New Haven County

Bullet Hill Schoolhouse // c.1762

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The Bullet Hill School, formerly known as the Brick School, is the oldest public building in Southbury, Connecticut and one of the oldest schoolhouses in America. Originally built in 1762 of locally made bricks, the two-story structure is a well-preserved example of a Colonial-era school building. Some sources date the building to 1790. The building remained in operation as a school for 179 years until December 1941 when the new Southbury Consolidated School, now Gainfield Elementary School, opened in January 1942. The Bullet Hill school is distinguished by its near-square proportions, locally made bricks laid up in Flemish bond, generous window sizes, and a hipped roof. The original cupola, now replaced, served as the model for Southbury’s 1977 Town Hall and other public buildings in town. Today, the former schoolhouse is maintained by the town and operated by the Historical Society as a living museum that is open for class visits and tours.

Reverend Graham-Howard Richmond House // c.1715

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Who doesn’t love a good Colonial house in Connecticut!? This house in Southbury was originally built at the beginning of the 18th century and was later altered and expanded in the fashionable Federal style at the end of the century. The house was built around 1715 by a Nathan Strong, who sold the property to Reverend John Graham who was the town’s pastor for over forty years. The house was later owned by antiques dealers Daniel and Marguerite Croucher. They used the former White Oak Schoolhouse (nextdoor) to store and sell some of their finds! After later owners, the property (which includes the schoolhouse) was purchased by Howard K. Richmond had been a graphic designer and art director in New York. He created the original layout and logo for Life magazine in 1936. He also did advertising and publicity work for Lord & Taylor, Bloomingdale’s, Elizabeth Arden and Saks Fifth Avenue. So many layers of history in over 300 years!

White Oak Schoolhouse // 1840

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When the first white settlers of present-day Southbury, Connecticut, traveled up the Housatonic on rafts in 1673, they spent their first night under a white oak tree in what is now Settlers Park. That section of Southbury became known as White Oak for this early history. As this part of town developed and the population grew, another schoolhouse was needed. In around 1840, this Greek Revival style school building was constructed and has stood proudly on Main Street in the nearly 200 years since. The school now shares the same lot as the Reverend Graham House and has most recently been occupied as an antiques store.

Curtiss-Fabrique House // 1810

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Located on Main Street in Southbury, this stately Federal style mansion stands out as one of the most unique and interesting in town! The house here was originally built in the 1760s as a more modest Georgian house by members of the Curtiss Family, one of the earliest families to settle in the area after land here was purchased from the Potatuck Native Americans. In the early 19th century, the house was modernized in the fashionable Federal style, giving the house the present appearance. The facade is dominated by an excellent doorway with a projecting Palladian portico above. The property was later owned by Benjamin Fabrique.

Dublin Hill Deck House // 1974

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I don’t share Mid-Century buildings on here enough, mostly due to the fact that so many of the houses of the period are secluded down winding driveways and surrounded by trees! This stunning house is located in Southbury, Connecticut, and is a great example of a Deck House. The Deck House was a housing type developed by architect Carl Koch. According to At Home With Tomorrow, he began his lifelong mission to create “the good, the beautiful, and the inexpensive” in housing while at Harvard under the guidance of Walter Gropius, who is famous for the development of the Modernist Movement in architecture. After the war, he turned his focus on the housing shortage, a symptom of the Great Depression, WWII, and returning Veterans with growing families and VA mortgage loan offers. His solution was for an affordable house of pre-fabricated parts to cut costs and provide streamlined construction. In 1953, his Techbuilt house was launched, after a decade of research. William Berkes and Robert Brownell had worked with Koch at Techbuilt after graduate school, but wanted to create a design of their own. They left Techbuilt in 1959 and founded Deck House, using the same principles. The exposed Douglas fir beams, wood panel ceilings and mahogany trim and window casements are what give the deck house a lot of its signature aesthetic. A wall of glazing, open floor plan with sloping roof rafters extending beyond the walls and a low placement in seemingly untouched nature are further elements that have endeared these houses to the modern homeowner.

Oatman Hotel // 1806

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It always amazes me that even getting lost driving the winding roads in obscure places, can reveal some of the most magical old buildings and history to uncover. This stunning Federal style mansion was built in 1806 and is located on the busy Southford Road in Southbury, Connecticut. The road was a span along a turnpike was the great thoroughfare between New Haven and Litchfield, Connecticut. Present-day Southbury was about halfway between the two, so lodging was always busy here. Knowing this, brother’s in-law, John Thompson and Benjamin Hurd had this turnpike hotel built to capitalize on the flow of weary travelers. Charles R. Oatman (1827-1904), who married Orinda T. Hurd, the daughter of Benjamin Hurd, acquired the property in 1870 and operated the hotel under his name as the Oatman Hotel. After successive owners, the name remained. It was sold in the 20th century and was converted back to single-family use, and maintains much of its original fabric, including a barn at the rear of the property. It could definitely use a new coat of paint!

Reuben Curtiss House // c.1840

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The Reuben Curtiss House is a classic example of a Greek Revival farmhouse from the mid-19th century, located in Southbury, Connecticut. Local history states that a house built here by Israel Curtiss (1716-1795) who farmed the land with his large family. In 1798, Israel’s large estate was distributed among three of his sons, Joseph, Benjamin, and Reuben. This was complicated by the fact that in the same year, both Joseph and Benjamin died, leaving the entire estate to Reuben. From about 1840 and possibly until he sold the property in 1866, Reuben B. Curtiss ran an academy here, known as “Buck Hill Seminary for Boys.” It was a large operation, as suggested by the size of the addition and confirmed by the 1850 federal census. At that time there were 23 students in residence, ranging in age from 8 to 12, along with four adult supervisors. It was likely that the former farmhouse was expanded and the present 1840s Greek Revival block was added which now is the main facade.

Former Middlebury Central School // 1898

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Having the tall order of being a neighbor to the later Westover School, the town of Middlebury’s Central School still packs an architectural punch. The school was built in 1898, replacing the former Union Academy building also near the town green. The school building is Neo-Classical in style with a projecting pedimented portico supported by four columns. A cupola extends through the roofline and shingle siding add some charm to the small two-room school building. The former school later housed the Middlebury Public Library and is now occupied by the Middlebury Historical Society.

Tranquility Farm – Farmhouse and Barn // c.1840

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Tranquillity Farm, spanning the rolling hills around Lake Quassapaug in Middlebury Connecticut, was originally a 303-acre model/gentleman’s farm developed by John Howard Whittemore, a successful industrial-era businessman in Naugatuck, and his wife Julia Spencer Whittemore. Whittemore was a major figure in Naugatuck, sponsoring a series of commissions of McKim, Mead & White for buildings in the city center. For his country farm estate, he again commissioned McKim, Mead & White to design a new country house, a farm superintendent’s house, boat house on the lake, and other outbuildings for a working farm. An older farm was purchased, which included a modest Greek Revival style farmhouse dating to the early-mid 19th century (seen here) and a large wooden barn. Both of these were kept and incorporated into the estate near the southern entrance to the property, possibly to harken visitors back to the charm of rural living. The sweeping landscape, featuring miles of distinctive stone walls lining the roads and crisscrossing the fields, was designed by Charles Eliot and completed by Warren H. Manning – both protégée of Olmsted.

“Highfield” // 1914

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The Highfield house is a historic building located in Middlebury, Connecticut. The House, surrounded by over 600 acres of land, was the former summer estate of Columbia University law professor Joseph and his wife, Elizabeth Chamberlain. They commissioned Theodate Pope Riddle, one of the first licensed female architects in America to build this comfortable English Arts and Crafts style cottage on a hill above a lake. It is likely that after the Westover School was completed in town, the Chamberlains were excited to see how Theodate could design them a summer house in the similar Arts and Crafts style. The estate was completed in 1914 and stands two-stories with the second floor concealed within the steeply pitched gable roof. Like Westover, the building was stuccoed. In the 1950s, the estate was purchased by a group of individuals who dedicated the complex as a family and country club with golf, tennis courts, and pool. It is known as the Highfield Club today.