The pergola’s lounge area looks out to the pool, house and bay.
The pergola’s lounge area looks out to the pool, house and bay.
Native perennials such as summer phlox and butterfly weed add seasonal color.
The bespoke, black-stained garden gate swings open to a stone-rimmed courtyard boasting a concrete-and-copper water feature from Lunaform.
A semi-circle of southern bayberry between the pergola and guest house/garage help create a sense of enclosure.
Last year, the owners reimagined the front entrance, installing a custom door.
Public spaces enjoy bay views.
A glass sculpture by Vincent Beaurin crowns the living area’s fireplace.
Stainless-steel countertops lend the kitchen an industrial edge.
The main home’s primary bedroom features a bespoke, gray-washed pine bed from Daniel Donnelly Modern Design.
In the owners’ bathroom, a marble-topped, knotty-pine vanity rests on pebbled flooring from Ann Sacks.
In the guest house, a wood accent wall features a Japanese shou sugi ban finish.
Jason Claire oversees Interior Matter’s operations from the guest house home office.
Claire discovered his mid-century Italian desk at Reform Vintage Modern in Philadelphia and unearthed the vintage Turkish rug on a 2010 trip to Istanbul.
Claire created the artwork hanging over the guest house bed by nailing vintage sand shovels, sourced on eBay, to an antique floor board.
Under the shady, post-and-beam pergola, a row of chaise longues from Knoll’s Richard Schultz 1966 collection invites relaxation.
Interior Photography by Anice Hoachlander | Outdoor Photography by Allen Russ
Set on a bluff overlooking the Chesapeake Bay, the home of Jason Claire and his husband tells a tale of evolution. Originally built as a weekend retreat from the couple’s DC-based life, it now serves as their primary residence—yet a sense of escape prevails. “We’ve created a relaxing space that almost makes us feel like we’re on vacation,” reveals the designer. “So much of it is the view. We’re fortunate to have a beautiful natural environment.” That panorama provides a pristine backdrop for Claire’s clean-lined, layered aesthetic.
After searching for a property with, as Claire puts it, “some sort of water situation,” the couple purchased the one-and-a-half-acre parcel in Chestertown, Maryland, in 2006. Five years later, they replaced a tired home on the site with a 2,300-square-foot modern cottage. “We wanted the interior space to be open and light, to have both glass for the views and walls for art,” he states. The kitchen, living and dining areas, and library flow in an L shape on the main floor; the owners’ suite lies to the left of the entry. Upstairs sit two guest bedrooms and a bath.
The pair also added a detached, two-story garage/guest house, originally leaving the upper floor unfinished. Not long after, Claire’s husband, a physician who specializes in global health, accepted a position in Switzerland. So they sold their house in DC and moved abroad, with the commitment to make Chestertown their full-time base upon their return.
While overseas for four years, Claire remotely orchestrated several improvements that, he discloses, “amped up some things we didn’t spend money on in the first round because it was a second home.” First, he asked architect Cathy Purple Cherry to devise a plan to finish the above-garage space. Her layout includes an open office, kitchenette, guest bedroom and bath. Downstairs, the architect also shaped a welcoming entryway. “We opened up that vertical space so light can shaft down through the stair to the first-floor foyer,” she explains. “That lower level engages the upper floor.”
Next, South Fork Studio enhanced the somewhat stark landscape, employing an array of native plants to add privacy and definition, as well as color and texture. The existing pool lying between the house and garage presented the biggest challenge. “The unique part of this project is that the pool is basically in the front yard,” notes principal Miles Barnard. “Anybody who comes to the house has to come through that area.” He devised a new bluestone path that fosters circulation around the renovated pool. A cedar pergola, installed after the couple’s return, offers shade and architectural interest. “It’s a really neat little oasis,” Barnard says of the finished spot.
Upgrades within the house included re-facing the kitchen cabinets, switching out some earlier lighting choices and installing a home-automation system. “We did those tweaks to make it feel more like a primary home,” explains Claire. “We wanted the spaces to be a little more sophisticated and less ‘beach house.’”
Claire also used the time in Europe “to feed my design curiosity and plant the seeds for whatever would come next.” Vastu, the DC furniture showroom he previously co-founded, closed in 2014 after both owners relocated. “In my head, I was collecting designs of hotels, restaurants, food, art—all the things that I was experiencing,” Claire recounts. “I was primed when I came back to start something new.”
That “something” turned out to be Interior Matter, the design business he launched in 2019 with former Vastu colleague Sarita Simpson. “We’re a modern firm,” Claire states. “We like clean lines and lightness, though the unexpected mixing of materials and periods is also a through line in our work.”
His aesthetic has evolved over the years from minimalism to a more layered approach, which he applies at home. White walls, warm woods and unfussy furnishings provide a timeless base, Claire maintains, for both “physical layers and layers of history, of experience.” He treasures “the stories behind the objects” gathered on the couple’s world travels. Original art plays a starring role in his meaningful tableaus. Along the guest-house stairway, for example, a charred-wood accent wall dramatically showcases pieces collected around the globe, plus one grade-school painting by Claire that won first place in a student art competition.
The designer works from home, thankful for the separation that “a one-minute walk down the path” to the guest house provides. He and his husband happily embrace the region’s low-key, outdoor lifestyle—lounging by the pool, dining on the deck and hosting crab feasts on the dock.
“When this was a second home and we’d come out for the weekend, our shoulders would relax once we got onto the Bay Bridge,” recalls Claire. “We’d be in the zone of being on the Eastern Shore. We’ve been very fortunate to make our lives work around that full-time.”
Interior Design: Jason Claire, principal, Interior Matter, Washington, DC. Renovation Architecture: Cathy Purple Cherry, AIA, LEED, AP, CAS, Purple Cherry Architects, Annapolis, Maryland. Renovation Contractor: Taylor Loughry Construction, Chestertown, Maryland. Landscape Architecture: D. Miles Barnard, ASLA, RLA, South Fork Studio Landscape Architecture, Chestertown, Maryland.