Tag Archives: Windyside

Lenox as a Resort – Yokun Ave. Cottages


Windy side - 1875
Windy side – 1875 (Lenox Library)

Windyside (111 Yokun)  was built  by Boston physician Richard Cranch Greenleaf (1845-1913) and his wife Adeline Emma Stone (1849-

Lenox Golf Club
Lenox Golf Club

1936).  It is notable as one of the few stick style wooden buildings still standing in Lenox.

History of the Lenox Club (and Windyside) Now Available
History of the Lenox Club (and Windyside) Now Available

For awhile, the it had the additional distinction of having one of the earliest American designed golf courses.

Upon Greenleaf’s death  in 1913 the house, outbuildings golf course and the entire ninety acres was purchased by the Club which moved in 1914 from its smaller club house on Walker St.

In 1924 the nine hole golf course was expanded to eighteen holes and the ‘Lenox Golf Club’ was formed in association with the Aspinwall and Curtis Hotels both of which used the course for their guests.
The arrangement lasted until 1932 when the Aspinwall Hotel burned. This event and the difficult financial situation caused by the Great Depression led to abandonment of the golf course which gradually became replaced by a heavily wooded forest.
Interest in the Club was revived and major improvements to the clubhouse and grounds were initiated in the 1980s.The course was expanded in the 1920’s and shared with the Curtis and the Aspinall.  The destruction of the Aspinall and the general financial mayhem of the 1930’s made the gold course unaffordable and it is now grown in.  Fortunately, the Lenox Club was revived in the 1980’s and the building survives as a private club.

Ethelwyn/Ethelwynde I and II

Ethelwyn - 1875
Ethelwyn – 1875
Henry Braem
Henry Braem

In 1875 Henry Braem (associated with the Cunrad Line and ambassador to Denmark) built the original Ethelwyn (or Ethelwynde) off Yokun Ave.  Then as now, his neighbor was Windyside (now the Lenox Club) built around the same time.

In the 1870’s Henry also built a model farm on Undermountain Road.

In 1893 he sold the estate to the widow of Robert Winthrop who was also the mother of Grenville Winthrop, who would go on to build Groton Place in 1905

"Grandma Winthrop" Lived at Ethelwyn owned Ethelwyn until 1925
“Grandma Winthrop” Owned Ethelwyn until 1925

on West. St.  The Wintwops were “those” Winthrop’s who led the great migration and had generations of wealth and notoriety.  Mrs. Wintrop (ne’ Kate Taylor) was wealthy in her own right.  Her father had been a partner of Cornelius Vanderbilt and first president of City Bank (predecessor of the modern Citibank).

Mrs. Winthrop was, not surprisingly, a social leader in Lenox and New York.  Among other things, she was active in the summer garden club competitions (think Downton Abbey).

Ethelwyn (Ethelwynde) II (111 Yokun) - 1928
Ethelwyn (Ethelwynde) II (111 Yokun) – 1928 (Lenox Library)

In 1928 the house was purchased by Halstead Lindsley.  He tore down the wood framed original house and had a local architect, Benjamin Greeley, construct the modern Tudor-style mansion that stands today.  Recently operated as an upscale cultural retreat, it is now a private home.

Stonover I and II

 Stonover - 1875
Stonover – 1875

Ethelwyn had Winndyside as a neighbor on one side and Stonover as a neighbor on the other. Still a lovely street today, Yokun Ave. was newly created in 1874-1875 and must have been quite spectacular from the 1870’s on.

John Parsons
John Parsons

Stonover was built by John Edward Parsons, (1829-1915) a New York Attorney. Among others, his clients included the American Sugar Company. He defended them to the Supreme Court in an anti trust case – very Gilded Age!
The estate spread from Yokun to Undermountain Road and encompassed

Drive on Stonover Property
Drive on Stonover Property

the area now known as Parson’s Marsh. the still standing Stonover Farm and over Lenox Mountain to what is now the Audubon Bird Sanctuary.

His son Herbert

Stonover Farm - Undermountain Road
Stonover Farm – Undermountain Road

inherited the farm (and died there in the 1920’s a freak accident). His daughters (Mary and Gertrude) inherited the house and after some adventuresome travel, re-invented it in 1921 with a Delano and Aldrich design.

Stonover II - 1921
Stonover II – 1921

They moved the house further back on the property, dispensed with the turrets and mansard roof and created a sleek stucco house that became a center of mid 20th century culture with speakers like Alexander Kerensky. Mary (Gertrude died in 1927 on a trip to Italy).

Mary donated the Pleasant Valley Bird Sanctuary in honor of her two deceased siblings.  In a move of less certain long term value, she became interested in re-populating local beavers (hence Parson’s Marsh.)

Stonover II was demolished in 1942 and replaced with a 20th century house.

Gusty Gable

Gusty Gables 1879
Gusty Gables 1879 (Lenox Library)

Shortly after Yokun Ave. opened Mary de Pester Carey Sr.  (in her ’60’s at the time), her daughter Mary de Pester Jr., and a close family friend, Katherine Buckley Sands pooled their resources to purchase a five acre plot and build

Charles McKim (1847-1909)
Charles McKim (1847-1909)

Gusty Gables.  The Colonial Shingle Style home is the only surviving Lenox design of Charles McKim.

The survivor of the three, Mary Carey, was an avid horsewoman and active in the Village Improvement Society. She, with Edith Wharton and Florence Sturgis awarded prizes for the best-kept village lawns and front gardens.

Gusty Gables (75 Yokun) as it Appears in 2016
Gusty Gables (58 Yokun) as it Appears in 2016

Carolyn Cobb, a later owner hired Pittsfield architect Henry Seaver to update the McKim design to a more formal Colonial Revival style.  The building survives as a private residence.



View of Stonover from Edgecombe Drive

The ladies of Gusty Gables must have been pleased when their New York friend, Miss Clementine Furniss decided to build Edgecombe next door.  The

Edgecombe - 1880
Edgecombe – 1880
Edgecombe Caretaker Cottage
Edgecombe Caretaker Cottage

whimsical and rambling building apparently still standing in the mid 1980’s  at the corner of Yokun and Sunset (it’s mentioned in Carole Owens’ The Berkshire Cottages) 

The caretaker’s cottage (much altered) still stands on Sunset.


For much more on the architecture of these houses and the people who lived in them, see

Houses of the Berkshires, 1870-1930, by Richard S. Jackson Jr. and Cornelia Brooke Gilder, Acanthus Press, 2006

The Berkshire Cottages, A Vanishing Era, by Carole Owens, Cottage Press, Inc. 1980

111 Yokun Ave., Richard C. Greenleaf House – c.1870

111 Yokun Av
111 Yokun Ave., Richard C. Greenleaf House – c.1870

From Surveys Completed 2011-2012 by the Lenox Historical Commission


This 2.5-story, wood-framed house with wood siding and corner boards is an excellent example of the Stick Style of architecture. It has a complex roof form with multiple gables and dormers that are clad with asphalt shingles and have exposed rafter ends. A jerkin-head roof detail on the east side extends down to provide a hood for a set of three attic windows. Two gabled dormers are on the front and one is on the rear. There are seven brick chimneys. The Stick Styling is evidenced by the wood banding at level of the window sills and high on the second floor, cross members in the large gables, exposed rafter ends, angled braces for the wide overhanging eaves and porch roof, cross bracing in porch railing, and watertable. These detail express on the exterior of the building its interior structure, which is the essence of the style. Above the high second floor banding the cladding is board and batten, below it is clapboard. The south side is the front facade and it has 2-story canted bay window on its west end, and a canted second floor bay window over the porch near its east end, which has a jerkin-head roof. The house has a porch that extends along the entire front (south) side and wraps around to the right side. Its roof is supported by chamfered pillars with collars. A right (east) side pavilion has a front gable roof features a Palladian window with four pilasters on the second floor; it has a peaked attic window above, and a projecting first floor beneath. On the first floor is a 3-part picture window with pilasters and a leaded fanlight in the upper sash over two lights flanked by double hung windows with diamond panes in the upper sashes. To the left of this pavilion is a triangular bay window on the second floor over the porch roof. There is a 2-story hipped roof rear ell with rear wall brick chimney. The foundation is stone. Some original tall, narrow windows arranged in pairs are extant, but many of the windows have been replaced or altered—such as a 3-part picture window to the left of that on the first floor of the right side pavilion with replaced glazing. Another change to the building is the removal of a projecting porch entry that angled 45 degrees out from its southeast corner. A balcony with exterior stair to grade has been added to the right of the right side pavilion. An open deck has replaced an original polygonal section of the porch at the southwest corner of the house.

A small wood-framed barn/garage built c.1875 is located behind the house. It has a steeply pitched front gable roof with large gable-roofed cupola. It has board and batten siding and its sliding doors for the vehicle bays are intact. Stone piers flank the driveway entrance off Yokun Avenue. The long driveway terminates in a circular section on the east side of the house in front of the barn. There are many mature coniferous and deciduous trees throughout the property and a more heavily wooded area behind the house.


Dr. Richard C. Greenleaf of Boston built Windyside, presumably as a summer home, although by the mid-1880’s he had made Lenox his permanent residence. An 1886 guidebook called it “one of the notable houses of the town”, and remarked on its interior “furnished in exquisite taste”. A large music room, added on to the house for his daughter’s wedding, contained a Roosevelt organ.

Greenleaf sold the house in 1921 to the Lenox Club, which relocated here from its Walker Street clubhouse. The Lenox Club has occupied the building ever since.


Lenox – Massachusetts Shire Town. David Wood, 1969 p.203

The Book of Berkshire. Clark W. Bryan, 1886 p.44

Lenox Club records

Lenox Assessor’s database