43 total properties
Did you mean the neighborhood Windermere?
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 8409 VIVARO ISLE WAY Windermere, FL MLS# G5112154
  • Recently Listed with Virtual Tour
1 of 92
OPEN HOUSE: Sunday 5/17 11:00 AM - 2:00 PM
$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 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
The time to sell is now! THE TIME TO SELL IS NOW!
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 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 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
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 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 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 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 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 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
OPEN HOUSE: Sunday 5/17 2:00 PM - 4:00 PM
$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 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 12718 WINDERMERE ISLES PLACE Windermere, FL MLS# O6399958
$1,490,000
4

Beds

4.0

Baths

3,487

Sq.Ft.

12718 WINDERMERE ISLES PLACE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 109 E 12TH AVENUE Windermere, FL MLS# O6394569
  • Virtual Tour
1 of 43
$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 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

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

$1,130,000
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 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 183

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 287
Townhouse 36
Condo 5
Commercial 1
Rental 91
Lots and Land 12
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 5/17/2026)

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 5/17/2026.