Winter Park Homes for Sale

The city of Winter Park was established in 1881 by northerners looking to escape the cold.  The downtown is unlike any other place in Central Florida, with various shoppes and restaurants on a brick paved street that face a large green space called Central Park.  Park Avenue isn't a commuter road, which creates a pedestrian friendly and safe atmosphere.  Central Park boasts various water fountains, rose garden, walking path, and performance stage.  The Winter Park Art festival is a popular tourist attraction that happens twice a year and is a good excuse for locals to quit work early and enjoy the action in the park.  

Real estate prices in Winter Park can be high, but there are many options to choose from that allow most everyone a chance to own property here. From condos to large waterfront estates, and everything in-between, Winter Park is a lively town that isn't inundated with tourism and is a more locally based community.

A series of lakes are connected through navigable canals and if you are lucky enough to afford a home on the water you will enjoy all it has to offer.  There is a public access called Dinky Dock that anyone can launch their boat from and enjoy it's small beach.  

Although Winter Park has some planned communities, the vast majority of neighborhoods are "Organic" and are a mixed bag of housing from multi-million homes to bungalow's.  With one of the best school systems around, easy commute to most areas, and a sense of community that isn't matched anywhere, Winter Park is certainly a top choice for living the good life.

Included below are homes for sale in Winter Park updated daily from the Orlando MLS. If you would like more information on any of these Winter Park homes for sale, 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 homes for sale come on the market.

Winter Park April 3, 2020
307
Listed
101
Avg. DOM
$284.60
Avg. $ / Sq.Ft.
$537,900
Med. List Price
307 Properties
Page 1 of 26
$1,225,000
Subdivision: Dixie Terrace
3
Beds
3F11/2
Baths
2,680
Sq.Ft.
2019
Year Built
2
Days on Site
O5855100
MLS
New home located just a block from Park Ave! Drive up to this beauty and fall in love. This 3 bedroom, 3.5 bath home boasts open spaces and clean lines inside and out. Highlights include upper and...
$389,000
Subdivision: Brookshire Heights
3
Beds
2
Baths
1,592
Sq.Ft.
1958
Year Built
2
Days on Site
O5854670
MLS
Newly remodeled Kitchen, CHECK! New stainless steel appliances, CHECK! Granite counter tops, CHECK! Sparkling Pool, CHECK! Amazing indoor Laundry/Mudroom, CHECK! New Paint, new Flooring, recessed...
$425,000
Subdivision: Charmont
3
Beds
3
Baths
1,314
Sq.Ft.
1949
Year Built
2
Days on Site
O5855171
MLS
This spacious yet quaint bungalow sits on a large lot in beautiful Winter Park Charmont area. The home is perfect as is but the lot is large and complete plans to build a custom 4290 sq ft home are...
$2,000,000
Subdivision: Stonehurst Estates
5
Beds
4F11/2
Baths
5,605
Sq.Ft.
2014
Year Built
2
Days on Site
O5854976
MLS
Beautifully custom built single story home offers 5 bedrooms, 4 and a half baths, two car attached garage, a two car detached garage/studio, and an amazing outdoor living and entertaining area. The...
$384,900
Subdivision: Winter Park Pines Rep
3
Beds
2
Baths
1,579
Sq.Ft.
1962
Year Built
2
Days on Site
O5855399
MLS
One story charmer located on a quiet street in Winter Park Pines. This 3 bedroom 2 bathroom home features 1,579 square feet of living space with beautiful tile floors throughout. Open living and...
$295,000
Subdivision: Tanglewood Sec 3 Rep
3
Beds
2
Baths
1,464
Sq.Ft.
1957
Year Built
2
Days on Site
O5855286
MLS
Meticulously maintained mid-century home looking for a new owner. An amazing location in the heart of Winter Park! This immaculate 3 bedroom 2 bath home with lush landscaping, beautiful oak trees...
4
Beds
2
Baths
2,052
Sq.Ft.
1987
Year Built
3
Days on Site
O5855139
MLS
Beautiful 4-bedroom 2-bathroom pool home in Quail Run SUBD. As you walk in the door you will be greeted by an amazing open concept floor plan tile and wood floor throughout at the house. Formal...
$799,900
Subdivision: The Ripples Add
7
Beds
5
Baths
3,788
Sq.Ft.
2007
Year Built
3
Days on Site
O5823549
MLS
VACANT AND MOVE IN READY!!! Please show at your convenience. This beautiful 7 bedroom pool home features a traditional layout with formal living and dining rooms, an open kitchen and family room, and...
$260,000
Subdivision: Cedar Ridge Unit 2
3
Beds
2
Baths
1,284
Sq.Ft.
1981
Year Built
3
Days on Site
O5855242
MLS
Welcome home to your adorable and well loved 3 bed 2 bath Winter Park pool home! This open and flowing floor plan offers a split plan complete with a kitchen that overlooks your new pool. With an...
$399,000
Subdivision: Brookshire Heights 2Nd Add
3
Beds
2
Baths
1,593
Sq.Ft.
1961
Year Built
3
Days on Site
O5855223
MLS
Gorgeous 3 bedroom, 2 bath pool home, located on a quiet low traffic street. Home features a split bedroom plan, vaulted ceilings in the family room, built in book shelves and quaint eat-in kitchen....
$368,000
Subdivision: Eastgate Sub
3
Beds
2
Baths
1,572
Sq.Ft.
1956
Year Built
3
Days on Site
O5855190
MLS
You can't beat this location! This recently renovated fenced-in 3 bed/ 2 bath Winter Park home offers the convenience you have been waiting for. Major updates in 2019 include new roof, new windows,...
$434,900
Subdivision: Winter Park Pines
4
Beds
2
Baths
2,171
Sq.Ft.
1969
Year Built
4
Days on Site
O5854744
MLS
Beautiful updated Winter Park home. This four bedroom two bathroom pool home has been almost completely renovated. The kitchen features granite counters, an island, built in oven, cook top and lots...