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Old Middletown High School
Masonic Temple Building, near South Green (Union Park)
South Congregational Church, near South Green
First United Methodist Church, near South Green
Church of the Holy Trinity (Episcopal)
Saint John's Roman Catholic Church
First Church of Christ Congregationalist
Russell Chapel, Indian Hill Cemetery
First Church of Christ Scientist, 151 College Street, originally built in 1832 as a house for Randolph Pease
Congregation Adath Israel (Conservative Jewish)
Saint Sebastian Church (Roman Catholic)
Wilcox Crittenden, Mill A
Wilcox Crittenden, Mills B and A
Wilcox Crittenden, Mill C
Samuel Wadsworth Russell House, 350 High Street. Now part of Wesleyan University.
Duane Barnes House. Now Davison Health Center, Wesleyan University.
Xi Chapter, Psi Upsilon Fraternity, Wesleyan University
College Row, Wesleyan University
Coite-Hubbard House, now home of the President of Wesleyan University
Inn at Middletown (former State Armory; wing at left was John R. Watkinson House, built c. 1810)
Former Farmers & Mechanics Bank, now Citizens Bank
Former Middletown National Bank, now Bank of America
Former post office, now part of Liberty Bank
Former Middletown Savings Bank, now part of Liberty Bank
Former City Savings Bank, now Middlesex County Chamber of Commerce
East side of Main Street slightly north of Washington Street
Mather-Douglas House, near South Green; Congregation Adath Israel in background at right
108–100 Washington Street, known as the Jeremiah Wetmore House or Starr-Weeks House, built 18th century
144 Broad St, former rectory of Holy Trinity, Dean Acheson's boyhood home
These historic house were moved to the south end of Main Street