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Builder Harold Chapdelaine tucked storage beneath the dining table’s banquette seat.
Builder Harold Chapdelaine tucked storage beneath the dining table’s banquette seat.Dan Cutrona

While debating whether to build a vacation home near family on secluded Chappaquiddick or relocate to bustling Edgartown, Becky Kidder Smith and Tom Smith found the perfect compromise: a woodsy plot just five minutes from town with two small buildings connected by a pergola. They snapped the property up and set about turning it into an outdoorsy retreat where they could relax and host friends.

The couple, who live in the Back Bay with their sons, Griffin, 11, and Graham, 6, assembled a Vineyard-based team led by interior designer Mary Rentschler that included architect Chuck Sullivan, builder Harold Chapdelaine, and landscaper Marcos Arado. Together they transformed the quirky, pagoda-like structures into an efficient pair of stylish houses, including reconfiguring outdoor spaces and constructing a 600-square-foot addition (bringing the home to about 2,200 square feet, combined).

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Thanks to what Rentschler calls the architect’s “instant vision” and the builder’s “MacGyver-like” ingenuity, a smart plan emerged for making the two spaces livable. For the main house, Sullivan designed two dormers that created a light-filled living room and more space on the second floor. At Rentschler’s suggestion, they also added a screened porch to extend the downstairs living and dining space and reworked the master bath, adding a private outdoor shower. To satisfy Kidder Smith’s desire to bring the outdoors in, they clad much of the interior with horizontal shiplap, and Chapdelaine sourced reclaimed Western red cedar telephone poles for ceiling rafters.

The expanded kids’ bathroom has a custom vanity and penny tile on the floor.
The expanded kids’ bathroom has a custom vanity and penny tile on the floor.Dan Cutrona

Over at the guesthouse, there had been only a tiny sleeping loft accessed by a ladder. To accommodate a proper guest bedroom, Sullivan designed a full second-floor addition. Rentschler outfitted the living space with funky wallpaper and upholstered sofas the size of twin mattresses, as effective for watching television as they are for kids’ beds. “Really,” Rentschler says, “this is Tom and the kids’ TV room with a guest bedroom over it.”

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The trickier design challenge was creating a transition between the buildings that invited easy flow back and forth. At first glance, the existing pergola seemed to be an open-air breezeway between the houses. However, instead of moving along a straightforward walkway, people were routed down wide gravel paths hemmed in by low stone walls. It was as if the buildings were surrounded by dry moats.

“The setup signaled that I shouldn’t venture over to the main house,” Chapdelaine says. “I knew that wasn’t the way Becky and Tom wanted to live.” The solution was to eliminate the stone paths and walls and then connect the pergola to each house. Now occupants can walk from either building right across to the other.

As the finishing landscaping touch, Arado created a bluestone patio with a built-in propane fire pit. The space is nestled between the houses and easily accessed from each, as well as from the pergola, by handsome granite slabs. It’s just what the couple had in mind — a fun and cozy gathering place to be enjoyed by family and guests.

The doors from the main house to the porch retract and stack on one another, essentially doubling the size of the living space.
The doors from the main house to the porch retract and stack on one another, essentially doubling the size of the living space. Dan Cutrona
Designer Mary Rentschler reconfigured the master bedroom closet as a built-in bank of dressers.
Designer Mary Rentschler reconfigured the master bedroom closet as a built-in bank of dressers.Dan Cutrona
A new staircase was built to access the second-floor addition. The bold wallpaper is by Porter Teleo.
A new staircase was built to access the second-floor addition. The bold wallpaper is by Porter Teleo.Dan Cutrona
Rentschler chose a neutral palette with punchy accents of blue for the main house.
Rentschler chose a neutral palette with punchy accents of blue for the main house.Dan Cutrona

More from the Globe Magazine’s Your Home Issue:

An Outer Cape home has a light touch on the land

This Wellesley home addition is super sleek yet budget savvy

An Edgartown home makes the most of two small buildings


Marni Elyse Katz blogs about design at StyleCarrot.com. Send comments to magazine@globe.com.

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