74 total properties
Did you mean the neighborhood Winter Park?
View 150 KILLARNEY BAY COURT 5-5 Winter Park, FL MLS# O6421106
$2,450
2

Beds

2.0

Baths

1,140

Sq.Ft.

150 KILLARNEY BAY COURT 5-5

Winter Park, FL

View 700 MELROSE AVENUE A5 Winter Park, FL MLS# O6428424
  • Recently Listed with Virtual Tour
1 of 21
$2,350
2

Beds

2.0

Baths

1,074

Sq.Ft.

700 MELROSE AVENUE A5

Winter Park, FL

View 301 S CAPEN AVE Winter Park, FL MLS# O6416050
  • Virtual Tour
1 of 26
$2,300
3

Beds

2.0

Baths

1,158

Sq.Ft.

301 S CAPEN AVE

Winter Park, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 151 N ORLANDO AVENUE 207 Winter Park, FL MLS# O6425110
  • Recently Listed with Virtual Tour
1 of 26
$2,300
2

Beds

1.0

Baths

710

Sq.Ft.

151 N ORLANDO AVENUE 207

Winter Park, FL

View 2730 PRINCE JOHN ROAD Winter Park, FL MLS# O6413831
$2,295
4

Beds

2.0

Baths

1,669

Sq.Ft.

2730 PRINCE JOHN ROAD

Winter Park, FL

View 151 N ORLANDO AVENUE 118 Winter Park, FL MLS# O6386414
$2,200
2

Beds

1.0

Baths

1,500

Sq.Ft.

151 N ORLANDO AVENUE 118

Winter Park, FL

View 7522 LAUREL SPRINGS DRIVE Winter Park, FL MLS# O6419181
$2,200
3

Beds

2.0

Baths

1,106

Sq.Ft.

7522 LAUREL SPRINGS DRIVE

Winter Park, FL

View 640 N PARK AVENUE 4 Winter Park, FL MLS# O6425848
$2,200
1

Beds

1.0

Baths

673

Sq.Ft.

640 N PARK AVENUE 4

Winter Park, FL

View Address not provided Winter Park, FL MLS# O6421826
$2,129
3

Beds

2.0

Baths

1,266

Sq.Ft.

Address not provided

Winter Park, FL

Courtesy of TAH FLORIDA LLC
View 151 N ORLANDO AVENUE 203 Winter Park, FL MLS# O6424654
  • Recently Listed with Virtual Tour
1 of 20
$2,100
2

Beds

1.0

Baths

800

Sq.Ft.

151 N ORLANDO AVENUE 203

Winter Park, FL

View 1261 RICHMOND ROAD Winter Park, FL MLS# O6419129
  • Recently Listed with Virtual Tour
1 of 16
$2,099
2

Beds

1.0

Baths

954

Sq.Ft.

1261 RICHMOND ROAD

Winter Park, FL

View 503 KILSHORE LANE Winter Park, FL MLS# O6412456
$2,050
2

Beds

1.0

Baths

1,125

Sq.Ft.

503 KILSHORE LANE

Winter Park, FL

View Address not provided Winter Park, FL MLS# O6423856
$1,997
1

Beds

1.0

Baths

650

Sq.Ft.

Address not provided

Winter Park, FL

View 3220 OAK LAWN PLACE PLACE 210 Winter Park, FL MLS# S5150258
$1,900
3

Beds

2.1

Baths

1,151

Sq.Ft.

3220 OAK LAWN PLACE PLACE 210

Winter Park, FL

View 7426 WYNNEWOOD SQUARE 195 Winter Park, FL MLS# O6410726
$1,800
3

Beds

2.0

Baths

1,117

Sq.Ft.

7426 WYNNEWOOD SQUARE 195

Winter Park, FL

Courtesy of SPRINGHILL PROPERTIES LLC
View 652 SAINT JHONS 652 Winter Park, FL MLS# TB8514256
$1,800
2

Beds

2.0

Baths

1,037

Sq.Ft.

652 SAINT JHONS 652

Winter Park, FL

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 612 TRINIDAD COURT 612 Winter Park, FL MLS# O6429437
$1,750
2

Beds

2.0

Baths

1,037

Sq.Ft.

612 TRINIDAD COURT 612

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 3045 AARON BURR AVENUE 12D Winter Park, FL MLS# S5150999
$1,650
2

Beds

2.0

Baths

1,062

Sq.Ft.

3045 AARON BURR AVENUE 12D

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

355

Estimated median home price

$725,000
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 - 100K7
$100K - 200K40
$200K - 300K22
$300K - 400K15
$400K - 500K33
$500K - 600K25
$600K - 700K32
$700K - 800K15
$800K - 900K12
$900K - 1M10
$1M - Max144

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family215
Townhouse21
Condo79
Commercial10
Rental72
Lots and Land22
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 8/3/2026)

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 8/3/2026.