Winter Park is the hottest suburb in Orlando. For years, this pocket of land adjacent to downtown Orlando has held the highest median prices in Orange County. With more square footage comes higher price tags; however, smaller homes needing some TLC can still be found for under $400,000. Homes regularly sell in the multi-millions.

Why is Winter Park so highly valued? Because the community is easily the most vibrant in Orlando. Nationally ranked arts festivals, world-class museums, and a lively downtown area are just a few great reasons Winter Park should be on your short list of places to live.

History and Location

Winter Park can trace its roots back to the 1880s, thanks to the creation of the South Florida Railroad. The main attraction to the city, the same today, is the many lakes and beautiful downtown. Rollins College, built in 1885 and located right next to downtown Park Ave, was the first college established in Florida!

Map and proximity to theme parks



Things to Do

Downtown Winter Park is located directly off Park Avenue next to Rollins College. The brick-lined street is home to the most vibrant downtown suburb in all of Orlando. Trendy restaurants and shops line the street, and it is a great place to spend an afternoon. On Saturdays, the Farmer’s Market is bustling in the morning.

The Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest juried outdoor art festivals, and is nationally ranked. The Morse Museum, also located on Park Ave, holds the most comprehensive collection of Tiffany art available anywhere in the world. Tiffany is famous for more than just jewelry – Tiffany stained glass is among the most beautiful you’ll find. Harry P. Leu Gardens and Mead gardens are beautiful places to see the amazing foliage only Florida can offer. The Orlando Science Center is also close by. In short, you won’t be lacking things to do in Winter Park.

Homes

Homes in Winter Park are just as beautiful as the city itself. Home owners take pride in their properties, resulting in highly desirable real estate. You can find every style of home here. From 1920s traditional, to 1940s ranch, to 1960s mid-century, to even newly built modern estates — there is something for every taste. No matter the style of the home, one thing remains common: all homes are beautifully restored and maintained.

One of my favorite things about Winter Park is how different every home is. Every house has its own personality. Even though the architecture is grand and stately, you’re not likely to own a home that looks just like your neighbor’s. Here you can find everything from lakefront mansions to quaint 2/1 cottages.

Why Live Here

Living in Winter Park is a lifestyle choice. The price point is higher, however, other neighborhoods strive to have the sense of community and artistic focus of Winter Park. While other suburbs work very hard to create community among residents, Winter Park has achieved it organically. Beautiful restaurants, gardens, lakes, and shops are just as important in Winter Park as the homes themselves.

Homes for sale in Winter Park, FL

If you have questions about moving to Central Florida and would like to speak with a real estate professional, please contact us.

New Listing - 2 weeks online
$110,900
Condo For Sale
Active
1
BED
1
TOTAL BATH
785
SQFT
333 NE Scottsdale Square #333
Winter Park, FL 32792
Winter Park Woods6-70 Subdivision
New Listing - 4 weeks online
$120,000
Land For Sale
Active
0.27
ACRES
SEMINOLE
COUNTY
1148 Valley Creek Run
Winter Park, FL 32792
Lost Creek Subdivision
$124,786
Condo For Sale
Active
1
BED
1
TOTAL BATH
785
SQFT
325 Scottsdale Square #325
Winter Park, FL 32792
Winter Park Woods Condo Subdivision
$124,786
Condo For Sale
Active
1
BED
1
TOTAL BATH
756
SQFT
281 Scottsdale Square #281
Winter Park, FL 32792
Winter Park Woods Condo Subdivision
$124,786
Condo For Sale
Active
1
BED
1
TOTAL BATH
756
SQFT
249 Scottsdale Square #249
Winter Park, FL 32792
Winter Park Woods Condo Subdivision
$124,786
Condo For Sale
Active
1
BED
1
TOTAL BATH
756
SQFT
171 Scottsdale Square #171
Winter Park, FL 32792
Winter Park Woods Condo Subdivision
$124,786
Condo For Sale
Active
1
BED
1
TOTAL BATH
756
SQFT
205 Scottsdale Square #205
Winter Park, FL 32792
Winter Park Woods Condo Subdivision
New Listing - 3 weeks online
$145,000
Condo For Sale
Active
2
BEDS
2
TOTAL BATHS
1,020
SQFT
278 Scottsdale Square #278
Winter Park, FL 32792
Winter Park Woods Condo Subdivision
$150,000
Condo For Sale
Active
1
BED
1
TOTAL BATH
638
SQFT
1695 Lee Road #D107
Winter Park, FL 32789
Waterfall Cove Subdivision
New Listing - a week online
$150,000
Condo For Sale
Active
1
BED
1
TOTAL BATH
678
SQFT
169 Lewfield Circle #169
Winter Park, FL 32792
Stratford A Winter Park Condo Subdivision
New Listing - 5 days online
$155,000
Condo For Sale
Active
2
BEDS
2
TOTAL BATHS
1,085
SQFT
126 Scottsdale Square #126
Winter Park, FL 32792
Winter Park Woods Condo Subdivision
New Listing - 7 days online
$160,000
Condo For Sale
Active
2
BEDS
1
TOTAL BATH
881
SQFT
1695 Lee Road #E203
Winter Park, FL 32789
Waterfall Cove Subdivision
New Listing - 2 weeks online
$164,900
Condo For Sale
Active
1
BED
1
TOTAL BATH
735
SQFT
1000 S Semoran Boulevard #703
Winter Park, FL 32792
Golfside Villas Condo Subdivision
New Listing - 2 weeks online
$180,000
Condo For Sale
Active
1
BED
1
TOTAL BATH
749
SQFT
3032 Antique Oaks Circle #148
Winter Park, FL 32792
Parkview Village Subdivision
New Listing - 2 weeks online
$195,000
Condo For Sale
Active
2
BEDS
1
TOTAL BATH
881
SQFT
1695 Lee Road #D113
Winter Park, FL 32789
Waterfall Cove/Winter Park Subdivision
New Listing - a week online
$195,000
Condo For Sale
Active
2
BEDS
2
TOTAL BATHS
756
SQFT
Address Withheld
Winter Park, FL 32792
Whisperwood 4 Subdivision
New Listing - 3 days online
$209,995
Condo For Sale
Active
2
BEDS
2
TOTAL BATHS
840
SQFT
3651 N Goldenrod Road #E105
Winter Park, FL 32792
Lancelot/Winter Park Subdivision
$210,000
Condo For Sale
Active
2
BEDS
2
TOTAL BATHS
940
SQFT
Address Withheld
Winter Park, FL 32792
Lancelot At Winter Park Subdivision
New Listing - 3 weeks online
$215,000
Condo For Sale
Active
2
BEDS
2
TOTAL BATHS
1,018
SQFT
3043 Antique Oaks Circle #170
Winter Park, FL 32792
Parkview Village Bldg 3043 Subdivision
$244,786
Condo For Sale
Active
2
BEDS
2
TOTAL BATHS
1,085
SQFT
172 Scottsdale Square #172
Winter Park, FL 32792
Winter Park Woods Condo Subdivision

Pete Werner

I'm an Orlando local and owner of The DIS (wdwinfo.com), DVCfan.com, DCLfan.com, and host of the DIS Unplugged podcast.

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