Historic Inventory Survey
Throughout 2016 and 2017 the Sturbridge Historic Resources Inventory was commissioned by the Town of Sturbridge, administered by the Sturbridge Historical Commission (SHC), prepared by the Pioneer Valley Planning Commission (PVPC), and supported by Sturbridge Community Preservation Act funds. The "Historic Resources Inventory Final Report" report discusses the methodology, results, and final recommendations of the four-phase project, which took place during this time frame.
In 2018 the Sturbridge Historic Resources Inventory was prepared by the Public Archaeology Laborartory (PAL). "The Final Report Sturbridge Community-wide Historic Properties Survey Update Phase II" discusses results of this phase.
Throughout 2024 and 2025 the Sturbridge Historic Resources Inventory was prepared by Easton Architects. This survey effort marks Phase III of the Stubridge Community Wide Historic Properties Survey Update. The goal of this project was to fill gaps in previous survey documentation through survey efforts targeting specific themes and areas identified by the Sturbridge Historical Commission. The "Community Wide Historic Properties Survey Update Survey Report" discusses the results of this phase.
The following list was narrowed to the most significant resources using the following criteria:
- Historic buildings that are potentially threatened, including some which were previously inventoried;
- Historic buildings which appear to be eligible for the National Register, either individually or related within a district;
- Historic buildings with special significance to Sturbridge; and/or
- Architecturally distinguished historic buildings, or those that are an excellent example of style, with moderate to good integrity.
The following list is made up of multiple surveying efforts.
Historic Area Inventory
Historic Building Inventory
Following is an inventory of some of the historic homes and buildings in the Town of Sturbridge. Further information on each property can be accessed by clicking on the "Historic Name." This is just a sample of historic structures in Sturbridge. For a complete list or more information about Massachusetts Cultural Resources, please visit the MACRIS site.
View the Historic Building Inventory in the GIS StoryMap here.
Street Number | Street Name | Historic Name | Year | Style | Notes |
|---|---|---|---|---|---|
| 26 | Allen Road | Joel & Martha Plimpton House | ca. 1786 | Cape form | |
| 54 | Allen Road | 54 Allen Road | 1997 | No Style | |
| 56 | Allen Road | 56 Allen Road | 1997 | No Style | |
| 58 | Allen Road | 58 Allen Road | 1998 | No Style | |
| 60 | Allen Road | 60 Allen Road | 1988 | No Style | |
| 62 | Allen Road | 62 Allen Road | 1988 | No Style | |
| 157 | Arnold Road | Sturbridge District School No. 5 | ca. 1831 | No Style | |
| 3 | Auger Street | ca. 1855 | No Style | ||
| 7 | Auger Street | 1857-1870 | No Style | ||
| 11 | Auger Street | Heck Residence | ca. 1850 | Late Federal | |
| 4 | Bates Court | ca. 1873 | Industrial Frame | ||
| 4 | Bates Court | Former Tenement House | ca. 1873 | Industrial Frame | |
| 8 | Bates Hill Road | 1836 | Federal | ||
| 10 | Bates Hill Road | ca. 1780 | Cape Form | ||
| 11 | Bates Hill Road | 11 Bates Hill Road | 1876 | No Style | |
| 12 | Bates Hill Road | 12 Bates Hill Road | 1880 | No Style | |
| 18 | Bates Hill Road | 18 Bates Hill Road | 1876 | No Style | |
| 19 | Bates Hill Road | 19 Bates Hill Road | 1870 | No Style | |
| 20 | Bates Hill Road | 20 Bates Hill Road | 1866 | No Style | |
| 34 | Beach Avenue | 34 Beach Avenue | 1988 | No Style | |
| 38 | Beach Avenue | 38 Beach Avenue | 1935 | Ranch | |
| 40 | Beach Avenue | 40 Beach Avenue | 1996 | No Style | |
| 42 | Beach Avenue | 42 Beach Avenue | ca. 1966 | No Style | |
| 48 | Beach Avenue | 48 Beach Avenue | 1940 | No Style | |
| 50 | Beach Avenue | 50 Beach Avenue | 1973 | Ranch | |
| 53 | Beach Avenue | 53 Beach Avenue | 2002 | No Style | |
| 55 | Beach Avenue | 55 Beach Avenue | 1920 | No Style | |
| 57 | Beach Avenue | 57 Beach Avenue | 1927 | No Style | |
| 61 | Beach Avenue | 61 Beach Avenue | ca. 1938 | No Style | |
| 63 | Beach Avenue | 63 Beach Avenue | 1940 | No Style | |
| 67 | Beach Avenue | 67 Beach Avenue | 1930 | No Style | |
| 73 | Beach Avenue | 73 Beach Avenue | 2001 | No Style | |
| 17 | Bennetts Road | Thomas Gray Cottage | 1930 | Craftsman | Original House (STU.221) was demolished in 2017. Garage remains extant. |
| 19 | Bennetts Road | 19 Bennetts Road | 1930 | No Style | |
| 21 | Bennetts Road | 21 Bennetts Road | 1950 | No Style | 2nd Story and deck constructed in 2015. |
| 29 | Bennetts Road | 29 Bennetts Road | 1965 | No Style | |
| 31 | Bennetts Road | 31 Bennetts Road | 2003 | No Style | |
| 35 | Bennetts Road | 35 Bennetts Road | 2006 | No Style | |
| 37 | Bennetts Road | 37 Bennetts Road | 1946 | No Style | |
| 39 | Bennetts Road | 39 Bennetts Road | 1996 | No Style | |
| 41 | Bennetts Road | 41 Bennetts Road | 1993 | No Style | |
| 43 | Bennetts Road | 43 Bennetts Road | 1945 | No Style | |
| 45 | Bennetts Road | 45 Bennetts Road | 1930 | No Style | |
| 47 | Bennetts Road | 47 Bennetts Road | 1989 | No Style | |
| 49 | Bennetts Road | 49 Bennetts Road | 1945 | No Style | |
| 51 | Bennetts Road | 1935 | Front-Gabeled Cottage | 2nd story constructed in 2023. | |
| 53 | Bennetts Road | 53 Bennetts Road | 1938 | No Style | |
| 55 | Bennetts Road | 55 Bennetts Road | 2018 | No Style | Constructed following the demo of an older building. |
| 57 | Bennetts Road | 57 Bennetts Road | 1990 | No Style | |
| 59 | Bennetts Road | 59 Bennetts Road | 2022 | No Style | Constructed following the demo of an older building. |
| 61 | Bennetts Road | 61 Bennetts Road | 1991 | No Style | |
| 63 | Bennetts Road | 63 Bennetts Road | 1977 | No Style | |
| 65 | Bennetts Road | 65 Bennetts Road | 1995 | No Style | |
| 67 | Bennetts Road | 67 Bennetts Road | 1933 | No Style | Massing suggests alterations made; date unknown. |
| 71 | Bennetts Road | 71 Bennetts Road | 2002 | No Style | |
| 2 | Brookfield Road | ca. 1855 | No Style | ||
| 8 | Brookfield Road | Fire Station | 1922 | Modern | |
| 8 | Brookfield Road | VFW Building | ca. 1900 | Modern Commercial | |
| 29 | Brookfield Road | 1939 | no style | ||
| 55 | Brookfield Road | Patrick and Mary Jarret House | 1878-1892 | Queen Anne | |
| 60 | Brookfield Road | Eliab and Fanny Marsh House | ca. 1814 | Federal | |
| 142 | Brookfield Road | Joseph Marsh House | ca. 1760 | Georgian | |
| 213 | Brookfield Road | Eliab and Fanny Marsh House | ca. 1975 | Georgian to Federal | |
| 231 | Brookfield Road | Jonathan Philips Curtis Farm | ca. 1804 | Cape altered to Ranch | |
| 249 | Brookfield Road | ca. 1913 | Craftsman | ||
| 285 | Brookfield Road | 1784-1795 | Cape form | ||
| 6 | Cedar Street | Sturbridge Veterinary Hospital | 1966 | Modern | |
| 83 | Cedar Street | Thomas Marsh Farm Building | ca. 1860 | no style | |
| 2-8 | Chamberlain Avenue | Jared Lamb Building | 1815-1825 | Federal | |
| 10 | Chamberlain Avenue | Simeon Allen House | ca. 1820 | Greek Revival | |
| 12 | Chamberlain Avenue | Allen-Bachellor House | ca. 1800 | Federal | |
| 12 | Champeaux | ca. 1762 | Georgian | ||
| 4 | Charlton Street | James Bachellor House | 1836 | Greek Revival | |
| 5 | Charlton Street | Jared Lamb House | ca. 1821 | Greek Revival | |
| 6 | Charlton Street | Alvan Bond House and Gifford Barn | ca. 1821 | Greek Revival | |
| 9 | Charlton Street | Merrick House and Cooper Barn | 1815-1825 | Federal | |
| 10 | Charlton Street | George Davis House and Barn | ca. 1812 | Greek Revival | |
| 13 | Charlton Street | Drew Corey Bullock Place | 1929 | Dutch Colonial | |
| 14 | Charlton Street | Rockwood House | 1935 | N/A | |
| 16 | Charlton Street | Otis Warner Shop | ca. 1835 | No Style | |
| 17 | Charlton Street | Roswell Warner House and Barn | 1815-1820 | Federal | |
| 18 | Charlton Street | Lewis Pelton House | ca. 1834 | Greek Revival | |
| 20 | Charlton Street | Albert Freeman House | 1918-1925 | No Style | |
| 3-5 | Church Street | Fiskdale Mills Worker Housing | 1870-1898 | No Style | |
| 3 | Church Street | Boudreau House | 1873 | Greek Revival | |
| 5 | Church Street | Mill Worker Housing | 1873 | Greek Revival | |
| 7 | Church Street | Kirby Estate | 1873 | Greek Revival | |
| 16 | Church Street | St. Anne's Church & Shrine | 1883 | Italian Gothic | |
| 16 | Church Street | St. Anne's Rectory | 1887 | No Style | |
| 20 | Church Street | St. Patrick's Church | 1883 | Victorian | |
| 20 | Church Street | St. Anne's Pavillion | N/A | No Style | |
| 20 | Church Street | St. Anne's Outdoor Shrine | N/A | No Style | |
| 1 | Commonwealth Ave | 1 Commonwealth Ave | 1875 | No Style | |
| 2 | Country Hill Road | 2 Country Hill Road | 1999 | No Style | |
| 4 | Country Hill Road | 4 Country Hill Road | 1961 | No Style | |
| 6 | Country Hill Road | 6 Country Hill Road | 1964 | No Style | |
| 7 | Country Hill Road | 7 Country Hill Road | 1969 | No Style | |
| 9 | Country Hill Road | 9 Country Hill Road | 1970 | No Style | |
| 11 | Country Hill Road | 11 Country Hill Road | 1970 | Split-Level (Bi-Level) | |
| 12 | Country Hill Road | 12 Country Hill Road | 1969 | Split-Level | |
| 15 | Country Hill Road | 15 Country Hill Road | 1970 | Cape | |
| 16 | Country Hill Road | 16 Country Hill Road | 1970 | Garrison Colonial | |
| 7 | Cove Drive | 7 Cove Drive | 2021 | No Style | |
| 9 | Cove Drive | 9 Cove Drive | 1965 | No Style | |
| 11 | Cove Drive | 11 Cove Drive | 1996 | No Style | |
| 13 | Cove Drive | 13 Cove Drive | 1967 | Ranch | |
| 15 | Cove Drive | 15 Cove Drive | 1975 | No Style | |
| 2 | Cricket Drive | 2 Cricket Drive | 1966 | Ranch | |
| 4 | Cricket Drive | 4 Cricket Drive | 1965 | Split-Level (Bi-Level) | |
| 5 | Cricket Drive | 5 Cricket Drive | 1965 | Ranch | |
| 6 | Cricket Drive | 6 Cricket Drive | 1966 | Split-Level (Bi-Level) | |
| 10 | Cricket Drive | 10 Cricket Drive | 1966 | Cape | |
| 11 | Cricket Drive | 11 Cricket Drive | 1965 | Cape | |
| 12 | Cricket Drive | 12 Cricket Drive | 1965 | Cape | |
| 14 | Cricket Drive | 14 Cricket Drive | 1965 | Split-Level (Tri-Level) | |
| 15 | Cricket Drive | 15 Cricket Drive | 1965 | Ranch | |
| 19 | Cricket Drive | 19 Cricket Drive | 1966 | Split-Level (Bi-Level) | |
| 21 | Cricket Drive | 21 Cricket Drive | 1966 | Split-Level (Bi-Level) | |
| 23 | Cricket Drive | 23 Cricket Drive | 1966 | Cape | |
| 24 | Cricket Drive | 24 Cricket Drive | 1967 | Garrison Colonial | |
| 27 | Cricket Drive | 27 Cricket Drive | 1966 | Ranch | |
| 28 | Cricket Drive | 28 Cricket Drive | 1967 | Split-Level (Tri-Level) | |
| 29 | Cricket Drive | 29 Cricket Drive | 1968 | Cape | |
| 30 | Cricket Drive | 30 Cricket Drive | 1966 | Cape | |
| 34 | Cricket Drive | 34 Cricket Drive | 1971 | Split-Level (Bi-Level) | |
| 36 | Cricket Drive | 36 Cricket Drive | 1969 | Split-Level (Tri-Level) | |
| 37 | Cricket Drive | 37 Cricket Drive | 1968 | Ranch | |
| 38 | Cricket Drive | 38 Cricket Drive | 1968 | Split-Level (Bi-Level) | |
| 42 | Cricket Drive | 42 Cricket Drive | 2003 | Split-Level (Tri-Level) | |
| 43 | Cricket Drive | 43 Cricket Drive | 1968 | Ranch | |
| 45 | Cricket Drive | 45 Cricket Drive | 1968 | Split-Level (Bi-Level) | |
| 48 | Cricket Drive | 48 Cricket Drive | 1969 | Split-Level (Tri-Level) | |
| 49 | Cricket Drive | 49 Cricket Drive | 1968 | Cape | |
| 51 | Cricket Drive | 51 Cricket Drive | 1968 | Split-Level (Bi-Level) | |
| 53 | Cricket Drive | 53 Cricket Drive | 1968 | Cape | |
| 54 | Cricket Drive | 54 Cricket Drive | 1968 | Split-Level (Bi-Level) | |
| 56 | Cricket Drive | 56 Cricket Drive | 1968 | Split-Level (Tri-Level) | |
| 60 | Cricket Drive | 60 Cricket Drive | 1971 | Split-Level (Bi-Level) | |
| 61 | Cricket Drive | 61 Cricket Drive | 1966 | Split-Level (Tri-Level) | |
| 62 | Cricket Drive | 62 Cricket Drive | 1967 | Split-Level (Bi-Level) | |
| 63 | Cricket Drive | 63 Cricket Drive | 1969 | Split-Level (Bi-Level) | |
| 64 | Cricket Drive | 64 Cricket Drive | 1968 | Split-Level (Tri-Level) | |
| 67 | Cricket Drive | 67 Cricket Drive | 1968 | Garrison Colonial | |
| 68 | Cricket Drive | 68 Cricket Drive | 1968 | Split-Level (Tri-Level) | |
| 69 | Cricket Drive | 69 Cricket Drive | 1968 | Split-Level (Tri-Level) | |
| 70 | Cricket Drive | 70 Cricket Drive | 1968 | Split-Level (Tri-Level) | |
| 71 | Cricket Drive | 71 Cricket Drive | 1968 | Cape | |
| 74 | Cricket Drive | 74 Cricket Drive | 1969 | Split-Level (Bi-Level) | |
| 75 | Cricket Drive | 75 Cricket Drive | 1968 | Split-Level (Tri-Level) | |
| 76 | Cricket Drive | 76 Cricket Drive | 1969 | No Style | |
| 77 | Cricket Drive | 77 Cricket Drive | 1969 | Ranch | |
| 80 | Cricket Drive | 80 Cricket Drive | 1968 | Split-Level (Tri-Level) | |
| 82 | Cricket Drive | 82 Cricket Drive | 1972 | Split-Level | |
| 83 | Cricket Drive | 83 Cricket Drive | 2005 | No Style | |
| 84 | Cricket Drive | 84 Cricket Drive | 1970 | No Style | |
| 87 | Cricket Drive | 87 Cricket Drive | 1971 | Split-Level (Tri-Level) | |
| 89 | Cricket Drive | 89 Cricket Drive | 1971 | Cape | |
| 91 | Cricket Drive | 91 Cricket Drive | 1974 | No Style | |
| 94 | Cricket Drive | 94 Cricket Drive | 1974 | Split-Level (Bi-Level) | |
| 95 | Cricket Drive | 95 Cricket Drive | 1971 | Ranch | |
| 97 | Cricket Drive | 97 Cricket Drive | 1976 | Cape | |
| 98 | Cricket Drive | 98 Cricket Drive | 1974 | No Style | |
| 99 | Cricket Drive | 99 Cricket Drive | 1981 | Garrison Colonial | |
| 100 | Cricket Drive | 100 Cricket Drive | 1976 | Cape | |
| 101 | Cricket Drive | 101 Cricket Drive | 2006 | No Style | |
| 102 | Cricket Drive | 102 Cricket Drive | 1979 | No Style | |
| 14 | Douty Road | late 1700s - early 1800s | Georgian | ||
| 16 | Eastern Avenue | 16 Eastern Avenue | 2013 | No Style | |
| 3 | Fall Road | 3 Fall Road | 1956 | Ranch | |
| 6 | Fall Road | 6 Fall Road | 1970 | Split-Level (Bi-Level) | |
| 26 | Farquhar Road | William R. Farquhar/W. and M. Edwards House | ca. 1944 | Colonial Revival | |
| 47 | Farquhar Road | Samuel, Jr. and Mary Morse House | ca. 1800 | Georgian | |
| 77 | Farquhar Road | James and Elizabeth Belknap House | ca. 1864 | Raised Cape | |
| 2 | Field Drive | 2 Field Drive | 1981 | No Style | |
| 3 | Field Drive | 3 Field Drive | 1983 | Ranch | |
| 8 | Fiske Hill Road | Otis E. Leach House | by 1931 | Classical Revival | |
| 12 | Fiske Hill Road | Harry H. Pickles House | pre 1931 | Classiscal Revival | |
| 15 | Fiske Hill Road | before 1944 | Greek or Classical Revival | ||
| 24 | Fiske Hill Road | Westwell Residence | ca. 1815-1817 | Federal | |
| 55 | Fiske Hill Road | ca. 1940 | Colonial Revival | ||
| 56 | Fiske Hill Road | Clifford A. Harvey House | 1954 | Cape | |
| 60 | Fiske Hill Road | Raymond M. Burnham House | 1922-1930 | Colonial Revival | |
| 63 | Fiske Hill Road | Alvino A. Alberti House | 1973 | French Revival/Chateauesque | |
| 66 | Fiske Hill Road | David Fiske House | 1786 | Federal with alterations | |
| 71 | Fiske Hill Road | First Well on Fiske Hill | 1730's | Plaque/Memorial | |
| 77 | Fiske Hill Road | 1832, 1937 | Federal to Colonial | ||
| 85 | Fiske Hill Road | Daniel Fiske II House | ca. 1811 | Colonial (Georgian) with alterations | |
| 96 | Fiske Hill Road | Plaque in Memory of Fiske Hill School | 1949 | Plaque/Memorial | |
| 108 | Fiske Hill Road | Fiske-Matys Residence | Early 1800s | Modern | |
| 120 | Fiske Hill Road | Capt. Simeon Fiske/Simeon F. Marsh House | ca. 1804 | Georgian with alterations | |
| 205 | Fiske Hill Road | Ebenezar Cutting/Edward Nichols House and Barn | 1812 | Georgian with alterations | |
| 1 | Glen Ridge Road | 1 Glen Ridge Road | 1970 | No Style | |
| 2 | Glen Ridge Road | 2 Glen Ridge Road | 1981 | No Style | |
| 3 | Glen Ridge Road | 3 Glen Ridge Road | 1981 | Split-Level (Bi-Level) | |
| 6 | Glen Ridge Road | 6 Glen Ridge Road | 1999 | Ranch | |
| 7 | Glen Ridge Road | 7 Glen Ridge Road | 1954 | Ranch | |
| 10 | Glen Ridge Road | 10 Glen Ridge Road | 1972 | Ranch | |
| 11 | Glen Ridge Road | 11 Glen Ridge Road | 1981 | No Style | |
| 12 | Glen Ridge Road | 12 Glen Ridge Road | 1983 | Ranch | |
| 2 | Grasshopper Lane | 2 Grasshopper Lane | 1979 | No Style | |
| 4 | Grasshopper Lane | 4 Grasshopper Lane | 1965 | Split-Level (Bi-Level) | |
| 5 | Grasshopper Lane | 5 Grasshopper Lane | 1965 | Split-Level (Bi-Level) | |
| 6 | Grasshopper Lane | 6 Grasshopper Lane | 1964 | Ranch | |
| 7 | Grasshopper Lane | 7 Grasshopper Lane | 1964 | Ranch | |
| 10 | Grasshopper Lane | 10 Grasshopper Lane | 1964 | Split-Level (Bi-Level) | |
| 11 | Grasshopper Lane | 11 Grasshopper Lane | 1965 | Split-Level (Bi-Level) | |
| 13 | Grasshopper Lane | 13 Grasshopper Lane | 1964 | Cape | |
| 15 | Grasshopper Lane | 15 Grasshopper Lane | 1964 | Ranch | |
| 16 | Grasshopper Lane | 16 Grasshopper Lane | 1965 | Split-Level (Bi-Level) | |
| 23 | Hall Road | Samuel and Lucy Hobbs House | ca. 1775 | Georgian | |
| 13 | Harrington Court | 13 Harrington Court | 1995 | No Style | |
| 14 | Harrington Court | 14 Harrington Court | 1977 | Contemporary | |
| 15 | Harrington Court | 15 Harrington Court | 1986 | Contemporary | |
| 1 | Haynes Street | Daniel Plimpton House | ca. 1800 | Utilitarian | |
| 3 | Haynes Street | Haynes Family House | 1830-1850 | Greek Revival | |
| 3 | Haynes Street | Barn | 1935 | Gambrel | |
| 5 | Haynes Street | Deacon Dunton House | ca. 1780 | Federal | |
| 12 | Haynes Street | Orchard Inn Area | 1964 - 1970 | Modern | |
| 2-6 | High Street | Fiskdale Mills Worker Duplex | 1870-1894 | No Style | |
| 4 | High Street | Fiske-Joseph Cartier- Walter Clarke - Oliver Vickers - Boone House | ca. 1873 | Simple Greek Revival | |
| 6 | High Street | ca. 1873 | Simple Greek Revival | ||
| 21 | High Street | Peloquin to Zuiss to Chicoine | 1873 | Greek Revival | |
| 8 | Hinman Street | ca. 1812 | Cape Cod | ||
| 14 | Hinman Street | Bates-Thorpe House | 1880-1890 | Late Victorian | |
| 6 | Holland Road | 6 Holland Road | 1850 | No Style | |
| 8 | Holland Road | 8 Holland Road | 1860 | No Style | |
| 9 | Holland Road | Fiskdale Upper Mill | 1865, 1869, 1875-1921, 1933-1952, 1975 | No Style | |
| 100 | Holland Road | George and Mary Eliza Holmes House | ca. 1850 | No style | |
| 220 | Holland Road | ca. 1880 | Federal | ||
| 222 | Holland Road | District #4 Schoolhouse | ca. 1855 | Uilitarian | |
| 224 | Holland Road | ca. 1793 | Federal | ||
| 6 | Jerry Road | 6 Jerry Road | 1985 | Split-Level (Bi-Level) | |
| 3 | Lakeshore Drive | 3 Lakeshore Drive | 1940 | No Style | |
| 11 | Lakeshore Drive | 11 Lakeshore Drive | 1985 | No Style | |
| 13 | Lakeshore Drive | 13 Lakeshore Drive | 1987 | Garrison Colonial | |
| 19 | Lakeshore Drive | 19 Lakeshore Drive | 1983 | Cape | |
| 21 | Lakeshore Drive | 21 Lakeshore Drive | 1985 | Ranch | |
| 23 | Lakeshore Drive | 23 Lakeshore Drive | 1985 | Cape | |
| 27 | Lakeshore Drive | 27 Lakeshore Drive | 1984 | Ranch | |
| 29 | Lakeshore Drive | 29 Lakeshore Drive | 1900 & 1960 | No Style | |
| 3 | Lakewood Trail | 3 Lakewood Trail | 1986 | No Style | |
| 4 | Lakewood Trail | 4 Lakewood Trail | 1985 | Cape | |
| 5 | Lakewood Trail | 5 Lakewood Trail | 2004 | No Style | |
| 6 | Lakewood Trail | 6 Lakewood Trail | 1986 | No Style | |
| 7 | Lakewood Trail | 7 Lakewood Trail | 1985 | No Style | |
| 8 | Lakewood Trail | 8 Lakewood Trail | 1986 | Cape | |
| 9 | Lakewood Trail | 9 Lakewood Trail | 1999 | No Style | |
| 10 | Lakewood Trail | 10 Lakewood Trail | 1988 | No Style | |
| 1 | Library Lane | 1 Library Lane | 1988 | No Style | |
| 3 | Library Lane | 3 Library Lane | 1967 | No Style | |
| 5 | Library Lane | 5 Library Lane | 1970 | Garrison Colonial | |
| 7 | Library Lane | 7 Library Lane | 1938 & 1970 | No Style | Two dwellings on the property. |
| 9 | Library Lane | 9 Library Lane | 1930 | No Style | |
| 10 | Library Lane | 10 Library Lane | 1970 | No Style | |
| 11 | Library Lane | 11 Library Lane | 1930 | No Style | |
| 13 | Library Lane | 13 Library Lane | 1935 | No Style | |
| 17 | Library Lane | 17 Library Lane | 1939 | Ranch | |
| 19 | Library Lane | 19 Library Lane | 1962 | No Style | |
| 23 | Library Lane | 23 Library Lane | 1962 | Ranch | |
| 25 | Library Lane | 25 Library Lane | 1937 | Ranch & No Style | Two dwellings on the property. |
| 29 | Library Lane | 29 Library Lane | 1942 & 2002 | No Style | Two dwellings on the property. |
| 7 | Long Avenue | 7 Long Avenue | 1910 | Unknown | |
| 12 | Long Avenue | 12 Long Avenue | 1958 | No Style | |
| 13 | Long Avenue | 13 Long Avenue | 2001 | No Style | |
| 14 | Long Avenue | 14 Long Avenue | 1947 | No Style | |
| 15 | Long Avenue | 15 Long Avenue | 1973 | No Style | |
| 16 | Long Avenue | 16 Long Avenue | 1940 | No Style | |
| 19 | Long Avenue | 19 Long Avenue | 1938 | No Style | |
| 20 | Long Avenue | 20 Long Avenue | 1926 | No Style | |
| 21 | Long Avenue | 21 Long Avenue | 1945 | No Style | |
| 22 | Long Avenue | 22 Long Avenue | 1910 | No Style | |
| 23 | Long Avenue | 23 Long Avenue | 1998 | No Style | |
| 24 | Long Avenue | 24 Long Avenue | 1927 | No Style | |
| 25 | Long Avenue | 25 Long Avenue | 1938 | No Style | |
| 26 | Long Avenue | 26 Long Avenue | 2017 | No Style | |
| 28 | Long Avenue | 28 Long Avenue | 1950 | No Style | |
| 29 | Long Avenue | 29 Long Avenue | 1935 | No Style | |
| 12 | Main Street | ca. 1869 | raised Cape | ||
| 60 | Main Street | 1946 | Minimal Traditional | ||
| 70 | Main Street | Eugene Gabree Investment House | ca. 1919 | Colonial Revival | |
| 75 | Main Street | Andre and Lillian Pinel House | 1941 | Minimal Traditional | |
| 82 | Main Street | John and Eva Ryan House | 1925 | Craftsman | |
| 171 | Main Street | Sylvanus W. Stone House | ca. 1855 | no style | |
| 204 | Main Street | 1937 | Tudor Revival | ||
| 258 | Main Street | Sturbridge Professional Center | 1970 | Neo-Federal | |
| 260 | Main Street | Dr. Jacob Corey House | 1805-1815 | Federal | |
| 262 | Main Street | Deacon George Davis House | 1815-1825 | Federal | |
| 265 | Main Street | East Schoolhouse | ca. 1832 | Federal | |
| 266 | Main Street | Roswell Warner House and Barn | ca. 1800 | Federal | |
| 267 | Main Street | No Name | 1829-1844 | No Style | |
| 269 | Main Street | John and Sally Paine House | ca. 1805 | Federal and Greek Revival | |
| 271 | Main Street | Fayette A. Eldridge House | 1918 | No Style | |
| 272 | Main Street | Benjamin D. Hyde House | ca. 1843 | Gothic Revival | |
| 274 | Main Street | John Coburn House | ca. 1783 | Federal | |
| 275 | Main Street | Chamberlain House | 1918 | Colonial Revival | |
| 277 | Main Street | Publick House Area | 1772, 1870, 1904-1911, 1938, 1965, 1971-1977, 2010, 2017 | Federal, Colonial Revival | |
| 277 | Main Street | Publick House | 1772 | Colonial | |
| 283 | Main Street | Wheelock-Champion-Bachellor House | ca. 1820-1857 | Greek Revival | |
| 293 | Main Street | Old Burial Ground | 1750 | Cemetery | |
| 301 | Main Street | Sturbridge Center School | 1855 | Greek Revival | |
| 306 | Main Street | Joshua Hyde Public Library | 1896 | Colonial Revival | |
| 308 | Main Street | Sturbridge Town Hall | 1836, 1858, 1910 | Greek Revival, Colonial Revival | |
310 | Main Street | Oliver B. Wight House | ca. 1832 | Greek Revival | |
| 320 | Main Street | Candy & Gift Shop | ca. 1955 | New-Greek Revival | |
| 331 | Main Street | Southbridge and Sturbridge Street Railway Substation | ca. 1898 | Colonial Revival | |
| 366 | Main Street | Brimfield Congrestional Church Conference Hall | ca. 1820 | Greek Revival | |
| 369 | Main Street | Wight Motel Area - East Lodge | 1963 | Colonial Revival | |
| 369 | Main Street | Wight Motel Area - Northeast Lodge | 1963 | Colonial Revival | |
| 369 | Main Street | Wight Motel Area - Mixed-Use Lodge | 1963 | Colonial Revival | |
| 369 | Main Street | Wight Motel Area - Southeast Lodge | 1963 | Colonial Revival | |
| 369 | Main Street | Wight Motel Area - Reeder House | 1963 | Colonial Revival | |
| 369 | Main Street | Wight Motel Area - Southwest Lodge | 1963 | Colonial Revival | |
| 371 | Main Street | 1836 | Greek Revival | ||
| 371 | Main Street | 1957 | Neo-Colonial | ||
| 379 | Main Street | 1958 | Pseudo Colonial | ||
| 407 | Main Street | George E. Richards House and Barn | ca. 1874 | Italianate | |
| 408 | Main Street | J. Dwight Underwood House | ca. 1884 | Queen Anne | |
| 413 | Main Street | George E. Richards Rental House | ca. 1886 | Italianate | |
| 419 | Main Street | Alpheus Wight Barn | ca. 1790 | Greek Revial | |
| 421 | Main Street | Snell Manufacturing Company Auger Shop/Wight-Snell Trailrace | 1855, 2007 & 2010 | No Style | |
| 423 | Main Street | D.W. Wight House | 1870-1894 | Greek Revival | |
| 425 | Main Street | F. Wight House | 1857 | Federal | |
| 433 | Main Street | 1912 | Greek Revival | ||
| 440 | Main Street | Sturbridge Trading Post | ca. 1957 | One-Story Modern | |
| 441 | Main Street | Village Farms | ca. 1950 | Road Stand | |
| 441 | Main Street | Snell Manufacturing Company Forge Shop/APCO Building/Securos Building | 1907 & 1928, 1945-1966, 1980, 1983 | No Style | |
| 446 | Main Street | Manderville Restaurant | ca. 1945 | Neo-Colonial | |
| 448 | Main Street | Cheese House | 1971 | Cheese Wheel Shape | |
| 450 | Main Street | George Holley House/Stageloft Repertory Theater Building | ca. 1880, 1981 | Greek Revival, No Style | |
| 454 | Main Street | Livingston Shumway House | ca. 1846 | Greek Revival | |
| 458 | Main Street | Snell Co. Employee Apartment House | ca. 1870 | Cottage | |
| 458 | Main Street | Apartment House | ca. 1870 | Cottage | |
| 464 | Main Street | Clarence Stone House | 1936 | Modern Cape Cod | |
| 468 | Main Street | Martin L. Phillips House and Barn | ca. 1900 | Queen Anne | |
| 472 | Main Street | Daniel Wight House/Wight Barn | ca. 1876 | Italianate | |
| 473 | Main Street | John and Lizzie Hooker House and Barn | ca. 1887 | Queen Anne | |
| 478 | Main Street | 478 Main Street | 1949 | Modern Garrison | |
| 479 | Main Street | Lucius Snell House | 1857-1870 | Italianate | |
| 480 | Main Street | 1874 | Italianate | ||
| 484 | Main Street | Jabez Westgate House and Barn | ca. 1840 | Greek Revival | |
| 500 | Main Street | Auto Museum | 1960 | Cinder Block | |
| 501 | Main Street | Moses and Lucy Morris House; Pink Haven Motel | 1830-1831, 1950, 1959 | No Style | |
| 502 | Main Street | Emory L. Bates House and Barn | ca. 1855 | Greek Revival | |
| 504 | Main Street | David and Rebecca Atherton House | ca. 1842 | Greek Revival | |
| 506 | Main Street | Parker's Garage | ca. 1930 | No Style | |
| 507 | Main Street | Sturbridge Second Adventist Church | ca. 1892 | No Style | |
| 509 | Main Street | Hiram and Seraph Hayward House | ca. 1846 | Greek Revival | |
| 510 | Main Street | ca. 1840 | No Style | ||
| 511 | Main Street | Hiram and Seraph Hayward House | ca. 1846 | Greek Revival | |
| 514 | Main Street | Truman Charles House | ca. 1841 | Greek Revival | |
| 518 | Main Street | Fiskdale Baptist Church Vestry | 1857-1870 | Greek Revival | |
| 524 | Main Street | Horatio N. Drake House | ca. 1835 | Greek Revival | |
| 528 | Main Street | ca. 1832 | Greek Revival | ||
| 530 | Main Street | ca. 1895 | Greek Revival | ||
| 531 | Main Street | Fiskdale Mill Blacksmith Shop | 1857-1870 | No Style | |
| 538 | Main Street | ca. 1836 | No Style | ||
| 538 | Main Street | Fiskdale House | pre-1857 | Greek Revival | |
| 544 | Main Street | Lemuel Lumbard Building | 1836-1857 | Greek Revival | |
| 546 | Main Street | Timothy Maloney Tenement | 1878-1898 | Queen Anne | |
| 548 | Main Street | Wheaton Knight House | 1857-1870 | Italianate | |
| 552 | Main Street | Josiah J. Fiske Building | ca. 1825 | Greek Revival | |
| 554 | Main Street | ca. 1870 | Greek Revival | ||
| 562 | Main Street | 1969 | Modern | ||
| 570 | Main Street | 1967 | Modern | ||
| 572 | Main Street | ca. 1874-1880 | Gothic Revival | ||
| 584-588 | Main Street | 1857 | Greek Revival | ||
| 588 | Main Street | Verry-Biron House | ca. 1870 | No Style | |
| 590 | Main Street | Former Tenement House | ca. 1870 | 4-family frame tenement | |
| 598-600 | Main Street | 1857 | No Style | ||
| 600 | Main Street | 600 Main Street | 1870 | Greek Revival | |
| 602 | Main Street | ca. 1830 | Simple Greek Revival | ||
| 618 | Main Street | 618 Main Street | ca. 1898 | No Style | |
| 621 | Main Street | 621 Main Street | ca. 1870 | No Style | |
| 622 | Main Street | 622 Main Street | ca. 1875 | No Style | |
| 626 | Main Street | 626 Main Street | 1891 | No Style | |
| 8 | Maple Street | Federated Church of Sturbridge and Fiskdale | 1910, 1954, 1960s | Colonial Revival | |
| 9 | Maple Street | Thomas Lyon/J.E. Purdy House | circa 1835-1845 | Possibly Greek Revival/Altered | |
| 10 | Maple Street | Congregational Parsonage | by 1869 | Greek Revival with Italianate details | |
| 14 | Maple Street | Chester H. Walker House | prior to 1870 | Greek Revival with Italianate details | |
| 17 | Maple Street | Benjamin C. Weld House and Barn | ca. 1850 | Greek Revival | |
| 5 | Mashapaug Road | 1787 and later alterations | Georgian/Folk Victorian | ||
| 104 | McGilpin Road | Probably 1826, by 1857 | Federal | ||
| 138 | McGilpin Road | John Smith House | by 1857 | Federal with additions | |
| 14 | McGregory Road | 1755 (NH); 1947; ca. 1968 | Colonial with alterations | ||
| 41 | McGregory Road | Richard B. Hardy House | 1966 | Garrison Colonial | |
| 14 | Mountain Brook Road | 14 Mountain Brook Road | 1980 | No Style | |
| 18 | Mountain Brook Road | 18 Mountain Brook Road | 1969 | Ranch | |
| 22 | Mountain Brook Road | 22 Mountain Brook Road | 1940 | No Style | |
| 28 | Mountain Brook Road | 28 Mountain Brook Road | 1999 | No Style | |
| 43 | Mountain Brook Road | 43 Mountain Brook Road | 1952 | No Style | |
| 45 | Mountain Brook Road | 45 Mountain Brook Road | 1945 | No Style | |
| 47 | Mountain Brook Road | 47 Mountain Brook Road | 1996 | No Style | |
| 121 | New Boston Road | 121 New Boston Road | 1956 | Ranch | |
| 123 | New Boston Road | 123 New Boston Road | 1981 | No Style | |
| 127 | New Boston Road | 127 New Boston Road | 1981 | Cape | |
| 129 | New Boston Road | 129 New Boston Road | 1981 | No Style | |
| 131 | New Boston Road | 131 New Boston Road | 1981 | No Style | |
| 133 | New Boston Road | 133 New Boston Road | 1989 | No Style | |
| 137 | New Boston Road | 137 New Boston Road | 1945 | Ranch | |
| 143 | New Boston Road | 143 New Boston Road | 1981 | Cape | |
| 149 | New Boston Road | 149 New Boston Road | 1956 | Ranch | |
| 151 | New Boston Road | 151 New Boston Road | 1952 | Ranch | |
| 153 | New Boston Road | 153 New Boston Road | 1956 | Ranch | |
| 340 | New Boston Road | Hyde Family House | by 1857 | Altered | |
| 22 | North Drive | 22 North Drive | 2003 | No Style | |
| 3 | Oaks Cove Road | 3 Oaks Cove Road | 1970 | No Style | |
| 3 | Old Stagecoach Road | between 1735 and 1772 | Colonial | ||
| 1 | Old Village Road | 1 Old Village Road | 1986 | No Style | |
| 3 | Old Village Road | 3 Old Village Road | 1971 | Ranch | |
| 6 | Old Village Road | 6 Old Village Road | 1973 | Garrison Colonial | |
| 7 | Old Village Road | 7 Old Village Road | 1966 | Garrison Colonial | |
| 10 | Old Village Road | 10 Old Village Road | 1973 | Ranch | |
| 11 | Old Village Road | 11 Old Village Road | 1970 | No Style | |
| 12 | Old Village Road | 12 Old Village Road | 1962 | Ranch | |
| 13 | Old Village Road | 13 Old Village Road | 1970 | Split-Level (Bi-Level) | |
| 14 | Old Village Road | 14 Old Village Road | 1967 | Split-Level (Bi-Level) | |
| 17 | Old Village Road | 17 Old Village Road | 1967 | No Style | |
| 18 | Old Village Road | 18 Old Village Road | 1966 | Split-Level (Bi-Level) | |
| 19 | Old Village Road | 19 Old Village Road | 1967 | No Style | |
| 21 | Old Village Road | 21 Old Village Road | 1970 | Cape | |
| 22 | Old Village Road | 22 Old Village Road | 1963 | No Style | |
| 24 | Old Village Road | 24 Old Village Road | 1968 | Garrison Colonial | |
| 25 | Old Village Road | 25 Old Village Road | 1970 | Garrison Colonial | |
| 30 | Old Village Road | 30 Old Village Road | 1972 | Cape | |
| 32 | Old Village Road | 32 Old Village Road | 1970 | No Style | |
| 35 | Old Village Road | 35 Old Village Road | 1983 | No Style | |
| 36 | Old Village Road | 36 Old Village Road | 1980 | No Style | |
| 38 | Old Village Road | 38 Old Village Road | 1972 | Garrison Colonial | |
| 39 | Old Village Road | 39 Old Village Road | 1973 | No Style | |
| 40 | Old Village Road | 40 Old Village Road | 1972 | Garrison Colonial | |
| 44 | Old Village Road | 44 Old Village Road | 1973 | No Style | |
| 45 | Old Village Road | 45 Old Village Road | 1978 | No Style | |
| 46 | Old Village Road | 46 Old Village Road | 1976 | Cape | |
| 47 | Old Village Road | 47 Old Village Road | 1977 | No Style | |
| 49 | Old Village Road | 49 Old Village Road | 1973 | No Style | |
| 50 | Old Village Road | 50 Old Village Road | 1975 | No Style | |
| 51 | Old Village Road | 51 Old Village Road | 1977 | No Style | |
| 52 | Old Village Road | 52 Old Village Road | 1984 | No Style | |
| 53 | Old Village Road | 53 Old Village Road | 1977 | No Style | |
| 54 | Old Village Road | 54 Old Village Road | 2005 | No Style | |
| 55 | Old Village Road | 55 Old Village Road | 1979 | Cape | |
| 56 | Old Village Road | 56 Old Village Road | 1974 | No Style | |
| 68 | Paradise Lane | Alva L. Burroughs House | Early to mid-20th century | Colonial Revival | Original House Demoed, new house built in 2024 |
| 70 | Paradise Lane | 70 Paradise Lane | 2016 | No Style | Constructed following the demo of an older building. |
| 71 | Paradise Lane | 71 Paradise Lane | 1910 | No Style | |
| 72A | Paradise Lane | 72A Paradise Lane | 2025 | No Style | According to Property Record Card, former building on property constructed in 1940. |
| 73 | Paradise Lane | 73 Paradise Lane | 2024 | No Style | Constructed following the demo of an older building. |
| 74 | Paradise Lane | 74 Paradise Lane | 2003 | No Style | Constructed following the demo of an older building. |
| 75 | Paradise Lane | 75 Paradise Lane | 1989 | No Style | |
| 76 | Paradise Lane | 76 Paradise Lane | 1991 | No Style | |
| 77 | Paradise Lane | 77 Paradise Lane | 2001 | No Style | |
| 80 | Paradise Lane | Clifford E. and Doris G. Gadaire House | 1946 | No Style | |
| 81 | Paradise Lane | 81 Paradise Lane | 2017 | No Style | |
| 82 | Paradise Lane | 82 Paradise Lane | 2024 | No Style | Constructed following the demo of an older building. |
| 84 | Paradise Lane | Ralph and Irene Gardner House | 1956 | No Style | |
| 84A | Paradise Lane | 84A Paradise Lane | 2014 | No Style | Constructed following the demo of an older building. |
| 86 | Paradise Lane | Herbert J. and Lillian M. Burgess House | 1942 | No Style | |
| 88 | Paradise Lane | Neil L. and Florence L. Prest House | 1930 | No Style | |
| 89 | Paradise Lane | 89 Paradise Lane | 1988 | No Style | |
| 90 | Paradise Lane | 90 Paradise Lane | 1940 | No Style | |
| 91 | Paradise Lane | 91 Paradise Lane | 1994 | No Style | |
| 92 | Paradise Lane | 92 Paradise Lane | 1985 | No Style | |
| 93 | Paradise Lane | 93 Paradise Lane | 2000 | No Style | |
| 94 | Paradise Lane | 94 Paradise Lane | 2014 | No Style | Constructed following the demo of an older building. |
| 95 | Paradise Lane | 95 Paradise Lane | 1992 | Split-Level (Bi-Level) | |
| 96 | Paradise Lane | 96 Paradise Lane | 1929 | No Style | |
| 97 | Paradise Lane | 97 Paradise Lane | 2001 | No Style | |
| 98 | Paradise Lane | 98 Paradise Lane | 2006 | No Style | |
| 102 | Paradise Lane | 102 Paradise Lane | 1990 | No Style | |
| 108 | Paradise Lane | 108 Paradise Lane | N/A | Not yet constructed | New dwelling not yet constructed. As part of the Zoning Board of Appeals application, the building at 106 Paradise Lane was also demolished. Former building at 108 constructed in 1940. |
| 110 | Paradise Lane | 110 Paradise Lane | 1940 | No Style | Existing building approved for demolition in 2025. Dwelling not yet demolished at time of survey (May 2025). |
| 114 | Paradise Lane | 114 Paradise Lane | 1970 | No Style | |
| 118 | Paradise Lane | 118 Paradise Lane | 2017 | No Style | Constructed following the demo of an older building. |
| 3 | Podunk Road | 3 Podunk Road | 1977 | No Style | |
| 5 | Podunk Road | 5 Podunk Road | 1977 | Ranch | |
| 7 | Podunk Road | 7 Podunk Road | 1981 | Split-Level (Bi-Level) | |
| 9 | Podunk Road | 9 Podunk Road | 1973 | Split-Level (Bi-Level) | |
| 15 | Podunk Road | 15 Podunk Road | 1974 | No Style | |
| 17 | Podunk Road | 17 Podunk Road | 1972 | Split-Level (Bi-Level) | |
| 19 | Podunk Road | 19 Podunk Road | 1973 | Split-Level (Bi-Level) | |
| 21 | Podunk Road | 21 Podunk Road | 1978 | No Style | |
| 25 | Podunk Road | 25 Podunk Road | 1976 | No Style | |
| 27 | Podunk Road | 27 Podunk Road | 1977 | Ranch | |
| 29 | Podunk Road | 29 Podunk Road | 1978 | Ranch | |
| 13 | Podunk Road | 1912 (barn), ca. 1946 (house) | Colonial Revival (Stylized Ranch) | ||
| 164 | Podunk Road | Sturbridge District School No. 7 Ainsworth School | ca. 1857 | No Style | |
| 177 | Podunk Road | Nichols Family House and Davis Family Barn | Prior to 1851 | Colonial with later alterations | |
| 251 | Podunk Road | Jonas Bemis/Silverberg Family Farm | mid-19th century with later alterations | Colonial with later alterations | |
| 35 | Racicot Lane | 35 Racicot Lane | 1966 | No Style | |
| 37 | Racicot Lane | 37 Racicot Lane | 1967 | No Style | |
| 39 | Racicot Lane | 39 Racicot Lane | 1950 | No Style | |
| 31 | Ridge Way | 31 Ridge Way | 1960 | Ranch | |
| 32 | Ridge Way | 32 Ridge Way | 1981 | No Style | |
| 33 | Ridge Way | 33 Ridge Way | 1983 | No Style | |
| 35 | Ridge Way | 35 Ridge Way | 1981 | No Style | |
| 37 | Ridge Way | 37 Ridge Way | 1950 | No Style | |
| 39 | Ridge Way | 39 Ridge Way | 1958 | No Style | |
| 40 | Ridge Way | 40 Ridge Way | 1981 | Cape | |
| 41 | Ridge Way | 41 Ridge Way | 1952 | No Style | |
| 42 | Ridge Way | 42 Ridge Way | 1989 | Ranch | |
| 43 | Ridge Way | 43 Ridge Way | 1950 | Ranch | |
| 46 | Ridge Way | 46 Ridge Way | 1989 | Garrison Colonial | |
| 47 | Ridge Way | 47 Ridge Way | 1975 | No Style | |
| 50 | Ridge Way | 50 Ridge Way | 1955 | Garrison Colonial | |
| 51 | Ridge Way | 51 Ridge Way | 1982 | No Style | |
| 52 | Ridge Way | 52 Ridge Way | 1984 | No Style | |
| 53 | Ridge Way | 53 Ridge Way | 1981 | Ranch | |
| 54 | Ridge Way | 54 Ridge Way | 2009 | No Style | Constructed following the demo of an older building. |
| 56 | Ridge Way | 56 Ridge Way | 1984 | Cape | |
| 58 | Ridge Way | 58 Ridge Way | 1981 | No Style | |
| 60 | Ridge Way | 60 Ridge Way | 1981 | No Style | |
| 28 | River Road | Lyman Janes House | ca. 1857 | No Style | |
| 130 | River Road | Sturbridge District School No. 11; Four Corners School | ca. 1857 | No Style | |
| 531 | Route 15 | Samuel Thompson House | possibly by 1857 to end of 19th century | Altered | |
| 8 | School Street | Fiskdale School | 1896 | Italianate, altered | |
| 10 | School Street | Moon House | N/A | N/A | |
| 210 | Shepard Road | 1805 | Georgian | ||
| 81 | Shore Road | 81 Shore Road | 1950 | No Style | |
| 85 | Shore Road | 85 Shore Road | 1950 | No Style | |
| 87 | Shore Road | 87 Shore Road | 1950 | No Style | |
| 89 | Shore Road | 89 Shore Road | 1944 | No Style | |
| 91 | Shore Road | 91 Shore Road | 1950 | No Style | |
| 93 | Shore Road | 93 Shore Road | 2015 | No Style | Constructed following the demo of an older building. |
| 97 | Shore Road | 97 Shore Road | 2025 | No Style | Constructed following the demo of an older building. |
| 99 | Shore Road | 99 Shore Road | 1940 | No Style | |
| 103 | Shore Road | 103 Shore Road | 1965 | No Style | |
| 105 | Shore Road | 105 Shore Road | 1940 | No Style | |
| 107 | Shore Road | 107 Shore Road | 1952 | No Style | |
| 109 | Shore Road | 109 Shore Road | 1940 | No Style | |
| 111 | Shore Road | 111 Shore Road | 1940 | No Style | |
| 115 | Shore Road | 115 Shore Road | 2005 | No Style | Constructed following the demo of an older building. |
| 119 | Shore Road | 119 Shore Road | 1991 | No Style | |
| 121 | Shore Road | 121 Shore Road | 1964 | No Style | |
| 123 | Shore Road | 123 Shore Road | 1954 | No Style | |
| 125 | Shore Road | 125 Shore Road | 1954 | No Style | |
| 129 | Shore Road | 129 Shore Road | 1963 | No Style | |
| 131 | Shore Road | 131 Shore Road | 1950 | No Style | |
| 135 | Shore Road | 135 Shore Road | 1950 | Cape | |
| 139 | Shore Road | 139 Shore Road | 1950 | Cape | |
| 145 | Shore Road | 145 Shore Road | 1987 | No Style | |
| 10 | Snell Street | 10 Snell Street | 1960 | Ranch | |
| 12 | Snell Street | 12 Snell Street | ca. 1966 | Split-Level (Bi-Level) | |
| 14 | Snell Street | 14 Snell Street | 1966 | Cape | |
| 18 | Snell Street | 18 Snell Street | 1966 | Ranch | |
| 1 | South Paradise Lane | 1 South Paradise Lane | 1992 | No Style | |
| 2 | South Paradise Lane | 2 South Paradise Lane | 1992 | No Style | |
| 16 | South Paradise Lane | 16 South Paradise Lane | 1927 | No Style | |
| 3 | South Shore Drive | 3 South Shore Drive | 1993 | No Style | |
| 6 | South Shore Drive | 6 South Shore Drive | 1979 | Cape | |
| 12 | South Shore Drive | 12 South Shore Drive | 1978 | Cape | |
| 15 | South Shore Drive | 15 South Shore Drive | 2002 | No Style | |
| 16 | South Shore Drive | 16 South Shore Drive | 1988 | Cape | |
| 17 | South Shore Drive | 17 South Shore Drive | 1986 | Outbuilding | |
| 19 | South Shore Drive | 19 South Shore Drive | 2002 | No Style | |
| 23 | South Shore Drive | 23 South Shore Drive | 2002 | Split-Level (Bi-Level) | |
| 31 | South Shore Drive | 31 South Shore Drive | 2007 | No Style | |
| 35 | South Shore Drive | 35 South Shore Drive | 1973 | No Style | |
| 37 | South Shore Drive | 37 South Shore Drive | 2005 | No Style | |
| 43 | South Shore Drive | 43 South Shore Drive | 2004 | No Style | |
| 46 | South Shore Drive | 46 South Shore Drive | 1965 | No Style | |
| 48 | South Shore Drive | 48 South Shore Drive | 1968 | No Style | |
| 49 | South Shore Drive | 49 South Shore Drive | 1999 | Split-Level (Bi-Level) | |
| 50 | South Shore Drive | 50 South Shore Drive | 2001 | No Style | Constructed following the demo of an older building. |
| 51 | South Shore Drive | 51 South Shore Drive | 1998 | Split-Level (Bi-Level) | |
| 52 | South Shore Drive | 52 South Shore Drive | 1961 | No Style | |
| 55 | South Shore Drive | 55 South Shore Drive | 2001 | No Style | |
| 58 | South Shore Drive | 58 South Shore Drive | 2010 | No Style | Constructed following the demo of an older building. |
| 59 | South Shore Drive | 59 South Shore Drive | 1999 | Split-Level (Bi-Level) | |
| 60 | South Shore Drive | 60 South Shore Drive | 1969 | No Style | |
| 64 | South Shore Drive | 64 South Shore Drive | 1999 | No Style | |
| 68 | South Shore Drive | 68 South Shore Drive | 1965 | No Style | |
| 70 | South Shore Drive | 70 South Shore Drive | 1965 | No Style | |
| 72 | South Shore Drive | 72 South Shore Drive | ca. 1966 | No Style | |
| 76 | South Shore Drive | 76 South Shore Drive | ca. 1966 | No Style | |
| 82 | South Shore Drive | 82 South Shore Drive | 1970 | No Style | |
| 84 | South Shore Drive | 84 South Shore Drive | 1970 | No Style | |
| 88 | South Shore Drive | 88 South Shore Drive | 2025 | No Style | Constructed following the demo of an older building. |
| 90 | South Shore Drive | 90 South Shore Drive | 1962 | Ranch | |
| 92 | South Shore Drive | 92 South Shore Drive | 1940 | Ranch | |
| 94 | South Shore Drive | 94 South Shore Drive | 1965 | Ranch | |
| 96 | South Shore Drive | 96 South Shore Drive | 1970 | No Style | |
| 98 | South Shore Drive | 98 South Shore Drive | 2001 | No Style | |
| 100 | South Shore Drive | 100 South Shore Drive | 2015 | No Style | Constructed following the demo of an older building. |
| 102 | South Shore Drive | 102 South Shore Drive | 1996 | No Style | |
| 104 | South Shore Drive | 104 South Shore Drive | 1973 | No Style | |
| 106 | South Shore Drive | 106 South Shore Drive | 1971 | No Style | |
| 108 | South Shore Drive | 108 South Shore Drive | 1989 | Octagon | |
| 110 | South Shore Drive | 110 South Shore Drive | 1985 | No Style | |
| 112 | South Shore Drive | 112 South Shore Drive | 1973 | No Style | |
| 5 | Stony Brook Drive | 5 Stony Brook Drive | 1971 | Split-Level (Bi-Level) | |
| 6 | Stony Brook Drive | 6 Stony Brook Drive | 1972 | Split-Level (Bi-Level) | |
| 8 | Stony Brook Drive | 8 Stony Brook Drive | 1971 | Split-Level (Bi-Level) | |
| 9 | Stony Brook Drive | 9 Stony Brook Drive | 1972 | Split-Level (Bi-Level) | |
| 12 | Stony Brook Drive | 12 Stony Brook Drive | 1971 | Split-Level (Bi-Level) | |
| 13 | Stony Brook Drive | 13 Stony Brook Drive | 1971 | No Style | |
| 16 | Stony Brook Drive | 16 Stony Brook Drive | 1972 | Split-Level (Bi-Level) | |
| 17 | Stony Brook Drive | 17 Stony Brook Drive | 1972 | Split-Level (Bi-Level) | |
| 18 | Stony Brook Drive | 18 Stony Brook Drive | 1971 | Split-Level (Bi-Level) | |
| 44 | Streeter Road | Lemuel L. Holmes/Frederick Holmes House | 1835, with later alterations | heavily altered | |
| 2 | Summit Avenue | 2 Summit Avenue | ca. 1846 - 1857 | Greek Revival | |
| 11 | Summit Avenue | Between 1870-1898 | Queen Anne | ||
| 16 | Summit Avenue | Early to late 19th century | Altered | ||
| 24 | Taft Street | Isaac Child Jr. House | ca. 1792 | Federal | |
| 5 | Tantasqua Shore Drive | 5 Tantasqua Shore Drive | 1965 | No Style |
|
| 6 | Tantasqua Shore Drive | 6 Tantasqua Shore Drive | 1961 | Contemporary | |
| 7 | Tantasqua Shore Drive | 7 Tantasqua Shore Drive | 1970 | No Style | |
| 8 | Tantasqua Shore Drive | 8 Tantasqua Shore Drive | 1960 | No Style | |
| 9 | Tantasqua Shore Drive | 9 Tantasqua Shore Drive | 1965 | No Style | |
| 12 | Tantasqua Shore Drive | 12 Tantasqua Shore Drive | 1960 | No Style | |
| 14 | Tantasqua Shore Drive | 14 Tantasqua Shore Drive | 1960 | No Style | |
| 15 | Tantasqua Shore Drive | 15 Tantasqua Shore Drive | 1960 | No Style | |
| 16 | Tantasqua Shore Drive | 16 Tantasqua Shore Drive | 1970 | Contemporary | |
| 18 | Tantasqua Shore Drive | 18 Tantasqua Shore Drive | 1966 | No Style | |
| 20 | Tantasqua Shore Drive | 20 Tantasqua Shore Drive | 1960 | No Style | |
| 26 | Tantasqua Shore Drive | 26 Tantasqua Shore Drive | 1972 | No Style | |
| 30 | Tantasqua Shore Drive | 30 Tantasqua Shore Drive | 2006 | No Style | |
| 32 | Tantasqua Shore Drive | 32 Tantasqua Shore Drive | 1976 | No Style | |
| 34 | Tantasqua Shore Drive | 34 Tantasqua Shore Drive | 1960 | No Style | |
| 36 | Tantasqua Shore Drive | 36 Tantasqua Shore Drive | 1960 | No Style | |
| 40 | Tantasqua Shore Drive | 40 Tantasqua Shore Drive | 1975 | Cape | |
| 42 | Tantasqua Shore Drive | 42 Tantasqua Shore Drive | 1993 | No Style | |
| 306 | The Trail | 306 The Trail | 1992 | No Style | |
| 307 | The Trail | 307 The Trail | 1999 | No Style | |
| 308 | The Trail | 308 The Trail | 1980 | No Style | |
| 309 | The Trail | 309 The Trail | 1978 | No Style | |
| 310 | The Trail | 310 The Trail | 1977 | No Style | |
| 312 | The Trail | 312 The Trail | 2002 | No Style | |
| 314 | The Trail | 314 The Trail | 1977 | No Style | |
| 316 | The Trail | 316 The Trail | 1876 | No Style | |
| 317 | The Trail | 317 The Trail | 1985 | Cape | |
| 320 | The Trail | 320 The Trail | 1964 | No Style | |
| 322 | The Trail | 322 The Trail | 1965 | Ranch | |
| 324 | The Trail | 324 The Trail | 1971 | No Style | |
| 326 | The Trail | 326 The Trail | 1970 | Ranch | |
| 327 | The Trail | 327 The Trail | 1974 | No Style | |
| 328 | The Trail | 328 The Trail | 2014 | No Style | |
| 329 | The Trail | 329 The Trail | 1984 | Cape | |
| 330 | The Trail | 330 The Trail | 1970 | Unknown | |
| 331 | The Trail | 331 The Trail | 1985 | Ranch | |
| 332 | The Trail | 332 The Trail | 1950 | No Style | |
| 335 | The Trail | 335 The Trail | 2004 | No Style | |
| 337 | The Trail | 337 The Trail | 2005 | No Style | |
| 339 | The Trail | 339 The Trail | 2004 | No Style | |
| 341 | The Trail | 341 The Trail | 2004 | No Style | |
| 99 | Wallace Road | Hamilton Woolen Co. House | Prior to 1857 | Georgian | |
| 111 | Wallace Road | Westville Schoolhouse; Sturbridge District School No. 10 | 1904 | No Style | |
| 116 | Wallace Road | Plimpton Farm | Prior to 1857 | Altered | |
| 63 | Walker Pond Road | 63 Walker Pond Road | 1965 | Split-Level (Bi-Level) | |
| 64 | Walker Pond Road | 64 Walker Pond Road | 1971 | Split-Level (Bi-Level) | |
| 67 | Walker Pond Road | 67 Walker Pond Road | 1971 | Garrison Colonial | |
| 70 | Walker Pond Road | 70 Walker Pond Road | 1965 | Garrison Colonial | |
| 73 | Walker Pond Road | 73 Walker Pond Road | 1972 | Cape | |
| 74 | Walker Pond Road | 74 Walker Pond Road | 1970 | Ranch | |
| 77 | Walker Pond Road | 77 Walker Pond Road | 1967 | Cape | |
| 81 | Walker Pond Road | 81 Walker Pond Road | 1966 | Split-Level (Bi-Level) | |
| 82 | Walker Pond Road | 82 Walker Pond Road | 1959 | Cape | |
| 85 | Walker Pond Road | 85 Walker Pond Road | 1961 | Cape | |
| 86 | Walker Pond Road | 86 Walker Pond Road | 1966 | Garrison Colonial | |
| 89 | Walker Pond Road | 89 Walker Pond Road | 1965 | Cape | |
| 91 | Walker Pond Road | 91 Walker Pond Road | 1972 | Split-Level (Bi-Level) | |
| 95 | Walker Pond Road | 95 Walker Pond Road | 1961 | No Style | |
| 101 | Walker Pond Road | 101 Walker Pond Road | 1970 | Cape | |
| 102 | Walker Pond Road | 102 Walker Pond Road | 1953 | Ranch | |
| 104 | Walker Pond Road | 104 Walker Pond Road | 1965 | No Style | |
| 108 | Walker Pond Road | 108 Walker Pond Road | 1970 | Split-Level (Bi-Level) | |
| 111 | Walker Pond Road | 111 Walker Pond Road | 1966 | Cape | |
| 112 | Walker Pond Road | 112 Walker Pond Road | 1965 | No Style | |
| 114 | Walker Pond Road | 114 Walker Pond Road | 1966 | Unknown | |
| 118 | Walker Pond Road | 118 Walker Pond Road | 1965 | No Style | |
| 126 | Walker Pond Road | 126 Walker Pond Road | 1970 | Contemporary | |
| 127 | Walker Pond Road | 127 Walker Pond Road | 1970 | Split-Level (Bi-Level) | |
| 129 | Walker Pond Road | 129 Walker Pond Road | 1970 | No Style | |
| 133 | Walker Pond Road | 133 Walker Pond Road | 1968 | No Style | |
| 135 | Walker Pond Road | 135 Walker Pond Road | 1968 | Split-Level (Bi-Level) | |
| 136 | Walker Pond Road | 136 Walker Pond Road | 1970 | Unknown | |
| 138 | Walker Pond Road | 138 Walker Pond Road | 1969 | Garrison Colonial | |
| 139 | Walker Pond Road | 139 Walker Pond Road | 1965 | Garrison Colonial | |
| 143 | Walker Pond Road | 143 Walker Pond Road | 1971 | Garrison Colonial | |
| 145 | Walker Pond Road | 145 Walker Pond Road | 1966 | Garrison Colonial | |
| 146 | Walker Pond Road | 146 Walker Pond Road | 1970 | Split-Level (Bi-Level) | |
| 147 | Walker Pond Road | 147 Walker Pond Road | 1972 | Garrison Colonial | |
| 148 | Walker Pond Road | 148 Walker Pond Road | 1971 | Garrison Colonial | |
| 149 | Walker Pond Road | 149 Walker Pond Road | 1987 | No Style | |
| 150 | Walker Pond Road | 150 Walker Pond Road | 1978 | No Style | |
| 151 | Walker Pond Road | 151 Walker Pond Road | 1973 | No Style | |
| 152 | Walker Pond Road | 152 Walker Pond Road | 1970 | Garrison Colonial | |
| 5 | Wells Park Road | 5 Wells Park Road | 1993 | Cape | |
| 7 | Wells Park Road | 7 Wells Park Road | 1964 | Cape | |
| 8 | Wells Park Road | 8 Wells Park Road | 1977 | Cape | |
| 10 | Wells Park Road | 10 Wells Park Road | 1965 | No Style | |
| 11 | Wells Park Road | 11 Wells Park Road | 1970 | Cape | |
| 14 | Wells Park Road | 14 Wells Park Road | 1970 | Split-Level (Bi-Level) | |
| 15 | Wells Park Road | 15 Wells Park Road | 1965 | Ranch | |
| 17 | Wells Park Road | 17 Wells Park Road | 1970 | Cape | |
| 20 | Wells Park Road | 20 Wells Park Road | 1981 | Split-Level (Bi-Level) | |
| 21 | Wells Park Road | 21 Wells Park Road | 1963 | Cape | |
| 22 | Wells Park Road | 22 Wells Park Road | 1958 | No Style | |
| 25 | Wells Park Road | 25 Wells Park Road | 1966 | Cape | |
| 28 | Wells Park Road | 28 Wells Park Road | 1965 | No Style | |
| 29 | Wells Park Road | 29 Wells Park Road | 1967 | Cape | |
| 31 | Wells Park Road | 31 Wells Park Road | 1965 | No Style | |
| 32 | Wells Park Road | 32 Wells Park Road | 1970 | Garrison Colonial | |
| 34 | Wells Park Road | 34 Wells Park Road | 1970 | Contemporary | |
| 35 | Wells Park Road | 35 Wells Park Road | 1964 | Garrison Colonial | |
| 36 | Wells Park Road | 36 Wells Park Road | 1964 | No Style | |
| 38 | Wells Park Road | 38 Wells Park Road | 1965 | Garrison Colonial | |
| 42 | Wells Park Road | 42 Wells Park Road | 1965 | Ranch | |
| 43 | Wells Park Road | 43 Wells Park Road | 1960 | Garrison Colonial | |
| 45 | Wells Park Road | 45 Wells Park Road | 1965 | No Style | |
| 46 | Wells Park Road | 46 Wells Park Road | 1969 | Split-Level (Bi-Level) | |
| 47 | Wells Park Road | 47 Wells Park Road | 1950 | Ranch | |
| 48 | Wells Park Road | 48 Wells Park Road | 1970 | No Style | |
| 52 | Wells Park Road | 52 Wells Park Road | 1970 | Split-Level (Bi-Level) | |
| 122 | Wells Park Road | 122 Wells Park Road | 1988 | No Style | |
| 67 | Westwood Drive | 67 Westwood Drive | 1995 | Cape | |
| 69 | Westwood Drive | 69 Westwood Drive | 1995 | Ranch | |
| 71 | Westwood Drive | 71 Westwood Drive | 1997 | Split-Level (Bi-Level) | |
| 77 | Westwood Drive | 77 Westwood Drive | 1980 | No Style | |
| 79 | Westwood Drive | 79 Westwood Drive | 1981 | Ranch | |
| 81 | Westwood Drive | 81 Westwood Drive | 1982 | Ranch | |
| 83 | Westwood Drive | 83 Westwood Drive | 1980 | Ranch | |
| 85 | Westwood Drive | 85 Westwood Drive | 1987 | Split-Level (Bi-Level) | |
| 87 | Westwood Drive | 87 Westwood Drive | 1982 | No Style | |
| 88 | Westwood Drive | 88 Westwood Drive | 2010 | No Style | Constructed following the demo of an older building. |
| 89 | Westwood Drive | 89 Westwood Drive | 1972 | No Style | |
| 90 | Westwood Drive | 90 Westwood Drive | 2003 | No Style | Constructed following the demo of an older building. |
| 92 | Westwood Drive | 92 Westwood Drive | 1967 | No Style | |
| 94 | Westwood Drive | 94 Westwood Drive | 1965 | No Style | |
| 95 | Westwood Drive | 95 Westwood Drive | 1985 | Ranch | |
| 96 | Westwood Drive | 96 Westwood Drive | 1965 | No Style | |
| 98 | Westwood Drive | 98 Westwood Drive | 1965 | No Style | |
| 99 | Westwood Drive | 99 Westwood Drive | 2003 | No Style | |
| 100 | Westwood Drive | 100 Westwood Drive | 1950 | No Style | |
| 104 | Westwood Drive | 104 Westwood Drive | 1976 | Ranch | |
| 106 | Westwood Drive | 106 Westwood Drive | 1940 | No Style | |
| 108 | Westwood Drive | 108 Westwood Drive | 1938 | No Style | |
| 110 | Westwood Drive | 110 Westwood Drive | 2014 | No Style | Constructed following the demo of an older building. |
| 112 | Westwood Drive | 112 Westwood Drive | 1981 | No Style | |
| 114 | Westwood Drive | 114 Westwood Drive | 1965 | No Style | |
| 116 | Westwood Drive | 116 Westwood Drive | 1969 | No Style | |
| 126 | Westwood Drive | 126 Westwood Drive | 1950 | No Style | |
| 10 | Whittemore Road | c. 1792; mid-to-late 20th century alterations | Altered | ||
| 35 | Willard Road | by 1857 | Altered | ||
| 7 | Woodlawn Drive | 7 Woodlawn Drive | 1970 | No Style | |
| 9 | Woodlawn Drive | 9 Woodlawn Drive | 1970 | No Style | |
| 12 | Woodlawn Drive | 12 Woodlawn Drive | 1985 | Cape | |
| 13 | Woodlawn Drive | 13 Woodlawn Drive | 1973 | No Style | |
| 14 | Woodlawn Drive | 14 Woodlawn Drive | 1970 | No Style | |
| 15 | Woodlawn Drive | 15 Woodlawn Drive | 1973 | Split-Level (Bi-Level) | |
| 16 | Woodlawn Drive | 16 Woodlawn Drive | 1970 | Contemporary | |
| 18 | Woodlawn Drive | 18 Woodlawn Drive | 1976 | No Style | |
| 19 | Woodlawn Drive | 19 Woodlawn Drive | 1973 | No Style | |
| 27 | Woodlawn Drive | 27 Woodlawn Drive | 1974 | Ranch | |
| 28 | Woodlawn Drive | 28 Woodlawn Drive | 1985 | Split-Level (Bi-Level) | |
| 30 | Woodlawn Drive | 30 Woodlawn Drive | 1985 | Cape | |
| 31 | Woodlawn Drive | 31 Woodlawn Drive | 1983 | No Style | |
| 33 | Woodlawn Drive | 33 Woodlawn Drive | 1973 | Split-Level (Bi-Level) | |
| 34 | Woodlawn Drive | 34 Woodlawn Drive | 1987 | No Style | |
| 37 | Woodlawn Drive | 37 Woodlawn Drive | 1969 | Split-Level (Bi-Level) | |
| 38 | Woodlawn Drive | 38 Woodlawn Drive | 1973 | Split-Level (Bi-Level) | |
| 42 | Woodlawn Drive | 42 Woodlawn Drive | 1970 | Split-Level (Bi-Level) |
