Webster Hill Area

The Webster Hill Area was documented by the Weston Historical Commission in 2005 and includes the following properties:
120 Church Street
7, 13, 19, 26, 32, and 36 Gypsy Trail
8, 16, and 27 Saddle Hill Road
11, 29, 37, 38, 49, 58, 60, 64, 74, 78, 83 Webster Road

Area Form
View the 2005 Webster Hill Area Form, including data sheets and photographs.
74 Webster Road
The Webster Hill Area, located in the northeast corner of Weston, developed in the 1910s and 1920s as a neighborhood of comfortable middle class homes. Webster Hill is one of the topographical high points in Weston. Webster Road, a loop road entering and exiting off Church Street, is marked at each entrance with handsome stone posts. The curve of Webster Road enhances the visual interest of the neighborhood. The roadway is steep, particularly “upper” Webster Road around #83, and large exposed boulders reflect the area’s glacial origins.

The Webster Hill Area is heavily wooded with large mature pines and hemlocks along with deciduous trees and mature rhododendrons and azaleas. Large lot sizes and naturalistic landscaping contribute to the wooded character. Houses are set back from the road, and most are designed to fit with sloping topography.

House Styles
Of the 21 houses, 15 were built before 1930 and most are Colonial Revival in style. Two houses are stone, three are stucco, and the remainder have shingle or clapboard exteriors. A number of early garages have survived. Styles demonstrate the variety possible within the Colonial Revival vocabulary and also include French Eclectic and Craftsman examples. Lot sizes range from 40,000 square feet on Gypsy Trail to as large as 8.5 acres on Saddle Hill Road, with most of the lots on Webster Road sized between two to four acres.
Webster/Goodale House
The oldest house in the Webster Hill Area, the Webster/Goodale House at 19 Gypsy Trail (1898/1913, MHC 782, Map #17), was built about 1898 as a small summer cabin, then enlarged and remodeled into a year-round house in 1913 in the Colonial Revival style. Later remodeling produced a rambling residence with numerous additions. The main entrance, located on the south facade of the main block, is marked by a handsome Colonial Revival entablature.
19 Gypsy Trail
Charles & Mary Plumer House
Development began in earnest in the early 1910s. The Plumers, who bought and subdivided the land, built the Charles and Mary Plumer House at 11 Webster Rd., formerly #23 (1911, MHC 789, Map #10, Photo #1), a two-story Colonial Revival with a hip roof, paired chimneys, and a pedimented center entrance roughly centered on the six-bay asymmetrical facade. A two-story sun porch on the west end and two-story wing on the east end make the house long and narrow in plan. Windows are 6/6 with shutters.
Stucco Houses
Three solidly constructed stucco houses were built next:
  • The Paul and Jesse Winsor House at 16 Saddle Hill Road (1912, MHC 787, Map #11, Photo #2 )
  • The Homer and Mary Lockwood House at 38 Webster Road (1913, MHC 792, Map #6, Photo #4)
  • The Jonathan and Lalia Powell House at 74 Webster Road (1913-14, MHC 797, Map #3, Photo #3).
16 Saddle Hill Road
Paul & Jesse Winsor House
Of these, the most significant is 16 Saddle Hill Road. With its hard southern yellow pine beams, concrete walls, asbestos shingle roof, expensive handmade green floor tiles in the family area, and plain Venetian red tiles in the large servants’ wing, the house was fireproof and virtually indestructible. It has remained largely intact. Designed in the Craftsman style, it features the wide overhanging eaves and show rafters typical of the style. A balcony on the second floor is cantilevered out on brackets and adorned with a decorative railing which is the house’s most important visual feature. Windows are generally double hung with 12/12 sash. On the first floor at either side of the central entrance door, small glass panes are used in large “picture” windows recessed within an arcade of segmental arches. A well-detailed one-vehicle early outbuilding features an elliptical fanlight window over wooden double doors, along with cross-hatched boarding along the sides. A later three-car garage is stucco with a shaped wall gable over the center bay. The house and outbuildings are located on a secluded 8.5 acre lot with mature landscaping, a gravel driveway, and stone walls.

Homer & Mary Lockwood House
The Lockwood House at 38 Webster Road, prominently located at the curve of the road, is a gracious two-story gable-across stucco Colonial Revival, painted yellow, with a slate roof. The asymmetrical facade features a semi-circular hood sheltering the entrance door. Window sash is 8/1. One- and two-story wings and sun porches add to the picturesque quality.

Jonathan & Lalia Powell House
The handsome five-bay, 2 1/2- story tan stucco Colonial Revival Powell House at 74 Webster Road has a number of notable features including a high hip roof, large one-story center entrance portico with balustrade and flanking oval windows, large double dormer on the front facade, and 6/1 windows with shutters.

John & Virginia Lilly House
A second major phase of development occurred in the 1920s. The John and Virginia Lilly House at 58 Webster Road (1920-21, MHC 794, Map #14) is a fine example of traditional Georgian Colonial architecture. The large 2 1/2-story, seven-bay center entrance Colonial features a central portico with balustrade sheltering double entrance doors with sidelights and transom. One-story side porches extend from each side. The entrance facade has three dormers, the largest in the center.
Walter Macomber Designs
Architect Walter Macomber designed two Colonial Revival houses in the mid-1920s:
  • The Robert and Grace Warren House at 60 Webster Road (1925-26, MHC 795, Map #5)
  • The Waldo and Evelyn Noyes House at 64 Webster Road (1925-26, MHC 796, Map #4)
Walter Macomber, the brother of Evelyn Noyes, was a Virginia architect who worked on the restoration of Williamsburg. Evelyn’s father, John Macomber, was the builder of #64.
60 Webster Road
Warren & Elizabeth Campbell House
About the same time the fieldstone Warren and Elizabeth Campbell House at 120 Church St. (1925-26, MHC 779, Map #1) was designed by reform-minded New York architect Ernest Flagg. Flagg (1857-1947) was the designer of the Corcoran Art Gallery, the Naval Academy in Annapolis, and the Singer Building in New York City and author of Construction of Small Houses. Flagg developed a technique of building masonry houses by pouring in concrete to bond the stones. He was an urban reformer interested in construction of multi-family dwellings and economical small houses. Flagg’s early training at the Ecole des Beaux-Arts in Paris is reflected in the French influences in the house.
120 Church Street