30 total properties
Did you mean the neighborhood Winter Park?
View 1507 GOLFSIDE DRIVE Winter Park, FL MLS# O6395355
$850,000
3

Beds

2.0

Baths

2,003

Sq.Ft.

1507 GOLFSIDE DRIVE

Winter Park, FL

View 1836 GRINNELL TERRACE Winter Park, FL MLS# O6395188
$999,000
Studio

Beds

0.0

Baths

1836 GRINNELL TERRACE

Winter Park, FL

View 1800 MAGNOLIA AVENUE Winter Park, FL MLS# NS1087637
  • Virtual Tour
1 of 65
OPEN HOUSE: Saturday 8/1 12:00 PM - 2:00 PM
$994,000
4

Beds

2.1

Baths

2,431

Sq.Ft.

1800 MAGNOLIA AVENUE

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
The time to sell is now! THE TIME TO SELL IS NOW!
View Lot #21 KAROLINA AVE Winter Park, FL MLS# O6387812
  • New Construction with Virtual Tour
1 of 9
$918,000
4

Beds

2.1

Baths

2,662

Sq.Ft.

Lot #21 KAROLINA AVE

Winter Park, FL

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

Beds

2.1

Baths

1,884

Sq.Ft.

1405 MILLER AVENUE

Winter Park, FL

View 1927 ELAND AVENUE Winter Park, FL MLS# O6381009
$820,000
5

Beds

3.0

Baths

2,242

Sq.Ft.

1927 ELAND AVENUE

Winter Park, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
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

View 731 MIDGET DRIVE Winter Park, FL MLS# O6368705
$940,000
Studio

Beds

0.0

Baths

731 MIDGET DRIVE

Winter Park, FL

Courtesy of EMPIRE NETWORK REALTY
View 560 OLOLU DRIVE Winter Park, FL MLS# O6344540
  • Virtual Tour
1 of 29
$925,000
2

Beds

2.0

Baths

1,086

Sq.Ft.

560 OLOLU DRIVE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 632 COUNTRY CLUB DRIVE Winter Park, FL MLS# O6250417
$1,050,000
3

Beds

2.0

Baths

2,342

Sq.Ft.

632 COUNTRY CLUB 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

368

Estimated median home price

$750,000
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 - 300K23
$300K - 400K17
$400K - 500K34
$500K - 600K24
$600K - 700K32
$700K - 800K15
$800K - 900K12
$900K - 1M11
$1M - Max153

Homes for Sale by Type in Winter Park, FL

Property TypeCount
Single Family227
Townhouse19
Condo79
Commercial11
Rental68
Lots and Land23
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms0

(Data as of 7/30/2026)

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 7/30/2026.