289 total properties
Did you mean the neighborhood Windermere?
View 7137 BEEK STREET Windermere, FL MLS# O6398814
  • Virtual Tour
1 of 33
$550,000
3

Beds

2.0

Baths

1,910

Sq.Ft.

7137 BEEK STREET

Windermere, FL

Courtesy of EXP REALTY LLC
View 8179 MARITIME FLAG STREET 101 Windermere, FL MLS# O6399551
$325,000
3

Beds

2.0

Baths

1,442

Sq.Ft.

8179 MARITIME FLAG STREET 101

Windermere, FL

Courtesy of CENTURY 21 CARIOTI
View 5825 OXFORD MOOR BOULEVARD Windermere, FL MLS# O6399697
$1,500,000
4

Beds

3.1

Baths

4,319

Sq.Ft.

5825 OXFORD MOOR BOULEVARD

Windermere, FL

Courtesy of EXP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2068 ROBERTS POINT DRIVE Windermere, FL MLS# O6397543
$2,250,000
5

Beds

4.0

Baths

4,876

Sq.Ft.

2068 ROBERTS POINT DRIVE

Windermere, FL

Courtesy of CENTURY 21 CARIOTI
View 12718 WINDERMERE ISLES PLACE Windermere, FL MLS# O6399958
$1,490,000
5

Beds

4.0

Baths

3,487

Sq.Ft.

12718 WINDERMERE ISLES PLACE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1925 BREEZY HILL DRIVE WINDERMERE FLORIDA 34786 Windermere, FL MLS# O6398784
$862,000
5

Beds

3.0

Baths

3,063

Sq.Ft.

1925 BREEZY HILL DRIVE WINDERMERE FLORIDA 34786

Windermere, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 8796 PEACHTREE PARK COURT Windermere, FL MLS# O6399023
$949,999
4

Beds

3.1

Baths

3,299

Sq.Ft.

8796 PEACHTREE PARK COURT

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 9011 CHAPMAN OAK COURT Windermere, FL MLS# S5148031
  • Adult Community with Virtual Tour
1 of 30
$629,000
4

Beds

2.0

Baths

2,050

Sq.Ft.

9011 CHAPMAN OAK COURT

Windermere, FL

Courtesy of TOWNE CENTER REALTY
View 9620 MAYWOOD DRIVE Windermere, FL MLS# O6399315
  • Virtual Tour
1 of 43
$2,400,000
4

Beds

3.0

Baths

3,004

Sq.Ft.

9620 MAYWOOD DRIVE

Windermere, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 13842 ORANGE CREST DRIVE Windermere, FL MLS# O6402132
  • Virtual Tour
1 of 48
OPEN HOUSE: Sunday 6/7 2:00 PM - 4:00 PM
$714,999
5

Beds

3.0

Baths

2,620

Sq.Ft.

13842 ORANGE CREST DRIVE

Windermere, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 6315 CLEARMEADOW COURT Windermere, FL MLS# O6398505
$618,000
3

Beds

2.0

Baths

2,077

Sq.Ft.

6315 CLEARMEADOW COURT

Windermere, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 11226 MACAW COURT Windermere, FL MLS# O6393210
  • Virtual Tour
1 of 77
$1,825,000
4

Beds

4.1

Baths

4,549

Sq.Ft.

11226 MACAW COURT

Windermere, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 1002 OAKDALE STREET Windermere, FL MLS# TB8495717
  • Virtual Tour
1 of 60
$975,000
4

Beds

3.0

Baths

3,516

Sq.Ft.

1002 OAKDALE STREET

Windermere, FL

Courtesy of KELLER WILLIAMS SUBURBAN TAMPA
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 910 LASCALA DRIVE Windermere, FL MLS# O6397847
  • Virtual Tour
1 of 54
$770,000
4

Beds

3.1

Baths

2,742

Sq.Ft.

910 LASCALA DRIVE

Windermere, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 109 E 12TH AVENUE Windermere, FL MLS# O6394569
  • Virtual Tour
1 of 43
$1,198,000
4

Beds

3.1

Baths

2,791

Sq.Ft.

109 E 12TH AVENUE

Windermere, FL

Courtesy of UPSIDE REAL ESTATE INC
View 4627 BLUE MAJOR DRIVE Windermere, FL MLS# O6397778
  • Virtual Tour
1 of 36
OPEN HOUSE: Sunday 6/7 11:00 AM - 2:00 PM
$570,000
4

Beds

3.0

Baths

2,411

Sq.Ft.

4627 BLUE MAJOR DRIVE

Windermere, FL

Courtesy of DENIZ REALTY PARTNERS LLC
View 212 W 1ST AVENUE Windermere, FL MLS# S5147532
  • Virtual Tour
1 of 21
$1,650,000
Studio

Beds

0.0

Baths

212 W 1ST AVENUE

Windermere, FL

Courtesy of HOME WISE REALTY GROUP, INC.
View 5106 TILDENS GROVE BOULEVARD Windermere, FL MLS# O6397273
$1,600,000
6

Beds

4.1

Baths

4,572

Sq.Ft.

5106 TILDENS GROVE BOULEVARD

Windermere, FL

Courtesy of TARA MOORE REAL ESTATE
View 825 OAKDALE STREET Windermere, FL MLS# O6396351
  • Virtual Tour
1 of 50
$792,500
3

Beds

2.0

Baths

1,664

Sq.Ft.

825 OAKDALE STREET

Windermere, FL

Courtesy of EXP REALTY 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

360

Estimated median home price

$1,188,500
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 0
$100K - 200K 0
$200K - 300K 1
$300K - 400K 22
$400K - 500K 30
$500K - 600K 32
$600K - 700K 25
$700K - 800K 18
$800K - 900K 18
$900K - 1M 15
$1M - Max 199

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 294
Townhouse 44
Condo 7
Commercial 1
Rental 93
Lots and Land 14
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 6/7/2026)

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

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties 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 6/7/2026.