29 total properties
Did you mean the neighborhood Winter Park?
View 1407 MILLER AVENUE Winter Park, FL MLS# O6406408
  • Recently Listed with Virtual Tour
1 of 44
$899,000
3

Beds

2.1

Baths

1,884

Sq.Ft.

1407 MILLER AVENUE

Winter Park, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
View 1960 WINTER PARK ROAD Winter Park, FL MLS# O6406091
$899,000
3

Beds

3.0

Baths

1,864

Sq.Ft.

1960 WINTER PARK ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1723 CHESTNUT AVENUE Winter Park, FL MLS# O6402563
  • Virtual Tour
1 of 40
$1,125,000
3

Beds

2.1

Baths

2,608

Sq.Ft.

1723 CHESTNUT AVENUE

Winter Park, FL

Courtesy of ANNE ROGERS REALTY GROUP INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2232 BANCHORY ROAD Winter Park, FL MLS# O6404702
  • Recently Listed with Virtual Tour
1 of 44
$1,160,000
4

Beds

3.0

Baths

2,597

Sq.Ft.

2232 BANCHORY ROAD

Winter Park, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 627 DUNBLANE DRIVE Winter Park, FL MLS# O6405036
  • Recently Listed with Virtual Tour
1 of 36
$899,000
4

Beds

3.0

Baths

2,086

Sq.Ft.

627 DUNBLANE DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1611 CHESTNUT AVENUE Winter Park, FL MLS# O6402502
  • Virtual Tour
1 of 45
$1,100,000
4

Beds

4.0

Baths

2,916

Sq.Ft.

1611 CHESTNUT AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1725 CAROLLEE LANE Winter Park, FL MLS# O6402656
  • Virtual Tour
1 of 41
OPEN HOUSE: Saturday 5/23 1:00 PM - 3:00 PM
$1,005,000
3

Beds

2.0

Baths

2,335

Sq.Ft.

1725 CAROLLEE LANE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1981 BLUE RIDGE ROAD Winter Park, FL MLS# O6402961
  • Recently Listed with Virtual Tour
1 of 52
$1,150,000
4

Beds

2.0

Baths

2,750

Sq.Ft.

1981 BLUE RIDGE ROAD

Winter Park, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 1960 WINTER PARK ROAD Winter Park, FL MLS# O6398264
$899,000
Studio

Beds

0.0

Baths

1960 WINTER PARK ROAD

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 2823 WRIGHT AVENUE Winter Park, FL MLS# O6398302
  • Virtual Tour
1 of 18
$899,900
Studio

Beds

0.0

Baths

2823 WRIGHT AVENUE

Winter Park, FL

Courtesy of TAL BUSIDAN PA
View 2702 PARKLAND DRIVE Winter Park, FL MLS# O6397997
  • Virtual Tour
1 of 48
$1,139,750
5

Beds

3.0

Baths

2,656

Sq.Ft.

2702 PARKLAND DRIVE

Winter Park, FL

Courtesy of NORDQUIST & COMPANY INC
View 1507 GOLFSIDE DRIVE Winter Park, FL MLS# O6395355
  • Virtual Tour
1 of 44
$899,000
3

Beds

2.0

Baths

2,003

Sq.Ft.

1507 GOLFSIDE DRIVE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1836 GRINNELL TERRACE Winter Park, FL MLS# O6395188
$999,000
Studio

Beds

0.0

Baths

1836 GRINNELL TERRACE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 250 CORTLAND AVENUE Winter Park, FL MLS# O6395137
  • Virtual Tour
1 of 46
$950,000
3

Beds

2.0

Baths

2,114

Sq.Ft.

250 CORTLAND AVENUE

Winter Park, FL

Courtesy of CREEGAN GROUP
View 1800 MAGNOLIA AVENUE Winter Park, FL MLS# NS1087637
$1,000,000
4

Beds

2.1

Baths

2,431

Sq.Ft.

1800 MAGNOLIA AVENUE

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 2823 WRIGHT AVENUE Winter Park, FL MLS# O6390670
  • Virtual Tour
1 of 19
$899,900
3

Beds

2.0

Baths

1,536

Sq.Ft.

2823 WRIGHT AVENUE

Winter Park, FL

Courtesy of TAL BUSIDAN PA
View Lot #21 KAROLINA AVE Winter Park, FL MLS# O6387812
  • New Construction with Virtual Tour
1 of 9
$944,890
4

Beds

3.1

Baths

2,662

Sq.Ft.

Lot #21 KAROLINA AVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1768 MONDRIAN CIRCLE Winter Park, FL MLS# O6375723
  • Virtual Tour
1 of 26
$1,099,000
3

Beds

3.1

Baths

2,193

Sq.Ft.

1768 MONDRIAN CIRCLE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 1405 MILLER AVENUE Winter Park, FL MLS# O6386405
  • Virtual Tour
1 of 46
$899,000
3

Beds

2.1

Baths

1,884

Sq.Ft.

1405 MILLER AVENUE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1836 GRINNELL TERRACE Winter Park, FL MLS# O6380457
$999,000
3

Beds

2.0

Baths

1,907

Sq.Ft.

1836 GRINNELL TERRACE

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

387

Estimated median home price

$785,000
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 3
$100K - 200K 50
$200K - 300K 22
$300K - 400K 22
$400K - 500K 29
$500K - 600K 23
$600K - 700K 28
$700K - 800K 20
$800K - 900K 16
$900K - 1M 8
$1M - Max 166

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 242
Townhouse 16
Condo 88
Commercial 7
Rental 72
Lots and Land 26
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 5/20/2026)

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 5/21/2026.