A short street connecting Muzzey and Clarke Streets, Raymond Street is one of a number of subdivisions which occurred close to the Center in the late 19th century in response to the need to provide housing for an expanding population. The laying out of Raymond Street in the early 1870s appears to have been a speculative venture by prominent citizens Hammon Reed and Freeborn Fairfield Raymond.
The street is lined by houses of mixed construction dates and materials although gablefront dwellings predominate. The houses at 20 Clarke Street (above) and at 6 Raymond Street were the first two houses built in the subdivision and date to 1872. Both were built by one of Lexington's most prolific local carpenters, David A. Tuttle (1820-1906). Local builder Abram C. Washburn built at least one house on the street. The 1893 house erected at 7 Raymond Street for Mrs. Harriet Lunt displays distinctive raking trim and gable decoration while 8 Raymond, also Queen Anne in style, mixes clapboards, wood shingles and stickwork. Indicative of the ease with which structures were moved and altered in the 19th century, the Colonial Revival structure at 5 Raymond Street was originally a barn, moved from Dr. Currier's former property at 21 Muzzey Street in the late 19th or early 20th century and remodeled into a house.
Additional construction occurred on Raymond Street in the early 20th century. Two c. 1920 brick houses with hip roofs and exposed rafters are visible at the northwest corner of Raymond and Muzzey Streets. The houses are quite similar in their mix of Craftsman and Colonial features although upon closer inspection #2 was constructed as a single-family dwelling while #4 was built to house two families.
Freeborn Fairfield Raymond's own house stood at the corner of Clarke and Raymond Streets. It was constructed in 1896 by Abram C. Washburn, but was razed in October 1956 to make way for the medical center that now stands on the site.