As we prepare for the 3rd annual “Historic Homes of “06880” tour next Sunday (November 2, 1 to 4 p.m.) — featuring 4 homes, all built between 1870 and 1938 — it’s interesting to take a look at the ages of all the homes sold in Westport thus far in 2025.
Exactly 1/3 (33.4%) of the 243 homes that changed hands were built between 1950 and 1970. 15.7% were built between 1900-1950, while 5% went up before 1900!
In other words, more than half the homes sold were built in 1970 or earlier, while just 18.6% of homes sold were built in 2010 or later.
The 4 homes on the Historic Tour date from 1870, 1904, 1907 and 1938. Each is an excellent representation of its time period. All have been restored with loving care — and enlarged to meet 21st century needs.

249 Greens Farms Road, a Bedford family gem.
Homes built in the 1920s housed an average of 4.3 people, and were approximately 1,000 square feet.
By 2014 — nearly 100 years later — home sizes had increased roughly 2 1/2 times, to an average of 2,650 square feet.
The average size of homes sold year to date in Westport is 3,851 square feet (above grade). The median size is 3,378 sf.
Homes priced in the $1.4 to $2 million dollar range remain the most sought after, deriving an average sales price of 5.5% over asking price. Homes in this price range average 2,848 square feet.

Hover over or click on to enlarge.
This information comes from our friends at KMS Team at Compass — sponsors of our November 2 Historic Homes tour.
They’ll be with “06880” representatives in the 4 homes next Sunday, ready to describe the history of each property, and answer questions about how “old” homes have been adapted for 21st century life.
To learn more about those 4 homes — 221 and 249 Greens Farms Road, both built by the legendary Bedford family, as well as 209 Wilton Road and and 155 Long Lots Road, and for tickets, click here.

155 Long Lots Road

Thought I would count how many of the total 243 houses were sold to an LLC – which normally means that the house is slated for demo and then a new built larger and expensive house. I counted 75 houses but could be off a few.
Bob Weingarten beat me to it; I’m sure many of those old houses are soon to be tear downs.
I fear the same….and all properties surely to be clear cut by developers who couldn’t care less.
Perhaps the new Administration can offer incentives to remodel rather than tear down for yet another monolith that only takes us further away from meeting affordable housing targets? I am sure most of these teardowns were in fact the most affordable housing in Westport and could be adapted to a more modern way of life with some thoughtful TLC.