In the late 1920s, Winslow Road was referred to as "the street of the brides" by the Cleveland Plain Dealer, as it "attracts more newly married couples of social prominence than any other street in Greater Cleveland." A 1929 article about life on Winslow Road described the weekday routine: a "light brigade of husbands" going to catch the Rapid train at 8, a gathering of women in the market at Kinsman and Lee Roads around 11, and an "influx of wives in their homes at 4:30" just in time to start dinner before their husbands arrived home. After living on Winslow Road for a couple of years though, most couples moved elsewhere in Shaker Heights. They did this so that they could "take an entire house" and "join the nabob class," while leaving behind the younger "bobs" and their two-family homes on Winslow.
Winslow Road is one of the more unique streets in Shaker Heights. It was designated a Historic District in 2007. The first house on Winslow was constructed there in 1924, and nearly 73% of the homes on the street were built by 1929. In total, the Winslow Road Historic District contains 170 two-family homes, three churches, and a city park. It is the only street in Shaker Heights that consists entirely of two-family houses. This was no accident -- the Van Sweringen Company carefully zoned Shaker Heights to control the suburb's development. Therefore, palatial homes on spacious lots would be able to coexist in Shaker Heights with more tightly packed-in duplexes, though the locations for these different types of lots would be carefully defined.
The two-family houses on Winslow Road, like all other houses in Shaker Heights, met high standards of construction and were designed by professional architects in either the English, French, or Colonial style. It is believed that no home on Winslow Road has ever been demolished in the street's nearly 90 years of existence.
Though all of the street's structures are two-family houses, each home on Winslow Road has only a single front entrance, giving it the appearance of a single-family home. The street features houses designed by prominent architects such as Charles Schneider (who designed Shaker Heights City Hall and Plymouth Church), the firm of Fox, Duthie, and Foose (designers of a series of "Master Model Homes" on Scottsdale Boulevard), and George Burrows. Burrows designed 43 houses on Winslow Road, the most of any architect.