Isaac Gleason House // 1805

Built in 1805 by Isaac Gleason (Glezen), this Federal style mansion was later expanded in the early 20th century in the Colonial Revival style as Wayland became more of a wealthy Boston suburb. Located on the appropriately named Glezen Lane, this house was constructed for Isaac Glezen (1769-1843), who farmed the land here. Other family members built homes nearby. As Wayland shifted from rural community to a wealthy Boston suburb in the early 20th century, the property was purchased by Charles Ashley Hardy and his wife, Alice. The couple would sell the property in 1918, which comprised of 89-acres of land and a chauffeur’s residence, was purchased by Albert H. Beck, a New York banker. The property was later subdivided and consists of many other large, single-family homes.

Griffin-Malloy House // 1720

This First Period Home on in Wayland, Massachusetts, can be found at 184 Glezen Lane and is one of the community’s oldest residences. The Griffin-Malloy Homestead dates to about 1720 and is a large, single-family farmhouse that is just over 300 years old! Records state that the house was built by early settler, Samuel Griffin and possibly expanded later by his son, Deacon Jonathan Griffin. After generations of Griffin Family ownership, the old farmhouse was purchased in 1877 by Timothy Malloy (1839-1909) an Irish immigrant who settled in Wayland and operated a farm here. The house as of the 20th century, retained much of its original wood paneled walls and fireplaces, and has been lovingly preserved by generations of great stewards. 

Cochituate School // 1910

The Cochituate School in Wayland, MA, was built in 1910 to educate the Cochituate Village’s growing student population. The industrial village was dominated by shoe manufacturing with workers largely consisting of first- and second-generation European immigrants who moved to New England for work. Boston architect, Willard P. Adden, designed the school, which replaced an earlier schoolhouse on the site that was outgrown. The two-story, brick school was expanded following WWII, when a long rear ell with classrooms and a cafeteria was designed by Perry, Shaw & Hepburn. In the 1990s, the old Cochituate School was renovated and converted to senior housing administered by the Wayland Housing Authority.

Damon-Griffin House // 1869

The Damon-Griffin House at 92 Commonwealth Road in Wayland, Massachusetts, is one of the exemplary buildings constructed in the Cochituate village in town, which prospered in the 19th century and centered around industry. This stately Second Empire style mansion is sited on a rise in the land overlooking Lake Cochituate and was completed in 1869 for George A. Damon (1826-1885), a wealthy businessman. George Damon died in 1885, and the house was sold to Wallace Griffin, one of the Griffin brothers who worked for the Bent Company, a prominent local shoe manufacturer. In 1890, Noble Griffin bought the house from his brother and, as his business prospered, proceeded to fix up the house as the showplace of a successful shoe manufacturer. In the mid-20th century, the Damon-Griffin House became a funeral home, and later was purchased by a developer who subdivided the land to build a suburban-style development of detached homes behind the house, and constructed an addition to the rear with more condominium units.

Grout-Heard House // c.1743

The Grout-Heard House on Cochituate Road in Wayland, Massachusetts, is one of the oldest extant residences in the community and architecturally significant as it shows the evolution of architectural tastes throughout the centuries. The house was built around 1743 for Jonathan Grout (1701-1748), a grandson of an original settler in the area, by the time of his marriage to Hannah Heard in 1743. Early records suggest that the house was originally just one bay deep and two-stories tall with a central entry. The property was sold in 1744 to Richard Heard, Jonathan’s brother in-law. In 1787, Silas Grout (1755-1820), a blacksmith, purchased the house and likely added rooms on the rear of the house. In 1822, Silas’ descendants added the side ell and the residence became a double-house in the mid-19th century. The house was moved from the site to make room for the 1870s Town Hall, and the rounded two-story side bay was added. After the Town Hall was razed in the 1950s, the Grout-Heard house was moved back to its original site in 1962. Since that date the Grout-Heard House has been the offices, research center, artifact repository and house museum of the Wayland Historical Society, who added a two-story Modern addition at the rear.

Warren Gould Roby House // 1888

The Warren Gould Roby House at 11 Concord Road in Wayland is located just north of the town’s public library building and is one of the community’s finest examples of the Colonial Revival style. The Roby family occupied this land going back to 1725, when Ebenezer Roby (1701-1772) came to Wayland and built a house on this site. His son, Dr. Ebenezer Roby, Jr. (1732-1786), inherited the large Georgian house which also had an office for his medical practice. The old homestead passed to Dr. Roby’s son, William Roby, and eventually to his grandson Warren Gould Roby who lived in Cambridge and worked as a metal merchant and would spend summers at the family homestead. The old colonial Roby House burned in 1886 which is when Warren Gould Roby (1834-1897) rebuilt a Queen Anne residence on the site. Before his death in 1897, Warren Roby donated a half-acre of his land to the south and $25,000 to the town for the purpose of constructing a library that would be as fireproof as possible, the result is the Wayland Public Library. After his death, the Roby heirs, who lived in Cambridge, sold the family estate to Daniel Brackett, a lawyer who also served as the Wayland Town Clerk and Assessor. It was likely Mr. Brackett who expanded the home in the early 20th century in the Colonial Revival style and form we see today.

Upland Farmhouse // 1929

The Nashoba Valley Winery in Bolton, Massachusetts, is one of Bolton’s most successful examples of the adaptation of an old agricultural property in the state. The land here was first developed as a farm in the early 19th century by Captain Martin Houghton (1779-1833). The farmland here, which has always had a scenic view, was called “Valley View Farm” later owner, William N. Felton (1835-1920). Sadly, the old farmhouse burned down in 1928, and the property was sold that year to Roy Clemens, an osteopathic doctor, who had this charming shingled cottage built in 1929. Roy and his wife, Laura, planted an apple orchard on the hills and named the property “Upland Farm”. Roy died in 1969 and Laura followed in 1981. With suburban development likely, the property was ultimately saved when it was purchased by Jack Partridge as the new home of the Nashoba Valley Winery, which was founded in Somerville in 1978. The winery specializes in fruit wines, and grows most of the fruits and berries for them on the property. The business expanded, adding a distillery, brewery and restaurant, and the beautiful grounds are often host to weddings and events.

Captain Caleb Moore House // c.1795

This stately Federal style residence constructed of brick sits atop a lovely hill in the town of Bolton, Massachusetts, and has been lovingly maintained by its owners for over 225 years. The home was built by Caleb Moore (1768-1826) just before his marriage to Achsah Whitney in 1796. Caleb was a merchant and later a shareholder and president of the Lancaster & Bolton Turnpike Corporation, chartered in 1805, to collect tolls for travellers from or to Boston from central Massachusetts. Caleb and Achsah had eight children, sadly, five of their children died as teenagers or young adults. The farmhouse was inherited by Alpheus Moore (1802-1882), who operated his late-father’s store and held a liquor license, possibly running the home as a tavern along the turnpike.

Bolton Public Library // 1903

The Bolton Public Library was established in 1859, when the town’s library collection was housed on a few shelves in the Selectmen’s room at the Town Hall. In the following decades it became clear to the community that a purpose-built library building should be constructed in town to house the growing collections there. At the time when wealthy benefactors donated funds for public libraries in towns and cities across New England, sisters Emma and Anna Whitney gifted their hometown of Bolton, $10,000 to build a dedicated library building in memory of their father, Captain Joseph Whitney in 1901. Completed in 1903, the Bolton Public Library was designed by the architectural firm Stone, Carpenter & Willson and built of local Bolton fieldstone in the Tudor Revival style. Of particular architectural merit is the red tile roof and three gabled bays with carved stucco and woodwork within half-timbered frames. The library was added onto in 2010 from plans by Lerner Ladds & Bartels Architects, who replicated key materials and forms so the new wing feels coherent with the original yet clearly differentiated.

Coolidge-Burnham House // 1822

This charming old home on Burnham Road in Bolton, Massachusetts, was built in 1822, but as a one-story three-quarter cape house with the additional story added later in the 19th century. The residence was built for William Coolidge, a Revolutionary War veteran. After successive ownership, the property was sold in 1855 to Reuben Burnham, a carpenter, who soon after added the second floor onto his new home, keeping the original cornice which now serves as a visual reminder of the home’s changes. Sadly, around 100 years later, the highway cut through the town, bisecting this property, which now abuts the busy road, but owners have maintained and preserved this stunning property which is evocative of the early days of Bolton.