I'm gonna do five ones that are close to me
>Gretna, Virginia
It was founded around 1904; however, it had been a train station for around 20 years prior.
The oldest building is Yates Tavern built around 1750 (wikipedia says late 17th to early 18th century, but that's not accurate)
>Altavista, Virginia
It's also a new town, founded in 1912 as a train station town.
The oldest building is Avoca Museum built in the 1755s. Charles Lynch, the guy who built it, got the land because of a grant from King George. Charles Lynch is famous because during Revolutionary War he established lynch courts that tried loyalists, and this came to be known as lynching.
>Lynchburg, Virginia
Founded in 1786 by John Lynch, (brother of Charles Lynch).
The Miller-Claytor House is the oldest, built in 1791
>Danville, Virginia
It doesn't have a technical founding. But the first proper settlement was in 1793.
I can't find the oldest building, but oldest I found was 1833.
>Straightstone, Virginia
This is where I live, and it's not an incorporated place.
But my family has at least inhabited been here since 1850s, and my grandmothers house is was built in early 20th century.
Also, for the buildings. A lot of this area suffered badly during ACW, so there are probably loads of buildings that used to exist, but were destroyed.
Additional shit
Danville and Lynchburg were both capitals of the Confederacy during the late Civil War.
Danville used to be considered one of the best tobacco markets in the US, if not the world.
The river that runs through Danville, the Dan River, is named after Dan from the Bible, and was discovered when trying to mark border with North Carolina in 1600s.
Chapstick (the brand) was invented in Lynchburg
Paleo-Indians also inhabited the area since 11000 BC, but they didn't leave structures.