Originally part of Falmouth and later Westbrook, Deering, Maine was incorporated in 1871. Deering’s independence was short‑lived and in 1899 the entire town was annexed to the City of Portland. Today, Deering remains one of Portland’s most convenient and desirable residential areas. Its many neighborhoods ‑‑ Deering Center, the Highlands, Woodfords Corner ‑‑ offer tree‑lined streets of historic homes for those who want to be convenient to all that Portland offers while living in a quiet, residential setting. Evergreen Cemetery and Baxter Woods offer trails for walking. Busy Stevens Avenue hosts restaurants, including neighborhood favorites the Press Room and the Tree House Café, and schools, houses of worship, and retail suppliers for life’s necessities.
“The Highlands” is one of the more private and picturesque of Deering’s neighborhoods. The site was once “Highfield,” the estate of Alexander W. Longfellow, brother of the famous poet and a successful artist, surveyor and cartographer in his own right. The land was divided in 1880 although Orland Street (the Avenue) was not created until some time later. The hilly terrain and rocky ledges made for poor farming but offer a dramatic setting for the many large‑scale residences built here after 1900. Curved roads and sloping sites add to the charm.