120 total properties
Did you mean the neighborhood Winter Park?
View 764 W COMSTOCK AVENUE Winter Park, FL MLS# O6379596
  • Recently Listed with Virtual Tour
1 of 39
$474,000
2

Beds

1.0

Baths

925

Sq.Ft.

764 W COMSTOCK AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 600 W WEBSTER AVENUE Winter Park, FL MLS# O6378330
$295,000
2

Beds

1.0

Baths

754

Sq.Ft.

600 W WEBSTER AVENUE

Winter Park, FL

Courtesy of REALTY ONE GROUP MVP
View 1500 GAY ROAD 5 Winter Park, FL MLS# S5143213
  • Recently Listed with Virtual Tour
1 of 17
$195,000
1

Beds

1.0

Baths

732

Sq.Ft.

1500 GAY ROAD 5

Winter Park, FL

Courtesy of TRANSCEND REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 2748 LION HEART ROAD Winter Park, FL MLS# O6379237
  • Recently Listed with Virtual Tour
1 of 49
OPEN HOUSE: Saturday 2/7 12:00 PM - 3:00 PM
$500,000
3

Beds

2.0

Baths

1,502

Sq.Ft.

2748 LION HEART ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
View 4872 ORANGE AVENUE Winter Park, FL MLS# O6380333
  • Recently Listed with Virtual Tour
1 of 18
$375,000
3

Beds

2.1

Baths

1,881

Sq.Ft.

4872 ORANGE AVENUE

Winter Park, FL

Courtesy of ALFA REAL ESTATE LLC
View 200 SAINT ANDREWS BOULEVARD 2302 Winter Park, FL MLS# O6377760
  • Recently Listed with Virtual Tour
1 of 18
$195,000
2

Beds

2.0

Baths

987

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 2302

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 1564 CAVENDISH ROAD Winter Park, FL MLS# O6380505
$470,000
2

Beds

1.0

Baths

1,140

Sq.Ft.

1564 CAVENDISH ROAD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2500 LEE ROAD 229 Winter Park, FL MLS# O6377616
  • Recently Listed with Virtual Tour
1 of 41
$255,000
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 229

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 630 KILLARNEY BAY COURT 3 Winter Park, FL MLS# O6375307
  • Recently Listed with Virtual Tour
1 of 55
$549,900
2

Beds

2.1

Baths

1,428

Sq.Ft.

630 KILLARNEY BAY COURT 3

Winter Park, FL

Courtesy of FLORIDA ONE REAL ESTATE LLC
View 2249 MINNESOTA AVENUE Winter Park, FL MLS# O6377279
  • Recently Listed with Virtual Tour
1 of 70
$435,000
4

Beds

2.0

Baths

1,536

Sq.Ft.

2249 MINNESOTA AVENUE

Winter Park, FL

Courtesy of MARKET CONNECT REALTY LLC
View 3315 AMBER WOOD WAY 104 Winter Park, FL MLS# O6376997
  • Recently Listed with Virtual Tour
1 of 26
$165,000
2

Beds

1.1

Baths

990

Sq.Ft.

3315 AMBER WOOD WAY 104

Winter Park, FL

Courtesy of 100% REAL ESTATE, INC
View 3207 LOWNDES DRIVE Winter Park, FL MLS# O6362285
  • Recently Listed with Virtual Tour
1 of 31
OPEN HOUSE: Saturday 2/7 10:00 AM - 12:00 PM
$509,000
3

Beds

2.0

Baths

2,028

Sq.Ft.

3207 LOWNDES DRIVE

Winter Park, FL

Courtesy of MILLER GRANT AND COMPANY
View 326 FITZHUGH ROAD Winter Park, FL MLS# O6372053
$475,000
4

Beds

3.0

Baths

1,835

Sq.Ft.

326 FITZHUGH ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2500 LEE ROAD 110 Winter Park, FL MLS# O6375907
$159,900
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 110

Winter Park, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 1500 GAY ROAD 18A Winter Park, FL MLS# O6376215
  • Recently Listed with Virtual Tour
1 of 21
$259,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 18A

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 7618 WAUNATTA COURT Winter Park, FL MLS# V4946886
  • Recently Listed with Virtual Tour
1 of 31
$465,000
3

Beds

3.0

Baths

1,970

Sq.Ft.

7618 WAUNATTA COURT

Winter Park, FL

Courtesy of PHOENIX REALTY ADVISORS LLC
View 2500 LEE ROAD 228 Winter Park, FL MLS# O6375288
  • Recently Listed with Virtual Tour
1 of 35
$249,900
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 228

Winter Park, FL

Courtesy of HOMEVEST REALTY
View 3220 NETHERWOOD DRIVE Winter Park, FL MLS# O6374172
$285,000
2

Beds

2.0

Baths

1,036

Sq.Ft.

3220 NETHERWOOD DRIVE

Winter Park, FL

Courtesy of THE FIRM RE
View 1695 LEE ROAD B216 Winter Park, FL MLS# O6374448
$134,900
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD B216

Winter Park, FL

Courtesy of EXP REALTY LLC
View 2833 PRINCE JOHN ROAD Winter Park, FL MLS# O6374734
$429,000
4

Beds

2.0

Baths

1,605

Sq.Ft.

2833 PRINCE JOHN ROAD

Winter Park, FL

Courtesy of EXIT REALTY PREMIER LEGACY

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

306

Estimated median home price

$695,250
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

PriceCount
$0 - 100K7
$100K - 200K33
$200K - 300K30
$300K - 400K16
$400K - 500K27
$500K - 600K18
$600K - 700K26
$700K - 800K19
$800K - 900K5
$900K - 1M8
$1M - Max117

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family176
Townhouse17
Condo78
Commercial6
Rental92
Lots and Land21
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 2/7/2026)

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

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 2/8/2026.