Winter Park Community

Winter Park is a suburban city located in Orange County, Florida, north of Orlando. It covers an area of 10 square miles and it has an estimated population of 30,000 habitants.

Winter Park was founded as a resort community by northern business magnates in the late 19th and early 20th centuries. Today, the arts- and culture-filled city of Winter Park includes Rollins College and the Charles Hosmer Morse Museum of Natural Art.

Winter Park also is destination for nature lovers. In Winter Park, you will find more than 70 parks, all home to various events, festivals and celebrations throughout the year, and available to anyone looking for a place to just sit and relax in the shades of the trees and enjoy a beautiful afternoon. Not only are there enough activities to keep you and your family happy, but all the Orlando attractions are just minutes away.

Most places are within walking distance, which is great if you want to take a stroll down the street and see all of the local shops and restaurants. So much shopping and so many different types of historical architecture. You get a small town feeling from the downtown area, and there's an great farmers market every Saturday.

Education

Homes

Included below are homes for sale in Winter Park. If you would like more information on any of these Winter Park real estate listings, just click the "Request More Information" button when viewing the details of that property. We can provide you with disclosures, past sales history, dates and prices of homes recently sold nearby, and more.

And, if you haven't already, be sure to register for a free account so that you can receive email alerts whenever new Winter Park listings come on the market.

Winter Park September 15, 2019
46
Listed
97
Avg. DOM
$235.39
Avg. $ / Sq.Ft.
$336,200
Med. List Price
46 Properties
Page 1 of 4
$284,900
Subdivision: Winter Park Pines
3
Beds
2
Baths
1,550
Sq.Ft.
1962
Year Built
5
Days on Site
O5810114
MLS
Three bedroom and 2 full baths with a large screened patio overlooking fenced backyard - Two car garage with garage door opener - Inside laundry room - Home has newer windows and doors - Block home...
$120,000
Subdivision: Stratford A Winter Park Condo
2
Beds
2
Baths
953
Sq.Ft.
1973
Year Built
4
Days on Site
O5811409
MLS
Must be owner occupied. Excellent location. Walk to grocery stores, pharmacies, shopping, coffee shops, restaurants, banks in the area. Short drive to Park ave, Farmer's Market. Rollins College,...
$69,000
Subdivision: Winter Park Woods Condo
1
Beds
1
Baths
756
Sq.Ft.
1974
Year Built
7
Days on Site
O5810516
MLS
Come take a look at this spacious 1 bedroom / 1 bathroom condo. Large living room area with sliding glass door leads out to your private balcony with extra storage room. Kitchen features all major...
Open 9/15
2808 Prince John Road #1 Winter Park, FL 32792
$340,000
Subdivision: Winter Park Pines Rep
3
Beds
2
Baths
1,564
Sq.Ft.
1963
Year Built
10
Days on Site
O5809137
MLS
Welcome home to the Winter Park Pines, where the mailman delivers to your door and sidewalks line both sides of the street. This home is tucked away on a beautiful, quiet, tree lined street. DO NOT...
$183,000
Subdivision: Gallery At Winter Park Sec 03
2
Beds
2
Baths
1,004
Sq.Ft.
1985
Year Built
10
Days on Site
O5809960
MLS
Fantastic 1st floor condo at The Gallery of Winter Park! Enjoy the beautiful water view from your living room, back porch and master bedroom. This split planned condo has spacious rooms, an ideal...
$4,350,000
Subdivision: Winter Park
10
Beds
12F21/2
Baths
8,325
Sq.Ft.
1905
Year Built
13
Days on Site
O5809404
MLS
A unique offering to say the least. Originally built in 1920, the woodwork highlights the best of lost skills retained in the massive renovation done in 2009. Sitting on over 1/2 acre this home is a...
$160,000
Subdivision: Winter Park Villas Condo
2
Beds
2
Baths
1,120
Sq.Ft.
1981
Year Built
17
Days on Site
O5808956
MLS
Very nice, clean town home located just south of University Blvd and SR 436. This two story , end unit was recently renovated with travertine floors, granite counter tops, stainless steel appliances...
$130,000
Subdivision: Winter Park Villas Condo
2
Beds
2
Baths
1,037
Sq.Ft.
1981
Year Built
17
Days on Site
O5808761
MLS
LOCATION LOCATION LOCATION!!! This updated Condo Cutie in the Winter Park Villas subdivision offers 2 Bedrooms 2 Baths with a Fireplace. Another plus the unit comes with a fenced in private backyard...
$1,099,000
Subdivision: Landmark Winter Park
2
Beds
2
Baths
1,758
Sq.Ft.
2008
Year Built
18
Days on Site
O5808372
MLS
URBAN LUXURY LIVING IN THIS CORNER PENTHOUSE SINGLE STORY SUITE. RECENTLY REMODELED BY TED MAINES INTERIORS WITH LUXURY SELECTIONS THROUGHOUT. 2 BEDROOMS, 2 FULL BATH, CHEFS KITCHEN WITH HIGH END...
$2,750,000
Subdivision: Winter Park
5
Beds
6F11/2
Baths
8,910
Sq.Ft.
2013
Year Built
20
Days on Site
O5808325
MLS
Masterful design and modern luxury are uniquely embodied in this Spectacular Mid-Century Modern Estate. Stylish simplicity, extensive use of glass, and open design forge a connection with nature....
$140,000
Subdivision: Winter Park Woods Condo Cb 6/70 Bldg I Unit 228
3
Beds
2
Baths
1,250
Sq.Ft.
1974
Year Built
20
Days on Site
O5808473
MLS
Completely renovated 3 Bedroom Loft Style condo for sale, new flooring, painting, main door, lights and fixtures, located on 436/Semoran Blvd only 10 min to Orlando Downtown. Perfect opportunity for...
$89,900
Subdivision: Stratford A Winter Park Condo
1
Beds
1
Baths
678
Sq.Ft.
1973
Year Built
23
Days on Site
O5807638
MLS
Adorable and clean end unit, 1 bedroom, 1 bathroom condo within the convenient and highly sought after community of The Stratford. New roof on entire building as well as gutter system. This is not an...