At a glance
| Location | Historic core of the City of Winter Garden, Orange County |
|---|---|
| Historic district | About 100 acres, 26 historic structures, NRHP listed 1996 |
| District boundaries | Woodland, Tremaine, Henderson and Lakeview streets |
| Trail | West Orange Trail runs along the Plant Street median |
| City millage | 4.8565 mills (2026-27) |
| ZIP | 34787 |
What downtown is like
The Winter Garden Downtown Historic District is bounded by Woodland, Tremaine, Henderson and Lakeview streets. Its buildings include the Garden Theatre, the Winter Garden Heritage Museum and the Dillard & Boyd Building, one of the oldest confirmed buildings, dating to 1912. The district has restaurants, shops, cafes, two museums and a performing arts venue.
The West Orange Trail, a 22-mile paved rail trail run by Orange County Parks and Recreation, runs through downtown along the Plant Street median, with a Winter Garden station. That makes downtown one of the few places in west Orange County where you can walk or cycle to dinner.
Homes near downtown
Most homes within walking distance are older single-family houses on established streets, with some newer infill. Expect a wide range of age and condition on the same block. Zillow's typical value for the nearby Tildenville neighborhood was $306,224 in August 2026, which shows how much older areas can differ from the city figure.
Zillow's typical home value for Winter Garden was $566,535 in August 2026, down 1.0% on the year, and $570,875 for ZIP 34787. Zillow does not publish a separate figure for this neighborhood in our data, so use closed sales inside the community over the last six months as your guide. Across the Orlando metro, homes took a typical 70 days to go pending and 28.0% of listings had a price cut, which gives buyers some room to negotiate.
Taxes and fees
Homes inside city limits pay the City of Winter Garden millage, which was raised from 4.5 to 4.8565 mills for 2025-26 and kept at 4.8565 for 2026-27. Older downtown streets generally predate CDDs, but confirm on the tax bill. Some newer infill may have an HOA. See our Orange County property tax page.
Downtown versus newer neighborhoods
Living near downtown trades newer construction and community amenities for walkability and an established street grid. Newer areas such as Horizon West usually offer larger, newer homes with pools and clubhouses but add HOA dues and often a CDD, and most are a drive from Plant Street. At a 7.03% rate with 20% down, principal and interest on Winter Garden's typical value is about $3,024 a month, so run the same numbers for any home you compare.
Checks for an older home
- Roof age, and whether the insurer will write a policy on it.
- Electrical panel, wiring type and plumbing materials.
- Permits for past additions or renovations. New finishes are not evidence about concealed systems.
- Whether the property is inside the historic district and what that means for exterior changes. Ask the city's planning department.
- Parking and event noise if you are close to Plant Street.
Use our home inspection checklist and compare with newer options in Horizon West.
Common questions
Is Downtown Winter Garden a historic district?+
Yes. The Winter Garden Downtown Historic District was added to the National Register of Historic Places on 1 August 1996. It covers about 100 acres bounded by Woodland, Tremaine, Henderson and Lakeview streets and contains 26 historic structures, including the Garden Theatre and the Winter Garden Heritage Museum.
Do homes near Downtown Winter Garden have CDD fees?+
Older homes on established city streets generally predate CDDs, but you should still check the property tax bill for any non-ad valorem assessments. Homes inside city limits pay the City of Winter Garden millage, which is 4.8565 mills for 2026-27, on top of county and school rates.
Can you walk to the West Orange Trail from downtown?+
Yes. The West Orange Trail runs through downtown Winter Garden along the Plant Street median and has a Winter Garden station. The trail is 22 miles long from Killarney to Apopka and is owned and run by Orange County Parks and Recreation.