The house at 380-382 Main Street in Cromwell was originally a center-chimney residence. Built between 1744 and 1758, probably by Israel Wilcox, it was sold by Charles Wilcox to Capt. Daniel Ranney in 1757. Capt. Ranney, who had become wealthy in the West Indies trade, died the following year and the house eventually was passed on to his grandson, Capt. James Butler and then was owned (1831) by Stillman K. Wightman, a lawyer who had married Butler’s daughter Clarissa. After his son Edward K. Wightman was killed in 1865 in the Civil War, Stillman K. Wightman made a long journey through a war-torn countryside to recover his son’s body in North Carolina. Greek Revival additions were made to the house around 1830. The property remained in the family until 1912. Colonial Revival alterations were made around 1920. The house, also called the William Ranney House, is haunted and was featured in an episode of the TV series “A Haunting.”
The Cornell Doud, Jr. House, at 20 West Street in Cromwell, was built circa 1807 on the site of a 1692 house that had long been home to the Ranney family. Comfort Ranney sold the old homestead to Doud, who replaced it with a center-chimney Federal-style house. In 1815 Doud, in partnership with Eben Wilcox, erected at distillery on the property. The house passed from the Doud family in 1883 and was later owned by Edmund Butterworth and then by his son Burton Butterworth.
Daniel Eels (1757-1851), a cooper, built a house on Main Street in Cromwell around 1782. He moved to Whitestown, New York in 1795 and sold the property, which then had a number of owners until 1802, when it was purchased by William Smith, who then sold it to his brother Capt. John Smith. The house (373 Main Street) may actually have been built at that time, instead of the earlier date of 1782. In the late nineteenth century, this Colonial/Federal house was altered in the Queen Anne style.
At 93 Shunpike Road, corner of Evergreen Road, in Cromwell is a brick Federal-style house constructed circa 1811 to 1815. The house was built by Eber Sage (1790-1848) on land deeded to him by his father, Solomon Sage. In 1835 Eber Sage’s house and farm were purchased by Samuel Kirby (1771-1849). In 1875 the property was sold from the Kirby family to Patrick Caffrey and remained in his family until 1944.
The building at 349 Main Street in Cromwell was built in 1853 as a Baptist church and later served as an American Legion Hall. The church was organized in 1802. According to Rev. Myron Samuel Dudley’s History of Cromwell (1880):
In 1803 the church built a plain frame edifice Meeting-House on the West Green, and held their public meetings there until 1833, when the house was moved to the central part of the village and placed on a lot nearly opposite the present site of the Post Office. Worship continued in this house until Nov. 3, 1853, on which day a new house of worship, located a little North of the old one, built during the pastorate of the Rev. C. W. Potter and largely through his instrumentality, was dedicated. This latter edifice was remodeled, somewhat, internally in 1872, and is the house of worship of the church at the present time.
The church disbanded in 1936 and the building’s steeple was removed.
Elisha Sage (1755–1801), of the Upper Houses of Middletown (now Cromwell) served in the Revolutionary War. A mason, he built bridges and worked on the construction of the Old State House in Hartford. Sage married Martha Montague. His house, at 64 West Street in Cromwell, was built circa 1776.
The house at 350 Main Street in Cromwell was built around 1870 on land purchased by Stephen P. Polley in 1869. Born in Chatham (Portland), Polley and his brother, Hiram Nelson Polley, moved to Wilmington, North Carolina, along with Levi Austin Hart of Southington and established Hart & Polley, a machine shop and metals manufacturing company. Stephen P. Polley later returned to Connecticut and founded the Cromwell Dime Savings Bank in 1871. He served as Cromwell’s town clerk from 1872 to 1878 and again from 1879 to 1881. After he died in 1887, his widow Catherine (from North Carolina) lived in the house until her death in 1891.