More historic than 22% of U.S. towns · #213 of 638 in Florida. What drives it
Most of Oakland was built recently: 4% of its homes predate 1940 and the median home dates from 2009. Below: maps from 1962 on and the census since 1910.
Founding year: the first Oakland post office (Blevins & Helbock, CC0).The full story ↓
History grade
What drives Oakland’s History grade
On its age, its old homes and the National Register, Oakland is more historic than 22% of U.S. towns, #213 of 638 in Florida. Its age holds the grade up; its share of homes from before 1940 pulls it down.
C−
HistoryA character grade: shown, never part of Oakland’s overall grade.
Few Florida towns list much on the Register (a typical Florida town has 0.0 per 10,000 residents, the U.S. 2.4), so Oakland’s 0.0 sits below most of its state (33% of Florida towns have fewer) while its 0 listings outnumber those of 23% of U.S. towns.
How sure. Graded on any two of the three inputs instead, the letter would range from C− to C. The pre-1940 share is a Census survey estimate (±3.4 points). The founding year is the first post office, not a stated founding date.
Founding year: the first post office (other dates in Quick answers). Homes: Census ACS 2020–24. National Register: National Park Service, May 2026 list; each listing counted once (boundary changes and added documentation belong to their listing), and a historic district counts its contributing buildings. How TownRatings grades history →
What stands out about Oakland’s past
Read from the archive, the National Register and the record. The page puts what stands out first.
In 1857, James Gamble Speer settled in Oakland after buying all the land between Lake Apopka and Johns Lake. In 1860, the Oakland post office opened and closed in 1867. During the Civil War, the post office at Oakland was the only one operating within the present-day boundaries of Orange County, as Orlando's was closed from 1861 to 1866. Oakland post office reopened in 1877. During a time of great growth in the region during the 1880s, Oakland emerged as the center of commerce in west Orange County. The Town of Oakland was officially on November 1, 1887. However, a fire in the business district and a subsequent period of freezes in rapid succession throughout the 1890s, along with the growth of nearby Winter Garden, seemed to ensure that Oakland would remain as little more than a sleepy community. In 1891, the Florida Legislature officially reincorporated after being chartered. In 1940,…
The Oakland post office opened in 1860, the earliest record of the town by name (U.S. post office records).
How does Oakland rank for history?
Oakland is more historic than 22% of U.S. towns, #213 of 638 in Florida. The History grade combines the town’s founding era, the share of homes built before 1940 and its National Register listings. It’s a character grade, so it isn’t part of the overall grade. How it works.
How old are the homes in Oakland?
4% of Oakland’s homes were built before 1940 (Census estimate, ±3.4 points), against a typical 0.6% for a Florida town; the median home was built in 2009.
Founding dates: Wikidata, Wikipedia, the U.S. post office records of Blevins & Helbock (CC0) and the Census. Homes by year built: Census ACS 2020–24. National Register of Historic Places: National Park Service (list of May 22, 2026). Old photos, postcards and papers: Wikimedia Commons, the Library of Congress and other public archives, credited on each item’s page. Maps: U.S. Geological Survey historical topographic maps (via Esri) and Sanborn fire-insurance maps (Library of Congress). History text and census tables: Wikipedia (CC BY-SA 4.0). Places that used to be: USGS Geographic Names Information System (2021).
From Wikimedia Commons (6), Wikipedia, U.S. Geological Survey historical maps, U.S. Census counts (via Wikipedia), the US Post Offices dataset (Blevins & Helbock) and the USGS Geographic Names Information System. Archive images are copied here with their credits and licenses, shown on each photo’s page. Refreshed monthly.
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