Villa Bella Vista // 1908

Villa Bella Vista in Chester, Connecticut, stands as a striking and deeply personal interpretation of an Italian Villa, designed not by a professional architect, but by its remarkable owner, Eila Pierre. Known even among friends as Madame Pierre, she was a turn-of-the-century feminist of independent means who defied convention at nearly every turn. Drawing inspiration from the indigenous farmhouse architecture of northern Italy, Pierre personally designed the well-preserved stuccoed stone house, which was later constructed by local Italian immigrant masons who settled in Chester. Born Ila Rowland Stone (1870–1931), she was newly married to Reverend Dwight Stone, a Yale-educated minister of the town’s Congregational Church. Within just two years of marriage, it unraveled. Reverend Stone resigned his post, and by 1906, the couple’s uncontested divorce, scandalous for the time, was finalized. Casting off both marriage and social expectations, Ila reinvented herself as Eila Pierre. Despite the scandalous divorce and cheating rumors, she chose to remain in Chester and build a summer home that reflected her independence and worldview. Plans for Bella Vista were underway as early as 1904, when she purchased land on Old Depot Road. To prepare for the design, Pierre embarked on an extended tour of northern Italy, studying villas firsthand and bringing along a young local stone mason, Martin Lanzi, who later built his home across from Madame Pierre’s mansion. Villa Bella Vista, completed in 1908, includes common architectural details in the Italian Villa style with the campanile, or tower, the colonnaded piazza, and stone masonry that define the Latin prototype, all unique to Connecticut, which makes this home so special.

Mitchell-Pratt House // 1820

This architecturally unique and stunning Federal­ style house in Chester, Connecticut, was built in 1820 on the Middlesex Turnpike by Abram Mitchell for $10,000, double what he originally hoped to pay for the residence. The principal builder was Samuel Silliman, a locally well-known master carver, who clearly showcased his skill inside and out, much of which has been preserved by two centuries of owners. In 1845, the property was purchased by George Spencer, and presented as a wedding gift for his daughter, Julia, who married Dr. Ambrose Pratt (1814-1891). Dr. Pratt became well-known for his practice of hydropathology and temporarily used his house as a sanitarium known as the Chester Water Cure. The house was acquired by the local Roman Catholic Church and became the parish center until the residence was purchased and moved away from the busy street to its current location in 1966. In the 1980s, the house was purchased by famed artist, Sol Lewitt. The house has a large spider web window, still containing the original glass over the door and full-height pilasters dividing bays and inside, many stunning carved mantles and woodwork.

Jonathan Warner House // 1798

The Jonathan Warner House in Chester, Connecticut, is one of the finest Federal style houses in the state and has been meticulously preserved for over two centuries. The house was built in 1798 by Jonathan Warner (1756-1828), a wealthy farmer who invested in merchant shipping ventures and also operated the nearby Chester–Hadlyme ferry transporting people across the Connecticut River for a fee. When he built his house Jonathan Warner used local workmen and timber, importing glass and paint from New York, wallpaper from Hartford, and stone and hardware were brought from Connecticut and New York. The farmhouse remained in the Warner family until 1922 when it was purchased by Malcolm Brooks, who retained all of the receipts and correspondence on the house’s construction and maintenance. Architecturally, the house stands out for its proportions and detailing, specifically at the front door with fanlight and sidelights, which are framed by fluted pilasters, pediment and dentil molding. There is a Palladian-esque window above the entry which is framed by two free standing Ionic columns on brownstone pedestals. What is your favorite detail of this house?

Gilbert-Zanardi House // 1830

This unique Greek Revival style house is located on North Main Street in Chester, Connecticut, and was built around 1830 for John Gilbert. Johnʼs sister (Abby Gilbert Daniels) lived in a Greek Revival house on Liberty Street that had been built a few years earlier and was said to have been designed by Ithiel Town, a renowned Connecticut architect who specialized in Greek Revival style designs. It is thought that Town may also be the architect of John Gilbert’s residence seen here. The temple-front facade of the residence sits on a raised basement with the side-hall entrance and full-height hung windows on the facade sheltered under a portico supported by four square Doric columns. In the early 20th century, the property was purchased by Antonio Zanardi, who immigrated to Chester from Italy and worked as a watchman in a local factory. Antonio and his wife, Claudina, had a large family and expanded the house with a side wing in the early 1900s, also adding greenhouses and growing grapes on the terraced rear yard.


Dunk Homestead // c.1672

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!

Chester House Hotel // c.1840

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.

Charles Daniels House // c.1826

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.

Buck-L’Hommedieu House // c.1755

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.

Leet-Ely House // c.1787

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. 

Chester Flatiron Building // 1913

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!