Glenwood-Brooklyn was developed by the Glenwood Land Company in the early twentieth century as street car suburbs of Raleigh. The district is architecturally significant for the range of early 20th-century house types, methods of construction, and styles. The Glenwood-Brooklyn neighborhood in its present form was conceived in 1905-07 and no resources are known to survive from before 1907. The period of significance runs from 1907 to 1940.

The area was built out largely by the middle of the twentieth century despites lulls during World War I and the depression. By the 1940s there were few available infill lots. Suburban development reduced pressure on the neighborhoods but also created in its wake disinvestment and conversions of single family owner occupied residences to multiple rental units. National Register listing also provided incentives for the conversion of properties to income producing uses. By the 1980s, new residential developments in the area and an increased desire to live closer to downtown began to reverse the trends of disinvestment. Coupled with periods of economic prosperity, that desire has spurred a number of tear downs to provide land for new construction, and rehabilitations of existing buildings, some of which provide existing square footage at the cost of architectural integrity.

The district's earliest houses, those built from 1907 to the mid-1910s, exhibit vernacular and Victorian influences; those with simple symmetrical massing with rear kitchen and dining room ells, and one-room-deep center-passage and tworoom plans appear to predominate. These houses can be one- and two-stories and include I houses and triple A houses representing a continuation of nineteenth century regional vernacular tradition where weather boarded frame construction was typical. Victorian influences include decorative (nonfunctional) gables, turned and sawn millwork ornament in porches and gables, and (less frequently) decorative sheathings such as novelty or German siding and shaped wood shingles. Common milled ornament in the district includes turned porch posts, sawn and spindlework porch post brackets, and louvered gable vents, the latter typically diamond-shaped in form but occasionally also quatrefoil (four lobed) and triangular.

Most of the district's Victorian houses are fairly reserved in character, not as flamboyant as some found in Raleigh's Oakwood neighborhood. Exceptions are largely found along Glenwood Avenue, the main boulevard of the neighborhoods. Several of the houses along Glenwood are a subset of Victorian architecture known as the Queen Anne style. Primary elements of the style found in the district include irregular massing and roof lines, turrets, and wraparound verandas. Secondary details include decorative window sash and classical allusions.

Victorian influence appears in a few houses built as late as the early 1920s, but generally speaking the style was eclipsed by the Craftsman style beginning in the mid-1910s. The characteristic Craftsman house type, nationwide as well as in the district, was the bungalow, a snugly proportioned house of one or one and a half stories. Almost all Craftsman bungalows have front porches, and most of these are engaged (incorporated) under the house roof. Other common Craftsman bungalow features include large dormers that expanded upstairs living space, porch supports with wood posts (usually tapered and sometimes clustered) on brick pedestals, wood-shingle sheathing in gables and on dormers, gable brackets (usually triangular in form, sometimes appearing like purlin ends), and doublehung windows with upper sash composed of three or more vertical panes. Unlike earlier houses in the district, Craftsman bungalows usually dispensed with rear wings by incorporating the kitchen and dining room into the house envelope.

Roughly one hundred Craftsman bungalows stand in the district, most clustered along the back streets of the Glenwood area. Two basic gable roof forms are represented: side-gable and front-gable. Side-gable roofs are typical of the earlier and more finely appointed bungalows whereas front-gable roofs appear on later and more modest examples. Although they were relatively modest in scale and proportion, several bungalows exhibit a high level of quality in their construction.

Unlike the vernacular Victorian houses that preceded them, the district's Craftsman bungalows were not strongly influenced by regional architectural traditions. Because the type was disseminated nationwide through plan books, magazine articles, and even as kits distributed by Sears Roebuck, Aladdin Homes and other mail-order firms, the same bungalow could appear anywhere. Glenwood Brooklyn has two documented kit houses. Not all Craftsman houses were bungalows; a few two-story Craftsman houses were constructed.

Next to the Craftsman style the Colonial Revival was the most popular idiom during the period between the world wars. In the district this style is usually expressed by brick construction with contrasting white trim, symmetrical compositions, and classically-derived detail. A few of the Colonial Revival houses in the district have gambrel roofs which evoke, directly or indirectly, the Dutch architecture of the Mid Atlantic region.

The district also contains a fair number of stylistic hybrids–buildings that incorporate features form more than one style and mixing elements of the Colonial Revival, Craftsman and/or Victorian styles.

Other period styles make cameo appearances in the district including the Tudor Revival style. Period cottages in the district range from Tudor Revival to the Arts and Crafts movement. While outside the period of significance, the district does contain a handful of Ranch style houses. The most recent infill construction generally respects the architectural traditions of the district. Much of the new construction has sympathetic setbacks and some are in a Neo-Victorian or NeoCraftsman style.

With the exception of a few stores, a church, a lab, a school and a firehouse, the district is largely residential in character. Though there are some apartments, both purpose built and conversions, the majority of the residences are single family and are one or two stories high. Most are frame but there are a significant number of masonry or masonry veneered buildings.

As a rule, houses in the Brooklyn section, west of Glenwood Avenue, tend to be smaller and more modest with simpler stylistic expressions and a greater number of vernacular forms. The area east of Glenwood Avenue contains more of the larger houses (excluding modern additions which are found in both areas). Glenwood Avenue itself has the largest concentration of large and high style homes.

Most streets have near uniform setbacks. New construction (postdating the period of significance) accounts for the most obvious exceptions including several multi-unit apartments which are sited in larger lots and more oriented to their place on the lot not in relationship to the street or the surrounding buildings.

Front porches are common, creating a transition zone from public to private space. Lots that contain parking and/or a garage generally have a drive perpendicular to the street with a garage in the rear of the lot. Some houses in the eastern portion of the district continue to be served by rear alleys. Surface parking lots and front yard parking are rare.

The neighborhood enjoys mature tree cover. Most street are laid in an orthogonal grid with a few curvilinear roads. Glenwood Avenue is the only street with a median and there are no public parks or green space within the district.