Just found this while Googling -- it's the text of the sale advertisement for Edward Herbert's land from 1872. Woodstock is item #3 in the list. If I can find an actual image of the newspaper listing I'll be sure and post that too.
This sale listing gives us some key details for establishing Woodstock's residential timeline. While houses and other structures are listed for Level Green and Whitehurst farm, there is no mention of a residence or current occupant for Woodstock. Instead, Woodstock is advertised as "well timbered" forest land with good farming potential.
Woodstock remained on the auction block for nearly 5 years. In March, 1877 Samuel Kimberly purchased the land for $2,000. Kimberly was a businessman, active in Norfolk society and politics: he was no farmer. In the following year he sold the waterfront property to Pheby Richards, and Elizabeth Addington secured the remaining 180 acres 5 months later. The rapid subdivision and resale by Kimberly bears the hallmark of a simple business transaction, so it is not likely that Samuel Kimberly took up residence here.
Pheby Richards and daughter Fannie were listed as Kempsville residents in the 1880 census (they were Norfolk residents in 1870). The census names Samuel Davis as a neighbor  and Abner T. Herbert as a neighbor , placing the Richards residence right on their Woodstock property. According to this evidence we can identify Pheby Richards as Woodstock's first permanant resident, ca. 1878. 
 the Davis farm was to the south, on the land that is now Woodstock Park, Providence Park and the Park-And-Ride.
 The Herbert's Sunnyside farm was to the west; now the Riverton neighborhood.
 My wife is quick to point out that Pheby Richards should be considered the first white resident of Anglo-European descent, since it is possible that native Americans lived here in pre-colonial times. While this is possible, I would counter that forest land would not be suitable for farming or livestock and would therefore not make for a hospitable dwelling of any permanence.