The area was settled in the early 18th century by the Ridgley and Warfield families forming large tobacco plantations: "Bushy Park", "Longwood", "Ellerslie" and others. In 1822, James B. Matthews purchased a 200-acre farm and stone home from Caleb Dorsey. He opened a post office on July 30, 1841, giving the area the name "Matthews Store" in the Howard District of Anne Arundel County, which operated until January 1874.[4][5] The Union Chapel was built in 1833. The Howard District of Anne Arundel county became the newly formed Howard County. Despite southern sympathies, the Civil War ended slave labor on the local farms. The Phrenakosmian Hall was opened, renamed to the Howard Institute serving 25 children. On January 13, 1874, the Glenwood postal stop opened.[4] It was renamed to Glenwood by James Matthew's son, Professor Lycurgus Matthews.[6][7]
In 1995, Glenwood land developer Randolph Ayersman made national news after police found that profits from drug sales were being used to buy and develop properties under A&A contracting in Glenwood.[8][9]
Glenwood is primarily a residential community consisting of 1,088 households[12] which are primarily single-family homes on larger lots. The majority of retail and commerce for Glenwood is situated along the Maryland Route 97 corridor that runs north–south through the community.