William Pollard House // 1899

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This high-style and ornamental house in Chester, Vermont, ranks among the state’s best examples of the Queen Anne style. The residence was constructed in 1899 for William Pollard (1854-1941), a local businessman who owned a shirtwaist manufactory in town with his brother, who lived next door. The painted-lady Victorian house features an asymmetrical plan highlighted by a three-story octagonal corner tower that is surrounded by a wrap-around porch with a delicate spindled frieze. The use of accent colors in the paint scheme further highlight the millwork details on the residence, which have all been preserved for well over a century. 

Chester Masonic Temple // 1907

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Built in 1907, this handsome building on Main Street in Chester, Vermont, has long been the home to the Olive Branch Lodge 64 of the Freemasons, an international fraternal organization. Colonial Revival in style, the building features corner pilasters that support a denticulated entablature along the eaves of the slate hip roof. A projecting portico over the front entrance is supported by classical Ionic columns. The 1920s marked a heyday for Freemasonry, especially in the United States. By 1930, over 12% of the adult male population of the United States were members of the fraternity. Following the Great Depression and WWII, membership sharply declined in fraternal organizations, like the Masonic Temple. A number of years ago, the Lodge here moved to a new building in a nearby town, and a local law firm purchased the building and spent 18 months renovating the building for use. Today, the historic character and even symbology remain on the building, while it houses a local business. 

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. 

Robbins & Marsh Store // c.1858

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Located in the Chester Depot Village, a commercial and civic assortment of buildings constructed in the mid-19th century between the often feuding North and South villages in Chester, Vermont, this handsome commercial building contributes to the character and history of the once thriving commercial center of town. Built across the tracks of the Central Vermont Railroad from the town’s depot, this Italianate style building dates to about 1858 when a P. H. Robbins opened an all-in-one store, selling everything from groceries to hardware and building products. Mr. Marsh was later joined by Frederick W. Marsh, who entered into the business, then named the Robbins & Marsh Store. The business thrived with the close proximity to the railroad depot with later alterations to the building including the addition of plate glass storefronts and a massive side awning porch. Business slowed after WWII, as rail service slowed and ultimately stopped in town. Today, the handsome building remains as an important visual anchor to the depot village. 

Chester Depot // 1872

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The first public train arrived in Chester, Vermont, on July 18, 1849, and in December, the Rutland & Burlington Railroad opened the first rail line across Vermont linking the Connecticut River valley at Bellows Falls and Lake Champlain at Burlington. A fire destroyed the first station in 1871, and the Vermont Central Railroad built the current station within a year. The State of Vermont purchased the line in 1963, leasing it in part to the Green Mountain Railroad. Exceptional in Vermont, this brick station retains its high-style Italianate design and continues in railroad use. The station can be classified as Italianate/Romanesque in style and has a corbeled cornice, windows capped by brick hood moldings, and a projecting trackside awning. It appears that the station is not in active use, does anyone know more?

Chester Academy – Chester Historical Society // 1884

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The town of Chester, Vermont, is one of the best small towns in the state for architecture lovers! Don’t believe me? I will prove it in this upcoming series. Located in Chester Village, the town’s center, this handsome brick building set off the main street, was built in 1884 as the town’s high school, replacing an 1814 private academy formerly on the site. The private academy closed in 1881, and the building was sold to the town, who by 1884, demolished the original structure and erected the current Italianate style building. The building served as the town high school until 1911, when a new high school was constructed nearby. The elementary and junior high school operated from here until the 1950s, when a modern school was constructed in town. Since 1950, the former academy building has been used by the Chester Art Guild, and currently is leased from the Town by the Chester Historical Society. The structure retains its architectural character down to the segmental arched windows and cupola.

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.

Simonsville Union Meetinghouse // 1848

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A once excellent example of a Gothicized, vernacular Greek Revival church in Vermont, the former Simonsville Meetinghouse in Andover, Vermont, has since been renovated into a private residence, removing almost all of the original fabric. Long ago in the Simonsville area of Andover, the residents desired to have a meeting house. There was a Baptist church in the village of Peaseville, but not all the Simonsville residents were Baptists, in fact, there were several religious denominations being followed. None of the religious groups had enough followers in Simonsville to be able to afford a minister and a church building, so they got together and combined their efforts and finances to erect a union meetinghouse that they would share. In April of 1847, the Simonsville Union Meetinghouse Society was formed and later that year, construction began, with the building completed in the spring of 1848. By the late 20th century, membership and use of the building dwindled, causing deferred maintenance and threatening the future of the church. The trustees of the church sold the building, and the church has since been renovated for private home. Sadly, the gothic belfry and historic window fenestration were altered in the renovation, but the entry and basic form remain.

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.