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Chichester Road Historic District Becomes New Canaan’s First National Register Historic District

By Jack Zussman | July 6, 2026

Midcentury Modern homes on Chichester Road have become New Canaan’s first historic district listed on the National Register of Historic Places, marking a milestone in the preservation of the town’s internationally recognized architectural heritage, advocates say.

Officially listed on March 2, the “Chichester Road Historic District” recognizes both the distinctive architecture and the natural landscape that helped make New Canaan a center of Midcentury Modern design. The new designation follows a nearly two-year effort led by the New Canaan Preservation Alliance, a nonprofit organization.

“The goals were to inform the public of the importance of preservation; to recognize the significance of the terrain and architecture on Chichester Road that has been well preserved; to honor the original architects who designed houses in the district between 1956 and 1964; and to enable the owners of these houses to receive tax credits for restoration of their properties,” Susan Pollish, secretary of the New Canaan Preservation Alliance, told NewCanaanite.com.

The district’s history dates to 1955, when architect John Black Lee purchased about 17 acres on Chichester Road and subdivided the property into six lots, according to the NCPA. Lee required that each home be designed by a modernist architect.

Constructed between 1956 and 1964, the six homes were designed by Lee, Hugh Smallen, Harrison DeSilver and James Evans. The homes remain on their original sites and have been carefully preserved, with additions that respect the architects’ original designs.

According to the New Canaan Preservation Alliance, the district’s wooded landscape, rocky outcroppings, rolling topography and winding streams were important to its design. Lee said in a 2012 interview, “All of these houses had something to do with the land they were on.”

Pollish said the district is historically significant because it was developed when New Canaan had become “a hotbed of American Mid-Century Design.”

“The development was comprised of single-family houses that were designed for like-minded, progressive, creative clients who were a part of a community with similar values,” she said.

Architecturally, Pollish said the district represents the work of a small group of architects whose innovative residential designs earned New Canaan international recognition. Their work drew influence from Bauhaus principles, Frank Lloyd Wright, Japanese architecture, the Arts and Crafts movement and the Chicago School of Architecture.

The effort to nominate the district began in June 2024. With funding from the Connecticut State Historic Preservation Office, the NCPA sponsored the nomination. Architectural historian James Sexton of Archaeological and Historical Services researched and wrote the nomination, while Pollish supervised the project on behalf of the alliance.

Although inclusion on the National Register is primarily honorary, Pollish said it offers practical benefits for property owners.

“It provides benefits to property owners by providing Connecticut state tax credits for restoration expenses for houses in the district,” she said.

The designation also comes as New Canaan continues to lose portions of its architectural heritage. According to the preservation alliance, the town is home to more than 100 Midcentury Modern houses built between 1948 and 1976, though about 20 have already been demolished.

For Pollish, the district’s designation is a reminder of the importance of protecting New Canaan’s architectural legacy.

“New Canaan has lost many of its architectural treasures from our early 1700s houses to our mid-twentieth century modern buildings,” Pollish said. “The New Canaan Preservation Alliance advocates for the preservation of our significant built and natural environments. This designation is an affirmation of our mission to advocate for the preservation of our treasured architectural and natural landscapes and the importance of preserving them today and in the future.”