Westport’s colonial history runs along the Kings Highway. In 1648 five settlers remembered as the Bankside Farmers arrived along the shore. In 1672 the Kings Highway was laid out, and in 1761 a bridge carried it over the Saugatuck. By 1811 Ebenezer Jesup had a wharf on the river, and in 1835 the town was incorporated from pieces of Fairfield, Weston and Norwalk.
Many of the houses that survive from those centuries stand near the old road. The Kings Highway North Historic District, listed on the National Register of Historic Places in 1998, counts 106 contributing buildings in Colonial, Federal and Greek Revival styles. Read closely, the district has three layers. The first is 18th-century farmhouses. The second is the Greek Revival growth of the 19th century. The third, laid over both around 1900, is the work of artists who bought old houses and remade them. The town protected the area as a local historic district in 1973 and extended it in 1990 and 2000.
The estates
Westport’s Gilded Age arrived by the water. The town’s own history records the Morris Ketchum estate of 500 acres with an Olmsted-style landscape, and George Laurence’s 180-acre Longshore estate of the 1880s, which became a country club in the 1920s. The town bought Longshore in 1960, and it is now Longshore Club Park, with its golf course and the Inn at Longshore. WSHU has reported that Frederick E. Lewis’s estate there hosted a 1917 benefit with Harry Houdini that raised $50,000, and that it is believed to have helped inspire the setting of The Great Gatsby.
On Beachside Avenue, E.T. Bedford built an estate with its own racetrack. In 1910 he bought Nyala Farm, 53 acres where he kept Guernsey cows. In the late 1960s Stauffer Chemical built an office park on the farm. Today it is the headquarters of Bridgewater Associates.
Beachside’s estates still set the town’s records. In November 2025 five parcels there sold for $54 million, the largest residential sale in Westport’s history.
The resort and the stonemason
Between 1910 and 1940 the land around Compo Beach and Owenoke became a summer colony. The Compo-Owenoke Historic District, listed on the National Register in 1991, covers 154 acres of houses designed largely by the architects Sanford Evans and Ernest G. Southey.
Inland, a builder named Frazier Forman Peters was working in fieldstone. Between 1924 and 1936 he built several dozen stone houses in Westport. Accounts put the number between 36 and 41. They are low, thick-walled and unmistakable, and they have not all survived. In 2012 his 1928 house at 14 Charcoal Hill Road became the subject of a demolition application. Two years later a book, Westport’s Legacy in Stone, catalogued the survivors.
The Shambaugh House at 12 Old Hill Road, designed by Charles E. Cutler around 1923, belongs to the same moment. It joined the National Register in 1999.
The moderns
After the Second World War Westport built modern houses, and later it began to tear them down.
Among the survivors is the Allen House at 4 Burritt’s Landing, designed in 1958 by Roy Binkley Jr., a protégé of Ludwig Mies van der Rohe. It is an H-shaped plan, with a landscape by Frank Okamura, built for Ernst and Marcia Peterson Herrmann. It was listed on the National Register in 2010.
Victor Lundy designed Westport’s Unitarian Church and, in 1962, Hillspoint Elementary School. Local modernists including Larry Michaels and Joseph Salerno built houses across town. The Westport Historical Society later mounted an exhibition on the era, titled “Westport Modern” and subtitled “When Cool Was Hot!”
What was lost
The most consequential loss was a house by Paul Rudolph. Rudolph designed the Micheels House at 16 Minute Man Hill in 1972, a house of 3,336 square feet by the Paul Rudolph Institute’s count, the National Trust for Historic Preservation called of “great significance.” In 2007, after a public fight in which Connecticut’s attorney general, Richard Blumenthal, sought an injunction, it was demolished. The buyers, David and Yvette Waldman, had paid $3.234 million. It was the first Rudolph house demolished after the architect’s death in 1997, and a 6,204-square-foot house replaced it.
Smaller losses continue. Victor Civkin’s house at 6 High Point Road is gone. This August the Westport Journal published its farewell notice for 11 Beachside Common, a 1971 custom contemporary that is being replaced by a 12,946-square-foot new house listed at $22,825,000.
The rules now
Westport’s tools for saving a house are limited, and owners and buyers should know them. Any building at least 50 years old and larger than 500 square feet is subject to a 180-day demolition delay, which can be waived if no one objects. The Historic District Commission can block a demolition only for properties in one of the town’s seven local historic districts or on its list of 22 local historic properties. Everywhere else, the delay buys time to find a buyer or a compromise, nothing more. Our story on saving an 1810 saltbox shows how one house on Riverside Avenue used that time.
Sources
- Town of Westport, Westport history, Historic District Commission, accessed Oct. 2026
- Wikipedia, Kings Highway North Historic District, accessed Oct. 2026
- Wikipedia, Westport, Connecticut, accessed Oct. 2026
- WSHU, The Great Gatsby, Great Neck and Westport, April 10, 2024
- 06880, Nyala Farm, accessed Oct. 2026
- Wikipedia, Compo-Owenoke Historic District, accessed Oct. 2026
- 06880, Frazier Forman Peters, accessed Oct. 2026
- Wikipedia, Frazier Forman Peters, accessed Oct. 2026
- Wikipedia, The Allen House, Westport, Connecticut, accessed Oct. 2026
- Paul Rudolph Institute for Modern Architecture, Micheels Residence, accessed Oct. 2026
- Wikipedia, Louis Micheels House, accessed Oct. 2026
- Wikipedia, Victor Lundy, accessed Oct. 2026
- 06880, Paul Rudolph, Jan. 29, 2010
- Westport Journal, Say goodbye to 11 Beachside Common, Aug. 14, 2026
- Town of Westport, Demolition delay ordinance, accessed Oct. 2026
- Wikipedia, National Register of Historic Places listings in Fairfield County, Connecticut, accessed Oct. 2026
