46 total properties
Did you mean the neighborhood Windermere?
View 6956 TRELLIS VINE LOOP Windermere, FL MLS# O6401639
$650,000
5

Beds

4.0

Baths

3,015

Sq.Ft.

6956 TRELLIS VINE LOOP

Windermere, FL

Courtesy of EAST PEARL REALTY
View 6840 HELMSLEY CIRCLE Windermere, FL MLS# S5142930
$649,000
4

Beds

4.0

Baths

2,847

Sq.Ft.

6840 HELMSLEY CIRCLE

Windermere, FL

Courtesy of IAD FLORIDA LLC
View 9011 CHAPMAN OAK COURT Windermere, FL MLS# S5148031
  • Adult Community with Virtual Tour
1 of 30
$649,000
4

Beds

2.0

Baths

2,050

Sq.Ft.

9011 CHAPMAN OAK COURT

Windermere, FL

Courtesy of TOWNE CENTER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 13622 DARCHANCE ROAD Windermere, FL MLS# S5146266
$629,900
3

Beds

2.0

Baths

2,147

Sq.Ft.

13622 DARCHANCE ROAD

Windermere, FL

Courtesy of AVANTI WAY REALTY LLC
View 12936 DROXFORD ROAD Windermere, FL MLS# O6376097
$629,000
5

Beds

3.1

Baths

2,960

Sq.Ft.

12936 DROXFORD ROAD

Windermere, FL

Courtesy of UNITED REAL ESTATE PREFERRED
View 11438 ARBORSIDE BEND WAY Windermere, FL MLS# O6395080
$627,500
4

Beds

2.0

Baths

2,019

Sq.Ft.

11438 ARBORSIDE BEND WAY

Windermere, FL

Courtesy of KELLER WILLIAMS ADVANTAGE 2 REALTY
View 8632 ABBOTSBURY DRIVE Windermere, FL MLS# O6406433
  • Recently Listed with Virtual Tour
1 of 32
$625,000
4

Beds

3.1

Baths

2,720

Sq.Ft.

8632 ABBOTSBURY DRIVE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 5224 LEMON TWIST LANE Windermere, FL MLS# O6393299
$624,900
4

Beds

3.1

Baths

2,812

Sq.Ft.

5224 LEMON TWIST LANE

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 6315 CLEARMEADOW COURT Windermere, FL MLS# O6398505
$618,000
3

Beds

2.0

Baths

2,077

Sq.Ft.

6315 CLEARMEADOW COURT

Windermere, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 14217 BRIDGEWATER CROSSINGS BOULEVARD Windermere, FL MLS# O6396155
$600,000
4

Beds

3.0

Baths

2,419

Sq.Ft.

14217 BRIDGEWATER CROSSINGS BOULEVARD

Windermere, FL

Courtesy of Lake Mary - WEICHERT, REALTORS® - Hallmark Properties
View 13237 FOSSICK ROAD Windermere, FL MLS# O6382389
$599,000
4

Beds

2.0

Baths

2,516

Sq.Ft.

13237 FOSSICK ROAD

Windermere, FL

Courtesy of EXP REALTY LLC
View 10765 Village Lake ROAD Windermere, FL MLS# O6139454
$598,000
4

Beds

3.1

Baths

2,317

Sq.Ft.

10765 Village Lake ROAD

Windermere, FL

Courtesy of JWJ REALTY 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 8323 LOOKOUT POINTE DRIVE Windermere, FL MLS# O6393407
$590,000
4

Beds

3.1

Baths

2,633

Sq.Ft.

8323 LOOKOUT POINTE DRIVE

Windermere, FL

Courtesy of WEST ORLANDO PROPERTY MANAGEMENT REALTY, LLC
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 6442 GOLDEN DEWDROP TRAIL Windermere, FL MLS# G5106279
$585,000
3

Beds

2.1

Baths

2,139

Sq.Ft.

6442 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of EMPIRE NETWORK REALTY
View 918 ALGARE LOOP Windermere, FL MLS# O6396400
  • Virtual Tour
1 of 73
$585,000
4

Beds

3.0

Baths

2,553

Sq.Ft.

918 ALGARE LOOP

Windermere, FL

Courtesy of SOUTHERN PRESTIGE REALTY INC
View 13118 SUNKISS LOOP Windermere, FL MLS# O6385211
$579,000
4

Beds

2.1

Baths

2,547

Sq.Ft.

13118 SUNKISS LOOP

Windermere, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 1516 HEMPEL AVENUE Windermere, FL MLS# O6342593
$575,000
Studio

Beds

0.0

Baths

1516 HEMPEL AVENUE

Windermere, FL

Courtesy of REAL BROKER, LLC
View 9802 6TH STREET Windermere, FL MLS# O6349678
$575,000
Studio

Beds

0.0

Baths

9802 6TH STREET

Windermere, FL

Courtesy of UPSIDE REAL ESTATE 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

341

Estimated median home price

$1,130,000
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 - 300K1
$300K - 400K16
$400K - 500K25
$500K - 600K33
$600K - 700K22
$700K - 800K25
$800K - 900K20
$900K - 1M16
$1M - Max183

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family287
Townhouse36
Condo5
Commercial1
Rental91
Lots and Land12
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 5/17/2026)

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 5/18/2026.