A “Quiet and Natural” Place

The Winsor Estate and Meadowbrook Road Area

Pamela W. Fox writer
Photography Courtesy of Weston Historical Society

The fourth in a series of articles in which we explore the people, history, and traditions that create Weston’s unique character

Robert Winsor’s 472-acre estate “Chestnut Farm” was once the second largest in Weston, stretching from Wellesley to Summer Streets. Meadowbrook Road extends the length of the former estate, which included the sites of the Weston Golf Club and Meadowbrook School. Today, houses of all sizes and styles overlook the fairways or blend into the wooded landscape. The natural beauty and serenity of the neighborhood is no accident but rather the result of careful planning by a far-sighted landowner and the preeminent Brookline landscape design firm of Olmsted Brothers.

When Robert Winsor and his wife Eleanor settled in Weston in 1883, he was a young Harvard graduate with just a few years experience at Kidder, Peabody & Co. He began his career there as a clerk but was quickly recognized and promoted because of his business acumen. Under Winsor’s leadership, Kidder, Peabody & Co. developed from an eminently respectable local investment bank to one of the greatest banking institutions of the time. Newspaper articles lauded him as “the J.P. Morgan of Boston” and “one of the country’s leading bankers.” He was praised as a man of foresight who had anticipated the need for improved transportation, utilities, banking, and communications.

The Winsors built a Shingle-style house that still stands on a hill overlooking Boston Post Road at the corner of Hemlock Road. Within a few years, Robert Winsor began purchasing additional property. Between 1887 and 1890, he acquired land at the corner of Wellesley Street and Boston Post Road. After laying out Winsor Way, he built houses at No. 1 and 10 and moved his widowed mother and five of his younger siblings to No. 10. Winsor assisted his siblings as they became established in homes and careers. His active support as trustee and fundraiser was instrumental in establishing two prestigious educational institutions, Winsor and Middlesex Schools, headed by his sister, Mary Picard, and brother Frederick respectively.

In 1898, the 30-year-old successful businessman made his first major land purchase, the 83-acre Bryden farm, including a Greek Revival farmhouse that still stands at 279 Meadowbrook Road. At the end of Winsor Way, he built a Tudor-style mansion covered in dark brown shingles, with picturesque gables facing in all directions. Chestnut Farm was featured in the 1902 Boston Sunday Herald article headlined “Weston Has Become the Lenox of the East,” which described “a beautiful estate, where comfort, not lavishness, is the keynote.”

Robert Winsor wanted his children to grow up in an unpretentious farm atmosphere. The estate was run as a gentleman’s farm and supplied fresh food for the family. The main barn was a substantial structure, more than 200 feet long. Nearby on what is now Hidden Road was a henhouse and a duck house. Winsor built a cottage at 248 Boston Post Road for his superintendent, Philip Spaulding, and several small staff houses at the upper end of Wellesley Street.

Over the next two decades, Winsor acquired additional land in Weston, until only General Charles Jackson Paine’s estate was larger. As early as 1910, the foresighted banker was thinking about future subdivision. That year he hired Olmsted Brothers to make a general plan for the property. Frederick Law Olmsted, Jr., principal partner for the job, recorded his client’s long-term plan: “He wants to keep place quiet and natural; but wants to build some woods-roads and gradually improve the place with the idea in mind of subdividing it as time goes on . . . into smaller places of (say) ten acres and upwards.”

Winsor asked the firm to lay out a road system that would be convenient for his own use and of value when the property was subdivided. The plans demonstrate the continued influence of naturalistic design principles advocated by Frederick Law Olmsted, Sr., father of American landscape architecture. The Olmsted Brothers firm located roadways and house lots based on topographical and geological features, taking advantage of any irregularity.

Olmsted Brothers also helped to design the four-acre artificial pond constructed beginning in 1909 on what is now Skating Pond Road. A reported 75 laborers worked on the swampy site to remove enough muck to make the pond deep enough for swimming. In winter, the skating pond was a local landmark. Early photographs show girls skating in leisurely fashion in their long flowing dresses and boys practicing hockey in a center section, set off by long boards. In his memoir Growing Up in Weston, Philip Coburn describes the curling rink at the west end, where “a horse drawn plane made the ice as smooth as glass.” With the flick of a switch on a nearby tree, anyone wishing to skate in the evening could turn on lights.

Next to the pond was a log shelter with log benches and a fireplace. Here, according to Coburn, “Mrs. Winsor sat in front of a table, serving hot coffee and tea to the grown-ups and marshmallows and cocoa to the children.” This pleasant custom continued until the Winsor boys went into the service in 1917. Reportedly, the Winsors’ reputation for hospitality brought an influx of strangers into the community and the pond had to be closed to the public.

Robert and Eleanor had four children who survived into adulthood: Robert Jr., Philip, Alexander “Sandy,” and Mary Pickard. Philip died of pneumonia in France while serving as an ambulance driver in the American Field Service. Robert and Sandy became partners at Kidder, Peabody, as did Mary’s husband, Walther H. Trumbull, Jr. Of the three homes built for the children within the estate, only one, at 209 Meadowbrook Road, survives today.

Robert Winsor was a founding member of the Weston Golf Club, established in 1894. The original location on Church Street posed some problems: the third fairway was a cow pasture, for example, and golfers had to watch their step. The land was leased from several owners, and one refused to allow Sunday play. When the club began looking for a new home, Winsor, who was president at the time, offered land within his estate. Contrary to popular belief, he did not donate the 50-acre parcel. He did help finance the purchase and construction of the original nine holes by holding a $38,500 mortgage, payable with interest. Included in the deed was a clause stating that “the granted premises shall be used only for a golf course or country club” and if this purpose were to change, the property would revert to himself or his heirs.

The club was fortunate to secure the services of Donald C. Ross to design the new course. Ross, a Scotsman, has been described as “one of the world’s outstanding golf architects.” Horse-drawn vehicles were used for earthmoving, and men with picks and shovels did the rest. By 1917, the original nine-hole golf course was complete. Farm operations were moved to the other end of the estate. The barn was converted into a clubhouse with a men’s locker room where the Guernseys once stood, a ladies’ dressing room where Winsor once kept his Morgan horses, and a bowling alley in the former sheep pens.

An additional nine holes, also designed by Ross, were completed in 1923. The Weston Golf Club would become a social center for the town’s business and professional elite. The resettlement of the club and golf course enhanced the residential value of Winsor’s remaining land by transforming ordinary farmland into desirable residential lots.

In 1918, Robert Winsor, now age 60, made a dramatic change in ownership of Chestnut Farm. Retaining 16 acres for his own use, he turned over the remaining 422 acres to the newly formed Weston Real Estate Trust, with himself and his three surviving children as trustees. Development of the property began in earnest in the 1920s. The Weston Roads Trust was formed to build and maintain the roads. All property owners were required, and are still required, to contribute as members of the roads trust. The 8.25 miles of private roads include Meadowbrook, Doublet Hill, Cart Path, Possum, Green, Cedar, Farm, Robin, Dellbrook, Dogwood, Hidden, and Skating Pond Roads, and Winsor Way.

A second institution that enhanced the neighborhood’s appeal was Meadowbrook School, which moved to its present site in 1924 and changed its name from Pigeon Hill School at that time. School facilities were used for a winter sports program including a lighted skating pond. For a few years in the mid-1920s there was even a toboggan chute extending from a high wooden stand at the top of the hill.

In 1922 the Weston Real Estate Trust invited architects to enter a competition for design of a “small house in the country.” A newspaper report about the contest noted that changes in lifestyle had altered perceptions as to what was necessary in a house:

The majority of families in the last few years have reduced the overhead expense of housekeeping by managing without a maid servant, seeking more compact living quarters, and by less entertaining of guests.

The Weston Real Estate Trust had a small sales office on Meadowbrook Road and published a brochure entitled Sites in WESTON for Large or Small Houses. The promotional piece reflects Winsor’s desire to protect the rural character of the land and states: “It is felt that large and small houses have the same chance for beauty and that the people who come to this community have the perception to adapt houses to the natural beauty of the surroundings.” Land cost $3,000 an acre. The trust has been described as “choosy” about who was allowed to purchase lots. Prospective buyers had to be of the accepted socioeconomic and religious background.

The stock market crash of October 1929 was devastating to the aging senior partner and his firm. Less than three months later, he died of a heart attack at age 71. The Depression brought land sales almost to a halt. Weston Golf Club struggled during the Depression and suffered another setback in 1938, when the clubhouse was severely damaged by fire. It was rebuilt without some of the architectural amenities. Many of the interior roads were not completed until after World War II. The Tudor mansion was demolished about 1948 and a brick house built on the site. That house was replaced in 2000 by a third mansion. Management of the Weston Real Estate Trust stayed in the family. Lots were sold slowly, by word of mouth. In 1986, after nearly 70 years of operation, the Winsor estate land had all been sold and the Weston Real Estate Trust was dissolved.