Developed primarily during a fifty-year period from 1880-1930, the Oakwood Historic District (designated in 1975) has the most diverse collection of architecture among Raleigh's historic districts. The neighborhood was built in the dense woods of northeast Raleigh known as "Mordecai Grove" and sold off in parcels after the Civil War. It developed incrementally, bit by bit, often lot by lot, with streets extended as needed, in contrast to Boylan Heights, which was platted in a single subdivision.

The street pattern is grid-like, but the blocks are of varying sizes and shapes. Some blocks are roughly square, while others are rectangular. This can lead to long stretches of sidewalk leading past home after home before an intersecting street is encountered. Most lots are small and narrow, especially between Bloodworth and East streets, and the houses are generally tightly spaced and often located close to the side lot lines. This dense grouping of buildings, which are also set close to the sidewalk, gives a certain intimacy and rhythm to the neighborhood. 

Bloodworth and East streets provide the major north-south spine of the district, with Elm Street the third internal north-south street. Boundaries of the district are largely set by where the historic pattern associated with Oakwood's development ends: adjacent commercial areas, vacant lots, buildings that represent other development patterns distinct from Oakwood, or open space. Person Street approximates the western boundary of the district, while Oakwood Cemetery and the rear lot lines east of Linden Street establish much of the eastern boundary. A recent extension of the district to the south carries across E. Edenton Street and New Bern Avenue to just south of Morson Street. Rear lot lines north of portions of N. Boundary and E. Franklin streets describe the northern limits of the district. Primary east-west streets through the district are E. Jones, E. Lane, Oakwood, Polk, and N. Boundary. Alleyways are rare in Oakwood.

 Many of the earlier streets have granite curbstones defining their edges, and the line of the curb is continuous through the narrow driveway curb cuts; the granite is simply depressed flush with the street surface to create the space for the driveway. Some of the curbs barely rise above the street as the streets have been resurfaced many times. A few of the driveway aprons are still paved with cobblestones or brick; most are concrete. Driveways themselves are most often gravel or concrete ribbon strips, squeezing beside the house to access the rear yard, and pushing the house close to the opposite side-lot line. Public sidewalks are generally concrete; a few brick walks still survive. There is typically a tree lawn between the public sidewalk and the curb where street trees are planted. Wooden electrical and telephone poles carry wires throughout the neighborhood along the streets and sometimes down alleys, supporting standard 'cobrahead' street lighting fixtures.

 The rolling topography of the neighborhood is the most varied among Raleigh's historic districts. Overlaid by the grid of streets, it provides a rise and fall to the experience of moving through the area, yet another element that contributes to the sense of diversity in Oakwood. The slopes in turn provide opportunities for numerous low retaining walls, sometimes of granite or brick, that are used to demarcate property lines and level the building site. Occasionally within the flatter, less sloping sections of the district, low concrete and stone dividers set nearly flush with the ground define property lines. A heavy, largely deciduous tree canopy shelters the neighborhood, shading the streets and buildings. Front yards are primarily lawn, bordered with planting beds; landscape plantings are generally informal, and often composed of simple foundation plantings.

 The compact nature of the neighborhood, along with the rolling land and the heavy tree canopy, creates an environment especially suited for the pedestrian. SidewaIks line both sides of most streets and houses huddle close to the walk, with front porches providing pause for interaction with neighbors. Recent years have seen the development of increasingly more private rear yard spaces as a counterpoint to the public front porches, with the erection of many privacy fences and outdoor decks. Two park areas no larger than one or two building lots, Vallie Henderson Garden and Oakwood Common, provide a bit of open space for pedestrians and children to enjoy. A larger open space for the neighborhood is provided by Oakwood Cemetery adjacent to the district's eastern boundary along Watauga Street.

 A wide range of architectural styles and building types are nestled within this tree-shaded setting. Many of the prominent buildings within the district are of recognizable "high style" architecture. Still, befitting its heritage as Raleigh's early middle-class neighborhood (Hillsborough and Blount streets were the upper middle class addresses), most of the dwellings in Oakwood are more simple, vernacular interpretations of these styles: frame construction covered with weatherboard using standard building parts available from local millwork and lumber suppliers. Because of this early standardization of building materials, many of the details found on Oakwood houses can be seen on a variety of structures in different parts of the neighborhood. Numerous outbuildings, garages, accessory buildings and even a couple of barns dot the rear yards of properties throughout the district.

 Generally speaking, the older housing stock is located within and close to the portion of the neighborhood that was part of the original 1792 city plan: south of North and Lane streets and west of East Street. This is also the area where most of the examples of "high style" architecture can be found, older structures built prior to the shift of upper middle class preference to Blount and Hillsborough streets. Here can be found examples of all the styles popularized during that long period of several decades that has been described as the "Victorian era," and which set the predominant image for the character of the district. Styles represented from this period include Colonial Revival, French Second Empire, Queen Anne, Eastlake, and Neo-classical Revival. Smaller, simpler vernacular cottages interpreting these styles are also present. A small commercial area at the intersection of Lane and Bloodworth streets continues to provide a touch of contrast to the otherwise uniformly residential character of the district.

 Because the neighborhood did develop in a lot-by-lot pattern, interspersed among the earlier dwellings are later "infill" styles from the late 1910s through the early 1930s, such as the Four-square and particularly the bungalow. Following a lull during the Depression and World War II, a few 1950s Federal Housing Administration (FHA) ranch-style houses were built, designed to meet federal specifications for mortgage insurability. Then, beginning in the mid 1980s, a number of new construction projects were built under the commission's design review procedures: several infill lots, and, on the site of the former Fallon's Greenhouses operation overlooking Oakwood Cemetery, the 23-lot Oakwood Green subdivision. This pattern of random development, a hallmark of Oakwood, has lead to a surprising diversity of scale within even small areas of the district, as larger, two-story homes are flanked by one-story cottages.

 Thus Oakwood, which contains Raleigh's only intact 19th century neighborhood, is also a surprisingly diverse neighborhood of long-term change. Its evolution is painted across a broad canvas, diversity borne of architectural and topographical variety, bound into a cohesive whole through repetition of detail and style, and a consistently intimate rhythm established along continuous streetscapes of tree-sheltered sidewalks.