[1][needs update] The neighborhood's residential architecture prominently features a number of late 19th century and early 20th century architectural styles, such as Greek revival, Craftsman, Colonial Revival, Queen Anne style, Cape Cod, Victorians, and ranches.

[5][6] Glenbrook retains a distinct identity, as "many residents see themselves as living not in a bustling city, but in a separate small town", according to a New York Times article about the community.

[1] In 1856, English pharmacist Charles Henry Phillips, best known for his invention of milk of magnesia, built a wax and camphor factory in present-day Glenbrook, along the banks of the Noroton River.

[7]: 2  The factory, located at 666 Glenbrook Road,[citation needed] would be sold to Sterling Drug, remain operational until 1975[7]: 3  or 1976.

[8] The initial ascent of modern-day Glenbrook began in 1866, when the construction of a railroad from Stamford's town center to nearby New Canaan fueled minor land speculation.

[1] He often visited to play poker with Ferdinand Ward, a business partner of his who owned a home at Strawberry Hill Avenue and Holbrook Drive.

Until the 1960s Stamford's now large neighborhoods, like Glenbrook, were often looked on as individual, unofficial towns, and residents would write their mailing addresses using the name "Glenbrook, Conn." instead of "Stamford, Conn."[citation needed]In the 1950s, the train station was moved from a spot near the Courtland Avenue overpass (on the New Haven Line) to its present location a bit to the northwest on the New Canaan Branch.

[10] In 2022, Mayor Caroline Simmons proposed converting the disused building into affordable housing, although the plan was ultimately scrapped.

A 2019 publication by the city government reported that the "Glenbrook-Belltown" neighborhood had a per capita income of $47,661, slightly below Stamford's total, but above Connecticut's.

[2] The Census Bureau's 2021 5-year American Community Survey estimated that the 06906 ZIP Code, which encompasses much of Glenbrook, had a median household income of $95,341, slightly below Stamford's total of $99,791.

[1][15][16] A 1989 New York Times article described the store as "a bizarre emporium of kitsch containing acres of architectural remnants, brick, used plumbing fixtures, antiques, garden statuary and some outrageous items of decor".

In August 2007, scenes for College Road Trip, a Disney film released in 2008, were shot on location in one of the Queen Anne style homes of Glenbrook.