One of the most popular features on the old WestportNow.com site was “Teardown of the Day.”
For nearly 2 decades local photographer Dave Matlow snapped images of area homes, just before they were knocked down.
He meticulously archived them.
Now he’s taken the project one step further.
Dave is photographing their replacements — from the same distance and angle.
Taken together, they show the changing face of Westport: the types of architecture we’ve lost, and what’s replaced them.
“Homes of ‘06880’: Then and Now” will be a regular feature here.
Thanks, Dave, for your diligence in documenting Westport — then and now.
Juniper Road, November 2014 …
… and February 2026.
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Hillspoint Road, 2005 …
… and Hillspoint Road, February 2026.
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Caccamo Lane, January 2012 …
and February 2026
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Colonial Road, September 2012 …
… 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.)
Great idea … looking forward to it. I would love to see my grandma’s Evergreen Parkway replacement.
This is a great feature. Unfortunately it looks like the trend is to replace with a generic McMansion-style home. I’d be curious to see what these same properties look like in another 20-30 years.
sad but inevitable. Great series of photos!
The “Teardown of the Day” feature was a real gut punch when you’d see your old friend’s homes being demolished…and then came the day when your house is the one falling to the wrecking ball, it was just devastating. I’m sure there are valid reasons to build a new, more modern home on the site of one built in the 40’s, 50’s or 60’s but some McMansion won’t replace my memories.
Just waiting to see ours. Thank you for this!
time doesn’t stand still
Dave Matlow is a town treasure for so many reasons!
Whoa! Fascinating. Thank you.
Anyone who bought a house in Westport during Covid will lose money. The cost of housing was inflated. Watch three years from now!
So many of these homes I remember housed families with three or more kids, when I grew up here. These new homes are certainly prettier and I assume more efficient and probably better built. They are at minimum, double the size of the original homes and dwarf the lots they are built on. I’m sure I would have preferred that as a kid, too. But I personally lament the loss of “air” around these homes and their neighborhoods. Seems like the design is conducive to keeping everyone indoors, probably in front of TVs and computers. Not outside, where we were.
Loved this! When I see a new house go up I always wish I had photoed the teardown.