From the moment the owners or their guests arrive, this Annapolis retreat sets a serene tone. Designed as an escape for a couple with grown children, it balances timeless Eastern Shore vernacular with easy-going amenities and style. “The overall vision was to create a modern interpretation of a classic Chesapeake Bay cottage,” says architect David Myers of Myers Greene Architects. “We wanted to evoke a sense of calm and tranquility upon arrival.”

The property built by Lynbrook of Annapolis is extraordinary—waterfront on both sides, with the bay to the north and the Little Magothy River to the south. “This meant there were opportunities on both sides of the house to have magnificent views,” Myers explains. “From the inside, it can feel like it’s on its own private island.”

This vacation residence revolves around connection—to nature, to family, to leisure. As the wife explains, “The home was designed for work, family, entertaining and relaxation. Downtime on the front porch and the back loggia is very special.”

The 3,500-square-foot, four-bath home was designed for seamless flow, with the kitchen, dining and family rooms opening to one another and extending directly to the pool and pool house on the ground floor. The compact layout minimizes hallways; nickel gap-clad ceilings and flush baseboards create a clean, modern look. The primary suite and guest bedrooms occupy the second floor.

The architecture responds to its site with thoughtful precision. “County regulations required that the house did not exceed a certain size, so efficiency became an even higher priority than usual,” notes Myers. “We wanted to do everything we could to optimize waterfront views on both sides.”
One challenge was garage placement. “The size of the lot meant that anything we did on the upper level was going to impede a view,” he says. “We proposed taking advantage of the natural grade to place the garage at the basement level. This allowed it to be out of sight and opened up more of the view. It also reduced lot coverage and afforded us the space needed to include a pool.”

Two sets of expansive bi-fold doors open on both waterfront exposures. “When the doors are open, the house seamlessly integrates with the landscape,” Myers notes. “And breezes that cross the peninsula through the house are hard to beat. It’s Chesapeake Bay living at its finest.”

Inside, designer Lauren Sparber of Jodi Macklin Interiors grounded living spaces in soft, organic tones and natural textures to complement the surroundings. “From the outset, the goal was to ensure the views remained the highlight,” she says. “Every decision—from materials to layout—was made to emphasize light, openness and a strong connection to the outdoors.”

Sparber describes the mood as “a laid-back, elevated atmosphere—a Hamptons feel in Annapolis. The palette is coastal and calm, while the textures add warmth and livability. It’s a true escape: refined, but never overly formal.” Custom furnishings and artisanal pieces punctuate the interiors: a light-blue, cerused oak dining table by Jiun Ho anchors the dining space, where a bold painting by Baltimore artist Ruri Yi makes a vibrant statement. In the family room, a black Aronson Woodworks console echoes the rolled-steel fireplace, offering depth and texture. The designer notes that the homeowners were collaborative yet trusting, encouraging unique touches like a floating bed in the primary suite that captures sunrise views.

The owners’ lifestyle also shaped the landscape, brought to life by McHale Landscape Design. The property’s dual waterfronts allowed for multiple outdoor “moments.” In the front, 13-foot sliding doors open from the living and family rooms to a bluestone patio. Elevated by an arched stone retaining wall and layered plantings, this terrace offers a welcoming overlook of the bay. In the rear, a vanishing-edge pool blends seamlessly with the river. Stone steps echo the front arches, connecting the pool to the lawn and waterfront.

“Working in and around the Chesapeake’s sensitive areas can certainly be challenging, but we view it as an opportunity,” notes McHale’s Andrew Moore. The plan concentrates development near the house while letting native plantings extend toward the water. A living shoreline along the Little Magothy resolved an existing erosion issue and integrates the property into the environment.

A conversation area with comfy chairs and a firepit provides another spot to enjoy the view, while patios and lawns accommodate gatherings. “Watching these outdoor spaces grow, evolve and become woven into the homeowners’ daily lives is what excites us most,” Moore says.

The residents point to favorite spots that reflect their vision: “I love the hanging chairs on the front porch,” says the husband. “The views, combined with all the flowers and plantings on the property, make it feel like you are a million miles away. Being here and enjoying it with family is amazing.”

Adds the wife, “Our bedroom is extra special—waking up, lifting the remote shades and watching the sunrise is dreamy. The house is everything we ever dreamed of and more.”