The area was supposedly named after the Battle of Guilford Court House in North Carolina, in which McDonald was wounded.

In 1907, the property was purchased by the Guilford Park Company who wanted to develop the area into a sophisticated suburban neighborhood on the edge of expanding Baltimore.

"[2] The company spared no expense on utilities, streets, drains and other infrastructure to create a modern and an attractive living destination for the Baltimore elite.

The houses were designed by some of the most prominent Baltimore architects of the era, included Edward L. Palmer, Bayard Turnbull, John Russell Pope, W. D. Lamdin and Laurence Hall Fowler.

On Sherwood's death in 1965, the Guilford Association acquired the gardens and later transferred them to another 501(c)(3) organization, Stratford Green, Inc., which made the park accessible to the public year-round.

In Laura Lippman's 1998 debut novel Baltimore Blues, Guilford is the home of a prominent lawyer and his socialite wife.

[18] His film Pink Flamingos was shot in part at the house, which served as Connie and Raymond Marble's home.