229 total properties
Did you mean the neighborhood Winter Park?
View 2010 SUMMERFIELD ROAD Winter Park, FL MLS# O6420140
  • Recently Listed with Virtual Tour
1 of 40
$594,500
3

Beds

2.0

Baths

1,889

Sq.Ft.

2010 SUMMERFIELD ROAD

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
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 313L SYLVAN DRIVE Winter Park, FL MLS# O6424300
  • Recently Listed
1 of 4
$1,750,000
Studio

Beds

0.0

Baths

313L SYLVAN DRIVE

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 4965 ORANGE AVENUE Winter Park, FL MLS# O6423739
  • Recently Listed with Virtual Tour
1 of 29
$379,900
4

Beds

2.0

Baths

1,444

Sq.Ft.

4965 ORANGE AVENUE

Winter Park, FL

View 708 BALMORAL ROAD Winter Park, FL MLS# O6423883
$1,690,000
4

Beds

3.0

Baths

2,786

Sq.Ft.

708 BALMORAL ROAD

Winter Park, FL

View 2803 RIDDLE DRIVE Winter Park, FL MLS# O6423829
  • Recently Listed
1 of 35
$589,000
3

Beds

2.1

Baths

1,637

Sq.Ft.

2803 RIDDLE DRIVE

Winter Park, FL

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 1415 GROVE TERRACE Winter Park, FL MLS# O6423553
  • Recently Listed with Virtual Tour
1 of 20
$2,200,000
Studio

Beds

0.0

Baths

1415 GROVE TERRACE

Winter Park, FL

View 439 N CAPEN AVENUE Winter Park, FL MLS# O6422949
  • Recently Listed with Virtual Tour
1 of 29
$849,000
3

Beds

2.1

Baths

1,861

Sq.Ft.

439 N CAPEN AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 2824 WOODSIDE AVENUE Winter Park, FL MLS# O6423146
$600,000
2

Beds

2.0

Baths

912

Sq.Ft.

2824 WOODSIDE AVENUE

Winter Park, FL

Courtesy of PARKSIDE PROPERTIES, LLC
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 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 730 W SWOOPE AVENUE Winter Park, FL MLS# S5152493
  • Recently Listed with Virtual Tour
1 of 35
$770,000
5

Beds

3.0

Baths

2,132

Sq.Ft.

730 W SWOOPE AVENUE

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 7500 WAUNATTA COURT Winter Park, FL MLS# TB8525179
  • Virtual Tour
1 of 34
$299,900
3

Beds

2.0

Baths

1,998

Sq.Ft.

7500 WAUNATTA COURT

Winter Park, FL

View 777 HALIFAX AVENUE Winter Park, FL MLS# O6422901
$1,500,000
5

Beds

4.1

Baths

3,109

Sq.Ft.

777 HALIFAX AVENUE

Winter Park, FL

View 7509 GLENMOOR LANE Winter Park, FL MLS# O6421887
  • Virtual Tour
1 of 45
$499,500
3

Beds

2.0

Baths

2,067

Sq.Ft.

7509 GLENMOOR LANE

Winter Park, FL

View 252 SCOTTSDALE SQ 252 Winter Park, FL MLS# O6421977
  • Recently Listed
1 of 3
$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 1622 ARBOR PARK DRIVE Winter Park, FL MLS# O6420937
  • Recently Listed with Virtual Tour
1 of 10
$695,000
Studio

Beds

0.0

Baths

1622 ARBOR PARK DRIVE

Winter Park, FL

View 1622 ARBOR PARK DRIVE Winter Park, FL MLS# O6420928
  • Recently Listed with Virtual Tour
1 of 10
$695,000
3

Beds

1.1

Baths

1,351

Sq.Ft.

1622 ARBOR PARK DRIVE

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

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

Price Count
$0 - 100K 4
$100K - 200K 41
$200K - 300K 18
$300K - 400K 14
$400K - 500K 25
$500K - 600K 21
$600K - 700K 24
$700K - 800K 11
$800K - 900K 11
$900K - 1M 5
$1M - Max 132

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 186
Townhouse 14
Condo 73
Commercial 7
Rental 72
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 7/10/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Multiple Listing Service of the St. Augustine Board of REALTORS®. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors includes the name of the listing brokers.

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

Data is updated as of 7/11/2026.

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.