The sign on the house at 55 Good Hill Road in Woodbury displays a date of 1685. That was the year Thomas Drakeley, Sr came to Woodbury. He gave one third of his property to his son, Thomas in 1725 and the house was probably built circa 1725-1730. The Drakeley family owned the house until 1918. The West Side School house once stood across from the Drakeley House. It is said that the school had no water so that the children had to use the Drakeleys’ well.
The J. Hebbard House in Windham Center is notable for its Late Georgian/Federal front door with fan light. Located at 11 Windham Green Road, the house was built c. 1783. It is also known as the Dr. Guild House. This is most likely Dr. Frank E. Guild, who is described in A Modern History of Windham County, Connecticut, Vol. II (1920):
Dr. Frank E. Guild was born in Thompson, August 14, 1853, son of Rev. John Burleigh Guild and Julia Ann Griggs. His father was a Baptist clergyman who preached at Clinton, Packerville and Thompson, in Connecticut. His son was graduated at State Normal School at New Britain in 1874, and from Long Island College Hospital in 1885, teaching school in the interim as a means to a professional education. Doctor Guild began medical practice in Windham, Conn., in October, 1886, and has continued there since, with oflices also at Willimantic. Has been president of Windham County Medical Society, vice president of the state society; member of town school board of Windham thirty years and chairman of the board for the past fifteen years. He was married April 28, 1887, to Harriet Clark, daughter of Edgar Clark of Putnam, who was a civil engineer and employed in surveying the Boston, Hartford and Erie Railroad. Doctor and Mrs. Guild are, respectively, S. A. R. and D. A. R. members, and Mrs. Gui1d’s grandmother was a real daughter. They have three children, Alan Clark, Harriet Griggs, and Julia Exton Guild.
Dr. Guild’s daughter, Dr. Harriet G Guild, became an authority on children’s kidney disease at Johns Hopkins and was the founder of the Kidney Foundation of Maryland.
At 3237 Bronson Road in the Greenfield Hill section of Fairfield is a Colonial Revival house built in 1882. It was once the home of Isaac Milbank, a gunsmith, who had his brick workshop behind the house. Later purchased by the Greenfield Hill Congregational Church for use as a school, the house has been much altered and an addition was built in 2012.
The substantial house at 93 Broad Street in East Hartford was built by Capt. John Kentfield (1743-1804) between 1784 and 1792. He had earlier built the house at 119 Naubuc Avenue, not far away. A later owner of the house on Broad Street was Josiah White, from Gildersleeve in Portland. Josiah married Rebecca Hills of East Hartford; his brother George and cousin Daniel married two of Rebecca’s sisters. Josiah White moved to Oneida County, New York in 1812.
The summer cottage at 6 Linden Point Road in the Stony Creek area of Branford was built in the 1870s or 1880s. The road to Flying Point was opened in 1870, opening the area to development. This was a period when Stony Creek was a popular summer colony. The cottage is an example of the Stick and Shingle styles. The house has been significantly remodeled/rebuilt in recent decades.
The main block of the Loomis-Pomeroy House, located at 1747 Boston Turnpike in North Coventry, is a transitional Federal-Greek Revival house. It was probably built c. 1833 by Eleazer Pomeroy (1776-1867), who had been operating a tavern in the vicinity since 1801. He deeded the house to his son George in 1843 and the Pomeroy family continued to own the house and farm until 1873. After passing through various owners, the property was acquired by James Otis Freeman in 1881. It was then owned by Freeman’s daughter Louise and her husband S. Noble Loomis and remained in the Loomis family until 1987. The Loomis farm, called Meadowbrook, extended to 100 acres, but was subdivided after 1968. Louise Loomis was librarian at the Porter Memorial Library across the street. In 1987, June Loomis bequeathed the house to the library association. It was eventually owned by the Town of Coventry, which leased to Coventry Preservation Advocacy for restoration and later sold it to support the Booth & Dimock Memorial Library.
The main part of the house at 243 Tolland Turnpike in Willington, in the Willington Common Historic District, was designed by architect Augustus Treusdel of Coventry and erected by builder Emery Williams for Deacon John Turner. This 1849 Greek Revival section was added to an earlier single-story building. Deacon John Turner was a stockholder in the Willington Glass Company. George V. Smith, who owned the house in the early twentieth century, was a lawyer and editor of the Connecticut Farmer.
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