Last week’s feature on torn-down older homes — and the new ones that replace them — highlighted North Bulkley Avenue.
This week, Dave Matlow — the series curator, and a pre-demolition archivist between 2004 and 2020 — takes us up and down Old Road.
That’s the equally historic (and “old,” for sure) street that intersects Bulkley North halfway down. Old Road begins on Maple Avenue North.
A reminder: “Then & Now” highlights homes of yesterday and today. Our neighbors live in houses old and new. 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.
January 2019 …
… and July 2026.
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March 2015 …
… and July 2026.
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February 2018 …
… and July 2026.
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November 2012 …
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Heading away from the Post Road on North Maple Avenue there were three homes on the right side of the road that were very similar. The first one on the corner of Old Road and North Maple Avenue was a disaster for years. I don’t know about the second house, but in the third house lived Diane Pepper, born in 1944. She was on a TV game show sometime in the 1950s and became a neighborhood celebrity. Her house was basically across the street from where the Jaeger family lived.
I knew Diane Pepper. Her father was my pediatrician.
Bravo Mikey! Bravo!
‘I’m a Pepper, you’re a Pepper, wouldn’t you like to be a Pepper too…!’
All the houses, old and newer, are/were beautiful but my only comment is where are young couples or single people going to find the old ‘starter’ homes of the 50s and 60s?? Those Cape Cods were adaptable for a growing income and family.
By the way, the house I called a disaster was demolished and not the red house pictured here. The old one was basically falling down by way of neglect! I think there were comments about that house in a previous 06880 post.
I just googled it. The rear wall of the house collapsed and the Westport Building Department issued a demolition permit for the structure, clearing the way to clear the site rather than fix up the old building.
Oops… I made a mistake. I commented on three homes on Maple Avenue, but it was the homes on Old Road that were pictured. I probably only got that one house correct, the one on the corner that was demolished. Sorry folks
I’m with Carol Waxman – all I see is Affordable/Not. It’s limiting the economic diversity of the town even further.
All these big houses are such a mistake. Delayed marriages, smaller families, more respect for the environment.
When you look down in the beach area you see smaller (comparatively) high end well thought out homes because space is limited.
I suspect the next teardown wave will be to replace these generic big boxes with smaller interesting structures that embrace nature. If I’m an architect / builder – that’s what I’m selling.
I remember a lot of these homes and they had a lot of charm, too bad a lot of copy + paste mcmansions are going in their place.
I grew up in the Red Cape. Such great memories of a neighborhood filled with kids of all ages that all played together. Although somewhat dated, my parents loved her and kept her pristine. My mom lived there until her late 80s when assisted living became the better option. Our hope was that a young couple would buy it and make it their own, but that was not to be.
Spot on, all of us who were raised in that other Westport can relate to this.
The blindingly white siding paired with blacked out window hardware fad seems to be fading a bit?