The Smallen House is set in a clearing on a gently sloping wooded site. The one-story house is simply finished with flush vertical wood siding painted white, large fixed sash, and flush doors. Geometric in its design, the shed-roofed house is sited to provide one floor of fenestration at its lowest pitch, and two floors of fenestration at its highest pitch. The main entrance is at the slope of the roof and consists of a flush door flanked by fixed sidelights and an irregularly shaped transom that follows the line of the low-pitched shed roof. The entrance is accessed by a wood deck anchored at one end by a mortared stone wall that bridges the slope at the front of the house.
The public living space is fenestrated with a five-bay glassed wall. A pair of full-height flush doors in the fourth bay leads to a wood deck terminating at a mortared stone wall; the remaining bays contain fixed sash. The opposite side facade is demarcated by two rows of horizontal sliding sash ribbon windows, indicating the split-level plan on the interior. At the rear of the house is a flat-roofed addition on concrete-block footers connected to the main building by a small hyphen with sliding glass doors. This addition is clad in V-channel vertical wood siding and fenestrated with horizontal sliding sash.
The property also has a one-story, flat-roofed, three-car garage/studio building. Sited on a hill, the building is designed to follow the slope of the land, creating an angled foundation similar to Smallen's Parsons House (1964). A wood deck at the side of the building leads to the entry to the lower-level studio.
The Smallen House was designed by architect Hugh Smallen for his family and completed in 1957. The Smallen House was part of a Modern enclave along Chichester Road. Architect John Black Lee purchased twenty acres of land in the mid-1950s to be subdivided into six building parcels with the stipulation was that houses constructed on the lots had to be of Modern design. Two other Smallen-designed houses are next door. The Smallen House parcel was purchased by Lee in July 1955 and sold to Smallen in September of that year. The builder for the project was Borglum & Meek.
The Smallen House was featured in the 1959 Modern House Tour in New Canaan. An May 14 article in the New Canaan Advertiser described the house: "...a nice division of sleeping areas is made possible by the way the architect planned his home to the sloping site. Going up one half flight of open structure walnut steps will be found the master bedroom, bath and a guest-study, while by descending a half flight one finds three bedrooms for the daughters of the family and an extra guest or maid's room. In both sleeping areas there are giant, walk-in closets, considered to be a monument to the architect's wife, that are expected to bring sighs of appreciation from most of the women who make the modern pilgrimage" (New Canaan Advertiser, 14 May 1959).
The house was also included in the 1965 Modern House Tour along with Smallen's Parsons House. In a May 13 article about the tour, Smallen called the design of the Small House as "the essential quality of interspacial relationships" (New Canaan Advertiser, 13 May 1965). The Smallen House was also featured in the October 1964 issue of House & Garden. This article discussed how the kitchen was divided from the dining room and entrance hall by partitions that did not extend to the ceiling, allowing light and air to flow through the house.
In 1962, a three-car garage was constructed on the property. A lower-level studio was added to the basement in 1969. In 1979, Smallen designed an addition for the house, but the assessor noted that it was of temporary construction with unfinished walls and floors. Hugh Smallen sold the property to Celia B. Berg in 1981. In 1986, the assessor noted that the existing studio was completed, but it is unclear if this refers to the house addition or the garage studio. In 1993, Clyde B. and Barbara A. Crebs acquired the house. Michael McDermott purchased the property in 2003, and David Strine purchased the house in 2007.