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 faces 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 its 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 May 25, 2020
305
Listed
110
Avg. DOM
$290.70
Avg. $ / Sq.Ft.
$595,900
Med. List Price
305 Properties
Page 1 of 26
$249,900
Subdivision: Villas Of Casselberry Ph 4
3
Beds
2F11/2
Baths
1,533
Sq.Ft.
1993
Year Built
2
Days on Site
S5034573
MLS
This Beautiful Mastercraft Florida Home has everything you are looking for. This 3 Bedroom, 2/1 Bathrooms Single Family Residence is located near Downtown WINTER PARK, Rollings College and UCF,...
$500,000
Subdivision: Quail Run
3
Beds
2F11/2
Baths
2,624
Sq.Ft.
1990
Year Built
3
Days on Site
O5866264
MLS
Snag this one quick! STUNNING home in a Bear Lake community in the sought after Tuskawilla area. Homes don't come up for sale in here very often! Almost everything has been updated in the last few...
$238,900
Subdivision: Villas Of Casselberry Ph 3
3
Beds
2F11/2
Baths
1,397
Sq.Ft.
1992
Year Built
4
Days on Site
O5865721
MLS
Adorable WATERFRONT gem in WINTER PARK! Rare opportunity to own in this fabulously located Winter Park, waterfront community! This darling 3 bedroom 2 bath boasts gorgeous views of the water and...
$410,000
Subdivision: Winter Woods Unit 03
4
Beds
3
Baths
2,176
Sq.Ft.
1970
Year Built
4
Days on Site
O5861907
MLS
You will want to snap up this split-level pool home located in the popular Winter Woods community in Winter Park! This home is simply stunning and will give you peace of mind with a new roof, new...
$1,695,000
Subdivision: Alexander Place
5
Beds
5
Baths
5,048
Sq.Ft.
1940
Year Built
4
Days on Site
O5865690
MLS
A downtown Winter Park location is home to a fabulous property of one of the most highly desirable streets with every lifestyle amenity Park Avenue offers and just a stroll away, all at your...
$1,445,000
Subdivision: Fountainhead
4
Beds
3
Baths
3,350
Sq.Ft.
1969
Year Built
4
Days on Site
O5866063
MLS
Stunning renovation inside and out on this one story home in downtown Winter Park. This four bed three bath is situated on a large 13,551 sq ft cul de sac lot that is an enjoyable walk to Park Ave....
$1,299,000
Subdivision: Jenkins Add
4
Beds
4F11/2
Baths
3,213
Sq.Ft.
2016
Year Built
4
Days on Site
O5866000
MLS
This Fabulous Home is conveniently located in the heart of Winter Par, on a large corner lot. This house is only a few years old built in 2016. This house has an open floor plan with the Kitchen and...
$435,000
Subdivision: Lake Forest Park
3
Beds
2
Baths
1,807
Sq.Ft.
1956
Year Built
4
Days on Site
O5866151
MLS
Welcome home! This spacious 3-bedroom 2 bath Lake Forest Park pool home has lots to offer, and with a few updates and personalized touches could be your sanctuary! Sitting on a .28-acre lot with...
$699,900
Subdivision: Lake Knowles Terrace
3
Beds
2F11/2
Baths
1,914
Sq.Ft.
1974
Year Built
4
Days on Site
O5866069
MLS
Beautifully renovated 3 bed/2 bath pool home for sale on a charming brick road in the heart of Winter Park s sought-after Tree Streets. Fully updated this year with all new floors and fixtures...
$379,900
Subdivision: Shores Lake Killarney Sec 02
3
Beds
2
Baths
2,482
Sq.Ft.
1957
Year Built
4
Days on Site
O5866082
MLS
FULL HD 3D TOUR AVAILABLE! CLICK TOUR LINK IN LISTING.What a Find! Bring the boat and/or water toys! You will fall in love with this Beautiful Winter Park home with full deeded lake access to Lake...
$249,900
Subdivision: Wrenwood Heights
3
Beds
2
Baths
1,148
Sq.Ft.
1972
Year Built
4
Days on Site
O5864752
MLS
This adorable ranch style home provides you with 3 bedrooms, 2 bathrooms, a garage, and a spacious back yard. Located on a quiet cul-de-sac just minutes from downtown Winter Park or Orlando, you...
$769,900
Subdivision: Fairbanks Park
4
Beds
3F11/2
Baths
2,445
Sq.Ft.
2014
Year Built
5
Days on Site
O5842401
MLS
This stunning custom built home has the curb appeal you've been looking for! From the moment you pull up you'll fall in love with the architectural design, professionally maintained landscaping and...