Sunday, October 18, 2026

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Teardowns

WestportNow Before and After: 18 Sue Terrace

WestportNow today begins a new series by Dave Matlow showing WestportNow Teardowns of the Day and their replacement houses. The new house at 18 Sue Terrace off Crescent Road is a notable property to debut the series.  As reported in a story on March 24, 2007 when the house was demolished, two neighboring families bought the property so they and not a developer would determine what would be built there. It was the WestportNow Teardown of the Day on June 14, 2006. Click on the photos or arrows to see the transformation. Dave Matlow for WestportNow.com

WestportNow Teardown of the Day: 2 Side Hill Road

2 Side Hill Road, Westport, CT 06880
Westport officials received paperwork to start the process for a permit to demolish the home at 2 Side Hill Road in the Old Hill section. The 3,142-square-foot, two-story, colonial was built in 1954 and is located on a 1.02-acre property. The property changed hands this month for $1.4 million. (CLICK TO ENLARGE) Dave Matlow for WestportNow.com

WestportNow Teardown of the Day: 258 Hillspoint Road

258 Hillspoint Road, Westport, CT 06880
Westport building officials received an application for a permit to demolish the home at 258 Hillspoint Road. The 2,271-square-foot, one-story, raised ranch house was built in 1966 and is located on a .98-acre property with a water view. The property changed hands in January for $4 million. (CLICK TO ENLARGE) Dave Matlow for WestportNow.com

Going Down: 7 Court of Oaks

WestportNow.com Image
The house at 7 Court of Oaks off Westport’s Morningside Drive North was demolished today. The 1,351-square feet house, a one-story ranch on 0.54-acres was built in 1925.  According to the owners who lived in the house. they plan to reside in its replacement. It was the WestportNow Teardown of the Day on Nov. 11, 2006. (CLICK TO ENLARGE) Dave Matlow for WestportNow.com

WestportNow Teardown of the Day: 60 North Ave.

60 North Avenue, Westport, CT 06880
An application for a permit to demolish the house at 60 North Ave. (also known as 4 Willow Walk), owned by the estate of the late Brett Somers, was under review at the Historic District Commission Tuesday night. The 1¾-story colonial-style house has 2,825 square feet and is located on a .74-acre property. Records indicate it was built in 1889. The HDC declined to delay the demolition. (CLICK TO ENLARGE) Dave Matlow for WestportNow.com

WestportNow Teardown of the Day: 104 Hillspoint Road

104 Hillspoint Road, Westport, CT 06880
Westport building officials received an application for a permit to demolish the home at 104 Hillspoint Road near Greens Farms Road. Built in 1920, the 1¾-story, Cape-style house has 2,232 square feet and is located on a 1.09-acre property. It changed hands in September for $1,145,000. Because the house is more than 60 years old, its demolition status will be reviewed by the Historic District Commission at its monthly meeting tonight. (CLICK TO ENLARGE) Dave Matlow for WestportNow.com

WestportNow Teardown of the Day: 14 Old Orchard Road

14 Old Orchard Road, Westport, CT 06880
Westport building officials received an application for a permit to demolish the home at 14 Old Orchard Road off Maple Avenue North. The 1,256-square-feet, one-story house was built in 1954 and is located on a half-acre property. The property changed hands in September for $700,000. (CLICK TO ENLARGE) Dave Matlow for WestportNow.com