213 total properties
Did you mean the neighborhood Windermere?
View 2009 WESTOVER RESERVE BOULEVARD Windermere, FL MLS# O6447265
$1,095,000
4

Beds

3.1

Baths

3,607

Sq.Ft.

2009 WESTOVER RESERVE BOULEVARD

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 613 E 6TH AVENUE Windermere, FL MLS# O6448614
$650,000
0.0

Baths

613 E 6TH AVENUE

Windermere, FL

Courtesy of UPSIDE REAL ESTATE INC
View 615 E 6TH AVENUE Windermere, FL MLS# O6448624
$650,000
0.0

Baths

615 E 6TH AVENUE

Windermere, FL

Courtesy of UPSIDE REAL ESTATE INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 13019 GARRIDAN AVENUE Windermere, FL MLS# O6451068
  • Recently Listed with Virtual Tour
1 of 57
$620,000
4

Beds

3.1

Baths

2,461

Sq.Ft.

13019 GARRIDAN AVENUE

Windermere, FL

Courtesy of LA ROSA REALTY LLC
View 12930 VENNETTA WAY Windermere, FL MLS# O6450743
$349,000
3

Beds

2.1

Baths

1,644

Sq.Ft.

12930 VENNETTA WAY

Windermere, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 11267 GRANDER DRIVE Windermere, FL MLS# O6450595
  • Recently Listed with Virtual Tour
1 of 34
$435,000
3

Beds

2.1

Baths

1,743

Sq.Ft.

11267 GRANDER DRIVE

Windermere, FL

Courtesy of AUTHENTIC REAL ESTATE TEAM
View 14038 EDEN ISLE BOULEVARD Windermere, FL MLS# O6450925
$709,000
4

Beds

3.0

Baths

2,749

Sq.Ft.

14038 EDEN ISLE BOULEVARD

Windermere, FL

Courtesy of EXP REALTY LLC
View 4936 WISE BIRD DRIVE Windermere, FL MLS# O6450351
$535,000
4

Beds

3.0

Baths

2,361

Sq.Ft.

4936 WISE BIRD DRIVE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 17538 BLACK RAIL STREET Windermere, FL MLS# O6449981
  • Recently Listed with Virtual Tour
1 of 72
$1,189,000
5

Beds

4.1

Baths

4,999

Sq.Ft.

17538 BLACK RAIL STREET

Windermere, FL

Courtesy of KARDOSH REALTY
View 13125 PENSHURST LANE Windermere, FL MLS# O6449706
  • Recently Listed with Virtual Tour
1 of 42
$599,000
3

Beds

2.0

Baths

1,948

Sq.Ft.

13125 PENSHURST LANE

Windermere, FL

Courtesy of CASTLE REALTY PROFESSIONAL GROUP LLC
View 4827 FLINT ROAD Windermere, FL MLS# O6449449
  • Virtual Tour
1 of 39
$559,000
3

Beds

2.0

Baths

2,085

Sq.Ft.

4827 FLINT ROAD

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 8867 HERENCIA ALLEY Windermere, FL MLS# O6449612
  • Recently Listed with Virtual Tour
1 of 35
$405,000
3

Beds

2.1

Baths

1,382

Sq.Ft.

8867 HERENCIA ALLEY

Windermere, FL

Courtesy of AAA GLOBAL VENTURES PA
View 7231 SANGALLA DRIVE Windermere, FL MLS# O6447329
  • Recently Listed with Virtual Tour
1 of 67
$1,348,000
5

Beds

4.1

Baths

3,835

Sq.Ft.

7231 SANGALLA DRIVE

Windermere, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 5944 CAYMUS LOOP Windermere, FL MLS# O6448123
  • Recently Listed with Virtual Tour
1 of 45
$1,050,000
4

Beds

3.0

Baths

2,984

Sq.Ft.

5944 CAYMUS LOOP

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 8276 MARITIME FLAG ST 1204 Windermere, FL MLS# O6449170
  • Recently Listed with Virtual Tour
1 of 31
$324,900
3

Beds

2.0

Baths

1,455

Sq.Ft.

8276 MARITIME FLAG ST 1204

Windermere, FL

Courtesy of HOMEVEST REALTY
View 8576 POWDER RIDGE TRAIL Windermere, FL MLS# O6447414
$597,000
4

Beds

3.1

Baths

2,661

Sq.Ft.

8576 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 11963 VERMILLION AVENUE Windermere, FL MLS# O6447919
  • New Construction with Virtual Tour
1 of 35
$430,000
3

Beds

2.1

Baths

1,676

Sq.Ft.

11963 VERMILLION AVENUE

Windermere, FL

Courtesy of METROPOLITAN R.E SOLUTIONS INC
View 12785 WESTSIDE VILLAGE LOOP Windermere, FL MLS# O6442356
  • Recently Listed with Virtual Tour
1 of 42
$769,000
4

Beds

3.1

Baths

2,996

Sq.Ft.

12785 WESTSIDE VILLAGE LOOP

Windermere, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 8168 BOAT HOOK LOOP 302 Windermere, FL MLS# O6445290
$297,997
2

Beds

2.0

Baths

1,161

Sq.Ft.

8168 BOAT HOOK LOOP 302

Windermere, FL

Courtesy of BLUE KEY PROPERTY MANAGEMENT
View 8179 MARITIME FLAG STREET 206 Windermere, FL MLS# O6447793
$350,000
3

Beds

2.0

Baths

1,332

Sq.Ft.

8179 MARITIME FLAG STREET 206

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

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

312

Estimated median home price

$1,089,500
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 - 100K1
$100K - 200K0
$200K - 300K4
$300K - 400K26
$400K - 500K23
$500K - 600K29
$600K - 700K33
$700K - 800K15
$800K - 900K7
$900K - 1M12
$1M - Max162

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family239
Townhouse40
Condo11
Commercial1
Rental104
Lots and Land21
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 10/29/2026)

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 10/29/2026.