Jabez Sargeant Jr. House // 1797

Deacon Jabez Sargeant (1720-1788) was born in Malden, Massachusetts, and later moved to the newly established town of Chester, Vermont in 1763. He is thought to have been the first settler of European ancestry in the town. Upon the outbreak of the Revolution, he served in Captain Little’s Company in 1778, returning home to Chester after. His son, Jabez Sargeant Jr. built this stately three-story late-Georgian residence in 1797 as a tavern along the Green Mountain Turnpike, a highway connecting Boston and Montreal. The dwelling originally fronted directly on the road, but was moved back sometime in the 19th or 20th centuries. The building boasted a large ballroom on the second floor, likely for community and fraternal organizations, and a tavern in the brick first floor. It is likely that Jabez and his family lived on the third floor. Outside, the property contained a large apple orchard and cider house, providing drinks to weary travellers. Although the tavern is built to a large size, it lacks many of the high-style features often found in large Georgian houses, telling for its time of construction in a sparsely developed area without seasoned builders.

Sherwin-Goldsmith House // 1844

The Stone Village of Chester, Vermont, is said to be the largest collection of stone buildings in the state. Built around 1844, the Sherwin-Goldsmith House is one of a few dozen “snecked ashlar” buildings in the region, where rubblestone is laid up with mortar using long stones called “snecks” to tie an outer and an inner wall together. The construction method is said to have been brought to the area by masons from Scotland and Ireland which is known there as ‘Celtic Bond’. Oral tradition state that Scottish masons from Canada introduced the technique to local masons while erecting a mill in nearby Cavendish in 1832. Local Chester resident, Dr. Ptolemy Edson became such a fan of the building that in 1834, he had his home, the first stone building in Chester, built in this method. He then would influence the rest of the North Village of Chester, where many of his neighbors, as well as the church and schoolhouse, built their structures in snecked ashlar. The Sherwin House is one of three near-identical houses built around the same time that are colloquially known as the “Three Sisters” because they were built for members of the same family. The Greek Revival form is toned down in this smaller side-hall house, which playfully uses large blocks of schist and mica which read as quoins at the corners. Simeon Sherwin (1813-1874) was a farmer, postmaster, and justice of the peace in Chester. Later owner, Olivia Goldsmith, wrote her bestseller, First Wives Club when she lived here. 

Mason C. Richardson House // c.1839

The Stone Village of Chester, Vermont, is said to be the largest collection of stone buildings in the state. Built around 1839, the Mason C. Richardson House is one of a few dozen “snecked ashlar” buildings in the region, where rubblestone is laid up with mortar using small long stones called “snecks” to tie an outer and an inner wall together. The construction method is said to have been brought to the area by masons from Scotland and Ireland which is known there as ‘Celtic Bond’. Oral tradition state that Scottish masons from Canada introduced the technique to local masons while erecting a mill in nearby Cavendish in 1832. Local Chester resident, Dr. Ptolemy Edson became such a fan of the building that in 1834, he had his home, the first stone building in Chester, built in this method. He then would influence the rest of the North Village of Chester, where many of his neighbors, as well as the church and schoolhouse, built their structures in snecked ashlar. Designed in the Federal style, the Richardson House is a vernacular, five-bay, two-story residence with central entrance and arched fanlight transom over the front door. Mason Richardson (1811-1881) was a merchant who lived here with his family while operating a store nearby.

Granville and Aurora Spaulding House // 1838

The Stone Village of Chester, Vermont, is said to be the largest collection of stone buildings in the state. Built around 1838, Granville and Aurora Spaulding House is one of a few dozen “snecked ashlar” buildings in the region, where rubblestone is laid up with mortar using small long stones called “snecks” to tie an outer and an inner wall together. The construction method is said to have been brought to the area by masons from Scotland and Ireland which is known there as ‘Celtic Bond’. Oral tradition state that Scottish masons from Canada introduced the technique to local masons while erecting a mill in nearby Cavendish in 1832. Local Chester resident, Dr. Ptolemy Edson became such a fan of the building that in 1834, he had his home, the first stone building in Chester, built in this method. He then would influence the rest of the North Village of Chester, where many of his neighbors, as well as the church and schoolhouse, built their structures in snecked ashlar. The Spaulding House is unique in that the main entrance does not face the street, as it fades the south east (side) facade. The couple married in 1839 and moved into this recently completed house to raise their family and work their farm. Like many other early stone houses built nearby in the 1830s, the Spaulding house blends Federal and Greek Revival motifs from the gable end facing the street and eaves returning to serve as a pediment as a nod to the emerging Greek Revival style, while retaining an arched entry off the street which echoes Federal period taste. 

Gideon M. Lee House // c.1836

The Stone Village of Chester, Vermont, is said to be the largest collection of stone buildings in the state. Built around 1836, the Gideon Lee House is one of a few dozen “snecked ashlar” buildings in the region, where rubblestone is laid up with mortar using small long stones called “snecks” to tie an outer and an inner wall together. The construction method is said to have been brought to the area by masons from Scotland and Ireland which is known there as ‘Celtic Bond’. Oral tradition state that Scottish masons from Canada introduced the technique to local masons while erecting a mill in nearby Cavendish in 1832. Local Chester resident, Dr. Ptolemy Edson became such a fan of the building that in 1834, he had his home, the first stone building in Chester, built in this method. He then would influence the rest of the North Village of Chester, where many of his neighbors, as well as the church and schoolhouse, built their structures in snecked ashlar. The first residence besides Dr. Edson’s home built this way in the village was this home, built nextdoor for Dr. Edson’s friend, Gideon Merrick Lee (1811-1880). Designed in a more vernacular version of the Federal style with emerging Greek Revival side-hall form, the Lee House features a charming entry with sidelights and a blind fan over the door.

Dr. Ptolemy Edson House // 1834

The Stone Village of Chester, Vermont, is said to be the largest collection of stone buildings in the state. Built in 1834, the Dr. Ptolemy Edson House is one of a few dozen “snecked ashlar” buildings in the region, where rubblestone is laid up with mortar using small long stones called “snecks” to tie an outer and an inner wall together. The construction method is said to have been brought to the area by masons from Scotland and Ireland which is known there as ‘Celtic Bond’. Oral tradition state that Scottish masons from Canada introduced the technique to local masons while erecting a mill in nearby Cavendish in 1832. Local Chester resident, Dr. Ptolemy Edson became such a fan of the building that in 1834, he had his home, the first stone building in Chester, built in this method. He then would influence the rest of the North Village of Chester, where many of his neighbors, as well as the church and schoolhouse, built their structures in snecked ashlar. Designed in the Federal style, the Edson House is a vernacular, five-bay, two-story residence with central entrance and arched fanlight transom over the front door.

Robbins House // c.1850

Originally built in the 1840s or 1850s, this stunning house on Main Street in Chester, Vermont, was “Victorianized” in the late 19th century through applied ornament, a tower, and porches. Historic maps show that this house was owned by Cyrus Robbins and his wife, who likely had the residence built in a vernacular example of the Greek Revival style, with a 2 1/2-story form with gable roof oriented towards the street. The corner pilasters remain as do the original facade windows with five on the first floor, three on the second, and a single window in the upper floor. By the late 1800s, the house was modernized with the addition of the wrap-around porch with decorative spindles and ornament and the octagonal turret with wood shingle conical roof. Today, the house is painted colors to highlight the Queen Anne appearance and details.

Amos Heald House // 1803

This large brick Federal period house in Chester, Vermont, was built in 1803 and is said to have been a stop on the Underground Railroad. The large residence was built for Amos Heald (1767-1849), who was born in Concord, Massachusetts, and when just a boy of nine years, Amos witnessed the Battle of Concord kicking off the American Revolution. In about 1777, his father, Daniel Heald, moved the family to Chester, Vermont, which was then named New Flemstead, to escape the conflict. Daniel Heald acquired land near the Williams River and built a large Federal style home. He later deeded his son, Amos, land on which he too would build a residence. Amos Heald lived in this brick home and served in many positions in town until his death. The estate was bequeathed to his son, Amos Heald Jr. (1804-1873), who also served in the town offices. Locals state that Amos would shelter escaped enslaved people from the south on their way north to Canada. After his death, his son Prescott took over the property and built a wood-frame addition off the rear stables and barns, which became the town clerk’s office during his tenure, as well as the office for his insurance business. Sometime in the 19th century, the house was renovated with the addition of porches, and later, the building became the Weathervane Inn.

Daniel Heald House // c.1785

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

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.