108 total properties
Did you mean the neighborhood Winter Park?
View 157 E NEW ENGLAND AVENUE 302 Winter Park, FL MLS# O6401783
$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
$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
The time to sell is now! THE TIME TO SELL IS NOW!
View 2500 LEE ROAD 232 Winter Park, FL MLS# O6404916
  • 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
  • Virtual Tour
1 of 29
$110,000
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
$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
View 7327 FOREST HILL COURT 223 Winter Park, FL MLS# O6403841
$185,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7327 FOREST HILL COURT 223

Winter Park, FL

Courtesy of M L VAZ REALTY INC
View 3282 OAK LAKE PLACE 3282 Winter Park, FL MLS# O6403912
$159,000
2

Beds

1.1

Baths

990

Sq.Ft.

3282 OAK LAKE PLACE 3282

Winter Park, FL

Courtesy of BUSBY REALTY LLC
View 7484 CANFORD COURT 8 Winter Park, FL MLS# O6402492
  • Virtual Tour
1 of 25
$250,000
3

Beds

2.1

Baths

1,578

Sq.Ft.

7484 CANFORD COURT 8

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 639 SAINT JOHNS COURT 639 Winter Park, FL MLS# O6402025
$199,900
2

Beds

2.0

Baths

1,120

Sq.Ft.

639 SAINT JOHNS COURT 639

Winter Park, FL

Courtesy of PLATINUM REALTY GROUP FLORIDA INC
View 1250 S DENNING DRIVE 117 Winter Park, FL MLS# O6401802
$240,000
2

Beds

1.1

Baths

908

Sq.Ft.

1250 S DENNING DRIVE 117

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 2889 ROUEN AVENUE Winter Park, FL MLS# L4961275
1 of 10
OPEN HOUSE: Saturday 6/6 1:00 PM - 3:00 PM
$375,000
3

Beds

2.0

Baths

1,144

Sq.Ft.

2889 ROUEN AVENUE

Winter Park, FL

Courtesy of HELLOSOLD LLC
View 3651 N GOLDENROD ROAD D102 Winter Park, FL MLS# O6401114
$159,000
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD D102

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View 1307 FORMOSA AVENUE Winter Park, FL MLS# O6400711
  • Virtual Tour
1 of 33
$373,800
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 7454 WYNNEWOOD SQUARE 188 Winter Park, FL MLS# O6386578
  • Adult Community with Virtual Tour
1 of 29
$229,000
3

Beds

2.1

Baths

1,151

Sq.Ft.

7454 WYNNEWOOD SQUARE 188

Winter Park, FL

Courtesy of APPLE 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

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

399

Estimated median home price

$775,000
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 42
$200K - 300K 25
$300K - 400K 25
$400K - 500K 28
$500K - 600K 26
$600K - 700K 32
$700K - 800K 22
$800K - 900K 15
$900K - 1M 9
$1M - Max 172

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 261
Townhouse 16
Condo 85
Commercial 7
Rental 69
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 6/5/2026)

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 6/5/2026.