The Chiltern Hundreds Area is a subdivision developed beginning in the mid-1920s in the southeast corner of Weston. The area encompasses 104 houses on approximately 145 acres. A small section of the original subdivision is located across the town line in Wellesley and is not included in this form. Designed in the early 1920s by well-known landscape designer Arthur Shurtleff (later Shurcliff), Chiltern Hundreds is characterized by quiet curved streets laid out roughly in a fan-shape, with many roads leading toward the Wellesley Farms train station.  The land slopes gently to the south and at its highest point is 300 feet above sea level.  Ridgeway Road, the principal route through the subdivision, provides a convenient connection to Commonwealth Avenue, once the main automobile route into Boston. Lot sizes range from about 0.14 acre to three acres, with most less than one acre. Because of commonalities in house size, setback, massing and materials, the area has a visual unity and sense of place. Two Shingle-style houses (153 Ridgeway Road and 64 OxBow Road) date from before the subdivision. The remainder of the houses in the Chiltern Hundreds Area were built between 1926 to 2003, with most dating before the mid-1950s. The most common house type is the Colonial Revival in all its manifestations, including Georgian, Federal, Dutch Colonial, Cape, and Garrison Colonials. Houses from the 1950s are generally Modern in style, most commonly one-story ranches with occasional split-level examples. The most common exterior materials are clapboard and wood shingles but brick, stone and stucco are also used. Some houses have been remodeled or demolished to make way for new, larger homes, but in general the area has remained largely intact.

From the 1860s to the 1920s, most of the Chiltern Hundreds subdivision land belonged to the estate of Charles Townsend Hubbard and later his son, Charles Wells Hubbard, and was maintained as part of a large gentleman’s farm. Both Hubbards subdivided off a few lots along Orchard Avenue (see Orchard Avenue Area, Form U) for relatives and friends, and in 1899, C. W. Hubbard subdivided off a lot on Ox Bow Road which he sold to S. F. Denton. Denton built a substantial shingle Colonial Revival house at 64 Ox Bow Rd (c.1900, MHC 1076, Map #69). The house at 153 Ridgeway Rd (1881-83/1920s, MHC 1093, Map #86) also predates the subdivision but was not moved to its present location until the1920s. The central core of this shingle house was originally the maid’s quarters (north wing) of the Shingle-style Hubbard mansion, Ridgehurst, at 80 Orchard Avenue (see Area Form U and MHC 378).

Prominent landscape architect Arthur Shurtleff (later Shurcliff) planned the Chiltern Hundreds subdivision in the early 1920s, and sales commenced in 1925. The first Weston lots to be purchased were those closest to the Wellesley town line, within walking distance of the Wellesley Farms Station. The first houses were generally modest in size, but many were well-constructed of brick or stone, with slate roofs. Notable 1920s Colonial Revival examples include 17 Locust Road (c. 1926, MHC 1057, Map # 50), a brick corner house with slate roof and entrance entablature with fanlight and broken scroll pediment; and 23 Old Colony Road (c. 1929, MHC 1061, Map #54), a two-story brick Colonial Revival with a slate roof and central entrance portico. Clapboard and shingle Colonial Revivals, generally painted white, include 4 Chiltern Road. (c. 1926, MHC 1009, Map #3) a shingled two-story Colonial with a one-story porches at each gable end;  5 Chiltern Rd (c. 1926, MHC 1010, Map #4), a Garrison Colonial with overhang;  8 Locust Road (c. 1929, MHC 1055, Map #48); and 234 Ridgeway Road (c. 1926, MHC 1106, Map #99), a two-story center entrance Colonial Revival with semi-circular portico.

The picturesque, asymmetrical Tudor style was used in the 1920s at 240 Ridgeway Road (c. 1927, MHC 1107, Map #100, Photo #1), a small1/2 story brick and half-timbered cottage where the asphalt-shingled roof wraps around the roof edges to imitate the appearance of thatch. A tall brick chimney with three chimney pots sits atop the clipped gable roof. Other examples of 1920s brick Tudors include 53 Dean Road (c. 1928, MHC 1040, Map #33), 244 Ridgeway Road (c. 1929, MHC 1109, Map # 102) and the Marie and John Lawless Jr. House at 3 Pembroke Road (c. 1927, MHC 1082, Map # 75, Photo #2). The latter is prominently sited at the corner of Pembroke and Old Colony Roads and features a brick first floor and half-timbered second-floor cross gable. No. 11 Locust Road (c.1927, MHC 1056, Map #49) is a stucco Tudor with high pitched front-facing gable roof. No. 43 Ox Bow Road (c. 1926, MHC 1070, Map #63) is a stucco Tudor with a clipped gable roof; and the adjacent 45 Ox Bow Road (c.1926, MHC 1071, Map #64) is a brick Tudor with half-timbered sloping wings, a slate hip roof, and small pane casement windows

Similar small houses were built during the early 1930s.  The north side of Pembroke Road features nicely proportioned Colonial Revival houses at 29 Pembroke Road (c. 1935, MHC 1087, Map #80); 33 Pembroke Road (c. 1934, MHC 1090, Map # 83), a small brick Col. Rev. with slate roof, 12/8 windows, and a fanlight over the entrance doorway; 37 Pembroke Road (c. 1934, MHC 1091, Map #84), a small shingled Colonial Revival; and  41 Pembroke Road (c. 1934, MHC 1092, Map #85), a Dutch Colonial.  English Tudor and English Country houses continued to be a popular option for 1930s builders. No. 224 Ridgeway Road (c. 1931, MHC 1103, Map #96) is a picturesque fieldstone Tudor with arched window openings, a slate roof, and rough irregular “antique” clapboard accents. No. 169 Ridgeway Rd. (c. 1934, MHC 1095, Map # 88) echoes English country houses; 54 Dean Road (c. 1932, MHC 1041, Map #34) is a charming fieldstone  1 1/2 story English Country cottage; 54 Ox Bow Road (c. 1931, MHC 1073, Map #66) is a well-preserved stucco Tudor with a high pitched front-facing gable roof; and 13 Old Colony Road (c. 1930, MHC 1060, Map #53) is an symmetrical brick Tudor with a steep gable roof facing front, irregularly-shaped bricks scattered to look handmade, casement windows, and fieldstones outlining the arched entrance door.

Other notable 1930s houses include 33 Dean Road (c. 1931, MHC 1034, Map #27, Photo #3), a two-story brick Neoclassical example with a two-story semi-circular portico, central entrance with leaded glass fanlight and sidelights, and slate roof with eyebrow dormer. No. 41 Ox Bow Road (c. 1931, MHC 1069, Map #62) is a two-story Mediterranean-style stucco house with a slate hip roof

The late 1930s and early 1940s saw the construction of handsome Colonial Revival houses located along Ridgeway Road and at important focal points such as the grassy islands at the intersections of Ridgeway Road with Chiltern and Dean Roads. No. 200 Ridgeway Road (c. 1939, MHC 1099, Map #92, Photo #4) is a two-story hip-roofed clapboard Colonial Revival with a distinctive broken scroll pedimented central entrance. No. 77 Dean Road (c.1938, MHC 1046, Map #39), a two-story brick Colonial Revival, anchors the corner of Ridgeway Road along with 80 Dean Road (c. 1939, MHC 1047, Map #40), another two-story Colonial Revival. No. 60 Chiltern Road ( c. 1938, MHC 1021, Map #15) is a two-story white clapboard corner house with slate roof, paired chimneys, and notable detailing including dentils and a center doorway with fluted pilasters and an elongated fanlight motif set within a triangular pediment. No. 90 Dean Road (c. 1942, MHC 1049, Map #42), a handsome 2 1/2-story stone Colonial Revival with a slate roof, anchors the corner of Dean and Columbine Road along with 91 Dean Road (c. 1940, MHC 1050, Map #43), a two-story well-detailed brick Colonial Revival with slate hip roof, delicate Adamesque semi-circular portico with fluted columns, decorative leaded glass sidelights flanking the center entrance door, dentil cornice, and 8/8 windows. No. 183 Ridgeway Road (c. 1940, MHC 1098, Map #91) is a two-story brick-end Colonial Revival with a notable entablature surrounding th center entrance door and 220 Ridgeway Road (c. 1937, MHC 1102, Map #95) is a Dutch Colonial with pent eave that exemplifies a house type common in the development.

Modern-style one-story ranches were first built within the development in the 1940s and became popular in the 1950s. Some examples borrow motifs seen in earlier Tudor houses in the neighborhood, such as the use of wide, irregular rough clapboards used to give the appearance of antiquity. The ranch house at 40 Dean Road (c. 1953, MHC 1037, Map #30, Photo #5) combines warm-colored stone with this type of irregularly-shaped clapboards. No. 228 Ridgeway Road (c. 1951, MHC 1104, Map #97) is a ranch with a brick center section accented by a board-and-batten gable with a scalloped lower edge and a “bird cote” motif in the gable peak.