This week, Dave Matlow — our “Then & Now” series curator, and a pre-demolition archivist between 2004 and 2020 — takes us all over town.
From Old Hill to Long Lots, he highlights 4 more homes that have fallen to the wrecking ball. And the new construction that replaced them.
A reminder: This is a community blog. Our neighbors live here. Some built those new structures; others are the second (or beyond) owners.
If you comment, please be kind. Taste is subjective. Wherever we live, everyone has loves their home.

Moss Ledge Road, July 2014 …

… and July 2026.
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Winding Lane, October 2018 …

… and July 2026.
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Joann Circle, October 2007 …

… and July 2028.
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Blind Brook Road, April 2005 …

… and July 2026. (All photos/Dave Matlow)
(“06880” regularly covers Westport real estate, history … and much more. If you enjoy features like this, please click here to support our work.)

if would be interesting to know the before/after square footage. while I assume most if not all would be bigger, some of these are huge
The original Joann Circle house was 2,062 sq.ft. The replacement is 6,942.
I know the Moss Ledge “then” house well. It belonged to the John MacDonald family back in the 70’s. I went to Staples with Mike who was one of seven or eight kids that grew up there. I spent a lot of time hanging out there my senior year, great times. The new build isn’t out of proportion with the property either for a change.