County Street is in the Ipswich Architectural Preservation District and has some of the oldest houses in town. The section between East and Summer Streets was originally called Cross St, and the section between the County Street bridge and Poplar Street was known as Mill St. The roads were connected when the County Street Bridge was constructed in 1861. It continues as County Road beyond the South Green.
When the County street bridge was built in 1860 it joined together Cross and Mill streets, which then became County street, and completely obliterated “Falls Island” which stood in the middle of the river and had always been a busy center of industry since Robert Calef built the first grist mill in 1715. Fulling, saw, grist and woolen mills flourished along with the several small enterprises across the street: saw, box and veneer mills. In time the mill burned down, the smaller mills closed their doors, and all that’s left to remind us of that long ago time are the three small houses, facing Elm street, and standing more or less on what was Fall’s Island.
10 County Street, the Dennis – Dodge House (1740) - The 1740 Dennis-Dodge house was owned by Captain John Dennis, whose father Thomas Dennis was a renowned woodworker and owned a home across the street. A succession of Dennis family members retained this property. Captain Ignatius Dodge (1816 - 1901) inherited the house. In the early 1800's, Eunice Hale maintained a school in the building. 11 County Street, the Bennett – Caldwell house (1725) - Joseph Bennett built this early Second Period house in 1725. In 1818 the house was sold to Capt. Sylvanus Caldwell, who engaged in maritime trade along the coast from Massachusetts to Maine for a half century. 15 County Street, the Rev. Levi Frisbie house (1788) - This house at 15 County Street was built in 1788 for Rev. Levi Frisbie, pastor of First Church in Ipswich. He continued in the pastorate thirty years until his death in 1806, succeeded by the Rev. David Tenney Kimball. 16 County Street, the Abraham Knowlton house (1726) - The original house is believed to have been constructed between 1725 and 1740. The house was in poor condition and in 2003 was restored by Ipswich architect Matthew Cummings. It is identical in construction to the Dennis-Dodge house a few doors away. 17 County Street, Daniels Shoe Factory (1843) - This house was built in 1843 near the EBSCO dam as Hoyt’s Veneer Mill. It was moved in 1859 to its present location on where it became the Perkins & Daniels Stocking Factory. Farley & Daniels succeeded in 1884. 25 County Street, the J. Caldwell house (c 1860) - The house at 25 County Street in Ipswich was built in approximately 1860 on a corner of the former Ipswich Jail grounds. The 1872 Ipswich map shows the owner as J. Caldwell. In 1910 the owner is N. S. Kimball. 3 County Street (1850) - The house does not appear on the Ipswich maps through 1910, at which time this tiny parcel was owned by Dr. Russell. It may be a wing of the Captain William Treadwell house which was removed from the other corner of East Street in order to widen the intersection. 47 County Street, the Benjamin Grant house (1723) - The Benjamin Grant House was added to the National Register of Historic Places in 1980. It appears to have been originally built as a half house. Benjamin Grant was born in 1701 in Ipswich to Robert and Mary Grant, who emigrated from England. Benjamin married Anne Perkins in 1722, and was killed in the French and Indian War in 1756. 5 County Street, the Rindge-Pinder-Leatherland house (1718) - Richard Rindge (also spelled Ringe) acquired the lot at 5 County St., with a house already on it, in 1718. Phillip Clark operated an undertaker's and cabinet shop here, and in the mid-19th Century it was a "shoe manufacturing" business owned by Ignatius Dodge who lived in the Thomas Dennis house next door. 7 County Street, the Thomas Dennis House (1663) - Shoreborne Wilson, a cooper, built a house and shop on this site about 1660. Thomas Dennis, the well-known master joiner, bought the property in 1663. The rear ell of the present house dates from that period, The 5-bay front section of the house dates to the 1750's. 9 County Street, the Benjamin Dutch house (1705) - This was built early in the 1700’s, and was owned by one of several men named Benjamin Dutch who owned and sold properties throughout town. The asymmetrical facade and timber frame are typical of First Period construction.