100 total properties
Did you mean the neighborhood Windermere?
View 8855 HERENCIA ALLEY Windermere, FL MLS# O6443503
  • Virtual Tour
1 of 22
$2,650
3

Beds

2.1

Baths

1,556

Sq.Ft.

8855 HERENCIA ALLEY

Windermere, FL

Courtesy of SANCTUM REALTY PROFESSIONALS LLC
View 13701 BECKMAN DRIVE Windermere, FL MLS# O6443113
  • Virtual Tour
1 of 33
$2,900
3

Beds

2.1

Baths

2,091

Sq.Ft.

13701 BECKMAN DRIVE

Windermere, FL

Courtesy of HOST MANAGEMENT GROUP LLC
View 8701 IRON MOUNTAIN TRAIL Windermere, FL MLS# O6443205
$5,200
7

Beds

4.1

Baths

4,507

Sq.Ft.

8701 IRON MOUNTAIN TRAIL

Windermere, FL

Courtesy of REALSOURCE PROPERTY MANGNT LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 8615 VIA TRIESTE DRIVE Windermere, FL MLS# S5157331
$2,700
3

Beds

3.0

Baths

1,891

Sq.Ft.

8615 VIA TRIESTE DRIVE

Windermere, FL

Courtesy of PREMIER CHOICE REALTY & MANAGEMENT LLC
View 7651 FORDSON LANE Windermere, FL MLS# O6442220
  • Virtual Tour
1 of 27
$2,650
3

Beds

2.1

Baths

1,748

Sq.Ft.

7651 FORDSON LANE

Windermere, FL

Courtesy of LA ROSA REALTY PREMIER LLC
View 9360 WOODBREEZE BOULEVARD Windermere, FL MLS# O6439664
$2,750
3

Beds

2.0

Baths

1,723

Sq.Ft.

9360 WOODBREEZE BOULEVARD

Windermere, FL

Courtesy of ICON REALTY ASSOCIATES INC
View 6310 GOLDEN DEWDROP TRAIL Windermere, FL MLS# S5157685
$3,300
3

Beds

2.1

Baths

1,977

Sq.Ft.

6310 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of AXEN REALTY LLC
View 8259 MARITIME FLAG STREET 7 Windermere, FL MLS# S5157575
$2,200
3

Beds

2.1

Baths

1,363

Sq.Ft.

8259 MARITIME FLAG STREET 7

Windermere, FL

Courtesy of ALTIS REALTY
View 6436 GOLDEN DEWDROP TRAIL Windermere, FL MLS# O6441890
$4,000
3

Beds

2.1

Baths

1,984

Sq.Ft.

6436 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 8256 MARITIME FLAG STREET 305 Windermere, FL MLS# O6440608
$2,550
3

Beds

2.0

Baths

1,332

Sq.Ft.

8256 MARITIME FLAG STREET 305

Windermere, FL

Courtesy of IAD REAL ESTATE
View 12355 LANGSTAFF DRIVE 12355 Windermere, FL MLS# A12085354
$2,600
3

Beds

2.1

Baths

12355 LANGSTAFF DRIVE 12355

Windermere, FL

Courtesy of FLORIDA FANTASY REAL ESTATE IN
View 7668 FAIRGROVE AVENUE Windermere, FL MLS# O6441765
  • Virtual Tour
1 of 17
$2,850
4

Beds

2.1

Baths

1,866

Sq.Ft.

7668 FAIRGROVE AVENUE

Windermere, FL

Courtesy of VESTI LLC
View 13633 RIGGS WAY Windermere, FL MLS# O6439827
  • Virtual Tour
1 of 29
$3,650
4

Beds

3.1

Baths

2,682

Sq.Ft.

13633 RIGGS WAY

Windermere, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 8428 IRON MOUNTAIN TRAIL Windermere, FL MLS# O6439629
$2,650
3

Beds

2.1

Baths

1,580

Sq.Ft.

8428 IRON MOUNTAIN TRAIL

Windermere, FL

Courtesy of SPRING REALTY ORLANDO
View Address not provided Windermere, FL MLS# O6437707
  • Virtual Tour
1 of 37
$2,375
3

Beds

2.1

Baths

1,429

Sq.Ft.

Address not provided

Windermere, FL

Courtesy of LA ROSA REALTY LLC
View 6020 MARLEON DRIVE Windermere, FL MLS# O6439210
  • Virtual Tour
1 of 44
$8,900
5

Beds

4.1

Baths

4,028

Sq.Ft.

6020 MARLEON DRIVE

Windermere, FL

Courtesy of UNITED REALTY GROUP INC
View 12986 HOLDENBURY LANE Windermere, FL MLS# O6438619
  • Virtual Tour
1 of 15
$2,699
4

Beds

2.0

Baths

2,074

Sq.Ft.

12986 HOLDENBURY LANE

Windermere, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 12543 CRUXBURY DRIVE Windermere, FL MLS# O6438155
  • Virtual Tour
1 of 12
$2,300
2

Beds

2.1

Baths

1,311

Sq.Ft.

12543 CRUXBURY DRIVE

Windermere, FL

Courtesy of BELLA VIEW REALTY LLC
View 13503 LAKE CAWOOD DRIVE Windermere, FL MLS# TB8542423
$8,250
5

Beds

5.1

Baths

5,312

Sq.Ft.

13503 LAKE CAWOOD DRIVE

Windermere, FL

Courtesy of BANNER INT'L REAL ESTATE
View 8351 BOWDEN WAY Windermere, FL MLS# O6437185
  • Virtual Tour
1 of 29
$6,500
4

Beds

3.0

Baths

2,578

Sq.Ft.

8351 BOWDEN WAY

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP

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

298

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

Price Count
$0 - 100K 1
$100K - 200K 0
$200K - 300K 4
$300K - 400K 27
$400K - 500K 23
$500K - 600K 27
$600K - 700K 29
$700K - 800K 16
$800K - 900K 7
$900K - 1M 12
$1M - Max 152

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 226
Townhouse 39
Condo 13
Commercial 1
Rental 97
Lots and Land 19
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 10/18/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

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 10/19/2026.