Winter Garden's historic downtown is one of the best small downtowns in Florida, and it did not happen by accident. A National Register district, a walking trail down the main street, and a restored theater give it a personality that most suburbs cannot fake.
Walk the trail, not the sidewalk
The West Orange Trail runs right down the median of Plant Street through the historic district. Park once and the whole downtown is your walk: shops on both sides, the trail in the middle, shade and people everywhere.
Catch a show
The Garden Theatre is a 1935 Mediterranean Revival landmark that still runs films and live performances. Check the calendar before you go; a movie in that room is a different experience than the multiplex.
Where to eat on Plant Street
- Thai Blossom: a longtime Plant Street favorite with a loyal following
- Urban on Plant: kitchen and bar in the heart of downtown
- Rosallie Le French Cafe: pastries and coffee for a slow morning
- MANGONI Italian Market Pizza: market and pizza near downtown
- Chef's Table at the Edgewater: fine dining on Lake Apopka if it is a special night
Why it matters to buyers
A downtown you can walk is a neighborhood you can sell, and Winter Garden proves it every weekend. For buyers, that walkability is one of the strongest reasons homes here hold their value.
Love the downtown life? Kelly can show you what is within walking distance of the trail, from historic bungalows to newer communities.
Explore Winter GardenTalk Later
Kelly Wheeler, the Real Estate Ninja, is a Clermont FL Realtor with eXp Realty (SL3352000). He works with buyers and sellers across Central Florida, from Clermont to Winter Garden to Davenport.