208 total properties
Did you mean the neighborhood Winter Park?
View 981 ARAGON AVENUE Winter Park, FL MLS# O6420093
  • Virtual Tour
1 of 7
$535,000
2

Beds

1.0

Baths

857

Sq.Ft.

981 ARAGON AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1000 S SEMORAN BOULEVARD 302 Winter Park, FL MLS# O6428713
$110,000
1

Beds

1.0

Baths

796

Sq.Ft.

1000 S SEMORAN BOULEVARD 302

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 1003 LAKE BELL DRIVE Winter Park, FL MLS# O6418278
  • Virtual Tour
1 of 30
$549,900
3

Beds

2.0

Baths

1,837

Sq.Ft.

1003 LAKE BELL DRIVE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View JESSICA COURT Winter Park, FL MLS# O6419256
  • Virtual Tour
1 of 11
$449,000
Studio

Beds

0.0

Baths

JESSICA COURT

Winter Park, FL

View 7488 WHISPERWOOD DRIVE 28 Winter Park, FL MLS# O6419151
$199,000
2

Beds

2.1

Baths

1,578

Sq.Ft.

7488 WHISPERWOOD DRIVE 28

Winter Park, FL

View 1500 GAY ROAD 3C Winter Park, FL MLS# O6417533
  • Virtual Tour
1 of 26
$235,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 3C

Winter Park, FL

View 2361 ROXBURY ROAD Winter Park, FL MLS# O6418164
  • Virtual Tour
1 of 34
$599,000
3

Beds

2.0

Baths

1,723

Sq.Ft.

2361 ROXBURY ROAD

Winter Park, FL

View 1278 S PENNSYLVANIA AVENUE 13 Winter Park, FL MLS# O6417455
  • Recently Listed with Virtual Tour
1 of 16
$799,000
3

Beds

2.1

Baths

1,957

Sq.Ft.

1278 S PENNSYLVANIA AVENUE 13

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 4756 TANGERINE AVENUE 4756 Winter Park, FL MLS# R4911483
$185,000
2

Beds

2.0

Baths

1,058

Sq.Ft.

4756 TANGERINE AVENUE 4756

Winter Park, FL

View 410 SAINT DUNSTAN WAY Winter Park, FL MLS# O6416796
$500,000
3

Beds

2.0

Baths

1,512

Sq.Ft.

410 SAINT DUNSTAN WAY

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1411 MILLER AVENUE Winter Park, FL MLS# O6416926
$899,000
3

Beds

3.1

Baths

1,824

Sq.Ft.

1411 MILLER AVENUE

Winter Park, FL

View 2323 DEVON COURT Winter Park, FL MLS# O6418530
  • Virtual Tour
1 of 35
$429,000
4

Beds

2.0

Baths

2,403

Sq.Ft.

2323 DEVON COURT

Winter Park, FL

View 7525 LODGE POLE TRAIL Winter Park, FL MLS# O6417303
  • Recently Listed with Virtual Tour
1 of 38
$600,000
4

Beds

2.0

Baths

1,936

Sq.Ft.

7525 LODGE POLE TRAIL

Winter Park, FL

View 1265 ARLINGTON PL Winter Park, FL MLS# O6415981
  • Virtual Tour
1 of 38
$810,000
3

Beds

3.1

Baths

2,030

Sq.Ft.

1265 ARLINGTON PL

Winter Park, FL

View 437 N CAPEN AVENUE Winter Park, FL MLS# O6414283
  • Virtual Tour
1 of 36
$849,000
3

Beds

2.1

Baths

1,904

Sq.Ft.

437 N CAPEN AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2500 LEE ROAD 104 Winter Park, FL MLS# TB8517242
  • Virtual Tour
1 of 23
$242,400
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 104

Winter Park, FL

View 2715 PRINCE JOHN ROAD Winter Park, FL MLS# O6415084
$494,900
3

Beds

2.0

Baths

1,565

Sq.Ft.

2715 PRINCE JOHN ROAD

Winter Park, FL

Courtesy of VIA PROPERTIES LLC
View 2831 MULFORD AVENUE Winter Park, FL MLS# O6414319
  • Virtual Tour
1 of 28
$635,000
4

Beds

2.1

Baths

1,647

Sq.Ft.

2831 MULFORD AVENUE

Winter Park, FL

View 151 NORTH ORLANDO AVENUE 142 Winter Park, FL MLS# O6412768
$199,900
1

Beds

1.0

Baths

582

Sq.Ft.

151 NORTH ORLANDO AVENUE 142

Winter Park, FL

View 1250 FORMOSA AVENUE Winter Park, FL MLS# O6412954
  • Virtual Tour
1 of 37
OPEN HOUSE: Friday 9/4 2:00 PM - 4:00 PM
$550,000
3

Beds

3.1

Baths

1,937

Sq.Ft.

1250 FORMOSA AVENUE

Winter Park, FL

Courtesy of EXP REALTY LLC

About Winter Park

Long considered one of the most desirable addresses in Central Florida, Winter Park has been experiencing a wave of new construction along with revitalization of historic areas.  In some instances, developers are choosing to raze older buildings and replace them with luxurious new homes, some that surpass the $1 million price range.  Handsome new residential villages can include exceptional amenities like lakefront parks, pools, and nature preserves.  Winter Park offers a number of amenities that are unusual for a smaller town, including the Rollins College.  This highly respected, private, liberal arts college with its lush campus enriches the entire community educationally, culturally, and economically.  However, the college is not the town's only point of pride.  One of the world's most comprehensive collections of the works of Louis Comfort Tiffany is permanently housed in the Charles Hosmer Morse Museum of American Art.  Aficionados of shopping are drawn to Park Avenue, a quaint district where an oak-shaded park and bandstand are surrounded by art galleries, museums, clothing stores, retail outlets, and wonderful boutiques.  

Listings in Winter Park, FL

369

Estimated median home price

$699,000
Winter Park FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winter Park, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Park, FL.

Homes for Sale by Price in Winter Park, FL

Price Count
$0 - 100K 3
$100K - 200K 41
$200K - 300K 22
$300K - 400K 14
$400K - 500K 38
$500K - 600K 31
$600K - 700K 37
$700K - 800K 11
$800K - 900K 11
$900K - 1M 10
$1M - Max 151

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 225
Townhouse 24
Condo 78
Commercial 9
Rental 76
Lots and Land 23
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 9/3/2026)

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

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 9/3/2026.