70 total properties
Did you mean the neighborhood Winter Park?
View 3374 CEDAR SPRINGS PLACE 155 Winter Park, FL MLS# O6424930
  • Recently Listed with Virtual Tour
1 of 25
$1,750
2

Beds

2.1

Baths

1,031

Sq.Ft.

3374 CEDAR SPRINGS PLACE 155

Winter Park, FL

View 151 N ORLANDO AVENUE 203 Winter Park, FL MLS# O6424654
  • Recently Listed with Virtual Tour
1 of 20
$2,200
2

Beds

1.0

Baths

800

Sq.Ft.

151 N ORLANDO AVENUE 203

Winter Park, FL

View 344 STARLING ROAD Winter Park, FL MLS# O6424771
  • Recently Listed
1 of 43
$4,500
3

Beds

3.0

Baths

1,345

Sq.Ft.

344 STARLING ROAD

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 1830 STAUNTON AVENUE Winter Park, FL MLS# O6424087
  • Recently Listed with Virtual Tour
1 of 14
$3,200
2

Beds

2.1

Baths

1,774

Sq.Ft.

1830 STAUNTON AVENUE

Winter Park, FL

Courtesy of COLDWELL BANKER REALTY
View Address not provided Winter Park, FL MLS# O6423856
  • Recently Listed with Virtual Tour
1 of 18
$1,997
1

Beds

1.0

Baths

650

Sq.Ft.

Address not provided

Winter Park, FL

View 3131 LOWNDES DRIVE Winter Park, FL MLS# O6423443
  • Recently Listed with Virtual Tour
1 of 38
$3,995
4

Beds

2.0

Baths

2,126

Sq.Ft.

3131 LOWNDES DRIVE

Winter Park, FL

View 508 DUNBLANE DRIVE Winter Park, FL MLS# O6423719
  • Recently Listed with Virtual Tour
1 of 19
$2,900
3

Beds

2.0

Baths

1,600

Sq.Ft.

508 DUNBLANE DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1000 S SEMORAN BOULEVARD 715 Winter Park, FL MLS# S5153133
  • Recently Listed with Virtual Tour
1 of 11
$1,200
1

Beds

1.0

Baths

735

Sq.Ft.

1000 S SEMORAN BOULEVARD 715

Winter Park, FL

View 660 OSCEOLA AVENUE 101 Winter Park, FL MLS# O6420593
  • Recently Listed with Virtual Tour
1 of 27
$9,500
3

Beds

3.1

Baths

2,714

Sq.Ft.

660 OSCEOLA AVENUE 101

Winter Park, FL

View 2942 ANTIQUE OAKS CIRCLE 86 Winter Park, FL MLS# O6422284
  • Recently Listed with Virtual Tour
1 of 24
$1,400
1

Beds

1.0

Baths

749

Sq.Ft.

2942 ANTIQUE OAKS CIRCLE 86

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View Address not provided Winter Park, FL MLS# O6421826
  • Recently Listed with Virtual Tour
1 of 17
$2,099
3

Beds

2.0

Baths

1,266

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of TAH FLORIDA LLC
View 630 KILLARNEY BAY COURT 3 Winter Park, FL MLS# O6421961
$2,695
2

Beds

2.1

Baths

1,428

Sq.Ft.

630 KILLARNEY BAY COURT 3

Winter Park, FL

View 123 SCOTTSDALE SQUARE 123 Winter Park, FL MLS# O6422391
  • Recently Listed with Virtual Tour
1 of 7
$1,200
1

Beds

1.0

Baths

785

Sq.Ft.

123 SCOTTSDALE SQUARE 123

Winter Park, FL

View 521 OHIO STREET Winter Park, FL MLS# O6421429
  • Recently Listed with Virtual Tour
1 of 25
$2,500
3

Beds

3.0

Baths

1,852

Sq.Ft.

521 OHIO STREET

Winter Park, FL

Courtesy of RE/MAX CENTRAL REALTY
View Address not provided Winter Park, FL MLS# O6421564
  • Recently Listed
1 of 15
$1,550
2

Beds

1.0

Baths

881

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of TRUSTHOME PROPERTIES INC
View 641 S LAKEMONT AVENUE Winter Park, FL MLS# O6420696
$2,250
3

Beds

2.0

Baths

1,450

Sq.Ft.

641 S LAKEMONT AVENUE

Winter Park, FL

Courtesy of Winter Park - WEICHERT, REALTORS® - Hallmark Properties
View 240 ORANGE TERRACE DRIVE Winter Park, FL MLS# O6421116
  • Recently Listed with Virtual Tour
1 of 30
$3,000
4

Beds

2.0

Baths

1,718

Sq.Ft.

240 ORANGE TERRACE DRIVE

Winter Park, FL

Courtesy of A+ REALTY PROFESSIONALS, INC
View 150 KILLARNEY BAY COURT 5-5 Winter Park, FL MLS# O6421106
  • Recently Listed with Virtual Tour
1 of 24
$2,450
2

Beds

2.0

Baths

1,140

Sq.Ft.

150 KILLARNEY BAY COURT 5-5

Winter Park, FL

View 4812 TANGERINE AVENUE 4812 Winter Park, FL MLS# O6420610
$1,700
2

Beds

2.0

Baths

1,058

Sq.Ft.

4812 TANGERINE AVENUE 4812

Winter Park, FL

View 301 S CAPEN AVE Winter Park, FL MLS# O6416050
  • Recently Listed with Virtual Tour
1 of 26
$2,400
3

Beds

2.0

Baths

1,158

Sq.Ft.

301 S CAPEN AVE

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

326

Estimated median home price

$799,500
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 - 200K40
$200K - 300K19
$300K - 400K15
$400K - 500K25
$500K - 600K23
$600K - 700K24
$700K - 800K12
$800K - 900K12
$900K - 1M6
$1M - Max144

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family199
Townhouse17
Condo75
Commercial7
Rental70
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 7/14/2026)

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 7/15/2026.