For years, Bulkley Avenue North boasted one of the best collections of small- and medium-sized homes in Westport.
Connecting Long Lots Road with Post Road East near the Southport border, it was filled with Capes, converted barns, and other structures built largely before the 1960s.
It’s now one of the streets with the sharpest contrasts in architectural styles. Some older houses have been demolished, replaced by larger ones on less-than-acre lots. They sit next to others that have not yet fallen to the wrecking ball.
All of Dave Matlow’s images this week come from Bulkley Avenue North.

September 2005 …

… and July 2026.
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April 2011 …

… and July 2026.
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August 2012 …

… and July 2026.
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August 2010 …

… and July 2026.
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The size change is eye opening. The red one was 1306 sq. ft.. Now it’s 5X that.
Evolving demographics are not your friend with all these massive homes. Delayed marriage, fewer kids. You read the news, or you watch what your own children are doing now if they’re in their 20’s / 30’s.
Funny that Wepo worries about gas powered leaf blowers and plastics. Any green anything has passed Westport by long ago.
The nice thing though is that they are plenty large enough to be turned into boarding houses or multifamily units when the demand for large houses wanes just like in the good old days.
These are particularly sad to see….
Just showing off . . . We just sold and our closing attorney told us most of her clients are two years in arrears on their mortgage(s). Keeping up with Jones’ on steroids.
The former Gudzik family home. Makes me sad…
The Gudzik home was maybe two houses away from the Old Road & Bulkley Avenue corner. I knew John and his parents. Is their house one of those shown? John had another brother, but I can’t remember his name.
Mike…Also retired from the WPD.. Awesome family.
You’re shaking up my memory here. The sister, Judith or Judy, married Bill Wanat. If you remember, when I posted a comment about that property on the corner of Roseville & the Post Rd, I mentioned a Bill Wanat parked his dump trucks on that property before the logs came. So Mike’s sister was Bill Wanat’s wife. She was a teacher. John Sr. used to play pinochle with my family members. John Sr was a long time Westport cop!
Here’s one more bit of information. John Sr’s sister was Mary Kowalsky. Mary Gudzik married Paul Kowalsky. They had that huge 12 acre property on South Morningside Dr, opposite where I lived. Kowalsky’s had a huge trucking company with his brothers. If I’m not mistaken, John Sr’s wife was a Zygmant. The Zygmants were an old time family friend Southport.
Oh, how sad. Seeing that beautiful red house replaced by that white monstrosity! I remember playing tidlywinks in the basement with Stretch Covington while his father worked on that gorgeous roof and his mother spent hours on that frontyard landscape. And it took Stretch’s brother, Shorty, a month to give the paint job that “distressed” look that these new houses can only dream of. What the picture doesn’t show is the illegal still in the backyard where the Covingtons made their home brew called Covington Corn Mash. Nothing was better on a hot day than a jigger of Cold Covington Corn Mash. Ahh, the good ole days…