The Stick-style house at 348 Hopmeadow Street in Simsbury was built in 1879 on the site of a c.1679 house, built by John Pettibone, Sr. The house was later owned by Rosetta Pettibone Bestor (1769-1825), wife of Dr. John Bestor. After her death, it was purchased by John Owen Pettibone in 1826. A large landowner, he was a probate judge of Simsbury and served in the State Senate. After his death in 1876, the property passed to his niece, Charlotte Pettibone Winslow, who tore down the old house and built the present one. She was the widow of Rev. Horace Winslow, who had retired and moved to Weatogue. According to the Commemorative Biographical Record of Hartford County (1901):

Mr. Winslow was married, May 8, 1850, at the Church of the Puritans, New York City, by the pastor, the Rev. George B. Cheever, D.D., to Charlotte Henrietta Pettibone, daughter of the late Capt. Jonathan and Mrs. Fanny Rosanna (Phelps) Pettibone, of Simsbury, Conn. Mrs. Winslow has for more than fifty years been a worthy and sustaining helpmate to her husband, and has always been interested in his work. She is of a kind and lovable disposition, and her devotion to her husband and children is unsurpassed. She was born at Weatogue, Simsbury, and was only three years old when she attended her first school, was a pupil of various private schools, and was graduated at the age of sixteen at Hartford Female Seminary, with first rank in her class. She also took courses in French, Music and Art while residing in Hartford, and later at New York City, being for a time a pupil at the private school of Madame Okill. About the year 1844, Miss Delia Bacon, of New Haven, sister of Rev. Leonard Bacon, D.D., conducted a class of young ladies in higher branches of study, This class Miss Pettibone joined, giving special attention to the Bible, to Shakespeare, and to philosophy, and the few months spent in New Haven were most delightful and profitable, as Miss Bacon was a lady of rare ability and attainments.

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Charlotte Pettibone Winslow House (1879)