Living in Oakland Park: homes, prices, HOA/CDD fees and what to check

At a glance

Oakland Park at a glance

Oakland Park is a newer community in the Winter Garden and Oakland area of west Orange County. An April 2026 roundup of Winter Garden new construction listed David Weekley Homes there from $811,990, with homes of 2,686 to 3,046 square feet on 55 to 70 ft lots, the highest base price in that roundup. By September 2026 David Weekley no longer listed Oakland Park among its Orlando communities, so most sales now are likely to be resales.

Is Oakland Park a good area?

For buyers who want a larger, newer home on a wider lot near the West Orange Trail and downtown Winter Garden, it is one of the few options. The trade-off is price: the reported base was well above Winter Garden's typical $566,535. Jurisdiction also needs checking, because the area straddles Winter Garden and the Town of Oakland.

Wider lots

Lots of 55 to 70 feet are wider than the 40 to 60 ft lots common in newer Horizon West communities such as Waterleigh, which leaves more room for a pool, a side-entry garage or a larger yard.

After the builder sells out

Once the builder leaves, the HOA passes to resident control. Ask whether turnover has happened, how reserves were funded at handover and whether any warranty items remain open.

What Oakland Park is known for

Its location. The Town of Oakland was settled early: a post office opened there in 1860, and during the Civil War it was the only one operating within present-day Orange County. The town incorporated in 1887. The West Orange Trail runs through downtown Oakland and the Oakland Nature Preserve on its way to Winter Garden's Plant Street, and it crosses Florida's Turnpike on a converted railroad bridge.

Winter Garden, Oakland or county

The Town of Oakland is a separate municipality with 3,516 residents at the 2020 census, up 38.5% from 2010. It uses ZIP codes 34760 and 34787, the same 34787 as Winter Garden, so a mailing address does not settle which government a home is in. Winter Garden's rate is 4.8565 mills for 2026-27; Oakland and the county set their own. Check the parcel with the Orange County Property Appraiser and see our Orange County tax guide.

Homes and prices

Resales of David Weekley homes

Expect two-story and large single-story plans in the reported 2,686 to 3,046 square-foot range. Compare closed sales of the same plan where you can.

How to price

Zillow publishes no Oakland Park figure in our data; the ZIP 34787 typical value was $570,875 in August 2026, which understates homes of this size. Use closed sales inside the community.

Schools and the trail

Schools

Records summarized for the Town of Oakland list Tildenville Elementary, Lakeview Middle and West Orange High as zoned schools, while the April 2026 roundup listed Independence Elementary for Oakland Park. The two sources disagree, so check the exact address with OCPS. The town also runs the Oakland Avenue Charter School.

West Orange Trail

Downtown Oakland is at about mile 2 of the trail, measured from Killarney Station at the county line, and Winter Garden Station on Plant Street is at mile 5. Check the actual route from the home to the nearest access point.

Pros and cons

Pro

Larger homes on wider lots near the trail and downtown Winter Garden.

Con

High reported prices, a town-or-city jurisdiction question and conflicting school information.

Compare nearby

See our Downtown Winter Garden guide for walkable older homes and our Winter Garden ZIP guide for how 34760 and 34787 overlap.

Common questions

Sources

• Pozek: New construction Winter Garden FL 2026, prices by builder (April 2026)
• Wikipedia: Oakland, Florida
• Wikipedia: West Orange Trail
• Citizen Portal: Winter Garden adopts 2026-27 millage at 4.8565 mills
• Zillow Research: Home value and market data (ZHVI), August 2026
• Orange County Public Schools: Student enrollment