314 total properties
Did you mean the neighborhood Windermere?
View 8386 IRON MOUNTAIN TRAIL Windermere, FL MLS# S5154426
$438,000
4

Beds

2.1

Baths

1,631

Sq.Ft.

8386 IRON MOUNTAIN TRAIL

Windermere, FL

Courtesy of MY REALTY GROUP, LLC.
View 6719 VALHALLA WAY Windermere, FL MLS# O6428554
$4,495,000
5

Beds

5.2

Baths

6,159

Sq.Ft.

6719 VALHALLA WAY

Windermere, FL

Courtesy of CELEBRITY GLOBAL REALTY LLC
View 13231 ROXBORO ROAD Windermere, FL MLS# O6427997
$579,000
3

Beds

2.0

Baths

1,706

Sq.Ft.

13231 ROXBORO ROAD

Windermere, FL

Courtesy of LA ROSA REALTY KISSIMMEE
The time to sell is now! THE TIME TO SELL IS NOW!
View 12102 MONTALCINO CIRCLE Windermere, FL MLS# O6428441
$3,100,000
4

Beds

4.1

Baths

4,296

Sq.Ft.

12102 MONTALCINO CIRCLE

Windermere, FL

Courtesy of EXP REALTY LLC
View 800 W 2ND AVENUE Windermere, FL MLS# O6422976
  • Virtual Tour
1 of 78
OPEN HOUSE: Sunday 10/11 12:00 PM - 2:00 PM
$5,999,000
5

Beds

4.1

Baths

5,511

Sq.Ft.

800 W 2ND AVENUE

Windermere, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 6208 TALARIA DRIVE Windermere, FL MLS# O6427527
  • Virtual Tour
1 of 40
$750,000
5

Beds

4.0

Baths

3,373

Sq.Ft.

6208 TALARIA DRIVE

Windermere, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 13006 SUNKISS LOOP Windermere, FL MLS# O6427757
  • Virtual Tour
1 of 52
$379,900
2

Beds

2.0

Baths

1,155

Sq.Ft.

13006 SUNKISS LOOP

Windermere, FL

Courtesy of MAY HO REALTY
View 8931 LOOKOUT POINTE DRIVE Windermere, FL MLS# O6427614
$740,000
5

Beds

4.0

Baths

2,989

Sq.Ft.

8931 LOOKOUT POINTE DRIVE

Windermere, FL

Courtesy of SPECIALIZED PROPERTY MANAGEMENT
View 7720 FICQUETTE ROAD Windermere, FL MLS# O6426088
  • Virtual Tour
1 of 41
$2,999,996
6

Beds

4.1

Baths

4,282

Sq.Ft.

7720 FICQUETTE ROAD

Windermere, FL

Courtesy of REVEL REALTY LLC
View 7222 STILL POND LANE Windermere, FL MLS# O6426722
  • Virtual Tour
1 of 32
$600,000
3

Beds

2.0

Baths

2,066

Sq.Ft.

7222 STILL POND LANE

Windermere, FL

Courtesy of ATRIUM REALTY, LLC
View 724 W 2ND AVENUE Windermere, FL MLS# O6426995
  • Virtual Tour
1 of 100
$7,500,000
6

Beds

7.1

Baths

6,874

Sq.Ft.

724 W 2ND AVENUE

Windermere, FL

Courtesy of THE SIMON SIMAAN GROUP
View 13250 BELLARIA CIRCLE Windermere, FL MLS# W7887812
  • Virtual Tour
1 of 99
$2,795,000
6

Beds

7.1

Baths

6,781

Sq.Ft.

13250 BELLARIA CIRCLE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 9021 VIA DI CANTI Windermere, FL MLS# O6437659
  • Virtual Tour
1 of 33
$550,000
5

Beds

3.1

Baths

2,268

Sq.Ft.

9021 VIA DI CANTI

Windermere, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 12085 SANDY SHORES DRIVE Windermere, FL MLS# O6426164
$1,225,000
5

Beds

3.0

Baths

2,831

Sq.Ft.

12085 SANDY SHORES DRIVE

Windermere, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 7712 FORDSON LANE Windermere, FL MLS# O6425885
  • Virtual Tour
1 of 37
$350,000
3

Beds

2.1

Baths

1,644

Sq.Ft.

7712 FORDSON LANE

Windermere, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 7537 BROFIELD AVENUE Windermere, FL MLS# O6426217
  • Virtual Tour
1 of 30
$659,000
4

Beds

3.1

Baths

2,610

Sq.Ft.

7537 BROFIELD AVENUE

Windermere, FL

Courtesy of SUNSHINE GROUP USA, INC
View 12417 MONTALCINO CIRCLE Windermere, FL MLS# O6425494
  • Virtual Tour
1 of 100
$1,595,000
4

Beds

3.1

Baths

3,166

Sq.Ft.

12417 MONTALCINO CIRCLE

Windermere, FL

Courtesy of LA ROSA REALTY LLC
View 6119 GROSVENOR SHORE DRIVE Windermere, FL MLS# O6421205
$15,900,000
8

Beds

8.3

Baths

14,068

Sq.Ft.

6119 GROSVENOR SHORE DRIVE

Windermere, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 8713 Crescendo Windermere, FL MLS# A12054326
  • Virtual Tour
1 of 24
$780,000
3

Beds

2.1

Baths

8713 Crescendo

Windermere, FL

Courtesy of REALTY ONE GROUP EVOLUTION
View 8344 BOWDEN WAY Windermere, FL MLS# O6425171
$1,065,000
4

Beds

4.0

Baths

3,646

Sq.Ft.

8344 BOWDEN WAY

Windermere, FL

Courtesy of ALIGN REAL ESTATE LLC

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

310

Estimated median home price

$1,032,500
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

Price Count
$0 - 100K 1
$100K - 200K 0
$200K - 300K 3
$300K - 400K 28
$400K - 500K 26
$500K - 600K 24
$600K - 700K 29
$700K - 800K 20
$800K - 900K 9
$900K - 1M 14
$1M - Max 156

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 236
Townhouse 42
Condo 11
Commercial 1
Rental 91
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 10/8/2026)

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 10/9/2026.