PropertyProperty detailsYear built
New Canaan, CT 06840
Built 1775
A clapboard-sided house, two additional buildings, and a 1.06-acre lot make up 204 Parade Hill Road near Oenoke Ridge. The Town of New Canaan Assessor dates the main residence to 1775 and the two smaller buildings, classified as cottages, to 1930 and 1951. Inside the main house, wide-plank floors and exposed beams sit alongside an updated kitchen and…
- Beds
- 4
- Baths
- 4
- Sq ft
- 3,260
- Acres
- 1.1
Before 18001775Closed
New Canaan, CT 06840
Built 1846
Extown Farm at 485 Laurel Road centers on a late-eighteenth-century farmhouse that became New Canaan's municipal poor house. In 1852, the Town of New Canaan bought Matthew Kellogg's 82-acre farm for $3,000 to provide housing and work for residents without other means of support. The 21-room house was divided between the overseer's family and residents, and some rooms…
- Beds
- 8
- Baths
- 8.5
- Sq ft
- 7,000
- Acres
- 17.5
1800–18491846Closed
New Canaan, CT 06840
Built 1850
At 132 Seminary Street, a nineteenth-century Italianate house combines an older, smaller building with a later gabled addition. Built between 1867 and 1879, the house was already standing when Irish gardener Owen Martin bought land and buildings here from the State of Connecticut in 1879. Its present form includes two stories, clapboard siding and staggered gable roofs. Extensive…
- Beds
- 2
- Baths
- 1.5
- Sq ft
- 1,432
- Acres
- 0.1
1850–18991850Closed
New Canaan, CT 06840
Built 1858
At 58 Seminary Street, the Watts Comstock House dates to about 1858. The north-facing, two-story dwelling has a five-bay front, clapboard siding, and a stone foundation. A small porch shelters its central entrance, where a paneled wood door is topped by a three-light transom. Additions extend east and south from the saltbox-form house. A separate twentieth-century garage stands…
- Beds
- 4
- Baths
- 3
- Sq ft
- 2,866
- Acres
- 0.2
1850–18991858Closed
New Canaan, CT 06840
Built 1870
87 South Avenue pairs a nineteenth-century Victorian residence with a separate cottage on a 0.34-acre parcel in central New Canaan. At the time of its 2023 sale, the main house featured a wraparound front porch, an entrance-hall stained-glass window, and a parlor with a marble fireplace. A gazebo stood on the grounds. The main residence and cottage were…
- Beds
- 5
- Baths
- 5
- Sq ft
- 4,334
- Acres
- 0.3
1850–18991870Closed
New Canaan, CT 06840
Built 1872
66 Seminary Street is an 1872 Second Empire house built by Watts Comstock as an intended home for New Canaan’s Baptist minister. Its mansard roof, gabled dormers and prominent corner tower give the small house a distinctive profile. The grounds also include a separate outbuilding dating to about 1890 and an early-twentieth-century picket fence. Comstock, a founder of…
- Beds
- 3
- Baths
- 3.5
- Sq ft
- 2,300
- Acres
- 0.2
1850–18991872Closed
New Canaan, CT 06840
Built 1875
284 Park Street is a late-nineteenth-century Queen Anne house associated with Irving Lockwood, whose businesses ranged from horse-and-carriage service to fuel and building supplies. Lockwood acquired the land from W. Stanley Lockwood in 1885. His livery sent carriages to meet trains, and he moved into the coal business in 1899. Myra Valentine enlarged the house in the 1930s,…
- Beds
- 5
- Baths
- 4.5
- Sq ft
- 3,715
- Acres
- 0.5
1850–18991875Pending
New Canaan, CT 06840
Built 1900
144 South Avenue is a Queen Anne-style house whose rehabilitation received a 2013 Team Award from the New Canaan Preservation Alliance. The award named homeowners Joanne Kennedy and William Bowers and credited a team working across the house and grounds. Jim Goebel of Marschalk Goebel handled design and contracting, Joanne Parsons of Site Systems provided landscape design, and…
- Beds
- 4
- Baths
- 4
- Sq ft
- 3,856
- Acres
- 0.3
1900–19241900Closed
New Canaan, CT 06840
Built 1900
20 Hoyt Street connects New Canaan’s residential history with the family behind Walter Stewart’s Market. Market founder Walter Stewart and his wife Nellie lived in the Hoyt Street house, later shared by their son Walter and his wife Audrey. Walter opened his Main Street grocery in 1907, and Nellie became New Canaan’s first woman elected to the Connecticut…
- Beds
- 4
- Baths
- 3.5
- Sq ft
- 3,020
- Acres
- 0.3
1900–19241900Closed
New Canaan, CT 06840
Built 1900
42 Hoyt Street was the home of John E. Hersam, founder of the New Canaan Advertiser. The house was standing by 1908, when a New Canaan directory pictured its open front porch, projecting two-story bay and intersecting gables. That July, Hersam launched the Advertiser, initially seeking better coverage of New Canaan’s baseball team. He also served as president…
- Beds
- 3
- Baths
- 2.5
- Sq ft
- 2,842
- Acres
- 0.2
1900–19241900Closed
New Canaan, CT 06840
Built 1910
10 Green Avenue was home to John Bryan Starr and his wife, Marilyn Ballou Starr, a longtime French teacher at New Canaan Country School. The couple moved to New Canaan in 1978. Marilyn taught French at the school for 25 years, including five years leading its foreign languages department, and retired in 2004. She later volunteered at the…
- Beds
- 3
- Baths
- 1.5
- Sq ft
- 1,742
- Acres
- 0.1
1900–19241910Closed
New Canaan, CT 06840
Built 1911
The residence at 322 Main Street underwent a substantial remodeling project in 2010–2011. A permit issued on July 16, 2010 authorized interior renovations and a two-car garage, with Country Club Homes named as the contractor. The Wilton builder worked with Michael Smith Architects on the project. In 2011, the work received the Home Builders Association of Connecticut’s HOBI…
- Beds
- 4
- Baths
- 4.5
- Sq ft
- 4,643
- Acres
- 0.4
1900–19241911Closed
New Canaan, CT 06840
Built 1924
The two-story, wood-shingled Colonial at 36 Mortimer Street dates to about 1924, with a detached garage dated to about 1925. The house stands on a 0.14-acre lot along Mortimer Street, part of Prospect Heights, a development begun in 1915 by Frank B. Gurley of Stamford. The street was named for Gladys Mortimer, secretary to Judge James E. Brinckerhoff,…
- Beds
- 3
- Baths
- 2.5
- Sq ft
- 2,170
- Acres
- 0.1
1900–19241924Closed
New Canaan, CT 06840
Built 1928
42 Old Stamford Road is a late-1920s Colonial-style house on a 0.27-acre lot in New Canaan. Its two-story front has a side-gabled roof, paired windows with shutter accents, and a small gabled entrance hood above a doorway with sidelights. A narrower two-story section steps back on the right, while a detached two-bay garage stands farther along the driveway.…
- Beds
- 3
- Baths
- 2.5
- Sq ft
- 2,132
- Acres
- 0.3
1925–19491928Closed
New Canaan, CT 06840
Built 1928
45 Seminary Street is a late-1920s Colonial Revival house known as the Emma C. Clark House. Three gabled dormers rise above its two-and-a-half-story, wood-shingled form. A centered portico with Tuscan columns frames an entrance with sidelights and a fanlight, while multi-pane windows give the front a balanced arrangement. A screened porch extends from the west side. Terraced grounds,…
- Beds
- 3
- Baths
- 2.5
- Sq ft
- 2,455
- Acres
- 0.2
1925–19491928Closed
New Canaan, CT 06840
Built 1929
The Frederick F. Fisher House at 40 Oenoke Ridge dates to 1929. One of the Church Hill neighborhood’s few brick houses, it has a two-and-a-half-story center beneath a slate roof, with lower wings on either side. Its off-center, projecting entrance combines a fanlight, sidelights, and a paneled door. Behind the brick exterior is a steel frame. The property…
- Beds
- 7
- Baths
- 7
- Sq ft
- 6,057
- Acres
- 2
1925–19491929Closed
New Canaan, CT 06840
Built 1937
35 Hawthorne Road is a Cape-style residence on a 0.4-acre parcel in New Canaan, dated to 1937 by the Town of New Canaan Assessor. The house was also named as the setting for a local civic gathering in 2013. The League of Women Voters of New Canaan announced a new-member coffee at Joanne Windas’s home here for March…
- Beds
- 4
- Baths
- 2.5
- Sq ft
- 4,136
- Acres
- 0.4
1925–19491937Closed
New Canaan, CT 06840
Built 1948
192 Cross Ridge Road is the Landis Gores House, completed in 1948 for the architect and his family. Gores was one of the Harvard Five, the architects associated with New Canaan’s early postwar modern houses. His home was among the six houses opened for the first Modern house tour in May 1949. The long, single-story house combines International…
- Beds
- 3
- Baths
- 3
- Sq ft
- 3,096
- Acres
- 4.2
1925–19491948Active
New Canaan, CT 06840
Built 1950
The Barlow House at 154 Indian Rock Road is an early-1950s design by John M. Johansen, one of New Canaan's Harvard Five architects. Set beside the Five Mile River, the single-story residence combines vertical siding and large areas of glass with views into the surrounding wooded landscape. Johansen had moved his practice to New Canaan in 1949, placing…
- Beds
- 4
- Baths
- 3.5
- Sq ft
- 3,112
- Acres
- 2.4
1950 and later1950Closed
New Canaan, CT 06840
Built 1954
257 Wahackme Road is the James Swallen House, constructed in 1954 using Carl Koch’s Techbuilt prefabricated design. Koch developed the prototype in 1953 as part of an effort to make modern houses more affordable. At the Swallen house, that standardized approach was later paired with a custom addition by Landis Gores, one of New Canaan’s Harvard Five architects.…
- Beds
- 4
- Baths
- 3.5
- Sq ft
- 3,388
- Acres
- 1.2
1950 and later1954Closed
New Canaan, CT 06840
Built 1956
The Beaven W. Mills House at 31 Chichester Road was built in 1956 to a design by William Francis Pedersen. On its wooded, sloping acre, the house combines a flat roof and vertical wood siding with broad areas of glass. High ceilings and a two-sided fireplace distinguish the living and dining spaces, while the hillside allows a walk-out…
- Beds
- 4
- Baths
- 3
- Sq ft
- 2,802
- Acres
- 1
1950 and later1956Closed
New Canaan, CT 06840
Built 1960
The Teaze House at 296 Frogtown Road is a Modern home designed by John Black Lee for David and Jane Teaze, overlooking the Noroton River. The New Canaan Museum & Historical Society holds Lee's architectural rendering, floor plan and elevations for David Teaze's Frogtown Road house, dated February 29, 1960. Pedro E. Guerrero also photographed the house. Lee…
- Beds
- 4
- Baths
- 4.5
- Sq ft
- 3,606
- Acres
- 2.5
1950 and later1960Closed
New Canaan, CT 06840
Built 1960
The Evans House at 44 Benedict Hill Road was designed by architect James Evans for his own family around 1961. Trained at Yale under Louis Kahn, Evans made his New Canaan residence an experiment in the relationship between roof structure and open living space. Its saddle-shaped hyperbolic paraboloid roof rests on two concrete piers at its low corners,…
- Beds
- 5
- Baths
- 3.5
- Sq ft
- 3,200
- Acres
- 4.6
1950 and later1960Active
New Canaan, CT 06840
Built 1962
431 Valley Road is the Corinne and George Liston Tatum Jr. House, designed by Hugh Smallen and built in 1962. Its flat roof, white wood siding, and broad areas of glass give the residence a low, open form closely connected to its grounds. Two large rooms were added in 1967. The house received public attention almost immediately. On…
- Beds
- 5
- Baths
- 4
- Sq ft
- 3,886
- Acres
- 2
1950 and later1962Closed
New Canaan, CT 06840
Built 1967
At 122 Woods End Road, the Latham House is a late-1960s design by Richard Bergmann for Ernest and Chaillie Latham, overlooking the Noroton River. Paired, steeply pitched roofs and broad windows distinguish its architectural profile. The commission helped launch Bergmann’s independent practice. The Lathams owned the Silvermine house that he and his wife were renting and offered it…
- Beds
- 5
- Baths
- 5
- Sq ft
- 6,764
- Acres
- 4.3
1950 and later1967Closed
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ABOUT THIS COLLECTION
A curated view of local history.
For now, this collection is limited to properties that have been listed for sale or sold since October 2021. It is not a complete inventory of older buildings or a statement of legal historic designation. The displayed Year Built is reported by SmartMLS and has not been independently verified. When reliable sources disagree, the property’s Historic Profile explains what is known.
