Nelson S. Hurlbutt House - 1922 - 8 Cannon Road - a 2½-story, Colonial Revival gambrel-roofed house with wood shingles, a three-bay facade and Tuscan-columned portico framing its central entry
Godfrey Academy - 1849 - 20 Cannon Road - moved in 1961 to its present location from Danbury Road.

Cannondale Station - 1892 - 22 Cannon Road - Victorian-era, one-story structure with a gable roof and wide, overhanging eaves supported by chamfered brackets and bargeboard with a geometric motif and a stickwork peak ornament.

Charles Gregory Store and Post Office - c. 1850 - 24 Cannon Road - 2½ stories, with a gable roof, clapboard, a "plain frieze and molded cornice with partial return", a rear wing added about 1895
A small, two-story, clapboard house behind Charles Gregory Store, built about 1900, with a gable roof.

Cannon Grange Hall - 1899 - 25 Cannon Road - Victorian, 1½-story structure with a "gable roof, clapboard with scalloped shingles in gable ends, stickwork peak ornament".

Charles Gregory Dam - 30 Cannon Road - c. 1910 - "coursed rubble spillway and abutments; wheel-pit with draft tube for turbine-based power system incorporated into west abutment.
Atop west abutment is former Charles Gregory gristmill that was extensively remodeled in the late 1920s and late 1970s."

Three contributing objects located at entrance to Cannon Crossing shopping area at 30 Cannon Road:
a "c.1900 turbine that was removed from Gregory Grist Mill wheelpit"
"two c. 1925 reservoir-head gasoline pumps"
Gregory Gristmill Tenant House - c. 1900 - 32 Cannon Road - two stories, with a "gable roof, clapboard with shingled gable ends".

B. F. Brown Boarding School - 1857 - 33 Cannon Road - Greek Revival entry, three stories, "gable roof, clapboard, high brick basement with brownstone window lintels, pilaster-and-lintel entry with sidelights and transom"
A barn behind the B. F. Brown Boarding School
Cannondale School - 1872 - 34 Cannon Road - one-story, "gable roof, clapboard, hip-roofed entry shelter on large brackets, pedimented window surrounds, ogee-roofed cupola with round-arched openings"; the building was moved to its present location in 1979 from the corner of Olmstead Hill and Danbury roads.

Helen Godfrey House - c. 1900 - 37 Cannon Road - Victorian era, 2½-story house with a "gable roof, wood shingle; porch (turned posts jigsawn brackets, molded rail on turned balusters) wraps around right side to meet 2-story cross-gabled ell".

Lockwood Academy - 1851 - 43 Cannon Road, also known as 42 Cannon Road - Built in a "vernacular" style "with greek Revival influence, 2½ stories, gable roof, clapboard, pilaster-and-linetl entry, simple steeped entablature with partial return"
Barn to the rear of the Lockwood Academy building
Marjorie W. Hands House - 1939 - 63 Cannon Road - Southern Colonial Revival - 2½ stories, "gable roof, clapboard with flush-boarded facade, central chimney, two-story inset gallery with plain square posts"
Cottage - c. 1940 - 68 Cannon Road - 1½ stories, gable roof, wood shingles
Jesse Gregory House - c. 1800 - 109 Cannon Road - Federal/Colonial Revival with 20th-century additions and alterations, 2½ stories, gable roof, clapboard, "original portion is 5-bay, central-hall plan with remnants of pilaster-and-lintel entry treatment; Tuscan-columned porches, windows and surrounds, entablature, and extensions to either side represent 20th-century alterations".
Nelson S. Hurlbutt House - 1922 - 8 Cannon Road - a 2½-story, Colonial Revival gambrel-roofed house with wood shingles, a three-bay facade and Tuscan-columned portico framing its central entry
Godfrey Academy - 1849 - 20 Cannon Road - moved in 1961 to its present location from Danbury Road.
Cannondale Station - 1892 - 22 Cannon Road - Victorian-era, one-story structure with a gable roof and wide, overhanging eaves supported by chamfered brackets and bargeboard with a geometric motif and a stickwork peak ornament.
Charles Gregory Store and Post Office - c. 1850 - 24 Cannon Road - 2½ stories, with a gable roof, clapboard, a "plain frieze and molded cornice with partial return", a rear wing added about 1895
A small, two-story, clapboard house behind Charles Gregory Store, built about 1900, with a gable roof.
Cannon Grange Hall - 1899 - 25 Cannon Road - Victorian, 1½-story structure with a "gable roof, clapboard with scalloped shingles in gable ends, stickwork peak ornament".
Charles Gregory Dam - 30 Cannon Road - c. 1910 - "coursed rubble spillway and abutments; wheel-pit with draft tube for turbine-based power system incorporated into west abutment. Atop west abutment is former Charles Gregory gristmill that was extensively remodeled in the late 1920s and late 1970s."
Three contributing objects located at entrance to Cannon Crossing shopping area at 30 Cannon Road:
a "c.1900 turbine that was removed from Gregory Grist Mill wheelpit"
"two c. 1925 reservoir-head gasoline pumps"
Gregory Gristmill Tenant House - c. 1900 - 32 Cannon Road - two stories, with a "gable roof, clapboard with shingled gable ends".
B. F. Brown Boarding School - 1857 - 33 Cannon Road - Greek Revival entry, three stories, "gable roof, clapboard, high brick basement with brownstone window lintels, pilaster-and-lintel entry with sidelights and transom"
A barn behind the B. F. Brown Boarding School
Cannondale School - 1872 - 34 Cannon Road - one-story, "gable roof, clapboard, hip-roofed entry shelter on large brackets, pedimented window surrounds, ogee-roofed cupola with round-arched openings"; the building was moved to its present location in 1979 from the corner of Olmstead Hill and Danbury roads.
Helen Godfrey House - c. 1900 - 37 Cannon Road - Victorian era, 2½-story house with a "gable roof, wood shingle; porch (turned posts jigsawn brackets, molded rail on turned balusters) wraps around right side to meet 2-story cross-gabled ell".
Lockwood Academy - 1851 - 43 Cannon Road, also known as 42 Cannon Road - Built in a "vernacular" style "with greek Revival influence, 2½ stories, gable roof, clapboard, pilaster-and-linetl entry, simple steeped entablature with partial return"
Barn to the rear of the Lockwood Academy building
Marjorie W. Hands House - 1939 - 63 Cannon Road - Southern Colonial Revival - 2½ stories, "gable roof, clapboard with flush-boarded facade, central chimney, two-story inset gallery with plain square posts"
Cottage - c. 1940 - 68 Cannon Road - 1½ stories, gable roof, wood shingles
Jesse Gregory House - c. 1800 - 109 Cannon Road - Federal/Colonial Revival with 20th-century additions and alterations, 2½ stories, gable roof, clapboard, "original portion is 5-bay, central-hall plan with remnants of pilaster-and-lintel entry treatment; Tuscan-columned porches, windows and surrounds, entablature, and extensions to either side represent 20th-century alterations".
Cannondale Historic District