When landscape designer Hilarie Holdsworth first encountered her client’s 1.79-acre Rockport property, a paved road ran straight through the site from one street to another. “It’s a very deep lot that goes from one street all the way back to another street,” explains Holdsworth, owner of Hilarie Holdsworth Design in Gloucester. Purchased in 2015, the property included an 1866 Victorian main house, a cottage, and a garage—all within walking distance of Bearskin Neck. While the location was ideal, the landscape required a complete reimagining.
Holdsworth began by removing the road entirely, creating a clean slate for a thoughtful, multilevel design. Working with a team of subcontractors, she introduced strategic topography and grade changes to transform the site into a cohesive, resort-like retreat tailored to her clients’ lifestyle. Just beyond the main house, a terrace-level outdoor living area sets the tone. An outdoor kitchen with an oversized grill anchors the space, while a monolithic hearthstone fireplace serves as its focal point. Built from Cape Ann granite quarried locally in Rockport and Gloucester, the fireplace reflects Holdsworth’s hands-on approach—she personally selects the stone from local quarries to ensure each piece meets her vision. A large dining table and ample seating complete the inviting setting.
“I like to use a lot of stone,” says Holdsworth. “When fall comes and the plants recede, stone provides structure. It gives a sense of permanence and makes the space feel like it’s always been there—it adds gravitas.” Reclaimed granite curb was also incorporated throughout the project, reinforcing this timeless quality. Draped over the fireplace, native, noninvasive Amethyst Falls wisteria produces dramatic clusters of purple blooms, softening the stone with seasonal color.
A series of steps leads up to a pool and hot tub level designed for both relaxation and movement. Chaise lounges offer a place to unwind, while bluestone pavers of varying lengths are inlaid within the grass between the pool and hot tub. This design choice is both aesthetic and functional. “People are constantly moving between the pool and hot tub,” Holdsworth explains. “The pavers expand the hardscape while allowing grass to soften the experience.” The pool itself is finished with Cape Ann granite coping and bluestone flatwork, maintaining material continuity across the site.
Beyond the pool, another set of steps ascends to a productive garden space tailored to the clients—a family of five with a passion for cooking and gardening. Seven bluestone raised beds are filled with herbs and tomatoes, creating a practical yet visually appealing kitchen garden. Nearby, a historic hexagonal outbuilding—once an outhouse— was relocated by crane and repurposed as a potting shed. Positioned on axis with a key interior view from the main house, it now serves as both a functional and visual focal point.
Plantings throughout the landscape were designed to soften the hardscape and create a sequence of intimate outdoor “rooms.” “The planting is designed to provide lush, long-season borders,” says Holdsworth, “with flowering trees, shrubs, and perennials that create cozy garden spaces.” Additional layers include bulbs and twelve ground-level planters filled with seasonal annuals.
A calming palette of pinks, blues, purples, creams, and greens reinforces the retreat-like atmosphere. Spring highlights include crabapple trees, hellebores, peonies, dwarf lilacs, azaleas, rhododendrons, speedwell, Knock Out roses, and vinca minor groundcover. Thyme planted between stepping stones lends the pathways an old English garden character—an intentional contrast to the site’s former life as a paved roadway.
What was once a utilitarian thoroughfare is now a richly layered landscape—one that balances structure and softness, permanence and seasonality, and ultimately transforms the property into a deeply personal and enduring retreat.