Westport is a town of teardowns and new construction.
“06880” reports often on both.
But there are still plenty of historic homes. For decades — centuries, even — owners have cared for them lovingly, restored them beautifully, and adapted them to today’s life.
On Sunday, November 1 (12 noon to 4 p.m.)., you can tour 5 of Westport’s most classic — and coolest — houses.
Our 4th annual “Historic Homes of 06880” tour — presented with our friends at KMS Team at Compass — is our most impressive yet.
We’ve added a 5th home to our usual 4. We added an extra hour too.
We’ve found 5 remarkable properties — from Greens Farms and Long Lots to Compo and Old Hill — that will prove that history lives, architecture is stunning, and our neighbors are very creative folks.
As you explore all 5 houses, you’ll learn the stories behind each one. Homeowners and docents will point out highlights of each home. You’ll get a brochure giving added background and info too.
Tickets are $75 each, $100 for 2. Proceeds help fund “06880”‘s work — which, as always, chronicles Westport’s past, present and future.
Click here for tickets. Questions? Email 06880blog@gmail.com.
And now … 2026’s “5 Historic Homes of 06880.”
311 Greens Farms Road
This house was built in 1790 by Peter Jennings. It passed later to Edwin Jennings, the first commercial greenhouse owner in Green’s Farms, known nationally for his pansies. It was the home of 4 generations of that family for more than 150 years, until its sale in 1948.
A later owner, Allan Pifer, was president of the Carnegie Corporation. He renovated the handsome fireplaces.
The present owners purchased the home in 2018. Working with Rocco DiLeo, they added an addition, connected by a narrow wing that includes the 14-inch white pine floorboards in the original home. Upstate they found reclaimed exposed timbers, complementing the post and beam timbers in the original home.
The owners were extremely conscientious, restoring almost every aspect of the home. With all original details replicated — including gas sconces — the architecture, scope and warm charm is enhanced throughout.
Moving from the lovingly maintained original portion, into the well-designed addition, highlights the seamless blend of 1790 and 2026 life.
311 Greens Farms Road
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50 Turkey Hill Road North
One of the most recognizable houses in Westport — on the Turkey Hill North/Long Lots Road corner, opposite St. Luke Church — this was built between 1788 and 1799. by the famous Burr family.
It was an inn and tavern, then given as a wedding present by Daniel Burr to his son Jonathan and his bride. It passed later into the equally famous Banks family, who owned it through 1920, and served for a while as a farm.
The current owners have restored other antique homes. They fell in love with the scale of the house. They renovated the oversized kitchen (originally a barn/shed for crops). The post and beam architecture is spectacular; the pine floors are original.
Fireplaces throughout are reminders of the days when they warmed the entire home. The one in the dining room features a very rare wood lintel. There are 7 bedrooms.
Outside, the current owners restored stone walls. Perennial gardens have bordered the property since the 1920s.
In back, the 19th century barn was redesigned as space for the owners’ parents.
50 Turkey Hill Road North
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50 Sylvan Road North
History bursts from every part of this 3-acre property.
The Tudor Revival was built by Charles Cutler more than a century ago for the president of Dun & Bradstreet. He designed (among others) the Patagonia building downtown (now the Compass office), and Greens Farms Elementary School.
Previous owners include actor Frank Gorshin (The Riddler on “Batman”), and billionaire Marc Lasry. The current owners have spent 3 years restoring the home and the grounds.
The stone walls are 2 feet thick. The 9 bedrooms and 8 bathrooms include carvings of Latin sayings and animals. There is even a room where the chauffeur could pull in and wait (he was not allowed anywhere else).
The grounds are as magnificent as the interior. Landscape architects Beate Hochman and Emilio Mandujano discovered and resurrected long-lost gardens, statues and fountains. A new farm building includes chickens and ducks, with a koi pond nearby.
50 Sylvan Road North
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56 Sylvan Road North
The “9 Hearths House” was built around 1791 by Noah Nash. (Fun fact: It actually has 11 hearths.) A famous later occupant was Daniel Webster. While living there, he created Westport’s Minute Man monument.
But Nash and Webster are not the only famous names to own this special property. The current owners are Mo and Jen Tooker — she is Westport’s former 1st selectwoman, now running for state comptroller.
Original wide wood plank floors and ceiling beams remain throughout the oldest section of the house (now the main living area). A mudroom and breakfast room were added in 2013.
The Colonial Revival received a Historic District Commission Preservation Award in 2014, for “meticulous care of the property.” Living space has been updated for a modern family, while the antique character of the house is felt everywhere.
56 Sylvan Road North
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217 Compo Road South
This home was built in 1855 by Rufus Bennett. His family dates back to the Revolutionary War; they watched the British march by on their way Danbury. It passed into the hands of Rufus Wakeman, a member of another famous Westport family.
In 2002 the house was saved from demolition. Realtor Jill O’Shea spent years fully restoring it. The current owners have re-designed this Victorian farmhouse, making it work well for themselves and their 2 young children.
Highlights include chestnut flooring, an exposed brick fireplace, a custom kitchen, gas lanterns, front porch and bluestone patio with a fire pit, enclosed by mature specimen trees and a perennial garden.
It is a great example of a home that’s a true antique outside, while inside it supports a modern lifestyle. The interior maximizes well-laid out, compact space. Hidden storage is key.
The current owners also renovated a carriage house/detached garage into a fully compliant accessory dwelling unit. It too is on display, as a thoughtful modern use of historic space.
217 Compo Road South
(Tickets are $75 each, $100 for 2. Proceeds help fund “06880”‘s work — which, as always, chronicles Westport’s past, present and future. Click here for tickets. Questions? Email 06880blog@gmail.com.)
