High Point Road is the longest cul-de-sac in Westport.
It’s also the street I grew up on.
It was quite a place. Nearly every home — about 70, by the time they were all built — had 2 or 3 kids, all around my sisters’ and my ages.
We rode bikes, played in yards (and in the “circle” at the end), wandered in and out of houses. Someone’s mother fed us dinner. Then we were outside again.
Staples High School was just over the hill, on the west side of the street. We took over the athletic fields as our own.
High Point is still filled with children. It’s still a great place to grow up.
Some of the original 1950s homes remain. But many others have been torn down.
From the time Dave Matlow began photographing houses set to be demolished, and the time he stopped 6 years ago, 14 High Point homes fell to the wrecking ball. Others have been razed since.
Here is a sampling:
May 2010 …
… and May 2026.
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September 2008 …
… and May 2026.
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June 2012 …
… and May 2026.
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May 2007 …
… and May 2026. (All photos/Dave Matlow)
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And here are bonus shots. This is #34, where I grew up:
June 2017 … (Photo/Dan Woog)
… and now.
Click here for a story I wrote in 2021, when my childhood home came down.
(“06880” regularly covers Westport real estate, history … and much more. If you enjoy features like this, please click here to support our work.)
Dan: Now that I know yours is one of the homes that came down, i really think this whole set together with your commentary should be a book — Evolution of a Suburb or some such…. it is really a fascinating picture of socio-anthropology, way behind “just” Westport…..
I don’t see this as evolution…..
Stunning. And not in a good way.
If only we had the “Before-the Before” pictures! The houses must have been real beauties. If the “Befores” are all better than the “Afters” just imagine how great the “Before-the Before” houses must have been. Think about it…
Geez.
The scale of the replacements isn’t long term sustainable. They were built by the “look at me” generation. The next crew is far more environmentally aware.