102 total properties
Did you mean the neighborhood Winter Park?
View 1812 KILLARNEY DRIVE Winter Park, FL MLS# G5112648
  • Recently Listed
1 of 10
$400,000
4

Beds

2.0

Baths

1,048

Sq.Ft.

1812 KILLARNEY DRIVE

Winter Park, FL

Courtesy of HANSON REAL ESTATE GROUP, INC.
View 700 MELROSE AVENUE H4 Winter Park, FL MLS# O6409318
  • Recently Listed with Virtual Tour
1 of 34
$290,000
2

Beds

2.0

Baths

1,074

Sq.Ft.

700 MELROSE AVENUE H4

Winter Park, FL

Courtesy of TAL BUSIDAN PA
View 700 MELROSE AVENUE J24 Winter Park, FL MLS# R4911307
  • Recently Listed with Virtual Tour
1 of 28
$390,000
1

Beds

1.0

Baths

987

Sq.Ft.

700 MELROSE AVENUE J24

Winter Park, FL

Courtesy of KIMBRIDGE REALTY, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2923 ANTIQUE OAKS CIRCLE 34 Winter Park, FL MLS# S5150301
  • Recently Listed with Virtual Tour
1 of 22
$190,000
2

Beds

2.0

Baths

1,105

Sq.Ft.

2923 ANTIQUE OAKS CIRCLE 34

Winter Park, FL

Courtesy of EXP REALTY LLC
View 151 N ORLANDO AVENUE 259 Winter Park, FL MLS# O6409651
  • Recently Listed with Virtual Tour
1 of 31
$239,000
1

Beds

1.0

Baths

582

Sq.Ft.

151 N ORLANDO AVENUE 259

Winter Park, FL

Courtesy of MAXLIFE REALTY LLC
View 7505 LAUREL SPRINGS DRIVE Winter Park, FL MLS# O6405854
  • Recently Listed with Virtual Tour
1 of 26
$400,000
3

Beds

2.0

Baths

1,471

Sq.Ft.

7505 LAUREL SPRINGS DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 2142 BLOSSOM LANE Winter Park, FL MLS# O6409144
  • Recently Listed
1 of 14
$399,900
3

Beds

2.0

Baths

1,363

Sq.Ft.

2142 BLOSSOM LANE

Winter Park, FL

Courtesy of THE WILKINS WAY LLC
View 1500 GAY ROAD 17D Winter Park, FL MLS# O6408516
  • Recently Listed with Virtual Tour
1 of 36
$259,900
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 17D

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 2973 SANBINA STREET Winter Park, FL MLS# O6407521
  • Recently Listed with Virtual Tour
1 of 36
$377,880
3

Beds

2.0

Baths

1,128

Sq.Ft.

2973 SANBINA STREET

Winter Park, FL

Courtesy of SUN PROPERTIES, INC.
View 1092 EASTBROOK BOULEVARD Winter Park, FL MLS# O6407251
  • Recently Listed with Virtual Tour
1 of 22
$410,000
3

Beds

2.0

Baths

1,122

Sq.Ft.

1092 EASTBROOK BOULEVARD

Winter Park, FL

Courtesy of JC FLORIDA REALTY LLC
View 340 KILLARNEY BAY COURT 4-4 Winter Park, FL MLS# O6407259
  • Recently Listed with Virtual Tour
1 of 37
$410,000
2

Beds

2.1

Baths

1,428

Sq.Ft.

340 KILLARNEY BAY COURT 4-4

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 7532 AZUREBROOK COURT Winter Park, FL MLS# O6406380
$410,000
3

Beds

2.0

Baths

1,402

Sq.Ft.

7532 AZUREBROOK COURT

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 2482 ROXBURY ROAD Winter Park, FL MLS# O6406443
  • Recently Listed with Virtual Tour
1 of 20
$400,000
2

Beds

1.0

Baths

913

Sq.Ft.

2482 ROXBURY ROAD

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 440 CAMBRIDGE BOULEVARD Winter Park, FL MLS# O6403694
  • Recently Listed with Virtual Tour
1 of 31
$380,000
2

Beds

1.0

Baths

988

Sq.Ft.

440 CAMBRIDGE BOULEVARD

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 819 DENSMORE DRIVE Winter Park, FL MLS# O6405658
  • Virtual Tour
1 of 39
$375,000
3

Beds

2.0

Baths

1,300

Sq.Ft.

819 DENSMORE DRIVE

Winter Park, FL

Courtesy of DON HARKINS REALTY LLC
View 2500 LEE ROAD 232 Winter Park, FL MLS# O6404916
  • Recently Listed with Virtual Tour
1 of 26
$164,900
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 232

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 721 DUNBAR STREET Winter Park, FL MLS# O6405338
  • Virtual Tour
1 of 36
$399,999
2

Beds

2.0

Baths

1,018

Sq.Ft.

721 DUNBAR STREET

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1695 LEE ROAD E116 Winter Park, FL MLS# O6399346
  • Recently Listed with Virtual Tour
1 of 29
$125,000
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD E116

Winter Park, FL

Courtesy of ALL REAL ESTATE & INVESTMENTS
View 4772 TANGERINE AVENUE 4772 Winter Park, FL MLS# O6405042
  • Recently Listed with Virtual Tour
1 of 27
$199,000
2

Beds

2.0

Baths

1,058

Sq.Ft.

4772 TANGERINE AVENUE 4772

Winter Park, FL

Courtesy of THE WILKINS WAY LLC
View 3371 RIVER VIEW WAY 46 Winter Park, FL MLS# O6403947
$205,000
3

Beds

2.1

Baths

1,151

Sq.Ft.

3371 RIVER VIEW WAY 46

Winter Park, FL

Courtesy of REALTY ONE GROUP EVOLVE

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

388

Estimated median home price

$787,500
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 2
$100K - 200K 49
$200K - 300K 23
$300K - 400K 23
$400K - 500K 29
$500K - 600K 22
$600K - 700K 29
$700K - 800K 20
$800K - 900K 15
$900K - 1M 10
$1M - Max 166

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 244
Townhouse 15
Condo 88
Commercial 7
Rental 74
Lots and Land 27
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 5/24/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

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.

Data is updated as of 5/24/2026.

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 5/24/2026.