55 total properties
Did you mean the neighborhood Winter Park?
View 145 SCOTTSDALE SQUARE Winter Park, FL MLS# O6424788
  • Recently Listed with Virtual Tour
1 of 30
$99,900
2

Beds

2.0

Baths

1,020

Sq.Ft.

145 SCOTTSDALE SQUARE

Winter Park, FL

View 7450 WYNNEWOOD SQUARE 189 Winter Park, FL MLS# O6425486
  • Recently Listed with Virtual Tour
1 of 41
$185,000
2

Beds

2.1

Baths

1,031

Sq.Ft.

7450 WYNNEWOOD SQUARE 189

Winter Park, FL

View 263 SCOTTSDALE SQUARE 263 Winter Park, FL MLS# O6424619
$80,000
2

Beds

2.0

Baths

1,020

Sq.Ft.

263 SCOTTSDALE SQUARE 263

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
The time to sell is now! THE TIME TO SELL IS NOW!
View 303 SCOTTSDALE SQUARE 303 Winter Park, FL MLS# O6424296
$80,000
2

Beds

2.0

Baths

1,020

Sq.Ft.

303 SCOTTSDALE SQUARE 303

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 3360 ROYAL STREET Winter Park, FL MLS# O6423106
$179,900
2

Beds

2.0

Baths

981

Sq.Ft.

3360 ROYAL STREET

Winter Park, FL

View 1250 S DENNING DRIVE 109 Winter Park, FL MLS# R4911491
  • Recently Listed with Virtual Tour
1 of 27
$190,000
1

Beds

1.0

Baths

658

Sq.Ft.

1250 S DENNING DRIVE 109

Winter Park, FL

View 1695 LEE ROAD B108 Winter Park, FL MLS# O6422568
  • Recently Listed with Virtual Tour
1 of 15
$89,999
1

Beds

1.0

Baths

638

Sq.Ft.

1695 LEE ROAD B108

Winter Park, FL

View 252 SCOTTSDALE SQ 252 Winter Park, FL MLS# O6421977
$85,000
2

Beds

1.1

Baths

1,085

Sq.Ft.

252 SCOTTSDALE SQ 252

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 1000 S SEMORAN BOULEVARD 306 Winter Park, FL MLS# R4911525
  • Recently Listed with Virtual Tour
1 of 13
$138,000
1

Beds

1.0

Baths

796

Sq.Ft.

1000 S SEMORAN BOULEVARD 306

Winter Park, FL

View 1000 S SEMORAN BOULEVARD 404 Winter Park, FL MLS# R4911526
  • Recently Listed with Virtual Tour
1 of 5
$138,000
1

Beds

1.0

Baths

776

Sq.Ft.

1000 S SEMORAN BOULEVARD 404

Winter Park, FL

View 1000 S SEMORAN BOULEVARD 408 Winter Park, FL MLS# R4911527
  • Recently Listed with Virtual Tour
1 of 11
$138,000
1

Beds

1.0

Baths

776

Sq.Ft.

1000 S SEMORAN BOULEVARD 408

Winter Park, FL

View 1695 LEE ROAD A116 Winter Park, FL MLS# O6420863
  • Recently Listed with Virtual Tour
1 of 18
$135,000
3

Beds

2.0

Baths

1,149

Sq.Ft.

1695 LEE ROAD A116

Winter Park, FL

Courtesy of REAL BROKER, LLC
View 3381 CEDAR SPRINGS PLACE 151 Winter Park, FL MLS# O6419959
  • Recently Listed with Virtual Tour
1 of 32
$179,900
2

Beds

2.1

Baths

1,031

Sq.Ft.

3381 CEDAR SPRINGS PLACE 151

Winter Park, FL

View Address not provided Winter Park, FL MLS# O6419422
$229,900
2

Beds

1.1

Baths

1,219

Sq.Ft.

Address not provided

Winter Park, FL

View 1500 GAY ROAD 3C Winter Park, FL MLS# O6417533
  • Virtual Tour
1 of 26
$248,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 3C

Winter Park, FL

View 4756 TANGERINE AVENUE 4756 Winter Park, FL MLS# R4911483
$195,000
2

Beds

2.0

Baths

1,058

Sq.Ft.

4756 TANGERINE AVENUE 4756

Winter Park, FL

View 151 NORTH ORLANDO AVENUE 142 Winter Park, FL MLS# O6412768
$199,900
1

Beds

1.0

Baths

582

Sq.Ft.

151 NORTH ORLANDO AVENUE 142

Winter Park, FL

View 4798 TANGERINE AVENUE 4798 Winter Park, FL MLS# S5150136
$180,000
2

Beds

2.0

Baths

1,058

Sq.Ft.

4798 TANGERINE AVENUE 4798

Winter Park, FL

View 2500 LEE ROAD 220 Winter Park, FL MLS# O6411927
$199,900
2

Beds

1.0

Baths

851

Sq.Ft.

2500 LEE ROAD 220

Winter Park, FL

View 2923 ANTIQUE OAKS CIRCLE 34 Winter Park, FL MLS# S5150301
$180,000
2

Beds

2.0

Baths

1,105

Sq.Ft.

2923 ANTIQUE OAKS CIRCLE 34

Winter Park, FL

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

315

Estimated median home price

$825,000
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

PriceCount
$0 - 100K6
$100K - 200K39
$200K - 300K17
$300K - 400K14
$400K - 500K23
$500K - 600K23
$600K - 700K23
$700K - 800K11
$800K - 900K13
$900K - 1M7
$1M - Max139

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family194
Townhouse16
Condo71
Commercial7
Rental71
Lots and Land21
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 7/15/2026)

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 7/16/2026.