Homes Of “06880”: Then & Now, Part 2

Readers reacted quickly to last week’s initial installment of “06880”‘s new series: “Homes of ‘06880’: Then & Now.”

They appreciated seeing photographer Dave Matlow’s archival images of homes he photographed for WestportNow’s “Teardown of the Day” — juxtaposed with their current-day replacements.

Dave is taking new shots, from the same distance and angle. Here are 4 more houses that are now gone, along with the new ones.

Darbrook Road, March 2005 …

… and February 2026.

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Deerwood Road, September 2020 …

… and February 2026.

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Burnham Hill, July 2011 …

… and February 2026.

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Blue Ribbon Drive, July 2011 …

… and February 2026.

(“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 “Homes Of “06880”: Then & Now, Part 2

  1. Hmmm. I think I’m maybe detecting a certain pattern here…

  2. Richard Johnson

    We need some better architects in town.

  3. Sandra Grunewald Jones...Staples 1964

    I find this very interesting since both my childhood home in Westport have changed dramatically…27 Guyer Rd. and 38 Bermuda Rd. are unrecognizable to day as they were in the 60’s

  4. David J.Loffredo

    Yes there are architectural gems in Westport. We restored a classic Victorian Farmhouse (next owners took it to even greater heights), and there are 100’s of others from Frazier Peters stone beauties, to mid century modern stunners. Even some of those 70’s contemporary “whoas” are in style now.

    We also had the tract houses of the 60’s. I great up in 4 Fillow Street (unchanged btw, love that) on a street full of houses with one of two designs. Super efficient for the builders, kids loved it because we knew where stuff was in our friend’s houses.

    Too many of the replacements look like over priced SIR Development crap. I’m sure it’s fun for people moving out of Manhattan looking for space, but this series is starting to remind me of the classic The Who lyric – “Meet the new boss, Same as the old boss”.

  5. Joyce Barnhart

    On a walking tour of the old whaling captains’ homes in Essex we were told that they’d been preserved because when the whaling industry collapsed, there wasn’t any money to change, modernize or “improve” the houses. The first Levittowns in Pennsylvania and New York were reviled for their cookie-cutter sameness but they served an important function for returning servicemen from WW2 and their young families. (Baby-boom, anybody?). Visit them now and the houses are all different from one another. It would be a serious challenge to find an unaltered original. Progress often means change.

  6. I love this new segment of the “old” and “new” homes…!

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