[2] Name on the Register[3] Image Date listed[4] Location City or town Description 1 Alsop House Alsop House October 6, 1970 (#70000686 ) 301 High St. 41°33′30″N 72°39′22″W / 41.558333°N 72.656111°W / 41.558333; -72.656111 (Alsop House ) Middletown Stately mansion built in "Greek-Tuscan Italianate" style in 1838-39, now owned by Wesleyan University . Designated a National Historic Landmark in 2009. 2 Arrawanna Bridge Arrawanna Bridge September 29, 2004 (#04001092 ) Berlin St. at the Coginchaug River 41°33′46″N 72°40′00″W / 41.562778°N 72.666667°W / 41.562778; -72.666667 (Arrawanna Bridge ) Middletown An early reinforced concrete bridge, of elegant open spandrel design, blocked from use and deteriorating as of 2004 nomination. 3 Broad Street Historic District Broad Street Historic District August 25, 1988 (#88001319 ) Roughly bounded by High, Washington, Broad and Church Sts. 41°33′29″N 72°39′10″W / 41.558056°N 72.652778°W / 41.558056; -72.652778 (Broad Street Historic District ) Middletown 4 Church of the Holy Trinity and Rectory Church of the Holy Trinity and Rectory August 14, 1979 (#79002615 ) 381 Main St. and 144 Broad St. 41°33′40″N 72°39′06″W / 41.561111°N 72.651667°W / 41.561111; -72.651667 (Church of the Holy Trinity and Rectory ) Middletown 5 Coite-Hubbard House Coite-Hubbard House December 20, 1978 (#78002846 ) 269 High St. 41°33′26″N 72°39′20″W / 41.557222°N 72.655556°W / 41.557222; -72.655556 (Coite-Hubbard House ) Middletown 6 Connecticut General Hospital for the Insane Connecticut General Hospital for the Insane August 29, 1985 (#85001920 ) Silver St. E. of Eastern Dr. 41°33′10″N 72°37′47″W / 41.552778°N 72.629722°W / 41.552778; -72.629722 (Connecticut General Hospital for the Insane ) Middletown 7 Connecticut Valley Hospital Cemetery Connecticut Valley Hospital Cemetery August 2, 2018 (#100002718 ) S of jct. of Silvermine Rd. & O'Brien Dr. 41°33′12″N 72°37′11″W / 41.5533°N 72.6196°W / 41.5533; -72.6196 (Connecticut Valley Hospital Cemetery ) Middletown 8 The Eclectic House The Eclectic House January 2, 2013 (#12001111 ) 200 High St., Wesleyan University 41°33′18″N 72°39′15″W / 41.55510°N 72.65419°W / 41.55510; -72.65419 (The Eclectic House ) Middletown 9 Highland Historic District Highland Historic District June 28, 1982 (#82003770 ) Atkins St. and Country Club Rd. 41°34′05″N 72°44′16″W / 41.568056°N 72.737778°W / 41.568056; -72.737778 (Highland Historic District ) Middletown 10 Nehemiah Hubbard House Nehemiah Hubbard House May 11, 1982 (#82003771 ) Laurel Grove Rd. and Wadsworth St. 41°32′17″N 72°40′52″W / 41.538056°N 72.681111°W / 41.538056; -72.681111 (Nehemiah Hubbard House ) Middletown 11 Main Street Historic District (Middletown) Main Street Historic District (Middletown) June 30, 1983 (#83001275 ) Roughly Main St. between College and Hartford Ave. 41°33′45″N 72°38′56″W / 41.5625°N 72.648889°W / 41.5625; -72.648889 (Main Street Historic District (Middletown) ) Middletown 12 Metro South Historic District Metro South Historic District January 24, 1980 (#80004064 ) Main and College Sts. 41°33′27″N 72°38′49″W / 41.5575°N 72.646944°W / 41.5575; -72.646944 (Metro South Historic District ) Middletown 13 Middletown Alms House Middletown Alms House April 29, 1982 (#82003772 ) 53 Warwick St. 41°32′56″N 72°39′09″W / 41.548889°N 72.6525°W / 41.548889; -72.6525 (Middletown Alms House ) Middletown 14 Middletown South Green Historic District Middletown South Green Historic District August 12, 1975 (#75001922 ) Union Park area, on S. Main, Crescent, Pleasant, and Church Sts. 41°33′21″N 72°38′56″W / 41.555833°N 72.648889°W / 41.555833; -72.648889 (Middletown South Green Historic District ) Middletown 15 Old Middletown High School Old Middletown High School August 23, 1985 (#85001826 ) Pearl and Court Sts. 41°33′30″N 72°39′13″W / 41.558333°N 72.653611°W / 41.558333; -72.653611 (Old Middletown High School ) Middletown 16 Jacob Pledger House Jacob Pledger House March 15, 1982 (#82003773 ) 717 Newfield St. 41°34′43″N 72°40′22″W / 41.578554°N 72.672897°W / 41.578554; -72.672897 (Jacob Pledger House ) Middletown 17 Plumb House Plumb House December 1, 1978 (#78002848 ) West of Middletown at 872 Westfield St. 41°33′49″N 72°42′06″W / 41.563611°N 72.701667°W / 41.563611; -72.701667 (Plumb House ) Middletown 18 Russell Company Upper Mill Russell Company Upper Mill February 6, 1986 (#86000150 ) 475 E. Main St. 41°32′37″N 72°38′20″W / 41.543611°N 72.638889°W / 41.543611; -72.638889 (Russell Company Upper Mill ) Middletown 19 Edward Augustus Russell House Edward Augustus Russell House April 29, 1982 (#82004336 ) 318 High St. 41°33′32″N 72°39′20″W / 41.558889°N 72.655556°W / 41.558889; -72.655556 (Edward Augustus Russell House ) Middletown Later ΚΝΚ fraternity, now offices of University Relations, Wesleyan University 20 Samuel Wadsworth Russell House Samuel Wadsworth Russell House October 6, 1970 (#70000688 ) 350 High St. 41°33′37″N 72°39′20″W / 41.560278°N 72.655556°W / 41.560278; -72.655556 (Samuel Wadsworth Russell House ) Middletown Greek revival mansion, designed by Ithiel Town ; now part of Wesleyan University . 21 Saint Luke's Home for Destitute and Aged Women Saint Luke's Home for Destitute and Aged Women April 29, 1982 (#82004337 ) 135 Pearl St. 41°33′42″N 72°39′18″W / 41.5617°N 72.6549°W / 41.5617; -72.6549 (Saint Luke's Home for Destitute and Aged Women ) Middletown 22 Sanseer Mill Sanseer Mill July 31, 1986 (#86002101 ) 215 E. Main St. 41°32′59″N 72°38′31″W / 41.5497°N 72.6419°W / 41.5497; -72.6419 (Sanseer Mill ) Middletown 23 Starr Mill Starr Mill December 14, 1993 (#93001379 ) Junction of Middlefield St. and Beverly Heights 41°32′55″N 72°41′28″W / 41.5486°N 72.6911°W / 41.5486; -72.6911 (Starr Mill ) Middletown 24 Starr Mill Road Bridge Starr Mill Road Bridge December 10, 1993 (#93001344 ) Starr Mill Rd. across the Cochinaug River 41°32′56″N 72°40′38″W / 41.5489°N 72.6772°W / 41.5489; -72.6772 (Starr Mill Road Bridge ) Middletown 25 Town Farms Inn Town Farms Inn May 4, 1979 (#79002614 ) Spring St. at River Rd. 41°33′28″N 72°37′20″W / 41.5578°N 72.6222°W / 41.5578; -72.6222 (Town Farms Inn ) Middletown 26 U.S. Post Office U.S. Post Office April 12, 1982 (#82004338 ) 291 Main St. 41°33′36″N 72°39′01″W / 41.56°N 72.6503°W / 41.56; -72.6503 (U.S. Post Office ) Middletown 27 Wadsworth Estate Historic District Wadsworth Estate Historic District July 25, 1996 (#96000775 ) 15, 30, 33, 59, 73, and 89 Laurel Grove Rd., Wadsworth Falls State Park, and 421 Wadsworth St. 41°32′02″N 72°40′44″W / 41.5339°N 72.6789°W / 41.5339; -72.6789 (Wadsworth Estate Historic District ) Middletown 28 William and Mary Ward House Upload image July 27, 2021 (#100006787 ) 45 Paterson Dr. 41°31′03″N 72°39′19″W / 41.5176°N 72.6552°W / 41.5176; -72.6552 (William and Mary Ward House ) Middletown 29 Washington Street Historic District Washington Street Historic District May 9, 1985 (#85001018 ) Roughly bounded by Washington and Main Sts., Washington Terrace, and Vine St. 41°33′41″N 72°39′31″W / 41.561389°N 72.658611°W / 41.561389; -72.658611 (Washington Street Historic District ) Middletown 30 Seth Wetmore House Seth Wetmore House September 10, 1970 (#70000689 ) CT 66 and Camp Rd. 41°33′09″N 72°41′19″W / 41.5525°N 72.688611°W / 41.5525; -72.688611 (Seth Wetmore House ) Middletown 31 Wilcox, Crittenden Mill Wilcox, Crittenden Mill December 3, 1986 (#86003349 ) 234-315 S. Main St., Pameacha, and Highlands Aves. 41°32′54″N 72°39′19″W / 41.548333°N 72.655278°W / 41.548333; -72.655278 (Wilcox, Crittenden Mill ) Middletown 32 Captain Benjamin Williams House Captain Benjamin Williams House December 1, 1978 (#09000143 ) 27 Washington St., 41°33′47″N 72°38′54″W / 41.563003°N 72.648428°W / 41.563003; -72.648428 (Captain Benjamin Williams House ) Middletown 33 Woodrow Wilson High School Woodrow Wilson High School August 6, 1986 (#86002270 ) Hunting Hill Ave. and Russell St. 41°32′25″N 72°38′57″W / 41.540278°N 72.649167°W / 41.540278; -72.649167 (Woodrow Wilson High School ) Middletown 34 Xi Chapter, Psi Upsilon Fraternity Xi Chapter, Psi Upsilon Fraternity November 4, 2009 (#09000870 ) 242 High St. 41°33′24″N 72°39′18″W / 41.556689°N 72.654908°W / 41.556689; -72.654908 (Xi Chapter, Psi Upsilon Fraternity ) Middletown 35 YMCA of Northern Middlesex County YMCA of Northern Middlesex County January 23, 2023 (#100008583 ) 99 Union St. 41°33′24″N 72°38′48″W / 41.5568°N 72.6468°W / 41.5568; -72.6468 (YMCA of Northern Middlesex County ) Middletown