Within the district, three notable sites include the Naugatuck Green and its associated monuments. The area also contains 160 structures, with 137 (86%) recognized as contributing to the district’s historical significance. The 23 non-contributing structures were primarily built after 1948. Key contributing buildings include 30 institutional and commercial structures—such as five churches, three schools, two banks, the town library, firehouse, and railroad station—and 76 historic residences.

Among the district's 23 contributing outbuildings are seven barns and carriage houses, many of which have been converted to garages or adapted for other purposes. The remaining outbuildings are garages added to properties between 1920 and 1940, further reflecting the area’s evolving character.

Barnum Court

#1 | 14 Barnum Court - 20th-century vernacular, c. 1900 Non-contributing

#2 | 15 Barnum Court - CONGREGATIONAL PARSONAGE, Greek Revival, c. 1840 (moved) Contributing

#3 | 18 Barnum Court - Vernacular Queen Anne, c. 1880 Contributing

#4 | 21 Barnum Court - Vernacular Queen Anne, c. 1880 Contributing

#5 | 23 Barnum Court - 19th-century vernacular, c. 1890 Contributing

#6 | 27 Barnum Court - 20th-century vernacular, c. 1900 Contributing

Cedar Street

#7 | 21 Cedar Street - Modern commercial, c. 1950 Non-contributing

#8 | 23-25 Cedar Street - AMERICAN LEGION BUILDING, Colonial Revival, 1948 Contributing

1/3W-1 - Vacant lot (former park)

l/lW-13 - Vacant lot (former park)

Church Street

#9 | 84-92 Church Street - BARNUM BUILDING (2nd), late 19th-century commercial, 1894 Contributing

#10 | 98-100 Church Street - BARNUM BUILDING, commercial Italianate, 1887 Contributing

#11 | 108 Church Street - Commercial, modern facade, 1990 Contributing

#12 | 122-124 Church Street - Late 19th-century commercial, 1880 Contributing

#13 | 128-130 Church Street - MASONIC BUILDING, Neo-Classical Revival, 1900 Contributing

#14 | 132-136 Church Street - G.C. MURPHY STORE, Art Moderne, 1935 Contributing

#15 | 152-172 Church Street - Modern commercial, c. 1950 Non-contributing

#16 | 159-171 Church Street - Modern commercial, 1941 Contributing

#17 | 173 Church Street - Rock Church (former theater), 1945/1970 Contributing

#18 | 174-210 Church Street - HOPSON BLOCK, Renaissance Revival, 1896 Contributing

#19 | 175 Church Street - JOHN M. PAGE BUILDING, 19th-century commercial, 1890/1986 Contributing

#20 | 189-215 Church Street - NEARY BUILDING, Neo-Classical Revival/Baroque Contributing

#21 | 210 Church Street - ST. MICHAEL'S PARISH HOUSE, Gothic Revival/Neo-Classical Revival, 1908 Contributing

#22 | 210 Church Street (garage) - 1920 Contributing

#23 | 210 Church Street - ST. MICHAEL'S EPISCOPAL CHURCH, High Victorian Gothic, 1875 (David R. Brown) Contributing

#24 | 9/7W-8 Naugatuck Green - 1832/1895 (McKim, Mead & White) Contributing

#25 | 9/7W-8 Civil War Memorial - 1885 (Ryegate Granite Company, Vermont) Contributing

#26 | 9/7W-8 Memorial Fountain - 1895 (McKim, Mead & White) Contributing

#27 | 9/7W-8 Soldier's Monument - c. 1960–c. 1990 Non-contributing

#28 | 9/7W-8 Bandstand - c. 1990 Non-contributing

#29 | 239 Church Street - Naugatuck Town Hall, modern, 1965 Non-contributing

#30 | 243 Church Street - HOWARD WHITTEMORE MEMORIAL LIBRARY, Neo-Classical Revival, 1894 (McKim, Mead & White) Contributing

#31 | 251 Church Street - NAUGATUCK SAVINGS BANK, Neo-Classical Revival, 1910 (Crowe, Lewis, & Wickenhofer) Contributing

#32 | 266 Church Street - L.S. PLATT HOUSE, Queen Anne, c. 1900 Contributing

#33 | 270 Church Street - Modern commercial, c. 1950 Non-contributing

#34 | 275 Church Street - NAUGATUCK NATIONAL BANK, Neo-Classical Revival, 1930 Contributing

#35 | 284 Church Street - YOUNG MEN'S CHRISTIAN ASSOCIATION BUILDING, Neo-Classical Revival, 1924 (Jallade, Lindsay & Warren) Contributing

#36 | 285 Church Street - U.S. POST OFFICE, Spanish Colonial Revival, 1915 (James A. Wetmore) Contributing

#37 | 294 Church Street - ST. FRANCIS SCHOOL, Colonial Revival, 1892/1900 Contributing

#38 | 295 Church Street - Southern New England Telephone Building, Colonial Revival, 1950 Non-contributing

#39 | 297 Church Street - Queen Anne, c. 1890 Contributing

#40 | 297 Church Street (carriage house) - c. 1890 Contributing

#41 | 304 Church Street - ST. FRANCIS OF ASSISI CHURCH, Gothic Revival, 1882-1890 (James Murphy) Contributing

#42 | 305 Church Street - Modern office park, c. 1967 Non-contributing

#43 | 318 Church Street - ST. FRANCIS RECTORY, Second Empire, 1901-1903 Contributing

#44 | 327 Church Street - J. H. WHITTEMORE COMPANY BUILDING, Colonial Revival, 1900 Contributing

#45 | 331 Church Street - Modern commercial, c. 1983 Non-contributing

#46 | 333 Church Street - Site of former J. H. Whittemore House Contributing

#47 | 333 Church Street - Modern bank, Neo-Victorian, 1996 Non-contributing

#48 | 380 Church Street - BRONSON B. TUTTLE HOUSE, Queen Anne, c. 1880 (Robert Wakeman Hill) Contributing

Division Street

#49 | 15/5W-1 Division Street - CONGREGATIONAL CHURCH, Baroque/Neo-Classical Revival, 1903 (McKim, Mead & White) Contributing

#50 | 15/5W-1 Division Street - CONGREGATIONAL CHURCH PARISH HOUSE, Romanesque Revival, 1887 (Robert Wakeman Hill) Contributing

Fairview Avenue

#51 | 38 Fairview Avenue - Queen Anne, c. 1890 Contributing

#52 | 38 Fairview Avenue (garage) - c. 1950 Non-contributing

#53 | 46 Fairview Avenue - Queen Anne, 1895 Contributing

#54 | 46 Fairview Avenue (garage) - c. 1950 Non-contributing

#55 | 54 Fairview Avenue - Late 19th-century vernacular, c. 1890 Contributing

#56 | 54 Fairview Avenue (garage) - c. 1930 Contributing

#57 | 60 Fairview Avenue - CHITTENDEN HOUSE, Dutch Colonial Revival, 1914 Contributing

#58 | 60 Fairview Avenue (garage) - 1914 Contributing

#59 | 70 Fairview Avenue - Colonial Revival, 1925 Contributing

#60 | 70 Fairview Avenue (garage) - 1925 Contributing

#61 | 82 Fairview Avenue - LEWIS W. WARNER HOUSE, Shingle (former), c. 1895 Contributing

#62 | 82 Fairview Avenue (garage) - c. 1930 Contributing

#63 | 90 Fairview Avenue - CHARLES SPENCER HOUSE, Queen Anne, 1890 Contributing

#64 | 90 Fairview Avenue (garage) - c. 1930 Contributing

#65 | 94 Fairview Avenue - HOWARD HART HOUSE, Queen Anne, c. 1890 Contributing

#66 | 94 Fairview Avenue (garage) - c. 1930 Contributing

#67 | 108 Fairview Avenue - CLAREMONT TOLLES HOUSE, Colonial Revival, c. 1920 Contributing

#68 | 108 Fairview Avenue (garage) - c. 1920 Contributing

#69 | 116 Fairview Avenue - FREEMONT TOLLES HOUSE, Queen Anne, 1894 Contributing

#70 | 126 Fairview Avenue - WILLIAM J. NEARY HOUSE, Queen Anne, c. 1900 Contributing

#71 | 126 Fairview Avenue (garage) - c. 1930 Contributing

#72 | 136 Fairview Avenue - RICHARD FREEMAN HOUSE, Queen Anne, c. 1900 Contributing

#73 | 148 Fairview Avenue - Queen Anne, c. 1900 Contributing

#74 | 148 Fairview Avenue (garage) - c. 1920 Contributing

#75 | 156 Fairview Avenue - BRITTON WARD HOUSE, Queen Anne, c. 1880 Contributing

#76 | 156 Fairview Avenue (garage) - c. 1925 Contributing

#77 | 170 Fairview Avenue - Hillside Covenant Church Parsonage, Four-Square, 1918 Contributing

#78 | 170 Fairview Avenue (barn/garage) - c. 1900 Contributing

Hillside Avenue

#79 | 15-17 Hillside Avenue - Queen Anne, c. 1895 Contributing

#80 | 16 Hillside Avenue - Queen Anne, c. 1895 Contributing

#81 | 18 Hillside Avenue - ROBERT SMITH HOUSE, Queen Anne/Gothic Revival, c. 1880 Contributing

#82 | 19-25 Hillside Avenue - Queen Anne, c. 1895 Contributing

#83 | 51 Hillside Avenue - NAUGATUCK HIGH SCHOOL, Neo-Classical Revival, 1905 (McKim, Mead & White) Contributing

#84 | 126 Hillside Avenue - SWEDISH BETHANY CONGREGATIONAL CHURCH, c. 1860/c. 1930 Contributing

#85 | 142 Hillside Avenue - Modern split-level, 1981 Non-contributing

#86 | 148 Hillside Avenue - 19th-century vernacular, c. 1880 Contributing

#87 | 148 Hillside Avenue (garage) - c. 1935 Contributing

#88 | 158 Hillside Avenue - 20th-century vernacular, c. 1910 Contributing

Maple Street

#89 | 41 Maple Street - NAUGATUCK FIREHOUSE, 1909 Contributing

#90 | 58 Maple Street - GOODYEAR INDIA RUBBER GLOVE COMPANY OFFICE, Neo-Classical Revival, 1895/1937 Contributing This building was torn down in 2014.

Meadow Street

#91 | 9/46W-1 Meadow Street - LEWIS PARK, 1894 (with children’s playground) Contributing

#92 | 83 Meadow Street - Colonial Revival, c. 1895 Contributing

#93 | 87 Meadow Street - Queen Anne/Colonial Revival, c. 1890 Contributing

#94 | 93 Meadow Street - Queen Anne, c. 1890 Contributing

#95 | 124 Meadow Street - SALEM SCHOOL, Second Renaissance Revival, 1893 (McKim, Mead & White) Contributing

#96 | 15/46W-9 Meadow Street - WORLD WAR I MONUMENT, Neo-Classical Revival, 1921 (Evelyn Beatrice Longman/Henry Bacon) Contributing

#97 | 142 Meadow Street - RUFUS LEWIS HOUSE, Carpenter Gothic, c. 1880 Contributing

#98 | 152 Meadow Street - Queen Anne, c. 1890 Contributing

#99 | 155 Meadow Street - ROBERT V. PARKER HOUSE, Vernacular Italianate, c. 1890 Contributing

#100 | 156 Meadow Street - E.J. STEELE GOODELL LINES HOUSE, Vernacular Queen Anne, c. 1890 Contributing

#101 | 159 Meadow Street - WALTER E. GERRISH HOUSE, Colonial Revival, c. 1895 Contributing

#102 | 161 Meadow Street (rear) - FRANKLIN WARREN HOUSE, Vernacular, c. 1910 Contributing

#103 | 163 Meadow Street - Italianate, c. 1865 Contributing

#104 | 164 Meadow Street - JOHN A. KENNEDY HOUSE, Queen Anne/Colonial Revival, c. 1900 Contributing

#105 | 165-167 Meadow Street - WILLIAM H. CRAMPTON HOUSE, Vernacular, c. 1910 Contributing

#106 | 170 Meadow Street - Colonial Revival, c. 1900 Contributing

#107 | 171 Meadow Street - 19th-century vernacular, 1898 Contributing

#108 | 173 Meadow Street - GEORGE S. ANDREW HOUSE, Vernacular, c. 1900 Contributing

#109 | 174 Meadow Street - WILLIAM KENNEDY HOUSE, Colonial Revival, 1905 Contributing

#110 | 178 Meadow Street - J. RUSSELL SAUNDERS HOUSE, Colonial Revival, c. 1890 Contributing

#111 | 178 Meadow Street (garage) - c. 1980 Contributing

#112 | 181 Meadow Street - CHARLES B. ANDREW HOUSE, Vernacular, c. 1900 Contributing

#113 | 182-184 Meadow Street - Colonial Revival, c. 1890 Contributing

#114 | 185 Meadow Street - PATRICK & WILLIAM BRENNAN HOUSE, Queen Anne/Colonial Revival, 1889 Contributing

#115 | 191-193 Meadow Street - MARY E. DOOLING HOUSE, Queen Anne/Neo-Classical Revival, c. 1915 Contributing

#116 | 192 Meadow Street - Vernacular Queen Anne, c. 1900 Contributing

#117 | 195 Meadow Street - HENRY D. PATTERSON HOUSE, Vernacular cross-gable, c. 1880 Contributing

#118 | 195 Meadow Street (garage) - c. 1940 Contributing

#119 | 198 Meadow Street - Modern bank, 1964 Non-contributing

#120 | 201 Meadow Street - FRANK GRANT HOUSE, Vernacular, c. 1900/1940 Non-contributing

#121 | 205 Meadow Street - Vernacular, c. 1870 Contributing

#122 | 207 Meadow Street - LAWLAUS-GALVIN HOUSE, Vernacular cross-gable, c. 1910 Contributing

#123 | 208 Meadow Street - METHODIST EPISCOPAL CHURCH, 1887/1926 Contributing

#124 | 214 Meadow Street - ANNIE B. TUTTLE HOUSE, Colonial Revival, c. 1915 Contributing

#125 | 222 Meadow Street (garage) - c. 1940 Contributing

#126 | 223 Meadow Street - SISTERS OF MERCY CONVENT, Neo-Classical Revival, 1912 Contributing

#127 | 226 Meadow Street - BEECHER-GARRICK HOUSE, Italianate, c. 1877 Contributing

#128 | 230 Meadow Street - Vernacular Queen Anne, c. 1910 Contributing

#129 | 231 Meadow Street - 19th-century vernacular, 1887 Contributing

#130 | 235 Meadow Street - SWEENEY HOUSE, Vernacular cross-gable, c. 1880 Contributing

#131 | 235 Meadow Street (garage) - c. 1920 Contributing

#132 | 250 Meadow Street - G.A. LEWIS CARRIAGEHOUSE & STABLES, c. 1890/1924 Contributing

#133 | 257 Meadow Street - Outbuilding/playing field Non-contributing

#134 | 262 Meadow Street - Restaurant, 1978 Non-contributing

#135 | 300 Meadow Street - TUTTLE CARRIAGEHOUSE (Tuttle Music Shed), Stick style, c. 1880 Contributing

#136 | 300 Meadow Street (garage) - 1976 Non-contributing

Meadow Court

#137 | 5 Meadow Court - 20th-century vernacular, c. 1930 Contributing

Park Place

#138 | 15 Park Place - 20th-century vernacular, c. 1900 Contributing

#139 | 17 Park Place - Vernacular Queen Anne, c. 1890 Contributing

#140 | 18 Park Place - Neo-Classical Revival apartment, c. 1900 Contributing

#141 | 18 Park Place (garage) - c. 1940 Contributing

#142 | 19 Park Place - Vernacular Queen Anne, c. 1890 Contributing

#143 | 22 Park Place - AMERICAN RED CROSS BUILDING, Colonial Revival, c. 1930 Contributing

Water Street

#155 | 195 Water Street - NAUGATUCK RAILROAD STATION, Spanish Colonial Revival, 1910 (Henry Bacon) Contributing

Winslow Court

#156 | 1 Winslow Court - 20th-century vernacular, 1920 Contributing

#157 | 3 Winslow Court - Gothic Revival, c. 1870 Contributing

#158 | 5 Winslow Court - Queen Anne, c. 1880 Contributing

#159 | 15 Winslow Court - 20th-century vernacular, 1928 Contributing

#160 | 15/47W-31 Winslow Court - Brick outbuilding, 1964 Non-contributing

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