41 total properties
Did you mean the neighborhood Windermere?
View 11923 LAKE BUTLER BOULEVARD Windermere, FL MLS# O6311003
$1,630,000
3

Beds

2.0

Baths

2,238

Sq.Ft.

11923 LAKE BUTLER BOULEVARD

Windermere, FL

Courtesy of JULIAN PROPERTIES, 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 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
The time to sell is now! THE TIME TO SELL IS NOW!
View 13124 FILLY COURT Windermere, FL MLS# O6303140
  • Virtual Tour
1 of 51
OPEN HOUSE: Saturday 5/23 1:00 PM - 3:00 PM
$1,575,000
5

Beds

3.0

Baths

3,300

Sq.Ft.

13124 FILLY COURT

Windermere, FL

Courtesy of HOME N OFFICES INTERNATIONAL
View 33 MAIN STREET Windermere, FL MLS# O6406887
  • Recently Listed
1 of 4
$1,575,000
4

Beds

2.0

Baths

2,130

Sq.Ft.

33 MAIN STREET

Windermere, FL

Courtesy of SAND DOLLAR REALTY GROUP INC
View 10948 DOWN PARK LANE Windermere, FL MLS# O6389820
$1,545,000
Studio

Beds

0.0

Baths

10948 DOWN PARK LANE

Windermere, FL

Courtesy of BHHS FLORIDA REALTY
View 11015 HAWKSHEAD COURT Windermere, FL MLS# O6405977
  • Recently Listed with Virtual Tour
1 of 42
$1,529,999
5

Beds

4.1

Baths

3,868

Sq.Ft.

11015 HAWKSHEAD COURT

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 1703 ROBERTS LANDING ROAD Windermere, FL MLS# O6346120
$1,520,000
4

Beds

4.1

Baths

3,288

Sq.Ft.

1703 ROBERTS LANDING ROAD

Windermere, FL

Courtesy of INTERNATIONAL NETWORK REALTY
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
View 9527 QUEENSBURY COURT Windermere, FL MLS# O6408997
  • Recently Listed with Virtual Tour
1 of 78
OPEN HOUSE: Saturday 5/23 1:00 PM - 4:00 PM
$1,499,900
5

Beds

4.2

Baths

5,378

Sq.Ft.

9527 QUEENSBURY COURT

Windermere, FL

Courtesy of THE PROPERTY PROS REAL ESTATE, INC
View 9119 BALMORAL MEWS SQ Windermere, FL MLS# S5146725
  • Recently Listed with Virtual Tour
1 of 64
$1,499,000
4

Beds

4.0

Baths

4,052

Sq.Ft.

9119 BALMORAL MEWS SQ

Windermere, FL

Courtesy of LA ROSA REALTY BEACHES LLC
View 12411 MONTALCINO CIRCLE Windermere, FL MLS# O6400067
$1,495,000
4

Beds

4.1

Baths

3,399

Sq.Ft.

12411 MONTALCINO CIRCLE

Windermere, FL

Courtesy of VISTA CAY REALTY COMPANY
View 11339 CAMDEN PARK DRIVE Windermere, FL MLS# O6388110
$1,490,000
5

Beds

4.0

Baths

3,492

Sq.Ft.

11339 CAMDEN PARK DRIVE

Windermere, FL

Courtesy of AMERICAN HORIZONS REALTY
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 2635 TRYON PLACE Windermere, FL MLS# O6402029
$1,475,000
6

Beds

4.1

Baths

4,027

Sq.Ft.

2635 TRYON PLACE

Windermere, FL

Courtesy of REIKI REALTY LLC
View 2509 RIDGEWIND WAY Windermere, FL MLS# O6402522
  • Recently Listed with Virtual Tour
1 of 39
$1,460,000
4

Beds

3.1

Baths

3,844

Sq.Ft.

2509 RIDGEWIND WAY

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 11617 CAMDEN PARK DRIVE Windermere, FL MLS# O6405409
  • Recently Listed with Virtual Tour
1 of 61
$1,450,000
6

Beds

4.1

Baths

3,463

Sq.Ft.

11617 CAMDEN PARK DRIVE

Windermere, FL

Courtesy of WATSON REALTY CORP
View 9548 CROWN PRINCE LANE Windermere, FL MLS# O6407352
  • Recently Listed with Virtual Tour
1 of 41
$1,450,000
4

Beds

4.0

Baths

3,997

Sq.Ft.

9548 CROWN PRINCE LANE

Windermere, FL

Courtesy of DOUGLAS ELLIMAN
View 1125 KELSO BOULEVARD Windermere, FL MLS# O6406003
  • Recently Listed
1 of 61
$1,425,000
4

Beds

3.1

Baths

3,660

Sq.Ft.

1125 KELSO BOULEVARD

Windermere, FL

Courtesy of Winter Park - WEICHERT, REALTORS® - Hallmark Properties
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

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

341

Estimated median home price

$1,196,000
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

PriceCount
$0 - 100K0
$100K - 200K0
$200K - 300K2
$300K - 400K17
$400K - 500K23
$500K - 600K31
$600K - 700K19
$700K - 800K25
$800K - 900K19
$900K - 1M16
$1M - Max189

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family287
Townhouse35
Condo6
Commercial1
Rental90
Lots and Land12
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 5/21/2026)

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 5/22/2026.