No. 2092 Bailey House on Dorchester Avenue, approximately 1935-1937 Dorchester Avenue. The house now has an address of 77 Bailey Street.
John Bailey acquired 6 ¼ acres of land in 1824 with the house already on it. He was elected that year to the U.S. House of Representatives from the 10th Congressional District, but the House refused to seat him, because he was not a resident of that district. That is most likely because he had moved to Dorchester. The house was in place by 1831, as represented on the 1831 map of Dorchester and Milton.
John Bailey was elected to the U.S. House of Representatives from the Massachusetts 10th Congressional district, serving from 1814 to 1817. Bailey was elected a member of the American Antiquarian Society in 1816. He became the clerk in the Department of State in Washington, D.C., from 1817-1823. He presented credentials as a Member-elect to the Eighteenth Congress, but the election was contested on the ground that he was not a resident of the district he purported to represent, and by resolution of March 18, 1824, the House declared he was not entitled to the seat. Bailey was subsequently elected as an Adams-Clay Republican to fill the vacancy in the seat that he had been denied; reelected as an Adams supporter to the Nineteenth and Twentieth, and as an Anti-Jacksonian Republican in the Twenty-first Congress. He was chair of the Committee on Expenditures in the Department of State during the Nineteenth Congress. John Bailey appeared in the 1830 U.S. Census as a resident of Dorchester. He was not a candidate for re-nomination in 1830, but he served as a member of the Massachusetts State senate from 1831 to 1834. He was the unsuccessful Anti-Masonic candidate for Governor in 1834. John Bailey died in Dorchester, Mass., June 26, 1835. His wife, Ann Bailey (ca. 1805-1835), died in late December of the same year.
The Baileys had three children, all minors at the time their parents died. Probate records indicate that a guardian was appointed for the children. Heirs of John Bailey appeared in the resident section of the tax assessing records through 1855. The 1861 Dorchester taxable valuation specifically says the heirs were non-resident.
Source: bioguide.congress.gov