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In the late 19th century, Willard Jennings developed Glen House as a summer resort within easy commute to Boston. A small portion of his original house remains at 245 Glen Road.
253 Glen Road (c. 1917) was one of eighteen houses along Glen Road built by members of the Jennings family on their family farmland.
This c. 1732 house was built by one of Weston's earliest settlers, Nathaniel Jennison, and later owned by the Jennings family. In 1924, it was moved across the street to 266 Glen Road.
Glen Farm, owned by Edward Jennings, was one of the largest dairies in Weston at the turn of the 20th century. His milk delivery wagons are pictured in front of the largest of two barns.
At the height of his operation, in 1903, Edward Jennings had 112 dairy cows.
This picture of Edward Jennings's two dairy barns was taken before a disastrous 1903 fire. Glen Road is in the foreground.
George Otis Wyman (1830-1905) was the son of Daniel Wyman, who bought a farm on Glen Road in 1850. It included #317 and property on three of the four corners.
317 Glen Road was constructed about 1812 and purchased in 1850 by farmer Daniel Wyman. His great-grandson, Nelson McNutt, purchased the Ford Model T wagon in 1919. (1921 photo)
317 Glen Road: the horse barn and the auto barn.
Nelson McNutt, Sophie Hamilton, Sophie's daughter May, and Florence, Evelyn, and Mary Elizabeth Wyman McNutt pose in front of 317 Glen Road in the early 1920s.
The Charles H. Jones estate, Fillmore Farm, at 458 Glen Road was developed beginning in 1901. The vegetable garden in the foreground was surrounded by a fieldstone wall.
Charles H. Jones was a shoe manufacturer and serious gentleman farmer. This rear view of his house at 458 Glen Road shows the man-made pond. The carriage house is at right; pump house at left.