98 total properties
Did you mean the neighborhood Windermere?
View 17514 BLACK RAIL STREET Windermere, FL MLS# O6410722
$3,995
4

Beds

2.0

Baths

2,373

Sq.Ft.

17514 BLACK RAIL STREET

Windermere, FL

Courtesy of SUNSHINE REALTY & PROP. MGNT
View 12784 GARRIDAN AVENUE Windermere, FL MLS# O6411120
  • Recently Listed with Virtual Tour
1 of 27
$3,100
4

Beds

2.1

Baths

1,970

Sq.Ft.

12784 GARRIDAN AVENUE

Windermere, FL

Courtesy of YORK MILLS REALTY LLC
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
The time to sell is now! THE TIME TO SELL IS NOW!
View 14252 CONFETTI DRIVE Windermere, FL MLS# O6410196
$3,099
1

Beds

1.0

Baths

320

Sq.Ft.

14252 CONFETTI DRIVE

Windermere, FL

Courtesy of HOMEVEST REALTY
View 11538 DELWICK DRIVE Windermere, FL MLS# O6410311
$6,150
6

Beds

4.1

Baths

4,028

Sq.Ft.

11538 DELWICK DRIVE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 12936 DROXFORD ROAD Windermere, FL MLS# O6409803
$3,600
5

Beds

3.1

Baths

3,038

Sq.Ft.

12936 DROXFORD ROAD

Windermere, FL

Courtesy of WEST ORLANDO PROPERTY MANAGEMENT REALTY, LLC
View 7708 FORDSON LANE Windermere, FL MLS# O6409598
$2,500
3

Beds

2.1

Baths

1,644

Sq.Ft.

7708 FORDSON LANE

Windermere, FL

Courtesy of UNIONE REALTY INC
View 7243 RAMBLING WATER WAY Windermere, FL MLS# O6409553
$3,300
5

Beds

3.1

Baths

2,396

Sq.Ft.

7243 RAMBLING WATER WAY

Windermere, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 13272 PENSHURST LANE Windermere, FL MLS# S5150230
$4,000
5

Beds

3.1

Baths

3,472

Sq.Ft.

13272 PENSHURST LANE

Windermere, FL

Courtesy of BLUEHOUSE REALTY GROUP LLC
View 7652 RIPPLEPOINTE WAY Windermere, FL MLS# O6409167
$2,750
3

Beds

2.1

Baths

1,743

Sq.Ft.

7652 RIPPLEPOINTE WAY

Windermere, FL

Courtesy of ADVANCE REALTY & MANAGEMENT LLC
View 9109 LEGADO DRIVE Windermere, FL MLS# O6408400
  • Virtual Tour
1 of 37
$2,900
3

Beds

2.1

Baths

1,687

Sq.Ft.

9109 LEGADO DRIVE

Windermere, FL

Courtesy of DIAMOND REAL ESTATE GROUP
View 11564 MIZZON DRIVE 902 Windermere, FL MLS# O6406185
$1,995
2

Beds

2.0

Baths

1,161

Sq.Ft.

11564 MIZZON DRIVE 902

Windermere, FL

Courtesy of GATE PROPERTIES & MANAGEMENT INC
View 8642 POWDER RIDGE TRAIL Windermere, FL MLS# O6401509
$2,850
4

Beds

2.1

Baths

1,890

Sq.Ft.

8642 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of METRO CITY REALTY
View 8122 WHITFORD COURT Windermere, FL MLS# O6406342
$7,995
4

Beds

3.1

Baths

3,062

Sq.Ft.

8122 WHITFORD COURT

Windermere, FL

Courtesy of WINDERMERE INTERNATIONAL REALTY
View 13544 RIGGS WAY Windermere, FL MLS# O6404050
$3,900
4

Beds

3.1

Baths

2,696

Sq.Ft.

13544 RIGGS WAY

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 11434 JASPER KAY TERRACE 1101 Windermere, FL MLS# O6404802
$2,500
3

Beds

2.0

Baths

1,442

Sq.Ft.

11434 JASPER KAY TERRACE 1101

Windermere, FL

Courtesy of PINK MIAMI REAL ESTATE
View 9031 LEGADO DRIVE Windermere, FL MLS# O6404941
  • 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 11807 VERMILLION AVE Windermere, FL MLS# O6404378
$2,700
3

Beds

2.1

Baths

1,822

Sq.Ft.

11807 VERMILLION AVE

Windermere, FL

Courtesy of HANG SENG REALTY , 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 8602 VIA TAVOLERIA WAY Windermere, FL MLS# O6404174
$2,900
4

Beds

3.1

Baths

1,936

Sq.Ft.

8602 VIA TAVOLERIA WAY

Windermere, FL

Courtesy of U KEY 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

362

Estimated median home price

$1,168,495
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 - 400K21
$400K - 500K31
$500K - 600K31
$600K - 700K30
$700K - 800K18
$800K - 900K19
$900K - 1M16
$1M - Max195

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family295
Townhouse45
Condo6
Commercial1
Rental98
Lots and Land15
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 6/15/2026)

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 6/16/2026.