Among the contributing properties, several are particularly important in the context of the district.
None have yet been listed individually on the National Register, but they are all local landmarks, carrying markers indicating what they are and their year of construction.

Samuel Allen Farm, 400, 401–407 Quaker Road.
Four buildings remain standing from this farm established sometime before 1820; all were built by 1852.
The currying shop, 400, is on the west side, with the main house, tenant house and an old barn.
All are similar buildings, four bays wide and from one-and-a-half to two stories high.

Thomas Dodge House, 428 Quaker Road.
Cabinetmaker Thomas Dodge and his wife Hannah, later inhabitants of the early settlement, built this three-by-two-bay house.
Since it is on sloping ground, it is two stories on the east but only one and a half on the west.

Meeting House, 420 Quaker Road.
Located on a slight rise above the road, immediately to the west of the Allen properties, the meeting house is a two-story clapboard-sided gabled structure with a full verandah around the south and east.
Inside, chamfered wooden posts support a gallery on three sides.
It is the oldest known building in the town of New Castle, dating to 1753.

Reynolds–Carpenter Farmhouse, 332 Quaker Road.
The southern end of the district is anchored by this five-bay, two-story gabled house, one of two likely built for one of Reynolds' seven sons.
Its rear wing was added in 1850 by Robert Carpenter.
North of it is a barn from the same era, now used as a garage.

Stony Hollow Farmhouse, 478 Quaker Road.
This house-and-barn combination is located at the north end of the district.
The clapboard-sided house contrasts with the shingled barn, but both are believed to have been built around 1820, with the house expanded later in the 19th century.

Sutton–Reynolds House, 354 Quaker Road.
Situated to the north of the Reynolds–Carpenter House, this similarly-sized house is also believed to have been built by Reynolds for another of his sons.
It is distinguished by the two chimneys that rise from either end.

Thorn–Dodge House, 386 Quaker Road.
The rear wing of this five-by-two-bay two-story clapboard-sided gabled house is the original structure built by Elnathan Thorn.
Henry Dodge moved it here when he built the current house in 1852.
Among the contributing properties, several are particularly important in the context of the district. None have yet been listed individually on the National Register, but they are all local landmarks, carrying markers indicating what they are and their year of construction.
Samuel Allen Farm, 400, 401–407 Quaker Road. Four buildings remain standing from this farm established sometime before 1820; all were built by 1852. The currying shop, 400, is on the west side, with the main house, tenant house and an old barn. All are similar buildings, four bays wide and from one-and-a-half to two stories high.
Thomas Dodge House, 428 Quaker Road. Cabinetmaker Thomas Dodge and his wife Hannah, later inhabitants of the early settlement, built this three-by-two-bay house. Since it is on sloping ground, it is two stories on the east but only one and a half on the west.
Meeting House, 420 Quaker Road. Located on a slight rise above the road, immediately to the west of the Allen properties, the meeting house is a two-story clapboard-sided gabled structure with a full verandah around the south and east. Inside, chamfered wooden posts support a gallery on three sides. It is the oldest known building in the town of New Castle, dating to 1753.
Reynolds–Carpenter Farmhouse, 332 Quaker Road. The southern end of the district is anchored by this five-bay, two-story gabled house, one of two likely built for one of Reynolds' seven sons. Its rear wing was added in 1850 by Robert Carpenter. North of it is a barn from the same era, now used as a garage.
Stony Hollow Farmhouse, 478 Quaker Road. This house-and-barn combination is located at the north end of the district. The clapboard-sided house contrasts with the shingled barn, but both are believed to have been built around 1820, with the house expanded later in the 19th century.
Sutton–Reynolds House, 354 Quaker Road. Situated to the north of the Reynolds–Carpenter House, this similarly-sized house is also believed to have been built by Reynolds for another of his sons. It is distinguished by the two chimneys that rise from either end.
Thorn–Dodge House, 386 Quaker Road. The rear wing of this five-by-two-bay two-story clapboard-sided gabled house is the original structure built by Elnathan Thorn. Henry Dodge moved it here when he built the current house in 1852.
Old Chappaqua Historic District