108 total properties
Did you mean the neighborhood Windermere?
View 11446 JASPER KAY TERRACE 1009 Windermere, FL MLS# O6358901
$1,800
2

Beds

2.0

Baths

1,161

Sq.Ft.

11446 JASPER KAY TERRACE 1009

Windermere, FL

Courtesy of CINO INTERNATIONAL INC
View 11562 AMIDSHIP LANE 208 Windermere, FL MLS# O6357378
$2,000
3

Beds

2.0

Baths

1,442

Sq.Ft.

11562 AMIDSHIP LANE 208

Windermere, FL

Courtesy of ALFANO PROPERTY MANAGEMENT
View 8156 BOAT HOOK LOOP 303 Windermere, FL MLS# O6357403
$2,000
3

Beds

2.0

Baths

1,442

Sq.Ft.

8156 BOAT HOOK LOOP 303

Windermere, FL

Courtesy of ALFANO PROPERTY MANAGEMENT
The time to sell is now! THE TIME TO SELL IS NOW!
View 11564 MIZZON DRIVE 104 Windermere, FL MLS# O6360568
$2,050
3

Beds

2.0

Baths

1,332

Sq.Ft.

11564 MIZZON DRIVE 104

Windermere, FL

Courtesy of WATSON REALTY CORP
View 8168 BOAT HOOK LOOP 725 Windermere, FL MLS# O6356119
$2,100
3

Beds

2.0

Baths

1,332

Sq.Ft.

8168 BOAT HOOK LOOP 725

Windermere, FL

Courtesy of REALSOURCE PROPERTY MANGNT LLC
View 8168 BOAT HOOK LOOP 107 Windermere, FL MLS# O6359665
$2,100
3

Beds

2.0

Baths

1,455

Sq.Ft.

8168 BOAT HOOK LOOP 107

Windermere, FL

Courtesy of WEST ORLANDO PROPERTY MANAGEMENT REALTY, LLC
View 8528 Danforth DRIVE Windermere, FL MLS# O6196396
$2,200
2

Beds

2.1

Baths

1,280

Sq.Ft.

8528 Danforth DRIVE

Windermere, FL

Courtesy of THE REALTY MEDICS
View 8180 BOAT HOOK LOOP 310 Windermere, FL MLS# O6318715
$2,300
3

Beds

2.0

Baths

1,442

Sq.Ft.

8180 BOAT HOOK LOOP 310

Windermere, FL

Courtesy of TOP TEAM REALTY, LLC.
View 8168 BOAT HOOK LOOP 707 Windermere, FL MLS# S5131775
$2,300
3

Beds

2.0

Baths

1,332

Sq.Ft.

8168 BOAT HOOK LOOP 707

Windermere, FL

Courtesy of TEAM DONOVAN
View 8265 MARITIME FLAG STREET 101 Windermere, FL MLS# O6357575
$2,300
3

Beds

2.1

Baths

1,644

Sq.Ft.

8265 MARITIME FLAG STREET 101

Windermere, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 5589 REMSEN CAY LANE Windermere, FL MLS# O5916546
$2,340
4

Beds

2.1

Baths

2,600

Sq.Ft.

5589 REMSEN CAY LANE

Windermere, FL

Courtesy of INVITATION HOMES
View 8716 DANFORTH DRIVE Windermere, FL MLS# O6368423
  • Recently Listed with Virtual Tour
1 of 29
$2,350
2

Beds

2.1

Baths

1,360

Sq.Ft.

8716 DANFORTH DRIVE

Windermere, FL

Courtesy of BEST ORLANDO PROPERTY MANAGEMENT LLC
View 7351 MILLSTONE STREET Windermere, FL MLS# S5137579
$2,400
3

Beds

2.0

Baths

1,510

Sq.Ft.

7351 MILLSTONE STREET

Windermere, FL

Courtesy of FRONTLINE FLORIDA REALTY, INC.
View 8180 BOAT HOOK LOOP 304 Windermere, FL MLS# O6358068
$2,400
3

Beds

2.0

Baths

1,455

Sq.Ft.

8180 BOAT HOOK LOOP 304

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 14284 DESERT HAVEN STREET 806 Windermere, FL MLS# O6357673
$2,450
3

Beds

2.1

Baths

1,840

Sq.Ft.

14284 DESERT HAVEN STREET 806

Windermere, FL

Courtesy of CINO INTERNATIONAL INC
View 7452 LEIGHSIDE DRIVE Windermere, FL MLS# O6334058
$2,500
3

Beds

2.1

Baths

1,910

Sq.Ft.

7452 LEIGHSIDE DRIVE

Windermere, FL

Courtesy of LJL REAL ESTATE, INC.
View 12910 CALDERDALE AVENUE Windermere, FL MLS# R4909829
$2,500
3

Beds

2.1

Baths

1,545

Sq.Ft.

12910 CALDERDALE AVENUE

Windermere, FL

Courtesy of SIMS REALTY LLC
View 7621 SUTHERTON LANE Windermere, FL MLS# S5138552
$2,500
3

Beds

2.1

Baths

1,520

Sq.Ft.

7621 SUTHERTON LANE

Windermere, FL

Courtesy of MY REALTY GROUP, LLC.
View 8145 SERENITY SPRING DRIVE GE Windermere, FL MLS# O6361898
$2,500
3

Beds

2.1

Baths

1,512

Sq.Ft.

8145 SERENITY SPRING DRIVE GE

Windermere, FL

Courtesy of SUNNY 365 REALTY GROUP
View 7708 BEXTON LANE Windermere, FL MLS# S5139994
  • Virtual Tour
1 of 11
$2,500
3

Beds

2.0

Baths

1,335

Sq.Ft.

7708 BEXTON LANE

Windermere, FL

Courtesy of ALTIS REALTY

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

286

Estimated median home price

$1,077,995
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 - 400K24
$400K - 500K21
$500K - 600K16
$600K - 700K21
$700K - 800K17
$800K - 900K20
$900K - 1M17
$1M - Max150

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family227
Townhouse37
Condo9
Commercial1
Rental109
Lots and Land12
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 12/31/2025)

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 1/1/2026.