53 total properties
Did you mean the neighborhood Windermere?
View 13320 FERNOW STREET Windermere, FL MLS# O6388986
  • Recently Listed with Virtual Tour
1 of 52
OPEN HOUSE: Saturday 3/14 10:00 AM - 12:00 PM
$730,000
4

Beds

3.1

Baths

2,745

Sq.Ft.

13320 FERNOW STREET

Windermere, FL

Courtesy of HOMEVEST REALTY
View 6573 HELMSLEY CIRCLE Windermere, FL MLS# S5145061
  • Virtual Tour
1 of 54
OPEN HOUSE: Saturday 3/14 11:00 AM - 1:00 PM
$639,900
4

Beds

3.1

Baths

2,664

Sq.Ft.

6573 HELMSLEY CIRCLE

Windermere, FL

Courtesy of WATSON REALTY CORP.
View 7264 BACKWOODS TRAIL Windermere, FL MLS# O6387913
  • Recently Listed with Virtual Tour
1 of 27
$650,000
4

Beds

2.1

Baths

2,214

Sq.Ft.

7264 BACKWOODS TRAIL

Windermere, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 13118 SUNKISS LOOP Windermere, FL MLS# O6385211
  • Recently Listed with Virtual Tour
1 of 52
$588,000
4

Beds

2.1

Baths

2,547

Sq.Ft.

13118 SUNKISS LOOP

Windermere, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 4773 BLUE MAJOR DRIVE Windermere, FL MLS# O6386132
$619,900
4

Beds

2.1

Baths

2,620

Sq.Ft.

4773 BLUE MAJOR DRIVE

Windermere, FL

Courtesy of LPT REALTY, LLC
View 13240 ROSKIN LANE Windermere, FL MLS# S5144759
  • Recently Listed with Virtual Tour
1 of 31
$739,000
4

Beds

3.1

Baths

3,108

Sq.Ft.

13240 ROSKIN LANE

Windermere, FL

Courtesy of HOMESMART
View 13013 OVERSTREET ROAD Windermere, FL MLS# O6380917
  • Recently Listed with Virtual Tour
1 of 47
$679,994
4

Beds

2.1

Baths

2,053

Sq.Ft.

13013 OVERSTREET ROAD

Windermere, FL

Courtesy of EXP REALTY LLC
View 12980 HOLDENBURY LANE Windermere, FL MLS# O6385797
$589,900
3

Beds

2.1

Baths

2,504

Sq.Ft.

12980 HOLDENBURY LANE

Windermere, FL

Courtesy of LIVE MVRK LLC
View 8552 POWDER RIDGE TRAIL Windermere, FL MLS# S5144276
  • Recently Listed with Virtual Tour
1 of 30
$690,000
4

Beds

2.1

Baths

2,612

Sq.Ft.

8552 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 13237 FOSSICK ROAD Windermere, FL MLS# O6382389
  • Recently Listed
1 of 41
$625,000
4

Beds

2.0

Baths

2,516

Sq.Ft.

13237 FOSSICK ROAD

Windermere, FL

Courtesy of EXP REALTY LLC
View 17520 BLACK RAIL STREET Windermere, FL MLS# O6384223
$777,000
4

Beds

2.0

Baths

2,380

Sq.Ft.

17520 BLACK RAIL STREET

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 6990 SMITHSHIRE LANE Windermere, FL MLS# O6380372
$675,000
4

Beds

3.1

Baths

2,986

Sq.Ft.

6990 SMITHSHIRE LANE

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 6518 SAWYER SHORES LANE Windermere, FL MLS# O6374607
$725,000
Studio

Beds

0.0

Baths

6518 SAWYER SHORES LANE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 6840 HELMSLEY CIRCLE Windermere, FL MLS# S5142930
$749,000
4

Beds

4.0

Baths

2,847

Sq.Ft.

6840 HELMSLEY CIRCLE

Windermere, FL

Courtesy of IAD FLORIDA LLC
View 6382 GOLDEN DEWDROP TRAIL Windermere, FL MLS# O6379533
$595,000
3

Beds

2.1

Baths

2,139

Sq.Ft.

6382 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 5018 RIVER GEM AVENUE Windermere, FL MLS# TB8469061
$785,000
3

Beds

2.1

Baths

2,379

Sq.Ft.

5018 RIVER GEM AVENUE

Windermere, FL

Courtesy of KELLER WILLIAMS SOUTH TAMPA
View 13912 DARCHANCE ROAD Windermere, FL MLS# O6377606
$709,999
4

Beds

3.1

Baths

2,699

Sq.Ft.

13912 DARCHANCE ROAD

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 9047 REFLECTION POINTE DRIVE Windermere, FL MLS# O6378672
$755,000
4

Beds

4.0

Baths

3,019

Sq.Ft.

9047 REFLECTION POINTE DRIVE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 12936 DROXFORD ROAD Windermere, FL MLS# O6376097
$649,000
5

Beds

3.1

Baths

2,960

Sq.Ft.

12936 DROXFORD ROAD

Windermere, FL

Courtesy of UNITED REAL ESTATE PREFERRED
View 17514 BLACK RAIL STREET Windermere, FL MLS# O6376756
$725,000
4

Beds

2.0

Baths

2,373

Sq.Ft.

17514 BLACK RAIL STREET

Windermere, FL

Courtesy of U S GLORY REALTY

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.