94 total properties
Did you mean the neighborhood Windermere?
View 7536 BENTONSHIRE AVENUE Windermere, FL MLS# O6408667
  • Recently Listed with Virtual Tour
1 of 26
$2,500
3

Beds

2.1

Baths

1,415

Sq.Ft.

7536 BENTONSHIRE AVENUE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 7708 FORDSON LANE Windermere, FL MLS# O6409598
  • Recently Listed
1 of 17
$2,500
3

Beds

2.1

Baths

1,644

Sq.Ft.

7708 FORDSON LANE

Windermere, FL

Courtesy of UNIONE REALTY INC
View 13040 OVERSTREET ROAD Windermere, FL MLS# S5144750
$2,595
3

Beds

2.1

Baths

2,203

Sq.Ft.

13040 OVERSTREET ROAD

Windermere, FL

Courtesy of MULTI CHOICE REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 14169 OASIS COVE BOULEVARD 101 Windermere, FL MLS# S5150239
  • Recently Listed with Virtual Tour
1 of 12
$2,595
3

Beds

2.1

Baths

1,647

Sq.Ft.

14169 OASIS COVE BOULEVARD 101

Windermere, FL

Courtesy of A+ HOME RENTALS LLC
View 7135 THICKET BRANCH ALLEY Windermere, FL MLS# O6389351
$2,600
3

Beds

2.1

Baths

1,569

Sq.Ft.

7135 THICKET BRANCH ALLEY

Windermere, FL

Courtesy of JULIAN PROPERTIES, INC.
View 12349 VIA DERNA PLACE Windermere, FL MLS# O6395622
$2,600
3

Beds

3.0

Baths

1,891

Sq.Ft.

12349 VIA DERNA PLACE

Windermere, FL

Courtesy of WORLD REALTY USA, INC
View 5513 SOMERSBY ROAD Windermere, FL MLS# O6406305
  • Recently Listed with Virtual Tour
1 of 39
$2,600
3

Beds

2.0

Baths

1,706

Sq.Ft.

5513 SOMERSBY ROAD

Windermere, FL

Courtesy of METRO CITY REALTY
View 12702 SALOMON COVE DRIVE Windermere, FL MLS# O6408108
$2,600
3

Beds

2.1

Baths

1,670

Sq.Ft.

12702 SALOMON COVE DRIVE

Windermere, FL

Courtesy of SUNNY 365 REALTY GROUP
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 8913 MATRIARCA ALY Windermere, FL MLS# S5145953
  • New Construction with Virtual Tour
1 of 30
$2,650
3

Beds

2.1

Baths

1,556

Sq.Ft.

8913 MATRIARCA ALY

Windermere, FL

Courtesy of LA ROSA REALTY ORLANDO LLC
View 7612 FAIRGROVE AVENUE Windermere, FL MLS# S5143482
$2,700
3

Beds

2.1

Baths

1,742

Sq.Ft.

7612 FAIRGROVE AVENUE

Windermere, FL

Courtesy of FLORIDA FANTASY REAL ESTATE INC
View 11807 VERMILLION AVE Windermere, FL MLS# O6404378
  • Recently Listed with Virtual Tour
1 of 25
$2,700
3

Beds

2.1

Baths

1,822

Sq.Ft.

11807 VERMILLION AVE

Windermere, FL

Courtesy of HANG SENG REALTY , INC
View 12825 GRACEHILL LANE Windermere, FL MLS# O6407539
  • Recently Listed with Virtual Tour
1 of 20
$2,700
3

Beds

2.1

Baths

1,617

Sq.Ft.

12825 GRACEHILL LANE

Windermere, FL

Courtesy of THOMAS LYNNE REALTY GROUP LLC
View 12357 VIA DERNA PLACE Windermere, FL MLS# O6405969
  • Recently Listed with Virtual Tour
1 of 33
$2,750
3

Beds

2.1

Baths

1,919

Sq.Ft.

12357 VIA DERNA PLACE

Windermere, FL

Courtesy of SUNNY 365 REALTY GROUP
View 9031 LEGADO DRIVE Windermere, FL MLS# O6404941
  • Recently Listed with Virtual Tour
1 of 27
$2,750
3

Beds

2.1

Baths

1,547

Sq.Ft.

9031 LEGADO DRIVE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 7652 RIPPLEPOINTE WAY Windermere, FL MLS# O6409167
  • Recently Listed with Virtual Tour
1 of 22
$2,750
3

Beds

2.1

Baths

1,743

Sq.Ft.

7652 RIPPLEPOINTE WAY

Windermere, FL

Courtesy of ADVANCE REALTY & MANAGEMENT LLC
View 7255 SHADEVIEW ALLEY Windermere, FL MLS# O6395878
$2,795
3

Beds

2.1

Baths

1,593

Sq.Ft.

7255 SHADEVIEW ALLEY

Windermere, FL

Courtesy of TRUSTHOME PROPERTIES 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
View 8470 IRON MOUNTAIN TRAIL Windermere, FL MLS# S5147220
$2,800
3

Beds

2.1

Baths

1,644

Sq.Ft.

8470 IRON MOUNTAIN TRAIL

Windermere, FL

Courtesy of LPT REALTY, LLC
View 13231 OVERSTREET ROAD Windermere, FL MLS# O6392297
$2,850
3

Beds

2.1

Baths

2,306

Sq.Ft.

13231 OVERSTREET ROAD

Windermere, FL

Courtesy of CINO INTERNATIONAL INC

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

339

Estimated median home price

$1,196,000
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 - 300K2
$300K - 400K17
$400K - 500K23
$500K - 600K30
$600K - 700K19
$700K - 800K25
$800K - 900K18
$900K - 1M17
$1M - Max188

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family285
Townhouse35
Condo6
Commercial1
Rental93
Lots and Land12
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 5/22/2026)

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 5/22/2026.