28 total properties
Did you mean the neighborhood Windermere?
View 1625 DOWN LAKE DRIVE Windermere, FL MLS# O6385420
  • Recently Listed with Virtual Tour
1 of 98
$1,400,000
5

Beds

5.1

Baths

3,383

Sq.Ft.

1625 DOWN LAKE DRIVE

Windermere, FL

Courtesy of THE ROSENBLOOM TEAM
View 9548 CROWN PRINCE LANE Windermere, FL MLS# S5144606
  • Recently Listed with Virtual Tour
1 of 22
$1,460,000
4

Beds

4.0

Baths

3,997

Sq.Ft.

9548 CROWN PRINCE LANE

Windermere, FL

Courtesy of LA ROSA REALTY LLC
View 8236 PROCIDA ISLE LANE Windermere, FL MLS# O6383546
  • Recently Listed with Virtual Tour
1 of 27
$1,250,000
6

Beds

4.0

Baths

4,176

Sq.Ft.

8236 PROCIDA ISLE LANE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 6533 CARTMEL LANE Windermere, FL MLS# O6381498
  • Virtual Tour
1 of 37
$1,298,000
4

Beds

3.1

Baths

3,751

Sq.Ft.

6533 CARTMEL LANE

Windermere, FL

Courtesy of THE AGENCY FL
View 5837 CAYMUS LOOP Windermere, FL MLS# O6380732
  • Recently Listed with Virtual Tour
1 of 36
$1,349,000
4

Beds

3.0

Baths

2,937

Sq.Ft.

5837 CAYMUS LOOP

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 6023 BLAKEFORD DR Windermere, FL MLS# O6381942
  • Virtual Tour
1 of 47
$1,525,000
5

Beds

3.0

Baths

3,013

Sq.Ft.

6023 BLAKEFORD DR

Windermere, FL

Courtesy of KEENE'S POINTE REALTY
View 6001 CAYMUS LOOP Windermere, FL MLS# O6379564
  • Virtual Tour
1 of 44
$1,599,000
5

Beds

5.0

Baths

3,520

Sq.Ft.

6001 CAYMUS LOOP

Windermere, FL

Courtesy of QUATTRO R E SOLUTIONS LLC
View 1134 KELSO BOULEVARD Windermere, FL MLS# O6378782
  • Virtual Tour
1 of 37
$1,590,000
2

Beds

2.0

Baths

2,044

Sq.Ft.

1134 KELSO BOULEVARD

Windermere, FL

Courtesy of REALTY AND COMPANY INT., LLC
View 12779 WESTSIDE VILLAGE LOOP Windermere, FL MLS# O6377817
$1,274,000
5

Beds

3.1

Baths

3,689

Sq.Ft.

12779 WESTSIDE VILLAGE LOOP

Windermere, FL

Courtesy of WEBB FLORIDA REALTY LLC
View 11658 HAMPSTEAD STREET Windermere, FL MLS# O6376140
$1,435,000
7

Beds

4.1

Baths

4,563

Sq.Ft.

11658 HAMPSTEAD STREET

Windermere, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 13596 GORGONA ISLE DRIVE Windermere, FL MLS# O6374555
$1,452,000
6

Beds

4.1

Baths

3,794

Sq.Ft.

13596 GORGONA ISLE DRIVE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 11472 PARK AVENUE NE Windermere, FL MLS# G5105731
$1,320,000
5

Beds

3.1

Baths

3,166

Sq.Ft.

11472 PARK AVENUE NE

Windermere, FL

Courtesy of Clermont - WEICHERT, REALTORS® - Hallmark Properties
View 17521 BLACK RAIL STREET Windermere, FL MLS# O6370115
$1,549,000
6

Beds

4.1

Baths

5,316

Sq.Ft.

17521 BLACK RAIL STREET

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 11334 CAMDEN LOOP WAY Windermere, FL MLS# O6367433
  • Virtual Tour
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 11947 LAKE BUTLER BOULEVARD Windermere, FL MLS# S5138619
$1,250,000
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
$1,390,000
4

Beds

3.1

Baths

3,809

Sq.Ft.

8375 BOWDEN WAY

Windermere, FL

Courtesy of B LIVE COMMERCIAL AND RESIDENT
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 1703 ROBERTS LANDING ROAD Windermere, FL MLS# O6346120
$1,590,000
4

Beds

4.1

Baths

3,288

Sq.Ft.

1703 ROBERTS LANDING ROAD

Windermere, FL

Courtesy of INTERNATIONAL NETWORK REALTY
View 311 E 8TH AVENUE Windermere, FL MLS# O6333319
  • Virtual Tour
1 of 59
$1,549,000
5

Beds

4.0

Baths

3,805

Sq.Ft.

311 E 8TH AVENUE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 11021 HAWKSHEAD COURT Windermere, FL MLS# O6328889
  • Virtual Tour
1 of 18
$1,299,000
5

Beds

4.0

Baths

3,557

Sq.Ft.

11021 HAWKSHEAD COURT

Windermere, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS

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

299

Estimated median home price

$1,050,000
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 0
$300K - 400K 16
$400K - 500K 22
$500K - 600K 28
$600K - 700K 24
$700K - 800K 26
$800K - 900K 20
$900K - 1M 9
$1M - Max 153

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 249
Townhouse 31
Condo 5
Commercial 1
Rental 107
Lots and Land 13
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 3/2/2026)

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 3/2/2026.