103 North Main (6/2005). This was long the home of the Rev. Clevius O. Pruden3, founder of Chatham Episcopal Institute (now Chatham Hall). Subsequent owner Patsy Motley Hamilton added the Neoclassical-related facade during the mid-1900's.
111 North Main (6/2005). Former rectory of Emmanuel Episcopal Church, diagonally across Main Street to the south. This Colonial Revival house was built in the 1920's to replace an earlier rectory which was moved to nearby 18 Lanier Avenue. It is now a private residence, owned by the Lewis family.
117 North Main (6/2005). Queen Anne - style characteristics from the original construction of the house are evident in the shaped shingles on the north wall and on the massive brackets on the front of the house. These early details seem to peer out from behind the later Neo-Colonial front porch and other renovations.
The house was for a long period the manse of the Chatham Presbyterian Church, across the street. Subsequent owners have included the Ervis Hall, Jr., family, whose television-producer daughters Karen Hall and Barbara Hall lived here during their teen years.
121 North Main (6/2005). This Colonial Revival house with Georgian detail was built by Danville architect T. Bryant Heard2 for Patton Coles3. Subsequent owners have been Dr. Haile Fitzgerald (dentist and mayor of Chatham) and his wife Madalene Vaden Fitzgerald (author of Pittsylvania: Homes and People of the Past), and Mr. and Mrs. Jack Holland.
125 North Main (6/2005).
131 North Main (6/2005). Magnolia Manor, built during the 1890's by William B. Shepherd, is the best example of Queen Anne architecture in Chatham. It was long the home of the Thompson and Broaddus families.
In 1989-1990, during the local filming of the movie Crazy People, this was the residence of acress Darryl Hannah. During the Civil War, when the home of Col. Coleman Bennett stood on this location, a cabin in the rear (now also gone) was the refuge of Letitia Tyler Semple, daughter of President John Tyler.
145 North Main (6/2005). William B. Shepherd's brother Hugh D. Shepherd, who operated a department store on the northwest corner of Main Street and Court Place, built this home next door to his brother's (see above).
151 North Main (6/2005).
102 North Main (6/2005). This home was built by Judge J. Doddridge Coles, of Ex Parte Virginia fame; he had formerly lived at Mansfield, now thought to be Chatham's oldest residence.
For much of the twentieth century this was the home of Preston and Minnie Moses, who operated the local newspaper The Star-Tribune.
106 North Main (6/2005). This American Foursquare was built by Chatham attorney David T. Williams, whose office was at 33 South Main Street.1 For a number of years it was the office of Chatham dentist Dr. Claude Whitehead.
112 North Main (6/2005). Undergoing renovation.
118 North Main (6/2005).
124 North Main (6/2005). Undergoing renovation. John Pride Hunt built this home for his wife Mollie Tredway Hunt after promising her that she would have the highest ceilings in Chatham, and he fulfilled his promise. This house also had the first bathtub in Chatham. Mr. Hunt was not a church-going man, but he allowed his wife to arrange for him to be baptized in his bathtub.4
128 North Main (6/2005). Chatham Presbyterian Church.
132 North Main (6/2005). Watson Memorial United Methodist Church's parsonage.
136 North Main (6/2005). Watson Memorial United Methodist Church.
144 North Main (6/2005). This classic “American Foursquare” house was built in the early 1900's by Chatham wagon-merchant Sandy White. The home was purchased in the 1930's by Arch Overbey, and for nearly 80 years has continued as a home for Overbey and his wife Catherine Motley Overbey.
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