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.
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.