Winter Park

Winter Park, Florida, is a blast! Located just north of Orlando, this city has everything you could want in a good time. You've got the hip and happening downtown area along Park Avenue, where you can find some wicked cool shops, galleries, and restaurants. And at night, the street comes alive with live music and entertainment - it's the perfect place to let your hair down and dance the night away!

But that's not all - Winter Park's parks and lakes are also a total hoot. Lake Virginia and Lake Osceola are the bomb for boating and paddleboarding. And you can't forget about Central Park - this lush green space in the heart of the city is totally chill. And if you're into artsy stuff, Winter Park has got you covered, too. Check out the Charles Hosmer Morse Museum of American Art, which has the biggest collection of Tiffany glass in the world!

There's always something going down in Winter Park, too. Don't miss the Winter Park Sidewalk Art Festival in March - it's one of the biggest and coolest outdoor art festivals in the whole country. Or hit up the Winter Park Farmer's Market for some farm-fresh goodies and live music. And that's just the tip of the iceberg - Winter Park has got loads of other events happening all year round!

In short, Winter Park is a total blast, and it's one of the best places to check out in Central Florida. Whether you're into shopping, eating, playing outside, or immersing yourself in culture, this city has got everything you need for a wicked good time. So what are you waiting for? Get your butt to Winter Park and let the good times roll!

And, for your convenience, feel free to register for a free account to receive email alerts whenever new Winter Park listings come on the market that match your specific criteria.

Winter Park March 24, 2023
157
Listed
74
Avg. DOM
$430.04
Avg. $ / Sq.Ft.
$750,000
Med. List Price
157 Properties
Page 1 of 14
$530,000
Neighborhood: Garden Lake Estates
3
Beds
2
Baths
1,644
Sq.Ft.
1983
Year Built
2
Days on Site
O6097228
MLS
Located in the picturesque Winter Park area of Florida, this stunning home boasts an UNPARALLED LAKEVIEW and is surrounded by lush tropical forest landscaping, providing a sense of privacy and...
Open 3/25
656 Randy Ln Winter Park,  FL 32789
$795,000
Neighborhood: Timberlane
3
Beds
2
Baths
2,060
Sq.Ft.
1958
Year Built
2
Days on Site
O6098541
MLS
PROFESSIONAL PHOTOS TO COME. Located on a quiet, tree lined street in Timberlane, a neighborhood in Winter Park that is known for its beautiful homes and excellent proximity to great schools,...
$4,200,000
Neighborhood: Sicilian Shores Rep 02
5
Beds
5F11/2
Baths
5,259
Sq.Ft.
2018
Year Built
2
Days on Site
O6094377
MLS
Nestled near the heart of Winter Park, this modern masterpiece exudes elegance and superb attention to detail throughout. This home was a Parade of Homes collaboration between IBK Construction & Z...
$525,000
Neighborhood: Slovak Village
1,920
Sq.Ft.
1982
Year Built
2
Days on Site
A4564973
MLS
Income producing duplex. Each side had 2 bedrooms and 1 and 1/2 baths. Both sides have been renovated. New flooring, kitchens with granite. New roof in 2022. Septic tanks serviced July 2022. Carport....
Open 3/26
1416 Aster Ct Winter Park,  FL 32792
$539,990
Neighborhood: Garden Lake Estates Unit 3
5
Beds
3
Baths
1,898
Sq.Ft.
1984
Year Built
2
Days on Site
T3425212
MLS
Back to Active. Buyer wasn't able to secure financing. Completely remodeled 5 bedrooms and 3 bathroom pool home on an oversized lot. As you walk in the front door you will see the beautiful...
$165,000
Neighborhood: Stratford A Winter Park Condo
1
Beds
1
Baths
678
Sq.Ft.
1973
Year Built
2
Days on Site
O6098687
MLS
Located in the Stratford, a well-maintained community in Winter Park between Maitland and Casselberry. The two story brick buildings give it a clean and bright look. The unit is located on the second...
$1,220,000
Neighborhood: Sylvan Lake Shores
3
Beds
2F11/2
Baths
2,801
Sq.Ft.
1887
Year Built
2
Days on Site
O6098884
MLS
Pre-inspected. Offered for the first time in over 30 years! Winter Park's only original, charming and completely remodeled historical farmhouse. Known as the Harris-Edison House , original...
$1,300,000
Neighborhood: Kenilworth Shores Section Seven
5
Beds
4F11/2
Baths
3,269
Sq.Ft.
2021
Year Built
2
Days on Site
O6098383
MLS
BETTER THAN NEW AND READY FOR YOU! BUILT IN 2021!! Designed and built by Winter Park architect and building contractor, Stevens, Inc., this CUSTOM CRAFTSMAN style home brings so much character from...
Open 3/25
202 Longbranch Ct Winter Park,  FL 32792
$850,000
Neighborhood: Lake Ann Estates Unit 3
4
Beds
3F11/2
Baths
2,855
Sq.Ft.
1988
Year Built
2
Days on Site
O6098357
MLS
This one of a kind Winter Park 4 bed/3.5 Pool contemporary two-story ranch estate is sure to impress! Sitting on nearly an acre in a secluded cul de sac makes this property a private oasis with...
$949,900
Neighborhood: Dubsdread Heights
4
Beds
2F11/2
Baths
2,546
Sq.Ft.
2019
Year Built
3
Days on Site
O6098645
MLS
Dreams do come true! 2019 Newer Build Winter Park and College Park Adjacent Paradiso! No HOA! Short term Airbnb and VRBO welcome! Modern Farmhouse style with almost 2600 sqft of spacious floorplan...
Open 3/25
1761 Greenwich Ave Winter Park,  FL 32789
$1,250,000
Neighborhood: Eastline
6
Beds
3F21/2
Baths
3,770
Sq.Ft.
1981
Year Built
3
Days on Site
O6098050
MLS
Like New! Remarkable 6 bed / 5 bath home in prime Winter Park 32789 location. Wonderful for entertaining and large families! Most attention to detail! Huge 92'x167' lot w/mature landscaping. Spacious...
$210,000
Neighborhood: Lancelot At Winter Park
2
Beds
2
Baths
840
Sq.Ft.
1990
Year Built
3
Days on Site
O6098761
MLS
Live in desirable Winter Park in this cute renovated 2/2 condo. This unit is ideal whether you are an investor or an owner-occupant. This is an opportunity to live in a charming neighborhood ZONED...