59 total properties
Did you mean the neighborhood Winter Park?
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
  • Recently Listed
1 of 2
$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

The time to sell is now! THE TIME TO SELL IS NOW!
View 1500 GAY ROAD 18D Winter Park, FL MLS# O6422691
  • Recently Listed with Virtual Tour
1 of 30
$275,000
2

Beds

2.0

Baths

1,026

Sq.Ft.

1500 GAY ROAD 18D

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
$148,000
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
$148,000
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
$148,000
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 3060 George Mason D Winter Park, FL MLS# A12044474
$107,000
2

Beds

2.0

Baths

1,062

Sq.Ft.

3060 George Mason D

Winter Park, FL

Courtesy of CAPITAL INTL REALTY LLC
View 3037 ANTIQUE OAKS CIRCLE 156 Winter Park, FL MLS# O6420008
  • Recently Listed with Virtual Tour
1 of 21
$154,900
1

Beds

1.0

Baths

749

Sq.Ft.

3037 ANTIQUE OAKS CIRCLE 156

Winter Park, FL

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 7488 WHISPERWOOD DRIVE 28 Winter Park, FL MLS# O6419151
  • Recently Listed with Virtual Tour
1 of 64
$230,000
2

Beds

2.1

Baths

1,578

Sq.Ft.

7488 WHISPERWOOD DRIVE 28

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 2500 LEE ROAD 104 Winter Park, FL MLS# TB8517242
  • Adult Community with Virtual Tour
1 of 24
$254,900
2

Beds

2.0

Baths

956

Sq.Ft.

2500 LEE ROAD 104

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 311 E MORSE BOULEVARD 6-12 Winter Park, FL MLS# O6413554
$275,000
1

Beds

1.0

Baths

570

Sq.Ft.

311 E MORSE BOULEVARD 6-12

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES

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

306

Estimated median home price

$735,000
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 - 100K4
$100K - 200K41
$200K - 300K18
$300K - 400K14
$400K - 500K25
$500K - 600K21
$600K - 700K24
$700K - 800K11
$800K - 900K11
$900K - 1M5
$1M - Max132

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family186
Townhouse14
Condo73
Commercial7
Rental72
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 7/10/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

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 7/11/2026.