32 total properties
Did you mean the neighborhood Windermere?
View 11947 LAKE BUTLER BOULEVARD Windermere, FL MLS# S5138619
$1,500,000
Studio

Beds

0.0

Baths

11947 LAKE BUTLER BOULEVARD

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 8375 BOWDEN WAY Windermere, FL MLS# S5137385
  • Virtual Tour
1 of 62
$1,490,000
4

Beds

3.1

Baths

3,809

Sq.Ft.

8375 BOWDEN WAY

Windermere, FL

Courtesy of B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE
View 101 LEE STREET Windermere, FL MLS# O6344558
  • Virtual Tour
1 of 63
OPEN HOUSE: Sunday 1/4 11:00 AM - 2:00 PM
$1,485,000
5

Beds

4.0

Baths

4,186

Sq.Ft.

101 LEE STREET

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 17538 BLACK RAIL STREET Windermere, FL MLS# O6349325
$1,480,000
6

Beds

4.1

Baths

4,522

Sq.Ft.

17538 BLACK RAIL STREET

Windermere, FL

Courtesy of GARCIA REALTY GROUP
View 6443 CARTMEL LANE Windermere, FL MLS# O6179128
  • Virtual Tour
1 of 31
$1,475,000
5

Beds

4.1

Baths

4,257

Sq.Ft.

6443 CARTMEL LANE

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 7135 HORIZON CIRCLE Windermere, FL MLS# O6327225
$1,449,000
4

Beds

3.1

Baths

3,359

Sq.Ft.

7135 HORIZON CIRCLE

Windermere, FL

Courtesy of THE BOSCH GROUP
View 10506 DOWN LAKEVIEW CIRCLE Windermere, FL MLS# S5130322
$1,350,000
4

Beds

3.0

Baths

3,888

Sq.Ft.

10506 DOWN LAKEVIEW CIRCLE

Windermere, FL

Courtesy of LA ROSA REALTY LLC
View 11474 CLAYMONT CIRCLE Windermere, FL MLS# S5140648
$1,350,000
5

Beds

4.0

Baths

3,238

Sq.Ft.

11474 CLAYMONT CIRCLE

Windermere, FL

Courtesy of WATSON REALTY CORP.
View 2206 Ridgewind WAY Windermere, FL MLS# O6189162
$1,347,000
5

Beds

4.0

Baths

3,443

Sq.Ft.

2206 Ridgewind WAY

Windermere, FL

Courtesy of LPT REALTY
View 11524 CLAYMONT CIRCLE Windermere, FL MLS# O6336789
$1,345,000
5

Beds

4.0

Baths

3,358

Sq.Ft.

11524 CLAYMONT CIRCLE

Windermere, FL

Courtesy of ALIGN REAL ESTATE LLC
View 11021 HAWKSHEAD COURT Windermere, FL MLS# O6328889
$1,299,000
5

Beds

4.0

Baths

3,557

Sq.Ft.

11021 HAWKSHEAD COURT

Windermere, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 11333 CAMDEN PARK DRIVE Windermere, FL MLS# O6322386
$1,298,000
5

Beds

4.1

Baths

3,449

Sq.Ft.

11333 CAMDEN PARK DRIVE

Windermere, FL

Courtesy of KARDOSH REALTY
View 6533 CARTMEL LANE Windermere, FL MLS# S5132324
  • Virtual Tour
1 of 35
$1,298,000
4

Beds

3.1

Baths

3,751

Sq.Ft.

6533 CARTMEL LANE

Windermere, FL

Courtesy of THE AGENCY ORLANDO
View 11334 CAMDEN LOOP WAY Windermere, FL MLS# O6367433
  • Recently Listed
1 of 70
$1,275,000
4

Beds

3.0

Baths

3,021

Sq.Ft.

11334 CAMDEN LOOP WAY

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 11318 FENIMORE COURT COURT Windermere, FL MLS# O6355539
$1,249,000
4

Beds

3.0

Baths

2,523

Sq.Ft.

11318 FENIMORE COURT COURT

Windermere, FL

Courtesy of FSM REALTY INVESTMENTS
View 10442 BIRCH TREE LANE Windermere, FL MLS# O6367335
  • Recently Listed with Virtual Tour
1 of 69
OPEN HOUSE: Sunday 1/4 12:30 PM - 3:00 PM
$1,249,000
4

Beds

3.0

Baths

3,505

Sq.Ft.

10442 BIRCH TREE LANE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 6146 GOLDEN DEWDROP TRAIL Windermere, FL MLS# O6368142
  • Recently Listed with Virtual Tour
1 of 73
OPEN HOUSE: Saturday 1/3 12:00 PM - 2:00 PM
$1,225,000
7

Beds

5.0

Baths

4,751

Sq.Ft.

6146 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 109 E 12TH AVENUE Windermere, FL MLS# O6368253
  • Recently Listed with Virtual Tour
1 of 73
$1,224,000
4

Beds

3.1

Baths

2,791

Sq.Ft.

109 E 12TH AVENUE

Windermere, FL

Courtesy of THE AGENCY ORLANDO
View 14238 CREST PALM AVENUE Windermere, FL MLS# G5099191
$1,222,740
6

Beds

4.0

Baths

4,222

Sq.Ft.

14238 CREST PALM AVENUE

Windermere, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 3443 WILD MYRTLE COURT Windermere, FL MLS# O6310904
$1,200,000
5

Beds

3.0

Baths

2,918

Sq.Ft.

3443 WILD MYRTLE COURT

Windermere, FL

Courtesy of JULIAN PROPERTIES, 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

283

Estimated median home price

$1,084,990
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 - 400K22
$400K - 500K22
$500K - 600K15
$600K - 700K21
$700K - 800K19
$800K - 900K18
$900K - 1M15
$1M - Max151

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family225
Townhouse36
Condo8
Commercial1
Rental101
Lots and Land13
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 1/3/2026)

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 1/4/2026.