Our drive down memory lane — specifically, past homes that have since passed into history — and a second drive by the houses that replaced them — continues this week.
“06880” photographer Dave Matlow has many photos in his archives. He’s been curious as to what’s taken their place. This week, he explores 4 more.

Rayfield Road, October 2004 …

… and March 2026.
==================================================

Salem Road, June 2019 …

… and March 2026.
==================================================

Pumpkin Hill, July 2010 …

… and March 2026.
==================================================

Meadowbrook Lane, April 2005 …

… and March 2026.
(“06880” regularly covers Westport real estate, history … and much more. If you enjoy features like this, please click here to support our work.)

Our house at 1 River Oaks Rd is still there.
It’s not like the new houses are replacing landmark-quality buildings. Many of these houses. old or new. probably seem much nicer if you’re inside, looking out. The owners will probably change things over time and the landscaping will grow and improve. Maybe there are tender memories attached to the old houses but new memories will be made by new people. Progress keeps us moving on. Sometimes that’s hard to accept.
For me, it’s about normal-sized houses being replaced by monstrosities. An average family home replaced by something that very few people can afford.
Meanwhile all the yelling about the need for affordable housing. As all the midsize homes get torn down. It’s either enormous or condo living. Less & less mid size choices all by developer design.
That’s really a function of the price of land in Westport. Even a midsize house would be priced out of reach for most people. Get rid of 1 and 2 acre zoning and break up those properties in to quarter acre lots and you might end up with more smaller/midsize houses at more affordable price points.
“Money doesn’t talk. It swears.”
Bob Dylan
Can you say cookie cutter They all look the same