The oldest building in Chester, Connecticut, is believed to be this First Period residence on North Main Street, which was originally built sometime after 1672, when land here was deeded to Thomas Dunk (1648-1683). The property was inherited by various members of the Dunk family, including Deacon Jonathan Dunk (1711-1781), who added onto what was originally a one-room, gambrel-roofed house as their families and wealth grew. The old Dunk Homestead is one of the many great landmarks in Chester and has been lovingly preserved for over 350 years!
This altered building in the center of Chester Connecticut’s village Main Street, has historically been known as the Chester House, a hotel and tavern to provide lodging and drinks to travelers passing through the area in the mid-late 19th century. The structure, built atop a raised stone foundation, was constructed in the Greek Revival style around 1840, and long had a sheltered two-story portico supported by four monumental columns under a gabled roof which resembled a pediment. In 1903, a fire destroyed the upper floor and the roof was removed, creating a flat roof design. Later in the 20th century, a shallow side gable roof replaced the flat roof and the columns on the facade were also removed, giving the building the appearance we see today. The hotel closed, but the historic structure remains an anchor to the town’s vibrant commercial center, and houses a local business.
The Charles Daniels House in Chester, Connecticut, is a sophisticated and excellently proportioned and designed example of a single-family residence in the Greek Revival style. Features like the Doric portico, flushboarding and frieze windows are components of a skillful design that has been credited to architect Ithiel Town, but this is unsubstantiated. The home was built around 1826 for Charles Daniels (1799-1838), a gimlet manufacturer, who had his factory nearby. Charles died in 1838, and the property was inherited by his second wife, Abby Gilbert, who also remarried and lived here with her new husband, Clark N. Smith, and they resided here until the early 1900s. Later, the residence was owned by the adjacent mill company, and used temporarily as a storage facility. The location adjacent to the deteriorating factory threatened the significant Daniels House, so in 1978, architect Thomas A. Norton had the house moved a short distance away onto the present site. The house was listed in the National Register of Historic Places and has been preserved, inside and out, by later owners.
Ezra L’Hommedieu (1772-1860) settled in Chester, Connecticut, in 1812 with his brother Joshua, and built a factory on the south branch of the Pattaconk Brook, which cut through the small village. The brothers manufactured gimlets (not the cocktail), a small wood-boring hand tool used to drill precise pilot holes for screws or nails, preventing wood from splitting and making driving fasteners easier. Ezra invented and patented the single-twist ship auger in 1812, which helped propel Chester into a prominent ship-building community. From his success, Ezra had this residence built on North Main Street in about 1835, which, like his brother’s house on Maple Street, blends Federal and Greek Revival styles elegantly.
This beautiful Federal style side-hall house is located on Maple Street in Chester, Connecticut, and (at least a part of it) was built by 1755 by Isaac Buck, who deeded half of the property to his son, Justus, during his lifetime. In the early 1800s, the property was purchased by Joshua L’Hommedieu (1787-1880), a manufacturer, who had the property redeveloped or redesigned in the Federal style giving it the appearance we see today. The house has its gable end oriented to the street with an elliptical fan and dentil block detailing.
One of the finest homes in Chester, Connecticut, can be found on Liberty Street, a short distance to the village green. The Federal style house dates to about 1787 and was built by Gideon Leet, a Revolutionary War veteran and joiner as his own residence. After Gideon’s death, the property was purchased by Dr. Richard Ely (1765-1816), who may have expanded the residence, and worked locally as a town doctor. The property remained in the Ely familyfor generations and minimal changes have occured to the exterior as a result of this. The modillon cornice, corner quoins, and fanlight transom sheltered under a columned portico add to the charm of this great house.
At the junction of West Main and Main Streets in Chester Village, Connecticut, this unique flatiron commercial building stands overlooking the Pattaconk Brook that cuts through the center of town. In 1913, this two-story block was built with ground floor retail and a second floor residence for owner, Elmer Pierce, who ran his pharmacy downstairs. By 1920, the building was owned by Jacob Feinstein, who raised his family on the second floor and had his clothing business, “Feinsteins” in the store below. Later, the retail space was occupied by Child Design, a wooden toy store, and after that, a lighting fixture store. Historic main street buildings are often incubators for small and local businesses, keep the chain stores near the highways!
James Baldwin (1742-1818) lived in present-day Chester, Connecticut, and upon the outbreak of the Revolution, joined the forces of Capt. Richard Douglass’ company as a private and fought for liberty. Upon the conclusion of the war, Baldwin returned to Chester and had this house built facing the village green. The transitional late-Georgian and Federal style house has a center chimney and very simple trim with an elliptical fanlight transom over the central door. The house has a wood shingle roof, typical of the early houses of the time. Pvt. Baldwin died in 1818 and his property was inherited by his daughter, Lydia Baldwin Sawyer and her husband, David Sawyer, and later in the 19th century by their eldest daughter, Lucina Morgan, and her husband, Jonathan. The home has been meticulously preserved by the later owners, important as one of the early surviving homes near the village green.
The Saybrook Colony was established in 1635 and covered a large geographic area near the mouth of the Connecticut River in Connecticut. This area was later subdivided into different towns after colonial era villages were established, each with their own church congregations. As was common in the colonial era, these divisions were centered on the establishment of separate church congregations. The Fourth Ecclesiastical Society of Saybrook in what is now the town of Chester, Connecticut, was established in 1742. As the town grew, this building was constructed in 1793 as Chester’s second meeting house and served as a church until 1846, when the third Meeting House was built. In 1847, the Town of Chester acquired this old meetinghouse and from that date until 1960, it was used as the Town Hall. In 1876, the old meetinghouse was renovated with a new, projecting main entrance added to the south side of the building when the Old Town Hall enjoyed its heyday as a theater and concert hall. The Old Town Hall witnessed many events under its roof, including hosting P.T. Barnum’s Tom Thumb, who performed here, as did musical events, high school proms, and school graduations. The building had become threatened following the construction of the new Chester Elementary School, which better-hosted events, in the 1960s. Luckily, in 1970, the newly formed Chester Historical Society acquired the building and restored it as a significant piece of the town’s rich history.
The former Mount Saint John School in Deep River, Connecticut, sits atop a hill on the western banks of the Connecticut River and is a visual landmark in every sense of the word. The school was founded by the Diocese of Hartford, who acquired the site in Deep River and began construction on the present building in 1907. Completed by 1908, the stone building (architect not known at this time), served as an industrial school for 100 boys in the Hartford region aged 8-16. The school, led by the Xaverian Brothers, was intended to educate troubled young men in the Catholic faith and learn working skills for a profession. The use changed numerous times throughout the 20th century, and ended up becoming the Mount Saint John School. Then under the Norwich Diocese, the school became known as the Mt. Saint John School. The school closed years ago and the historic building and surrounding campus’ future are uncertain.
Buildings of New England 