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…
Interesting question. However, all the High Point Road homes were built on vacant land — empty lots, farmland and/or woods. I think many of the homes built in the 1950s and ’60s were also the first ones on their land.
And couldn’t Westport use some of those empty lots and farmland and woods today? That was what Westport was and should still be! Some call it building on that land Progress. I call it despoiling the natural beauty of Westport. High Point Road would have made one heck of a Community Garden!!
This was a Pizza Hut now it’s all covered with daisies
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.
I love my street and home! High Point is the BEST! This house will most likely remain in my family for years to come as my kids both said that they want to plant their own families here! To each their own. We did not build our house for anyone else but ourselves and if you knew us as owners, you would know that. We don’t care what anyone else thinks of our build nor do we care about your home. Enjoy your own lives!
I actually think it is very rude to take pictures of people’s houses and post nasty comments about them. I think it is obnoxious to say rude things about fellow residents as taxpayers. I am actually disgusted by this.
That’s a fair point Stephanie – I have always wondered about how the people who [innocently] bought one of these new homes and live there feel when their house is profiled as disgusting McMansion.
I also sympathize with those who bemoan the loss of older, smaller homes in Town, especially where it seems to disrupt a tight-knit neighborhood.
The question of who is to blame for these tear-downs / McMansion replacements (if you are among those who are upset about this – and not everyone is) typically lands on the builder – who is just motivated by the marketplace, or the new owner – who simply bought a new home that suited their tastes in this town we all love. Neither seems deserving of the ire.
On the other hand, if you think these new homes are too big / too tall for the lot, that’s something your elected Planning and Zoning commission can address.
When my parents bought our home on Fillow street in 1956, it cost $21k, or $256k in today’s dollars. Tell me, are there ANY starter homes in Westport? With a median price now at $2M, no, there aren’t any. Congratulations Westport, you’ve become Greenwich.
The houses on High Point are beautiful, however pricey they may be currently. Here in Cincinnati we call identical properties “starter homes.” That will correct itself once the bubble bursts as it inevitably does when stratospheric appreciation fizzles out (and Trump has pushed the country over the abyss). As a fellow “Dan Fan” and a contemporary member of the High Point Higherarchy you know, Dan (Woog, not Katz) is one of the original residents of High Point. He’s managed to live a full, productive and most of all, guilt free life sans the demons that inevitably come when you realize that you are the victim of out of control spending. I was a Paul Samuelson fan as a student in Elliott Kraut’s Econ 101 at Staples (the High School not the office superstore). What we are all experiencing are the consequences of too much money chasing too few goods and services. Do what most “Old Westporters” have done: Move to Bridgeport where housing is affordable. Or if you prefer to live among the cool and collected, check out listings in Jack Backiel’s neighborhood.
I am from Cincinnati as you well know Eric. These are not starter homes like in let’s say Westchester or Montgomery. These are homes people worked hard in their jobs and careers to build to their liking. Don’t like it.. easy fix. You don’t know anything about anyone who lives in these homes! I do! They are good people! Try not to be so judgemental; it’s freeing! Many people I know in these homes on this street give to many wonderful charities and causes. Have a nice day!
oh and Cincy ,the home to Proctor and Gamble, is all about consumerism! That’s what supports that town! Westchester Mc starter homes has a main street filled with fast food and strip malls! Yee haw consumerism.
I am so straightened out. Thank You!!!!
I only lived on High Point Rd for a couple of years in the mid 70s, while my Dad was working in New York, and then we returned to the UK—those two years gave me some of the happiest memories of my life. I attended Burr Farms School, had a great group of friends, and High Point Road was a wonderful place to live. We lived in the third old house in this blog, and though I was sad to see that it had been replaced (along with hearing that the school had gone as well), no one can replace my happy memories, so I will treasure those. I’m glad Westport is still a great place to live, and hope it continues to be, whatever your houses look like.
Dan, know how you feel…having grown up in Westport on a great street Edgewater Hillside and now seeing all the new builds overlooking the Mill Pond. Hope the kids growing up there and on Highpoint have as much fun as we did!!!!
How did we ever manage to live in such small often single story houses ?!
Easy. Everybody shared a bedroom.
I think what you mean, Eric, is “everybody shared bedrooms.”
Dan,
I’m punctuationally challenged.