At a glance
| Location | West Orange County, Winter Garden and Oakland area |
|---|---|
| Builder reported | David Weekley Homes (April 2026 roundup) |
| Reported base price | From $811,990 (April 2026) |
| Nearby town | Town of Oakland, 3,516 residents (2020 census) |
| Trail | West Orange Trail passes through downtown Oakland |
What we could verify
An April 2026 roundup of Winter Garden new construction listed David Weekley Homes at Oakland Park with a base price of $811,990. By September 2026, David Weekley's Orlando-area listings no longer included Oakland Park. We could not confirm HOA dues or CDD status from official sources, so those are items to check.
Winter Garden, Oakland or county
The Town of Oakland is a separate municipality, incorporated in 1887, with 3,516 residents at the 2020 census. It uses ZIP codes 34760 and 34787, the same 34787 as Winter Garden. A home in this area could be inside Winter Garden, inside Oakland or in unincorporated Orange County, and each has a different millage. Check the parcel on the Orange County Property Appraiser site. Winter Garden's rate is 4.8565 mills for 2026-27.
Location and amenities
The West Orange Trail, a 22-mile paved rail trail, passes through downtown Oakland and the Oakland Nature Preserve on its way to Winter Garden. Downtown Winter Garden's historic district is a short trip east. See our Downtown Winter Garden guide.
Public records summarized for the Town of Oakland list Tildenville Elementary, Lakeview Middle and West Orange High as zoned Orange County schools. Confirm zoning for the exact Oakland Park address with the OCPS locator.
Buying after the builder leaves
Once a builder sells out, the HOA usually passes to resident control. Ask whether turnover has happened, how reserves were funded at handover and whether any warranty items remain open with the builder.
Prices and resale
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.
What to check before you buy
- Look up the parcel on the Orange County Property Appraiser site and note the millage code and any non-ad valorem assessments.
- Read the latest property tax bill. CDD assessments, where they exist, usually appear there as separate lines.
- Ask the seller or HOA for the current HOA budget, dues and what they cover.
- Order an HOA estoppel certificate early in the contract period.
- Check the FEMA flood zone for the exact lot, especially near lakes and ponds.
- Confirm school zoning with the Orange County Public Schools locator for the exact address.
See our Orange County property tax guide and Winter Garden ZIP guide.
Common questions
Is Oakland Park in Winter Garden or Oakland?+
It depends on the parcel. The area straddles Winter Garden and the separate Town of Oakland, and both use ZIP 34787. Look up the home on the Orange County Property Appraiser site to see whether it is inside Winter Garden, inside Oakland or in unincorporated Orange County, because each has a different millage.
How much are homes in Oakland Park?+
An April 2026 new-construction roundup listed David Weekley Homes at Oakland Park from $811,990. The builder no longer listed the community in September 2026, so most sales will now be resales. Compare closed sales inside the community over the last six months before making an offer.
Is Oakland Park near the West Orange Trail?+
The West Orange Trail passes through downtown Oakland and the Oakland Nature Preserve before reaching Winter Garden. How close a specific home is depends on its street, so check the walking or cycling route from the address rather than relying on the community name.