Vermont historic Houses

Daniel Heald House // c.1785

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Daniel Heald (1739-1833), one of the earliest settlers in the town of New Flamstead (later renamed Chester) Vermont, established his farm on the west side of the upper Williams River. He moved to rural Vermont from Concord, Massachusetts, where he was one of the Patriot soldiers who at the Concord bridge, fought against the British troops while his wife and children who had fled from their home viewed the battle from a neighboring hill. He, with his family, emigrated to Vermont in about 1776 and eventually would serve as town clerk from 1779 to 1799 and as town representative from 1783 to 1797. Around 1785, he built this residence, oldest wood-frame house in North Chester, a two-story, central-chimney house with saltbox roof sloping to the rear. When his son, Amos Heald, was of age, some of the property was deeded to him, where he built a stately Federal style residence that stands across the street to this day. Both of the Heald houses tell the early history of Chester through well-preserved houses.

Comfort C. Dresser House // 1799

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Built just before the turn of the 19th century, this handsome five-bay vernacular Federal period house is located on the charming Main Street of Chester, Vermont, and is one of the oldest extant houses in the village. The residence was built in 1799 by Comfort Carpenter Dresser (1777-1856), who with his family, moved from Bridgewater, Massachusetts, to the town of Chester, where he found work as a carpenter and housewright, a fitting profession due to his middle name. The family resided here for nearly 30 years until they moved to New Hampshire. The beautiful home, painted a bright white sometime in the 20th century, features a front door with sidelights, 12-over-12 sash windows, and a symmetrical facade, common for the style. 

Simonsville Schoolhouse // 1856

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One-room schoolhouses like this example in the Simonsville area of Andover, Vermont, have been commonplace throughout rural portions of New England where children of most ages would share the classroom and be taught everything from basic spelling to math. The Simonsville schoolhouse was built in 1856 and is a typical example of a vernacular one-room schoolhouse in rural New England, with no frills or ornament, just a house of learning. The Simonsville Schoolhouse was converted to a residence sometime in the latter half of the 20th century and has been renovated, keeping the basic form and interior floorboards from the 1850s. The school-turned-home is currently (2025) listed for sale.

Marie Hill Farmhouse // c.1810

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Located in the charming rural town of Andover, Vermont, the Marie Hill Farmhouse is one of the most interesting and charming residences in the area. Built around 1810, the brick farmhouse was designed in the Federal style, with a symmetrical five-bay facade, brick end chimneys, and a fanlight over the front door. The property was purchased by New Yorkers, Laurence Pfluger and his wife Mary “Marie” Pfluger, who operated the farm, raising dairy cows. Laurence would ship eggs, dairy and meat to his market in New York from this farm, which did quite well financially. The farmhouse was “modernized” by the turn of the 20th century with the addition of the two-story octagonal towers on the facade, front and side porches, along with the decorative slate spelling out “Marie Hill Farm” after his Marie Pflueger. The residence was later converted into a guesthouse, a use that remains to this day, still retaining the iconic name and branding in the southern gable.

Rowell’s Inn // 1826

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An outstanding example of a two-story, brick Federal style house with a five bay, front gable elevation, Rowell’s Inn of Andover, Vermont, is arguably the most famous landmark in town. The inn was constructed in 1826 by Edward L. Simons, for whom Simonsville, the area village, is named. Mr. Simons operated the building as a stagecoach inn and tavern for those traveling along major highways through the state. The building was also the home to the local post office, with Mr. Simons serving as the first postmaster. The inn, which had been in operation almost continuously since 1826, was purchased in 1910 by Frederick Rowell, hence the name, Rowell’s Inn. It is not clear when the distinctive wooden porch was added, which includes two-story full-length porches with a third-story porch set within a broad elliptical arch set in a flush-board pediment. The historic porch was altered years ago before it was purchased by the present owners, who renamed the building, The Inn Between, continuing its legacy as a stop for weary travelers.

Jaquith Homestead // c.1820

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Erected in the 1820s by Joshua Jaquith, a prosperous mill owner who operated a sawmill and grist mill on the river directly behind his house, this residence in Andover, Vermont, exemplifies vernacular Federal period residential architecture in rural New England. The residence is said to have been carved up inside into apartments in the mid-1800s but was restored by Alden Jaquith, the third generation of the family later in the 19th century back into a single-family residence. The handsome brick home is symmetrical with a five-bay facade, 12-over-12 sash windows, and large end chimneys. Of particular note are the relief arches above first floor windows and above the door and the attached sidelight windows.

Leland Homestead // 1843

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The small, rural Town of Baltimore, Vermont, was originally a part of Cavendish but due to the geography and a mountain separating the village from the main town, residents here voted in 1793 to set off as its own town. The nomenclature of the town name, Baltimore is not clear, as the city in Maryland was named for George Calvert, first Baron Baltimore, who was granted that colony in 1632, but there is no evident connection between the two communities. The word Baltimore itself is Celtic for “large town”; appropriate for Calvert’s colony, perhaps, but hardly for this Vermont town, which is one of the smallest in the state in terms of population or square miles. The town has always been a community without a distinctive village center and has long been primarily farmland, with properties bounded by stone walls and forests. This stone house on Harris Road in Baltimore was built in 1843 by Joshua Leland and his wife, Betsy Boynton. A history of the town speaks of the house, “It was one of the most attractive houses ever built in Baltimore, a well-built front hall and stairway, four fair-sized pleasant rooms downstairs, three well-arranged chambers and a convenient back stairway, all well-finished”. The home, with its date of construction over the front door, remains one of the most historic and well-preserved buildings in the town of just over 200 residents.

Bread Loaf Campus – Treman Cottage // c.1890

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This is the last building to be featured on the Bread Loaf Campus! For more early history and context of the complex, check out the post on the Bread Loaf Inn. By 1900, owner Joseph Battell’s enterprise exceeded the capacity of the original inn, and cottages were added to accommodate more guests visiting his new permanent home in the mountains of Ripton, Vermont. Special friends who summered regularly at Bread Loaf purchased lots with water and sewage rights, and with Battell’s assistance, built their own family cottages to spend their summers. This is Treman Cottage, a shingled beauty which appears to have been built for a friend (though I am not sure who), and has since become the faculty cottage on the campus. As we wrap up this series, here is an interesting fact about the mountain campus: All buildings here that are painted the ochre color were built during Mr. Battell’s lifetime (by 1915), with later buildings painted white.

Bread Loaf Campus – Maple Cottage // c.1900

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Welcome back to the Bread Loaf Campus! For more early history and context of the complex, check out the post on the Bread Loaf Inn. By 1900, owner Joseph Battell’s enterprise exceeded the capacity of the original inn, and cottages were added to accommodate more guests visiting his new permanent home in the mountains of Ripton, Vermont. Located adjacent to the Mansard-roofed Birch Cottage, one of the most visually striking buildings in the campus is Maple Cottage, which reads more porch than cottage, but it’s 100% perfect. It was the last cottage built by Battell for his family and friends to stay at when visiting. They must have loved evenings on the three-floors of porches looking out over the Green Mountains.

Bread Loaf Inn // 1882

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The Breadloaf Inn is a rare intact example of Vermont’s Victorian resort architecture that also has important associations with the environmental movement and for American literature. Located in the quiet town of Ripton, Vermont, this impressive structure was built in 1882 by eccentric philanthropist Joseph Battell. Mr. Battell attended Middlebury College in the early 1860s but he was forced to abandon his studies due to ill health. On the advice of his doctor, Battell spent a weekend at a farmhouse in nearby Ripton where the clear mountain air would help cure his ailing lungs. He so loved the beauty of the surrounding hills that he decided to buy the old farmhouse, which became known as the Bread Loaf Inn, named for Bread Loaf Mountain not far away. Over the years, numerous new buildings, porches, and barns were added in order to accommodate Battell’s many friends and guests. The Inn, which was remodelled from the farmhouse in 1882, and the surrounding mountains served as Battell’s home and sanctuary for the rest of his long life. He amassed land holdings of over 30,000 acres of forest, preserving it in perpetuity until his death in 1915, becoming the state’s largest landowner when he died. Battell’s vast mountain estate was left to Middlebury College, who brought the seasonal inn back to life as the summer Breadloaf School of English. In 1926 the college added the Breadloaf Writers’ Conference, drawing such luminaries as poet Robert Frost, who spent summers at a cabin nearby. The complex is maintained by Middlebury College to this day, who do a great job at preserving the original buildings.