3

Beds

2.1

Baths

1,569

Sq.Ft.

7249 SHADEVIEW ALLEY

Windermere, FL

Courtesy of REMAX PREMIER PROPERTIES
View 12072 VIA CASELLI LN Windermere, FL MLS# O6382432
$2,800
4

Beds

3.0

Baths

1,885

Sq.Ft.

12072 VIA CASELLI LN

Windermere, FL

Courtesy of HANG SENG REALTY , INC
View 7609 SUTHERTON LANE Windermere, FL MLS# O6382713
$2,800
3

Beds

2.1

Baths

1,545

Sq.Ft.

7609 SUTHERTON LANE

Windermere, FL

Courtesy of 1 ELEVEN REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 8408 ABBOTSBURY DRIVE Windermere, FL MLS# O6388448
  • Recently Listed with Virtual Tour
1 of 9
$2,800
4

Beds

3.0

Baths

2,343

Sq.Ft.

8408 ABBOTSBURY DRIVE

Windermere, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 8128 JAILENE DRIVE Windermere, FL MLS# O6379411
$2,799
4

Beds

3.0

Baths

2,214

Sq.Ft.

8128 JAILENE DRIVE

Windermere, FL

Courtesy of PREMIUM PROPERTIES R.E SERVICE
View 11619 WATER RUN ALLEY Windermere, FL MLS# O6384489
  • Recently Listed with Virtual Tour
1 of 31
$2,780
3

Beds

2.1

Baths

1,570

Sq.Ft.

11619 WATER RUN ALLEY

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 13845 ANCILLA BOULEVARD Windermere, FL MLS# O6386180
  • Recently Listed with Virtual Tour
1 of 33
$2,775
2

Beds

2.0

Baths

1,155

Sq.Ft.

13845 ANCILLA BOULEVARD

Windermere, FL

Courtesy of CT HOMES REALTY CORPORATION
View 13841 ANCILLA BOULEVARD Windermere, FL MLS# O6386275
  • Recently Listed with Virtual Tour
1 of 28
$2,775
3

Beds

2.1

Baths

2,332

Sq.Ft.

13841 ANCILLA BOULEVARD

Windermere, FL

Courtesy of CT HOMES REALTY CORPORATION
View 13718 BECKMAN DRIVE Windermere, FL MLS# S5136490
$2,750
3

Beds

2.1

Baths

1,912

Sq.Ft.

13718 BECKMAN DRIVE

Windermere, FL

Courtesy of MD3 HOMES LLC
View 12813 GRACEHILL LANE Windermere, FL MLS# O6385408
  • Recently Listed with Virtual Tour
1 of 18
$2,750
3

Beds

2.1

Baths

1,748

Sq.Ft.

12813 GRACEHILL LANE

Windermere, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 14235 DESERT HAVEN STREET 3503 Windermere, FL MLS# O6386593
  • Recently Listed with Virtual Tour
1 of 39
$2,750
3

Beds

2.1

Baths

2,028

Sq.Ft.

14235 DESERT HAVEN STREET 3503

Windermere, FL

Courtesy of KELLER WILLIAMS LEGACY REALTY
View 8973 MATRIARCA ALLEY Windermere, FL MLS# O6387553
  • Recently Listed with Virtual Tour
1 of 29
$2,750
3

Beds

2.1

Baths

1,690

Sq.Ft.

8973 MATRIARCA ALLEY

Windermere, FL

Courtesy of AAA GLOBAL VENTURES PA
View 8174 ENCHANTMENT DRIVE 1601 Windermere, FL MLS# O6355768
$2,700
3

Beds

2.1

Baths

1,852

Sq.Ft.

8174 ENCHANTMENT DRIVE 1601

Windermere, FL

Courtesy of MS LAND & BUILDING LLC
View 13261 ROXBORO ROAD Windermere, FL MLS# S5143584
$2,700
3

Beds

2.0

Baths

1,706

Sq.Ft.

13261 ROXBORO ROAD

Windermere, FL

Courtesy of MULTI CHOICE REALTY LLC
View 9005 VIA DI CANTI UNIT A DRIVE Windermere, FL MLS# O6383666
$2,700
4

Beds

3.0

Baths

1,955

Sq.Ft.

9005 VIA DI CANTI UNIT A DRIVE

Windermere, FL

Courtesy of METROPOLITAN R.E SOLUTIONS INC
View 8326 IRON MOUNTAIN TRAIL Windermere, FL MLS# S5145711
  • Recently Listed with Virtual Tour
1 of 32
$2,697
3

Beds

2.1

Baths

1,631

Sq.Ft.

8326 IRON MOUNTAIN TRAIL

Windermere, FL

Courtesy of TRANSCEND REALTY
View 11642 WATER RUN ALLEY Windermere, FL MLS# S5141662
$2,650
3

Beds

2.1

Baths

1,624

Sq.Ft.

11642 WATER RUN ALLEY

Windermere, FL

Courtesy of VS INTERNATIONAL PROPERTIES
View 12623 LANGSTAFF DRIVE Windermere, FL MLS# O6383047
$2,650
2

Beds

2.1

Baths

1,239

Sq.Ft.

12623 LANGSTAFF DRIVE

Windermere, FL

Courtesy of ELITE REALTY ENTERPRISES LLC
View 7605 RIPPLEPOINTE WAY Windermere, FL MLS# O6376581
$2,600
3

Beds

2.1

Baths

1,920

Sq.Ft.

7605 RIPPLEPOINTE WAY

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 13285 GORGONA ISLE DRIVE Windermere, FL MLS# O6379997
$2,600
3

Beds

2.1

Baths

1,547

Sq.Ft.

13285 GORGONA ISLE DRIVE

Windermere, FL

Courtesy of REALTY HUB

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

$1,030,000
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 - 400K17
$400K - 500K25
$500K - 600K30
$600K - 700K24
$700K - 800K26
$800K - 900K19
$900K - 1M14
$1M - Max158

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family258
Townhouse37
Condo3
Commercial1
Rental100
Lots and Land14
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 3/12/2026)

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 3/13/2026.