26 total properties
Did you mean the neighborhood Winter Park?
View 7505 LAUREL SPRINGS DRIVE Winter Park, FL MLS# O6405854
  • Recently Listed with Virtual Tour
1 of 26
OPEN HOUSE: Saturday 5/23 11:00 AM - 1:00 PM
$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 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
$415,000
3

Beds

2.0

Baths

1,122

Sq.Ft.

1092 EASTBROOK BOULEVARD

Winter Park, FL

Courtesy of JC FLORIDA REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
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 157 E NEW ENGLAND AVENUE 302 Winter Park, FL MLS# O6401783
  • Recently Listed with Virtual Tour
1 of 33
$425,000
940

Sq.Ft.

157 E NEW ENGLAND AVENUE 302

Winter Park, FL

Courtesy of SANDRONI HOLDINGS REAL ESTATE LLC
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 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 2889 ROUEN AVENUE Winter Park, FL MLS# L4961275
$399,500
3

Beds

2.0

Baths

1,144

Sq.Ft.

2889 ROUEN AVENUE

Winter Park, FL

Courtesy of HELLOSOLD LLC
View 1307 FORMOSA AVENUE Winter Park, FL MLS# O6400711
  • Virtual Tour
1 of 33
$374,500
2

Beds

1.0

Baths

1,150

Sq.Ft.

1307 FORMOSA AVENUE

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 814 DENSMORE DR Winter Park, FL MLS# O6399773
  • Virtual Tour
1 of 24
$425,000
4

Beds

2.0

Baths

1,610

Sq.Ft.

814 DENSMORE DR

Winter Park, FL

Courtesy of ORANGE SLICE PROPERTIES
View 811 OVERSPIN DRIVE Winter Park, FL MLS# O6400009
  • Virtual Tour
1 of 9
$349,000
2

Beds

1.0

Baths

749

Sq.Ft.

811 OVERSPIN DRIVE

Winter Park, FL

Courtesy of RICK SINGH REAL ESTATE
View 3172 CROWN JEWEL COURT Winter Park, FL MLS# O6397498
$339,900
3

Beds

2.1

Baths

1,406

Sq.Ft.

3172 CROWN JEWEL COURT

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 3054 BLUEBROOK DRIVE Winter Park, FL MLS# O6398450
  • Virtual Tour
1 of 27
$410,000
3

Beds

2.0

Baths

1,939

Sq.Ft.

3054 BLUEBROOK DRIVE

Winter Park, FL

Courtesy of WEATHERSPOON REALTY INC
View 2007 EDWIN BOULEVARD Winter Park, FL MLS# O6396498
  • Virtual Tour
1 of 16
$369,900
3

Beds

1.1

Baths

1,296

Sq.Ft.

2007 EDWIN BOULEVARD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2007 EDWIN BOULEVARD Winter Park, FL MLS# O6396307
  • Virtual Tour
1 of 10
$369,900
Studio

Beds

0.0

Baths

2007 EDWIN BOULEVARD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 4923 N MAGNOLIA AVENUE Winter Park, FL MLS# O6396378
$390,000
3

Beds

2.0

Baths

1,559

Sq.Ft.

4923 N MAGNOLIA AVENUE

Winter Park, FL

Courtesy of A+ REALTY PROFESSIONALS, INC
View Address not provided Winter Park, FL MLS# S5145631
  • Virtual Tour
1 of 11
$430,000
4

Beds

2.0

Baths

1,296

Sq.Ft.

Address not provided

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

387

Estimated median home price

$790,000
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 50
$200K - 300K 22
$300K - 400K 22
$400K - 500K 29
$500K - 600K 23
$600K - 700K 27
$700K - 800K 20
$800K - 900K 16
$900K - 1M 8
$1M - Max 167

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 242
Townhouse 16
Condo 88
Commercial 7
Rental 72
Lots and Land 26
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 5/19/2026)

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 5/19/2026.