The median sale price of a Westport home is climbing toward $2 million.
The cost of new builds is even higher.
Which is why the appeal of older homes — those with “good bones” and timeless charm — has never been higher.
Our friends at KMS Team at Compass say that a growing number of buyers are bypassing new construction, in favor of the town’s historic and vintage homes.
There are several reasons.
One is affordability and value. Buyers get more space, character and land for their investment, compared to new builds.

This Clapboard Hill Road property includes the original home, and an expansion. Perimeter trees ensure privacy, on the corner of Greens Farms Road.
With a recent increase in housing inventory, and homes staying on the market for an average of 45 days, buyers have more choices and negotiating power than in recent years.
Purchasing an older home can mean a lower property tax basis too — especially if the assessed value is less than a comparable new build.
This translates into significant savings over time, making historic properties even more attractive to price-conscious buyers.
Architectural character and historic charm are considerations as well. Homes in historic districts like Kings Highway North and Old Hill — where they date back to the 19th, even 18th, centuries — feature original woodwork, wide-plank floors and hand-crafted mantels — that are difficult (and costly) to replicate today.
Iconic properties like the Allen and John Osborn Houses showcase enduring craftsmanship and unique design that help define Westport’s architectural heritage.

The John Osborn House – the oldest home in Westport, located on Long Lots Road — took years to restore. It is believed to have been built between 1683 and 1687. (Photo by Larry Untermeyer)
Many of Westport’s older homes are situated on larger lots, with mature trees and landscaping.
They’re often in walkable, established neighborhoods close to the Saugatuck River, downtown and beaches. They offer a sense of community and history that new subdivisions often lack.
Of course, some historic homes need “rehabilitation.” Owners may qualify for Conncticut’s Historic Homes Rehabilitation Tax Credit, which covers up to 30% of qualified expenses (to $30,000).
The home must be a primary residence with a historic designation, and the project must meet certain criteria.
Restoring a historic Westport home — from updating kitchens and bathrooms to restorin original features — means blending modern comfort with classic style.
The rewards are personal. But they also contribute to the town’s legacy.
Today that appeals to homebuyers in Westport of all ages, and from here and far.
(You can see some of those historic, restored properties on our 3rd annual “Historic Homes Tour,” sponsored by “06880” and KMS Team at Compass. The date is November 2. Details will be announced soon.)

Maybe the same philosophy should be adopted towards schools? Instead of blowing 120 million dollars on a new grammar school, fix and improve what you have at half the cost. My prediction also is that less young children will be attending Westport’s public schools over the coming years.
Sometimes it’s more involved and more expensive to remodel existing structures to update them especially when trying to match and/or tie it together based on today’s building codes. We have built new and done renovations on older structures and it was more involved and took longer than building new. You need talented craftsmanship as things aren’t built today the same way they were back then both in good and bad ways. I think it’s great that more people are looking to buy older homes with more history!
Beth, Aren’t older homes grandfathered in with regard to new building codes?
Absolutely not. Once you pull a permit anything it involves has to be brought up to code.
We thoroughly renovated a 1901 home. Would have been way cheaper to rip it down and start from scratch.
Okay.. the key phrase here is “ pull a permit.” Without pulling a permit, and just living in the same house for years, are you grandfathered?
Grandfathered is the wrong concept because that implies compliance. Most homes in Westport have some element that’s not up to current codes, no one enforces you to update your wiring or your plumbing, etc.
And yes you can do projects, usually interior ones, without a permit so there’s no one to check.
However at least in my experience, once any project gets more involved and you call in the pros, they’ll insist on pulling a permit because it jeopardizes their license, most likely invalidates their insurance, etc. And once that happens, anything that they touch has to be brought up to today’s code. That doesn’t mean, by the way, that the inspector won’t walk thru a half dozen untouched non compliant rooms to get to the project.
Thanks to all for your clarifications.
Jack- in my experience in restoring 311 Post Road East current building codes are most definitely in force so yes , I can attest to the fact that demolishing and rebuilding would have been way cheaper but no where near as satisfying!
30% of $30000 as a tax credit is a joke- not even worth the effort in applying.
As one who remodeled an old home, our experience was very positive and achieved at a far lower cost than a tear down/rebuild. I believe builders promote tear downs since the effort is easier for them and generates larger profits. We have many architects in Town who enjoy and who are capable in doing renovations and restorations. I believe it is a very open question as to which approach is better and less costly. Our bias should always be to preserve.
You are brilliant. Why not form a steering committee of LOCAL architects to spearhead the design of “The Hamlet”? Let Roan chew on that idea for awhile.
I’m hoping Eric Buchroeder SHS ‘70 (I.Q. Of 168) can attend the Compo Beach get-together on July 17th.