34 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 2940 DE BROCY WAY Winter Park, FL MLS# O6408085
  • Recently Listed with Virtual Tour
1 of 55
$785,000
3

Beds

2.0

Baths

2,679

Sq.Ft.

2940 DE BROCY WAY

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
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
The time to sell is now! THE TIME TO SELL IS NOW!
View 739 ROUGHBEARD ROAD Winter Park, FL MLS# O6404545
  • Recently Listed with Virtual Tour
1 of 42
$800,000
5

Beds

3.0

Baths

2,194

Sq.Ft.

739 ROUGHBEARD ROAD

Winter Park, FL

Courtesy of SERHANT
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 1437 MILLER AVENUE Winter Park, FL MLS# O6403858
$750,000
5

Beds

4.0

Baths

2,150

Sq.Ft.

1437 MILLER AVENUE

Winter Park, FL

Courtesy of ORLANDO REAL ESTATE LLC
View 2324 LEE ROAD Winter Park, FL MLS# O6403791
  • Recently Listed with Virtual Tour
1 of 36
$750,000
2,124

Sq.Ft.

2324 LEE ROAD

Winter Park, FL

Courtesy of CARLISLE REALTY, LLC
View 1780 BRYAN AVENUE Winter Park, FL MLS# O6402643
  • Recently Listed with Virtual Tour
1 of 8
$849,000
Studio

Beds

0.0

Baths

1780 BRYAN AVENUE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 1725 CAROLLEE LANE Winter Park, FL MLS# O6402656
  • Recently Listed with Virtual Tour
1 of 41
$1,005,000
3

Beds

2.0

Baths

2,335

Sq.Ft.

1725 CAROLLEE LANE

Winter Park, FL

Courtesy of FANNIE HILLMAN & ASSOCIATES
View 1900 WINTER PARK ROAD Winter Park, FL MLS# O6402566
  • Recently Listed with Virtual Tour
1 of 22
$849,900
4

Beds

2.0

Baths

1,511

Sq.Ft.

1900 WINTER PARK ROAD

Winter Park, FL

Courtesy of RE/MAX ASSURED
View 1785 WALNUT AVENUE Winter Park, FL MLS# O6399577
$825,000
Studio

Beds

0.0

Baths

1785 WALNUT AVENUE

Winter Park, FL

Courtesy of BHHS FLORIDA REALTY
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
$899,900
Studio

Beds

0.0

Baths

2823 WRIGHT AVENUE

Winter Park, FL

Courtesy of TAL BUSIDAN PA
View 1507 GOLFSIDE DRIVE Winter Park, FL MLS# O6395355
$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 350 CORNWALL RD Winter Park, FL MLS# O6394524
  • Virtual Tour
1 of 36
$775,000
4

Beds

3.0

Baths

2,038

Sq.Ft.

350 CORNWALL RD

Winter Park, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 250 CORTLAND AVENUE Winter Park, FL MLS# O6395137
$950,000
3

Beds

2.0

Baths

2,114

Sq.Ft.

250 CORTLAND AVENUE

Winter Park, FL

Courtesy of CREEGAN GROUP
View 2119 HOWARD DRIVE Winter Park, FL MLS# O6390345
$850,000
4

Beds

2.0

Baths

2,479

Sq.Ft.

2119 HOWARD DRIVE

Winter Park, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 2823 WRIGHT AVENUE Winter Park, FL MLS# O6390670
$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

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

386

Estimated median home price

$792,500
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 - 100K3
$100K - 200K50
$200K - 300K21
$300K - 400K21
$400K - 500K31
$500K - 600K23
$600K - 700K27
$700K - 800K19
$800K - 900K16
$900K - 1M8
$1M - Max167

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family241
Townhouse16
Condo87
Commercial7
Rental71
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 5/18/2026)

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 5/18/2026.