Nearing retirement, a California couple packed their bags for Maryland to be closer to family. It helped that the wife’s father had recently sold them a waterfront parcel on Kent Island, near the confluence of Tanner’s Creek and Eastern Bay. The existing house there had served as a happy gathering spot for decades. Yet its new owners envisioned something even better and decided to start from scratch.

“We wanted to build a destination home that would continue to be a focal point in our family—a place where we could do most of the entertaining,” reveals the wife, who recently hung up her hat from the e-commerce industry. “But there were also things that really mattered to us, and there was a certain way we wanted to live.” They hired Hammond Wilson to conjure up their permanent dream digs. Interior designer Erin Paige Pitts, Focus Construction and Campion Hruby Landscape Architects soon joined the team.

Architects Leo Wilson and Marshall Harris devised a plan that caters to owners and guests alike. They sited the house along the water to capitalize on the spectacular Stevensville setting. The main living spaces flow in a linear, one-room-deep fashion via a spine that runs from end to end across the front. On the first floor, the foyer gives way to open living and dining spaces. The kitchen/breakfast area sits to the right; a wine room lies to the left. The second floor—accessed by two sets of stairs and an elevator—houses the primary suite and an office for the husband, who’s newly retired from a career in IT, at one end, followed by two guest suites and a bunk room. A gym and theater rest above the three-car garage, positioned at a right angle to the main volume.

“The arrangement allowed us to orient almost every room along that axis to the water views,” Wilson explains. “Then we opened up the waterfront side with a lot of windows and doors.” Transom windows above those swaths of glass invite additional sunlight into the spaces.

A tower was among the owners’ requests. The architects responded with a three-and-a-half-story element that houses the main stair and leads up to an all-weather observation room as well as an outdoor platform. Wilson points out that the couple “wanted to take advantage of the long view out to the bay, so the tower provides that.”

For the two oenophiles who came to the Eastern Shore by way of Napa Valley, a wine storage and tasting room was non-negotiable. They sought both a cave-like aura and a sightline to the creek. A domed ceiling and Venetian plaster walls capture the desired feel. Meanwhile, double doors frame a picturesque view and open onto an al fresco seating area, also accessible from the living room.

Several other spaces strengthen the indoor-outdoor connection. A patio off the dining room steps down to the lawn and water beyond. Adjacent to the kitchen, a screened porch links to the main outdoor-entertainment area, which features a new swimming pool and stone fireplace plus a terrace with zones for gathering, lounging and dining. The owners’ bedroom boasts a private balcony offering an impressive panorama.

Campion Hruby’s planting plan enhances and preserves the bay landscape. “We used a palette of mostly native trees, shrubs, perennials and grasses,” says principal Bob Hruby. “It’s ornamental, but it also fulfills our mitigation requirements in terms of construction disturbance.”

Embodying a coastal Shingle style, the home’s exterior meshes with its surroundings too. Engineered NuCedar shingles replicate traditional cedar shakes. Detailing—such as the series of gabled dormers across the back—“is intended to make you think about historic architecture, things of the past,” Wilson suggests.

Inside, Pitts answered her clients’ call for comfort and approachability without sacrificing style. “They asked for a hybrid look, California-meets-the-Chesapeake,” the designer recounts. Her translation: a gray-and-taupe color scheme with a smattering of blue and just enough interest. “It’s tonal, soothing and quiet, which feels good,” she notes. “At the same time, I wanted it to have a lot of depth, so I brought in texture and some pattern.”

Her schemes combine upholstery clad in nubby indoor-outdoor fabrics, woven goods, natural-fiber rugs and tactile wallpaper. Lighting selections bring the drama. The dining room, for instance, showcases a chevron-inlay wall covering made from genuine wood veneer and a statement chandelier featuring abaca rope.

Pitts threw “a wild card” into her design proposal: two platform swings that would hang from the living room ceiling to savor the view. Her clients were all in. “I presented two options—one with settees in front of the window and the other with swings,” she recalls. “They wanted the swings, no hesitation.”

A pizza oven and a large island topped the kitchen’s must-haves list. “We both love to cook, but like to keep it really casual,” discloses the wife. “That’s how we entertain.” A pizza-sauce-proof quartz from Cambria tops the cabinetry.

In the primary suite, Pitts created what she describes as “a restful retreat,” again marrying neutrals with texture; the fireplace’s silver-travertine surround is a shining example. The luxurious bathroom teems with marble, from its flooring to its shower tile.

The completed 7,200-square-foot abode works well for two—or a crowd. “While it’s a large house, it doesn’t feel overwhelming,” notes the wife. “We use and enjoy all the spaces.”