The 210 acres of land that are now Guilford were purchased in 1872 by Arunah S. Abell, founder of The Sun. It remained in the Abell family for 35 years, until 1907, when it was sold to the Guilford Park Company. The Guilford Park Company wanted to prevent this beautiful tract of land, lying in the line of the city's rapid growth to the north, from being sold in small parcels for merely speculative building operations of the usual type, and they determined that the property should be developed as a whole along the lines of the best modern methods of city planning. In 1911 the Guilford Park Company joined with the Roland Park Company and thus Guilford came under a management that had demonstrated in Roland Park the wisdom of safe-guarding a neighborhood by properly restricting the uses to which the land may be put and of adding to it the improvements that contribute so greatly to the comfort of living in it, and the attractiveness of its aspect as a whole.
Planning of the landscape design for Guilford was under the immediate direction of Mr. Frederick Law Olmsted, Jr. of the famous firm of Olmsted Brothers. The community reflects Olmstedian landscape design principles in its curvilinear streets and respect for existing topography and vegetation. The Guilford plan provided for three parks "for general use of the residents," two containing about one and one-quarter acres each and the other about three acres. Over the past ninety years two additional parks were created including the well regarded Sherwood Gardens and the Gateway Park. By December 1913, only seven months after the opening of Guilford, one-eighth of the entire development had been purchased by home seekers, appreciating the beauty, convenience, and security of this development. However, 1914 also brought war to Europe and it was not until April, 1925, that the completion of streets and utilities in the entire development was announced. The homes of Guilford were designed by some of the greatest Baltimore architects of the era. They included Edward L. Palmer, Bayard Turnball, John Russell Pope, W. D. Lamdin and Laurence Hall Fowler. Building materials range from brick and stone to stucco with carefully defined details. The homes are designed in predominantly early 20th century revival styles that reflect European influences. The Guilford Association maintains the neighborhood's integrity through the covenants in the Deed and Agreement, exercising oversight and guidance that have resulted in the unique community and quality living environment.