Some of Westport’s greatest concentrations of mid-20th century houses can be found in the eastern end of town, near the Southport line.
“Then & Now” curator and pre-demolition archivist Dave Matlow returned there recently, to document 4 more examples of new construction replacing teardowns. The images are part of a project he worked on from 2004 to 2020.
A reminder: This is a community blog. Our neighbors live here. Some built those new structures; others are the second (or beyond) owners.
If you comment, please be kind. Taste is subjective. Wherever we live, everyone has loves their home.
One home on Woodhill Road, February 2019 …
… and August 2026.
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A second home on Woodhill Road, October 2011 …
,,, and August 2026.
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Elizabeth Drive, September 2007 …
… and September 2026.
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Westfair Drive, October 2015 …
… and Westfair Drive, August 2026. (All photos/Dave Matlow)
(“06880” regularly covers Westport real estate, history … and much more. If you enjoy features like this, please click here to support our work.)
The one thing about building a large house on Westfair Dr, the lots are small, so one is limited on how wide the new house can be. That’s evident in the last picture.
The average square foot house in 1972 in the USA was 1660, now it is 2,440 square feet. Americans are having far less children. WTF? Big is better? Nope, here it is merely showing off with the bank’s money. 2008 again?
Scooter, As a former educator, the grade for your comment is A+++++++++++++
Don’t worry Scooter. Every new home comes with a wiffle ball, bat a dog named Lassie, and of course two boys, Wally and the Beav.
Why do so many folks who don’t live in Westport give a sh*t what other people do?
Allí, 1) We’re entitled to our opinion and I have a 123 year connection to Westport 2) We’re pointing out possible monetary mistakes some people are making.
Ali, Let this sink in. The Wright Brothers flew the first plane in December 1903, eight months after my grandfather moved to Westport. So my connection to Westport was before the airplane. So can I have your coveted permission to comment on 06880?
No Jack. You don’t have my permission.
You’re one comment over the limit.
Adhere or go away.
If you stopped trying to show off and brag so much, Mrs. Morrison, perhaps us expatriate Westporters would be less critical for your current sh@t stinks. And plenty of June Cleavers walking the town these days in yoga pants with their golden retriever, bored waiting for her boys’ swim team practice to end so she can make her Pickel ball game.
I LOVE YOU MAAAAN!!!!!
Scooter Rules!!!!
The problem with nouveaux Westporters is they think they are the only ones with a social conscience.
We may have moved away but we aren’t going away.
Get used to it.
Scooter Rules!!!!
Alli… You’re my new Hero today … lol
👏🏻👏🏻👏🏻👏🏻👏🏻👏🏻👏🏻
Indeed, go Alli (& Patricia)!
If a young couple wants to move to Westport with thoughts of raising a family, on what streets in town are the “starter homes.” Not the (state legal standard) “affordable” dwellings (which are almost exclusively apartments), but the homes that, say, a couple of young professionals can afford to move into?
The honest answer is that they don’t. Fairfield is the next best option, unless someone’s parents are funding the transition, and many do.
No young family moves to Westport until they have a kid heading towards Kindergarten, and then while maybe the school district doesn’t matter since all 5 elementary schools are great, the house has to be clean and safe and livable.
When we returned in 2000 with a 3 year old, our budget was $1M and our agent showed us the 8 houses we could afford. I still remember all the options, and we picked the one that was move in ready and never looked back.
The real number today is probably double that. For a house you don’t need to immediately remediate, that’s safe for a little kid.
I miss the days of the young family neighborhoods. I grew up on Fillow Street and still have friends from up and down the road.
Those days are long gone.
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