Landscape architect Dan Gordon is no stranger to working in some of New England’s most charming coastal towns. And on each project, the setting’s personality—a blend of cultural cues, architectural precedence, existing topography, and native flora—imbues the final result with a distinctive terrior. The result is a truly custom landscape with a clear connection to place.  

For an oceanfront lot in Chilmark, set high on Martha’s Vineyard’s northwestern coast overlooking Vineyard Sound and the Elizabeth Islands, Gordon employed the same process, soaking in the local flavor. Compared to the bustle of its ferry-fed neighbors, Chilmark is quiet, with pastoral stone walls, buzzing meadows, and scrub oak forests to complement its coveted coastlines. It offers privacy for residents and postcard scenery for visitors. It’s the very definition of bucolic.

The clients tasked island-based Hutker Architects with redeveloping the site. An existing cottage was donated for affordable housing, and the resulting compound now includes a main home, separate guest house, and standalone garage. A tidy one story on the approach, the new main home embraces its ocean views to the rear via a generous, curving balcony and walkout lower level. The existing pool terrace steps town with the topography even further, preserving the ocean views as the main attraction.

Collaborating closely with Hutker Architects, Gordon, principal of Dan Gordon Landscape Architects, based in Wellesley, Massachusetts, and Patrick Taylor, a senior associate, worked to maximize the property’s views with a cohesive, flowing series of outdoor spaces. They created a dedicated approach, navigated grading issues, selected plantings, and revamped the pool area. 

One of their primary goals at the outset: preserve standout natural features, namely the oaks and ledge outcroppings, a result of glacial erratics common to the island’s north side, notes Gordon. “The oaks are hundreds of years old and beautifully sculptural,” he adds. Keeping them as part of the finished landscape was challenging from a construction standpoint, but vital to maintaining the property’s sense of place. “It was worth making the extra effort to protect them; they impart a maturity that’s irreplaceable,” asserts the landscape architect. 

For the property’s new arrival sequence, a long drive winds through scrub oak forest and ends with a pea stone auto court. A mosaic walkway of hand-cut bluestone prefaces the front door, while simple stepping-stone paths lead to the guest house and down and around to the rear gardens. “We kept it very organic, without a lot of formal geometry,” says Gordon. “Our goal was to pick up on that relaxed up-island feel.”

Dry-stacked walls of rounded fieldstone—an homage to Chilmark’s agrarian vernacular—shape the side path leading down around the house to the pool. “The walls help terrace the land for improved grading and circulation. As the lot drops away, the design scissors into two paths: You can stay high towards the house or go low down to the pool,” describes Gordon.

The home’s primary outdoor feature is its pool. Island Pools fully renovated it with new finishes and coping while the landscape architecture team updated its surrounding garden. A circular mosaic bluestone terrace with broken edges intersects the pool, leaving the far end with a simple deck of grass. This artistic effect strengthens the geometric connection between the pool, main residence, and the stone stairs stretching between the two.

“Initially, it was just a pool with a picket fence and a pergola at one end; it was very rectangular,” recalls Gordon. “We tried to create, with the paving and plantings, a much more natural and organic garden retreat.”

Eschewing anything heavy or formal, the design team opted for a simple wire fence with wooden gates. Explains Gordon: “We used plantings on the uphill side to shield the pool enclosure, and we tucked the fence into the grade on the downhill side, so you don’t feel like you’re enclosed.” At the pool’s outer corner, a retaining wall takes the place of fencing altogether, leaving only the view as the land falls away towards the beach below. 

For plantings, the landscape architecture team opted for hydrangea, Russian sage, and roses to provide color during the summer months. Fountain grasses, ink berry, and lowbush blueberry along the borders help soften the property’s edges, easing the transition between built and native landscape. 

While clematis and honeysuckle wind up the pergola, an outdoor sculpture by island artist Steve Lohman reaches up from the pool garden beds. It’s a diving figure crafted from a continuous line of wire— “like a drawing made without raising the pencil from the paper,” notes Gordon. “It’s fascinating how he represents a figure so simply with one material.”

Preserving and developing the lot’s striking views were priorities throughout the design process; however, Gordon and his team still honored the property’s original developer: Chilmark, and that extreme ocean setting. 

“We look at all the details and lifestyle needs, but the big picture of what we do with walls and stone and plants is to create beautiful spaces that really fit contextually,” says Gordon. “That’s how we realize a site’s full potential for our clients.”

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