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Benjamin Bosworth House // 1800

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One of the most unique houses in Connecticut is this massive Federal style residence located in the small town of Eastford. Built next to the Congregational Church of Eastford (1829-2023), which burned down in 2023 by arson, the massive house has been known as both the Benjamin Bosworth House and Squire Bosworth’s Castle due to its first owner, Benjamin Bosworth (1762-1850). According to the Bosworth Family, the house was built in 1800 by Bosworth was a wealthy merchant, who hired Vini Goodell, a local carpenter to design and build the large Federal home. The house was completed by 1801 when the local Masonic group met in the building. As Bosworth was also a merchant, he used the basement as a storeroom. The house is also unusual for its monitor roof, a rarity in Federal period construction, which reads like a second structure on the house, due to the building’s size. After Bosworth’s death, the house was occupied by his niece, and was later purchased by Elisha Grant Trowbridge in 1897. Trowbridge was a grand-nephew of General Nathaniel Lyon (1818-1861), a local hero who was the first Union general killed during the Civil War. Trowbridge, an engineer, lived here until he died in 1963 at the age of 96. Later owners have had the monumental task of restoring and maintaining this behemoth of a house, to great success.

Abner Richmond House // c.1803

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This high-style Federal house sits across from the former Westford Baptist Church in Ashford, Connecticut. The house was built around 1803 for Abner Richmond (1761-1834) and his wife Eunice, who purchased 92-acres of land here one year earlier. Abner descended from John Richmond (1594-1664), one of the original white settlers of Taunton, Massachusetts in 1637. About ten years after he built his farmhouse, the town of Ashford paid the Richmond’s money for hardship caused by laying out a road right in front of the homestead. This 1812 occurrence possibly allowed the couple to invest further into the property, where they converted some of the rooms into a tavern, which was later accessible by the new Boston and Hartford Turnpike. The turnpike began in East Hartford and made its way through Ashford before winding its way to Boston. The house was documented as having 19th century stenciling on the walls, which survived underneath wallpaper (go figure). The new owners have clearly given the Richmond House some love and care, down to the perfect paint color.

Miller-Abbot House // 1789

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More impressive than elegant, this unusually large Federal house in Warren, Rhode Island was the home to two important military leaders, Nathan Miller and Joel Abbot. Nathan Miller (1743-1790) was a Brigadier General of the Rhode Island Militia during the Revolutionary War. He was a deputy in the Rhode Island State Assembly for six years, and he represented Rhode Island in the Continental Congress in 1786. After his death in 1790, the general’s daughter, Abigail, and her husband, Charles Wheaton inherited and enlarged the property. Their daughter Laura married Joel Abbot in 1825 and resided here afterwards. Joel Abbot (1793–1855) was a Naval officer in the War of 1812, and commanded a ship during Commodore Perry‘s 1853-1854 visit to Japan, opening the Asian country up to trade with the western world. The large home has maintained its charm and the dated chimney is just too perfect!

Samuel and Patty Randall House // c.1810

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This stately three-story Federal style mansion sits on Baker Street in the lovely town of Warren, Rhode Island. The house was funded by James Maxwell, of the local family of merchants and slave traders, for his daughter Martha “Patty” Maxwell and her soon-to-be husband, Samuel Randall. The house was gifted as a wedding present to the new couple, and an expensive one at that! Judge Randall operated a school nextdoor and established “The Telescope,” Warren’s third newspaper nearby the house. The pop of color at the entry and the Victorian-era door hood work so well on this facade as well.

Old Cooper Shop // c.1800

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This stunning Greek Revival house in Warren, according to historians, was built c.1800 as a cooper shop! A cooper as a professional, would make wooden barrels, tubs, and casks from wooden staves from their shops. This shop, which was originally a vernacular structure, was later renovated around 1833 into a Greek Revival style residence. On its facade, the house has two-story applied pilasters which break up the bays and smooth flushboard siding which makes the house even more stately!

High Ridge Manor // 1893

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Edward Payson Dutton (1831–1923) was a prominent American book publisher who founded the E. P. Dutton bookselling company in 1852 in Boston, Massachusetts. The business sold fiction and non-fiction, and within a short time expanded into the selling of children’s literature. In 1864, he opened a branch office to sell books in New York City and in 1869 moved his company’s headquarters there and entered the book publishing business. The company did very well, allowing Edward and his wife, Julia the means to build this large summer “cottage” in Ridgefield, Connecticut to escape the rustle and bustle of New York City. The couple purchased the lot in 1893 and appear to have built it soon after. High Ridge Manor is a stunning example of the Queen Anne and Shingle styles of architecture with its asymmetrical plan, continuous shingle siding with rubblestone foundation and chimney, gambrel roof, and towers.

Bailey Homestead // c.1815

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Located on a hill overlooking the Head Tide Village of Alna, Maine, this stately brick farmhouse has sat for roughly 200 years. According to old maps of the area, the property was occupied by the Bailey Family as far back as the land was surveyed in 1813. The property was owned by Ezra Bailey, who possibly built the house soon after as the village began to develop. By 1857, the property and its house were owned by I. H. Bailey, seemingly Ezra’s son, Isaac, who married his first cousin, Laura Palmer. The couple resided in the old homestead until they sold it in 1866, moving to Boston. The brick, Federal style house has a four bay facade with the entry door surrounded by a recessed arched relief. Above the door is a blind fan with sidelights.

John Banister House // 1751

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This deep, gambrel-roofed house is among my favorites in Newport. The house was built in 1751 for John Banister (1707-1767), a Boston-born merchant who moved to Newport in 1736, marrying Hermoine Pelham (1718-1765), a granddaughter of Gov. Benedict Arnold, that next year. Banister quickly established himself as a leading Newport merchant, trading with England, the West Indies, engaging in privateering and the slave trade. In 1752, he held one of the last public slave auctions in Rhode Island at his store, describing them in advertisements as “the finest cargo of slaves ever brought into New England”. The couple also built a country estate in Middletown, Rhode Island. John and Hermione had two sons, John and Thomas, who grew up in this home. John inherited the house after his father’s death in 1767, but the two brothers would soon find themselves on opposite sides of the battle for independence. Thomas was a loyalist, and even enlisted in the British army during the occupation of Newport, while John supported American independence. In retaliation for his patriot views, the occupying British forces seized this house, along with John’s farm in nearby Middletown. The house became the headquarters of General Richard Prescott during the occupation, although John later reclaimed his property following the British evacuation of Newport in 1779. The house has a later Federal entry, but otherwise is one of the best-preserved Colonial homes in Newport. It is a single-family home.

Amos Chase House and Mill // 1836

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The Amos Chase House and Mill are located in Weare, New Hampshire, on the banks of the Piscataquog River. The house is oriented facing the road, while the mill is behind it, on the bank of the river. The mill is the only surviving 19th-century mill building in Weare. The house was built about 1836 by Amos Chase, as was a mill. That mill burned in 1844; the present mill was built by Chase as a replacement a few years later. This mill was the only one in the town to survive the New England Hurricane of 1938, although its waterwheel was washed away. Amos Chase was a tool manufacturer and one of several members of a locally prominent family operating small mills in the town. His son later used the mill in the manufacture of baskets. The large Greek Revival style home has all the hallmarks of the style, from the pediment facing the street, to the pilasters at the entrance and corners.

Bailey Farmhouse // c.1767

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One of the oldest homes in Weare, New Hampshire is this large, Georgian farmhouse apparently constructed around 1767 by Samuel Bailey. Samuel’s father, Ebenezer Bailey, had purchased a property called “Lot 54, Range 1” in Weare, New Hampshire, which he then divided among his sons, Daniel, Samuel and Ebenezer Jr. for their own settlement in about 1767. Samuel received this lot in South Weare, upon which, the twenty-two-year-old and his wife established a farm and a family of at least eight children. Samuel died in 1824 and the farm was inherited by his son, Amos Wood Bailey, who continued operations here. Today, the large five-bay Georgian farmhouse is connected to a massive barn. It is a really spectacular property.