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Winter Park Homes

Winter Park is a beautiful upscale community located northeast of Orlando, and is the oldest master-planned community in Florida. Founded by wealthy New England industrialists in the late 1800s as a resort destination, continues to draw visitors from around the world with its mild, temperate winters, museums, golf course, chain of lakes, scenic bout tours, bike trails, art festivals, and beautiful, brick-lined Park Avenue . Winter Park is home to the Charles Hosmer Morse Museum of American Art, which hosts the largest collection of Tiffany glass in the world, and draws tens of thousands of visitors every year to the Bach Festival, Sidewalk Art Festival, and Winter Park Concours d'Elegance.The Winter Park chain of lakes covers 2,781 acres and includes Lake Virgina,Lake Osceola,Lake Maitland,Lake Mizell, and Lake Minnehaha.

Its main street includes civic buildings, retail, art galleries, a private liberal arts college, museums, a park, a train station, a golf course country club, a historic cemetery, and a beach and boat launch. Many structures are more than 100 years old. The scenic Olde Winter Park area is punctuated by small, winding brick streets, and a canopy of old Southern Live Oak and Camphor trees, draped with Spanish Moss.

With its outdoor cafes, upscale boutiques, exotic restaurants, high end clothing stores, shoe shops, museums, delis, and gift shops, it is always bustling with shoppers and diners.

Every Saturday a popular Farmers Market is held at 200 West New England Avenue in Winter Park. It features indoor and outdoor vendors and is held at a renovated 1920’s freight train depot.

Winter Park has an Amtrak train depot located on Morse Avenue, next to a beautiful park right off of Park Avenue. It is used by the Silver Star and Silver Meteor passenger trains.

Homes for Sale in Winter Park

430 Results
7
Beds
10 | 1
Baths
10,060
SqFt
(50)
 
 
#O5737785 | Single Family Home
 
5
Beds
6 | 1
Baths
5,006
SqFt
(50)
 
 
#O5724510 | Single Family Home
 
4
Beds
4 | 1
Baths
9,838
SqFt
(17)
 
 
#O5734401 | Single Family Home
 
5
Beds
5 | 1
Baths
4,681
SqFt
(24)
 
 
#O5729258 | Single Family Home
 
6
Beds
7 | 1
Baths
7,677
SqFt
(38)
 
 
#O5728849 | Single Family Home
 
4
Beds
4 | 3
Baths
4,686
SqFt
(18)
 
 
#O5731923 | Single Family Home
 
5
Beds
5 | 2
Baths
6,589
SqFt
(33)
 
 
#O5714430 | Single Family Home
 
6
Beds
6 | 2
Baths
7,666
SqFt
(25)
 
 
#O5706509 | Single Family Home
 
3
Beds
3 | 2
Baths
4,237
SqFt
(26)
 
 
#O5734148 | Condo
 
5
Beds
4 | 1
Baths
4,810
SqFt
(25)
 
 
#O5509686 | Single Family Home
 
4
Beds
3 | 1
Baths
4,057
SqFt
(27)
 
 
#O5532667 | Single Family Home
 
3
Beds
3 | 2
Baths
4,160
SqFt
(8)
 
 
#O5537925 | Condo
 
5
Beds
6 | 1
Baths
8,910
SqFt
(24)
 
 
#O5536500 | Single Family Home
 
5
Beds
6 | 3
Baths
7,631
SqFt
(24)
 
 
#O5552108 | Single Family Home
 
5
Beds
6
Baths
4,517
SqFt
(25)
 
 
#O5731163 | Single Family Home
 
3
Beds
3 | 1
Baths
3,253
SqFt
(16)
 
 
#O5734114 | Condo
 
5
Beds
5 | 2
Baths
5,307
SqFt
(3)
 
 
#O5717304 | Single Family Home
 
5
Beds
3 | 1
Baths
5,409
SqFt
(28)
 
 
#O5559096 | Single Family Home
 
5
Beds
5 | 2
Baths
6,345
SqFt
(50)
 
 
#O5732670 | Single Family Home
 
4
Beds
3 | 2
Baths
4,875
SqFt
(25)
 
 
#O5731623 | Single Family Home
 
6
Beds
5 | 1
Baths
6,378
SqFt
(40)
 
 
#O5570431 | Single Family Home
 
4
Beds
5 | 1
Baths
6,242
SqFt
(41)
 
 
#O5716286 | Single Family Home
 
3
Beds
2 | 2
Baths
3,808
SqFt
(6)
 
 
#T3111029 | Single Family Home
 
2
Beds
3 | 2
Baths
3,244
SqFt
(8)
 
 
#O5522049 | Condo
 
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The data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of My Florida Regional Multiple Listing Service, Inc. 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 consumers' 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.
MFRMLS - My Florida data last updated at October 14, 2018 8:18 PM ET