Inside a 100-Year-Old Waterfront Home Renovated for Today’s Lifestyle

In Westport, a home is rebuilt from top to bottom for fun in the sun.

Westport Living Room
NanaWall doors slide open across the back of the first floor living space. Photography by Neil Landino Jr.

Some might say that it was a folly to buy this century-old home, but for one Westport couple, it was a joy. The pair have lived in the town’s backcountry for nearly 25 years but had kept an eye on properties by the beach as well. When the wife saw this cottage on a downpouring day in early 2018, she knew it was special. “It was a little wobbly, but it was precious,” she says. Where other potential buyers saw rotted-out timbers, sagging floors and walls bent by high winds, she saw gorgeous beams, coastal character and the chance to give an older home a new chapter as their weekend house.

Westport Beach House
Raised by more than seven feet, the home now has three stories of living space. SunPower solar photovoltaic installation was by PurePoint Energy. Photography by Neil Landino Jr.

It was the clients’ can-do attitude that made the project such a pleasure, and a large part of why architect Robert Dean—who built their main home and has worked with them on several other projects since—enjoys collaborating with them. “They have a very enthusiastic way of life,” says Dean. “And they love this stuff.”

Westport Kitchen
A ropey light fixture from Hangout Lighting over the island fits in with the home’s coastal style. The countertops are Compac polished Calacatta through Stone Meister of CT. Photography by Neil Landino Jr.

A long history of flood damage had left the structure very fragile. To revive it, “it needed absolutely everything,” notes Dean. Another buyer might have torn it down and started again, but the couple were committed to keeping as much of the original character as possible—and to enjoying the process. The most difficult and important step was lifting the home out of flood risk by raising it up about seven-and-a-half feet—a challenging task given that it lacks vehicular access and equipment had to be carefully squeezed down a narrow footpath. The house was raised by hydraulic jack over the course of an afternoon, where it remained for nearly two months while a sturdier foundation was constructed below. After a painstaking excavation, 11 supporting piers now anchor it deep into the ground. As each hole was dug, it needed to be continuously pumped out because it would fill with water at every high tide. Though it was muddy and tedious work, “I loved it,” says the husband, a hands-on homeowner who often jumped in to help, even taking a turn on the digger.

Once the house was on solid footing, the team could turn their attention to the interior layout. The new elevation created even more stunning views of the water, and the first floor was opened up significantly to take advantage of it and provide a more contemporary flow. Pine flooring throughout creates a continuous space that fits today’s open-plan lifestyle, with materials (including original floorboards) that maintain the character of the past. A folding NanaWall opens the back of the house completely to the balcony and breezes outside. In tight quarters, clever storage solutions are everywhere, including a hidden utility closet under the stairs, accessed through a hinged bookcase.

Westport Bedroom
The primary bedroom has sliding glass doors that open onto a balcony with a view of the beach. Photography by Neil Landino Jr.

While her husband was more interested in the construction, the wife took the lead on interior finishes. She designed for fun and sun, with ample space for dining and lounging, including a comfy sectional facing the water view and a collection of colorful artworks. A funky Smeg refrigerator and open kitchen shelving feels at home at the beach, as does the ropey light fixture over the deep blue island. In the bedrooms, bed frames with built-in drawers add more storage space. Dean managed to give the primary bedroom its own ensuite bath, and a vaulted ceiling with weathered wood paneling adds spaciousness and drama.

Westport Paddle Boards
In a nod to the home’s location and history, the team used a pebble-dash stucco finish on the lower part of the supporting piers using locally sourced oyster shells. Photography by Neil Landino Jr.

Though the team encountered some challenges during the renovation, not all their discoveries were bad: In the attic, a series of letters and checks signed by Harry F. Sherwood were found, dated as far back as 1928. As a result, the Westport Museum for History & Culture will soon christen the home “The Sherwood Cottage.”

The complexity of this project was “10 out of 10” says Dean, but for all involved, so was the enjoyment. The homeowners, “have a lot of joie de vivre,” he says, “and it’s reflected in the result.”