Oakland, FL Guide 2026: Homes, Lots, Taxes & Getting to Plant Street

Is Oakland part of Winter Garden?

No. Oakland is its own town, with its own town government and its own tax rate, on Winter Garden's west side near Lake Apopka. Oakland Town Hall is at 230 N Tubb Street. The confusion comes from mailing addresses. Most of the town uses Winter Garden's 34787 ZIP code: of the town's 2,356 parcels on Orange County Property Appraiser records, 1,683 have a 34787 address and 673 have Oakland's 34760 (accessed Oct 6, 2026).

The mailing address does not tell you the jurisdiction. Look up the parcel on the Orange County Property Appraiser site and check its mill code before you rely on town rules or tax estimates. Call or text 407-706-5000 and we will confirm the jurisdiction for any address.

What do homes cost in Oakland?

The Town of Oakland had 94 detached-home and townhome sales in the 12 months ending Oct 2, 2026, at a median $656,500 and $285.74 per square foot (Stellar MLS, matched to Orange County Property Appraiser town-limits parcels). The middle half sold between $506,875 and $1,500,000. Detached homes, 90 of the 94 sales, had a median $681,500. The median sale went under contract in 32 days and closed at 98.5% of list price.

New construction pulls the top end up. The 77 town sales of homes built in 2024 or earlier had a median $600,000 and a median 36 days to contract, while the 17 homes built in 2025 or 2026 had a median $2,417,730. Builder closings are often entered in the MLS at or near closing, so their days on market are not a useful guide.

A ZIP-only search can mislead here. ZIP 34760 had just 17 sales over the same 12 months, and 12 of them were new builds in Briley Farm or Grove at the Harvest District, so a 34760-only figure is a small sample and not typical of the town. Call or text 407-706-5000 for current Oakland comps.

What kinds of homes and lots are in Oakland?

Most town sales were detached homes: 90 of 94, with 4 townhome sales. The median home sold was built in 2019 and had about 2,706 heated square feet. On Orange County Property Appraiser parcel data (accessed Oct 6, 2026), the median improved detached-home lot in the Town of Oakland is 0.218 acres (about 9,486 square feet), and the middle half fall between 0.138 and 0.289 acres. In the older 34760 part of town, the median lot is 0.288 acres. Homes built in 2015 or later sit on a median 0.139 acres, compared with 0.287 acres for homes built before 2015.

Watch subdivision names, too. A plat with "Oakland" in its name, such as Oakland Park, is not necessarily inside the Town of Oakland, and many in-town subdivisions use Winter Garden addresses. Check the parcel's jurisdiction on the Property Appraiser site. For homes in and around town, see our Oakland, FL real estate page.

How much are property taxes in the Town of Oakland?

On the Orange County Property Appraiser's 2025 final millage table, the Town of Oakland levied 6.7000 mills, and the total for Town of Oakland parcels was 18.1378 mills. Parcels inside the City of Winter Garden totaled 16.2943 mills on the same table. On $100,000 of taxable value, that is about $1,814 in Oakland versus about $1,629 in Winter Garden, before homestead exemptions and flat assessments.

HOA dues and any CDD assessment depend on the subdivision, so pull the tax bill and HOA documents for the specific parcel. Our Winter Garden property taxes guide explains homestead, Save Our Homes and portability.

How do you get from Oakland to Plant Street and the rest of Orlando?

By car, our free-flow map check on Oct 6, 2026 measured about 3.0 miles and 6 to 8 minutes from Oakland Town Hall to Plant Street and Main Street in downtown Winter Garden. By bike or on foot, the West Orange Trail connects the two. Orange County Parks describes the trail as 22.32 paved miles from the Orange/Lake County line through Killarney and Oakland, through Winter Garden and on to Apopka. On the City of Winter Garden's trail map, the Oakland Nature Preserve is at mile 1.4, the Oakland Outpost at mile 2.2 and Winter Garden Station at mile 5.2, about 3 trail miles apart.

For longer trips, Oakland drivers usually reach Florida's Turnpike and SR 429 through Winter Garden. The Central Florida Expressway Authority describes SR 429 as a nearly 23-mile route from US 441 in Apopka to I-4 in Osceola County, with Turnpike access. See our commute and roads guide and Plant Street vs Horizon West.

What is being built near Oakland?

For recent project news, see our coverage of Briley Farm Phase 2 and new development in Oakland and Winter Garden. Plans and timelines change, so check the current status of any project near a home you are considering.

Looking at a home in Oakland or just outside it? Call or text 407-706-5000 and we will confirm the jurisdiction, taxes and comps before you write an offer.