“Then & Now”: #24

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.)

7 responses to ““Then & Now”: #24

  1. 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

  2. Tom Duquette, SHS '75

    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.

  3. Mikey-Boy Brunetti

    As Yogi once famously said….

  4. That is what struck me. It’s not whether or not I like the new style but it seems like the size is so huge compared to the older homes. Just the cost to heat or cool the newer homes must be quite costly. And I assume the size is not necessarily related to having large families to house.

    • Russell Gontar

      The size of the replacements has increased significantly as can be plainly seen. And almost all of the replacements homes in this series strongly favor forward facing, multi peaks. Is there a single architectural firm providing the same basic same design over and over again? What is the appeal of this style? No judgement here, but it is curious.

  5. The company is called “Ditto & Sons.”

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