We enter our 6th month documenting the changing streetscape of Westport.
As the teardowns — and new construction — keep coming,”06880″ photographer Dave Matlow documents it all.
Brookside Drive, March 2019 …
… and July 2026.
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Clinton Avenue, March 2014 …
… and July 2026.
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Twin Falls Lane, August 2007 …
… and July 2026.
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Northgate, October 2020 …
… and July 2026.
(“06880” regularly covers Westport real estate, history … and much more. If you enjoy features like this, please click here to support our work.)
These never ending massive replacement homes will become an issue.
Trends are not your friend. 5 years ago, Kindergarten enrollment was 400, now it’s 342. Big families are not in vogue as people get married later and later.
Real estate values have skyrocketed and interest rates have settled in, so the unaffordable index for new families is through the roof.
The continued new build of apartment and condo units is interesting as empty nesters sell their homes and hope their kids with grandkids move nearby, but that too has fizzled out.
Good luck.
David, If I ever wrote what you just wrote I’d get slammed with, “ If you don’t have anything nice to say, don’t say anything at all.” The problem is not only are you correct, but you’ve underestimated the problem. Not since 1935 has the United States lost population. More people are fleeing the United States than are coming here. I’ve said this before, if you bought in town in the last five years, you will lose money on your property!
Florida is even worse. The Sunshine State is seeing a mass exodus of its working-age population and younger demographics. Dade county has lost 73,000 residents. Movers are citing skyrocketing housing costs, and soaring home insurance premiums. I’m glad I got out of there! The hospitals are horrible in Florida too. It’s a buyers market and I think you’ll see home prices tank in Westport.
Jack, you’re a story teller. I am too. Don’t fight it. And don’t stop. Sorry Dan. Eric and others too, keep them coming.
Westport has forever been a unicorn place which is why it’s fun to see the multi-generational posts. If you read Dan’s blog, you’re lucky to have found it.
I was a kid there in the 60’s and 70’s. Left for a few decades and then returned to raise our crew because for me it was the only place. I think that kids today will return in 30 years and do the same.
The big house trend is a problem tho. In my small sample size of three Westport bred daughers, marriage is coming later and later and kids even later after that.
Smaller high end homes is what they’ll all want, not massive footprint generic boxes.
Northgate 2020 would be in HOT demand in the unincorporated areas of Oregon City today. I couldn’t afford the rental if I was also affording a car. Yeah, “unincorporated” is really a thing west of Tidewater America. It’s where the land-land-land is that really matters.
To quote Yogi Berra: It’s deja vu all over again. But, hey, if keeps them out of trouble, let ’em bitch and moan and complain and grumble and gripe and then let ’em start all over again….
There was a segment a couple of days ago about the demise of the Italian neighborhoods, primarily in the Saugatuck area. The most nostalgic part of the whole story for me is that the Italian community not only built the town, it nurtured most of us kids who grew up there in the 50’s, 60’s and 70’s. We were so lucky to have them as our neighbors and friends. The families and their generosity to the town and most of all to its children deserves a book and a museum would be nice but I doubt the new Museum of History and Culture would have much interest in getting involved.
Eric, I know the story was about Italians from Saugatuck. However, in my opinion, the most famous Italian from Westport did NOT live in Saugatuck and thus could not be included in the story! I asked Dan to mention this person, but Dan said the story was about Italians only in Saugatuck. I have to respect Dan’s decision, so I can’t comment and mention the name. (Think 1.2 billion dollars.)
Jack,
Your point is well-taken that there were legendary Italian families and stellar individuals of Italian descent from all over town. But the spiritual “ground zero” of the Italian American community in Westport was located in Saugatuck. I doubt there are many of us “old-timers” who would disagree with that. Ironically, the “hamlet” developers are pretty much finishing the job that began when the thruway cut through Saugatuck.
Eric, You have an excellent point, but Nick Tiberio was mentioned and he lived near the golf range. He wasn’t from Saugatuck and was mentioned. Reistino (sp) and Masiello weren’t from Saugatuck either and they were mentioned.
Jack,
We could go blind trying to compile a comprehensive list of great Italians and their families from all over Westport. I’ve always had a theory, however unproven, that I am an Italian orphan that was left on my parents’ doorstep on Treadwell Ave. in Saugatuck. I share so many of their characteristics: Looks. Intelligence. Sex-appeal. Modesty. But who knows? I could even be a Backiel.
In 1972, the average home in the good ole USA was 1,321 square feet. Now, it is 2,743. And the younger generations are having less children. Go figure? Westport is obviously an outlandish exception. We sold our 1962 split level in 2025 and it was torn down, replaced by a now 10K square foot home with 7 bedrooms. I foresee in 50 years one house on the original 12 house street, almost returning to our farming heritage but this time the big money folks will be the owners. As Buffet said: We are in a class warfare and the rich are winning. Big time.