44 total properties
Did you mean the neighborhood Windermere?
View 14341 CREST PALM AVENUE Windermere, FL MLS# G5112469
$1,130,643
4

Beds

4.0

Baths

3,153

Sq.Ft.

14341 CREST PALM AVENUE

Windermere, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 8409 VIVARO ISLE WAY Windermere, FL MLS# G5112154
  • Recently Listed with Virtual Tour
1 of 92
$1,235,000
6

Beds

4.1

Baths

4,176

Sq.Ft.

8409 VIVARO ISLE WAY

Windermere, FL

Courtesy of WATSON REALTY CORP., REALTORS
View 1515 LAKE WHITNEY DRIVE Windermere, FL MLS# O6405903
$1,350,000
5

Beds

5.0

Baths

3,931

Sq.Ft.

1515 LAKE WHITNEY DRIVE

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
The time to sell is now! THE TIME TO SELL IS NOW!
View 1554 LAKE RHEA DRIVE Windermere, FL MLS# O6406297
  • Recently Listed
1 of 59
$1,400,000
4

Beds

3.0

Baths

3,427

Sq.Ft.

1554 LAKE RHEA DRIVE

Windermere, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 2127 LILYPAD LANE Windermere, FL MLS# O6403899
  • Virtual Tour
1 of 60
$1,250,000
4

Beds

3.0

Baths

3,349

Sq.Ft.

2127 LILYPAD LANE

Windermere, FL

Courtesy of UNITED REAL ESTATE PREFERRED
View 14348 CREST PALM AVENUE Windermere, FL MLS# G5111548
  • New Construction with Virtual Tour
1 of 5
$1,109,990
4

Beds

3.1

Baths

3,721

Sq.Ft.

14348 CREST PALM AVENUE

Windermere, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 4474 BEGONIA COURT Windermere, FL MLS# O6402227
  • Virtual Tour
1 of 41
$1,170,000
5

Beds

4.1

Baths

4,380

Sq.Ft.

4474 BEGONIA COURT

Windermere, FL

Courtesy of SOGO REAL ESTATE SERVICES LLC
View 13932 FLORIGOLD DRIVE Windermere, FL MLS# O6399812
  • Virtual Tour
1 of 53
$1,189,000
6

Beds

4.0

Baths

3,577

Sq.Ft.

13932 FLORIGOLD DRIVE

Windermere, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 6379 SWANSON STREET Windermere, FL MLS# O6400522
  • Virtual Tour
1 of 47
$1,119,000
5

Beds

4.0

Baths

3,804

Sq.Ft.

6379 SWANSON STREET

Windermere, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 2219 RIDGEWIND WAY Windermere, FL MLS# O6400508
$1,299,000
6

Beds

3.1

Baths

3,364

Sq.Ft.

2219 RIDGEWIND WAY

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 9663 GOTHA ROAD Windermere, FL MLS# O6399130
  • Virtual Tour
1 of 100
$1,299,900
5

Beds

3.1

Baths

3,731

Sq.Ft.

9663 GOTHA ROAD

Windermere, FL

Courtesy of ANNE ROGERS REALTY GROUP INC
View 715 MAGNOLIA STREET Windermere, FL MLS# S5147648
  • Virtual Tour
1 of 44
$1,175,000
5

Beds

4.0

Baths

3,390

Sq.Ft.

715 MAGNOLIA STREET

Windermere, FL

Courtesy of IRIS INTERNATIONAL
View 109 E 12TH AVENUE Windermere, FL MLS# O6394569
  • Virtual Tour
1 of 43
OPEN HOUSE: Monday 5/18 5:00 PM - 7:00 PM
$1,225,000
4

Beds

3.1

Baths

2,791

Sq.Ft.

109 E 12TH AVENUE

Windermere, FL

Courtesy of UPSIDE REAL ESTATE INC
View 14371 CREST PALM AVENUE Windermere, FL MLS# G5110664
  • New Construction with Virtual Tour
1 of 42
OPEN HOUSE: Saturday 5/23 1:00 PM - 5:00 PM
$1,114,989
4

Beds

3.0

Baths

3,100

Sq.Ft.

14371 CREST PALM AVENUE

Windermere, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 6152 GOLDEN DEWDROP TRAIL Windermere, FL MLS# O6396835
$1,130,000
8

Beds

5.0

Baths

4,830

Sq.Ft.

6152 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of VESTI LLC
View 11537 CLAYMONT CIR Windermere, FL MLS# O6395210
$1,400,000
5

Beds

4.0

Baths

3,164

Sq.Ft.

11537 CLAYMONT CIR

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 8411 WOBURN COURT Windermere, FL MLS# O6391980
  • Virtual Tour
1 of 41
$1,200,000
4

Beds

3.0

Baths

2,582

Sq.Ft.

8411 WOBURN COURT

Windermere, FL

Courtesy of THE AGENCY FL
View 11536 CLAYMONT CIRCLE Windermere, FL MLS# O6392958
  • Virtual Tour
1 of 68
$1,250,000
4

Beds

3.0

Baths

2,882

Sq.Ft.

11536 CLAYMONT CIRCLE

Windermere, FL

Courtesy of MATT ALLEN REAL ESTATE LLC
View 8351 BOWDEN WAY Windermere, FL MLS# O6393659
  • Virtual Tour
1 of 71
$1,199,000
4

Beds

3.0

Baths

2,599

Sq.Ft.

8351 BOWDEN WAY

Windermere, FL

Courtesy of KELLER WILLIAMS REALTY AT THE LAKES
View 106 PALM STREET Windermere, FL MLS# O6391350
  • Virtual Tour
1 of 35
$1,399,000
5

Beds

4.1

Baths

3,082

Sq.Ft.

106 PALM STREET

Windermere, FL

Courtesy of KELLER WILLIAMS WINTER PARK

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

342

Estimated median home price

$1,130,322
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 0
$100K - 200K 0
$200K - 300K 1
$300K - 400K 16
$400K - 500K 25
$500K - 600K 33
$600K - 700K 22
$700K - 800K 25
$800K - 900K 20
$900K - 1M 16
$1M - Max 184

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 288
Townhouse 36
Condo 5
Commercial 1
Rental 90
Lots and Land 12
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 5/18/2026)

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.