58 total properties
Did you mean the neighborhood Winter Park?
View 3027 AARON BURR AVENUE L1 Winter Park, FL MLS# O6390662
$159,000
2

Beds

2.1

Baths

1,090

Sq.Ft.

3027 AARON BURR AVENUE L1

Winter Park, FL

Courtesy of STIRLING INTERNATIONAL REAL ES
View 3217 OAK LAWN PLACE 211 Winter Park, FL MLS# O6390713
$175,000
3

Beds

2.0

Baths

1,117

Sq.Ft.

3217 OAK LAWN PLACE 211

Winter Park, FL

Courtesy of SHORES REAL ESTATE
View 200 SAINT ANDREWS BOULEVARD 312 Winter Park, FL MLS# S5145794
$170,000
1

Beds

1.0

Baths

793

Sq.Ft.

200 SAINT ANDREWS BOULEVARD 312

Winter Park, FL

Courtesy of ROMAN'S PRO REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2918 ANTIQUE OAKS CIRCLE 25 Winter Park, FL MLS# O6389113
$189,000
2

Beds

2.0

Baths

1,018

Sq.Ft.

2918 ANTIQUE OAKS CIRCLE 25

Winter Park, FL

Courtesy of PREMIER MANAGEMENT GROUP INC
View 4858 TANGERINE AVENUE 4858 Winter Park, FL MLS# O6388649
$209,900
2

Beds

2.0

Baths

1,058

Sq.Ft.

4858 TANGERINE AVENUE 4858

Winter Park, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 7336 FOREST HILL COURT 240 Winter Park, FL MLS# O6386461
$169,900
2

Beds

1.1

Baths

990

Sq.Ft.

7336 FOREST HILL COURT 240

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 2500 LEE ROAD 122 Winter Park, FL MLS# O6384082
  • Virtual Tour
1 of 25
$179,000
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 122

Winter Park, FL

Courtesy of PINEAPPLE PLACE REALTY, LLC
View 7117 SWALLOW RUN G1 Winter Park, FL MLS# O6385942
$236,800
3

Beds

2.1

Baths

1,565

Sq.Ft.

7117 SWALLOW RUN G1

Winter Park, FL

Courtesy of COMPLETE FLORIDA REALTY LLC
View 4768 TANGERINE AVENUE 4768 Winter Park, FL MLS# S5144503
$179,000
1

Beds

1.0

Baths

753

Sq.Ft.

4768 TANGERINE AVENUE 4768

Winter Park, FL

Courtesy of PROPERTY OUTLET INTERNATIONAL
View 1000 S SEMORAN BOULEVARD 715 Winter Park, FL MLS# S5144243
$122,990
1

Beds

1.0

Baths

735

Sq.Ft.

1000 S SEMORAN BOULEVARD 715

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 2924 ANTIQUE OAKS CIRCLE 46 Winter Park, FL MLS# S5144196
$195,000
2

Beds

2.0

Baths

1,105

Sq.Ft.

2924 ANTIQUE OAKS CIRCLE 46

Winter Park, FL

Courtesy of CENTURY 21 EDGE
View 1695 LEE ROAD E215 Winter Park, FL MLS# O6383089
  • Virtual Tour
1 of 82
$149,990
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD E215

Winter Park, FL

Courtesy of FOWLKES REALTY CO
View 278 SCOTTSDALE SQUARE 278 Winter Park, FL MLS# O6383638
$99,000
2

Beds

2.0

Baths

1,020

Sq.Ft.

278 SCOTTSDALE SQUARE 278

Winter Park, FL

Courtesy of CREEGAN GROUP
View 1500 GAY ROAD 5 Winter Park, FL MLS# S5143213
  • Virtual Tour
1 of 17
$170,000
1

Beds

1.0

Baths

732

Sq.Ft.

1500 GAY ROAD 5

Winter Park, FL

Courtesy of TRANSCEND REALTY
View 2500 LEE ROAD 229 Winter Park, FL MLS# O6377616
  • Virtual Tour
1 of 41
$245,000
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 229

Winter Park, FL

Courtesy of REALCOM REAL ESTATE SERVICES INC
View 1695 LEE ROAD B210 Winter Park, FL MLS# O6375872
  • Virtual Tour
1 of 27
$99,000
1

Beds

1.0

Baths

638

Sq.Ft.

1695 LEE ROAD B210

Winter Park, FL

Courtesy of GM SUNSHINE REALTY LLC
View 7468 CANFORD COURT 24 Winter Park, FL MLS# O6373850
$189,999
2

Beds

1.1

Baths

1,365

Sq.Ft.

7468 CANFORD COURT 24

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 1695 LEE ROAD B204 Winter Park, FL MLS# O6375348
$120,000
2

Beds

1.0

Baths

1695 LEE ROAD B204

Winter Park, FL

Courtesy of MTRE GROUPE LLC
View 2500 LEE ROAD 237 Winter Park, FL MLS# V4946519
$169,000
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE ROAD 237

Winter Park, FL

Courtesy of LPT REALTY LLC (DB)
View 2500 LEE RD. 222 Winter Park, FL MLS# O6368580
$189,500
1

Beds

1.0

Baths

645

Sq.Ft.

2500 LEE RD. 222

Winter Park, FL

Courtesy of HOMESMART

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

402

Estimated median home price

$780,000
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 43
$200K - 300K 24
$300K - 400K 26
$400K - 500K 30
$500K - 600K 25
$600K - 700K 31
$700K - 800K 22
$800K - 900K 15
$900K - 1M 9
$1M - Max 174

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 266
Townhouse 15
Condo 84
Commercial 7
Rental 73
Lots and Land 24
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 6/3/2026)

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 6/4/2026.