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 September 29, 2023
167
Listed
69
Avg. DOM
$429.62
Avg. $ / Sq.Ft.
$674,900
Med. List Price
167 Properties
Page 1 of 14
Open 9/30
1320 Bessmor Rd Winter Park,  FL 32789
$1,349,000
Neighborhood: Winter Park Village
5
Beds
3
Baths
2,577
Sq.Ft.
2021
Year Built
1
Day on Site
O6145243
MLS
This custom 5-bedroom, 3-bath home just steps from Winter Park's exclusive Vias neighborhood features interior architectural accents throughout, including hardwood floors, architectural ceilings, and...
Open 9/30
1000 S Kentucky Ave Winter Park,  FL 32789
$900,000
Neighborhood: Fairbanks Park
4
Beds
3
Baths
2,861
Sq.Ft.
1925
Year Built
1
Day on Site
O6145714
MLS
Seize a truly rare opportunity to own a distinguished member of the historic homes registry, in the heart of Winter Park. This splendid residence seamlessly marries the timeless allure of yesteryears...
Open 9/30
7551 Bent Bow Trl Winter Park,  FL 32792
$589,000
Neighborhood: Arrowhead Cove
4
Beds
2
Baths
1,936
Sq.Ft.
1972
Year Built
1
Day on Site
O6145834
MLS
This completely renovated home is located on a large corner lot, in the popular Arrowhead community in Winter Park with the sought-after school district of Lakemont Elementary, Maitland Middle, and...
Open 10/1
1741 Glencoe Rd Winter Park,  FL 32789
$2,749,000
Neighborhood: Forest Hills
4
Beds
4F11/2
Baths
4,692
Sq.Ft.
2007
Year Built
1
Day on Site
O6145633
MLS
A thoughtfully reimagined Winter Park custom home with transitional style & Mediterranean architectural influences awaits. Built by renowned Bates Driscoll Homes & designed by Gary Hancock, no detail...
Open 9/30
2524 Sweetwater Trl Winter Park,  FL 32789
$629,900
Neighborhood: Dommerich Hills Fourth Add
3
Beds
2
Baths
1,728
Sq.Ft.
1965
Year Built
1
Day on Site
O6145306
MLS
Nestled in the beautiful city of Winter Park, this delightful 3 bedroom, 2 bathroom POOL home is Florida living at its finest. Boasting a spacious layout, lush landscaping, and convenient location,...
Open 9/30
381 Perth Ln Winter Park,  FL 32792
$549,995
Neighborhood: Kenilworth Shores Sec 03
3
Beds
2
Baths
1,502
Sq.Ft.
1978
Year Built
1
Day on Site
O6145352
MLS
Come see this beautifully maintained home in the heart of Winter Parks Kenilworth Shores. Situated just a short walk from Ward Park, Cady Way Trail, Advent Health Wellness Center, Brookshire...
$699,000
Neighborhood: Parklando #3
4
Beds
4
Baths
3,130
Sq.Ft.
1926
Year Built
2
Days on Site
O6145304
MLS
Look no further, bring your own builder and build your dream home on this a quiet Cul-De-Sac in Winter Park! Over 1/3 acre homesite on private street and walking distance to the nearby Audubon Park...
$560,000
Neighborhood: Blk C Pt Rep 02
3
Beds
2
Baths
1,668
Sq.Ft.
1953
Year Built
2
Days on Site
S5092216
MLS
One or more photo(s) has been virtually staged. Drawing inspiration from the sophistication of the mid-century modern era, 1319 Orchid Ave is more than just a home; it's a statement piece nestled in...
$475,000
Neighborhood: Enclave At Hawks Crest
3
Beds
2F11/2
Baths
2,308
Sq.Ft.
2019
Year Built
2
Days on Site
O6144417
MLS
One or more photo(s) has been virtually staged. Welcome to the Enclave at Hawks Crest, a newly built GATED luxury townhome community in sought-after Winter Park! Delivering this largest floor plan in...
$3,950,000
Neighborhood: Morse & Pennsylvania Twnhms
4
Beds
4F11/2
Baths
4,390
Sq.Ft.
2021
Year Built
2
Days on Site
O6145505
MLS
This stunning DETACHED ELEVATOR CITY home, meticulously crafted by the renowned Phil Kean Design Group, presents itself as an opulent haven in the heart of Downtown Winter Park, FL. With innovative...
Open 9/30
350 N Phelps Ave Winter Park,  FL 32789
$849,900
Neighborhood: Sylvan Heights
4
Beds
3
Baths
2,267
Sq.Ft.
1953
Year Built
2
Days on Site
O6140002
MLS
Welcome to this gorgeous remodeled home with a huge fenced in backyard in highly sought after Winter Park! This open concept, split-plan home boasts four bedrooms, three full bathrooms, a large...
$259,900
Neighborhood: Winter Park Villas Condo
2
Beds
2
Baths
1,037
Sq.Ft.
1981
Year Built
3
Days on Site
O6143853
MLS
Welcome to this charming 2-bedroom, 2-bathroom condo located in the desirable Winter Park Villas community. This well-maintained unit and recently renovate offers a comfortable and convenient...