Beyond the home’s backdoor and through a split rail fence, summer visitors are greeted by an unobtrusive pool and a former art studio dubbed the “Pleasure Pavilion,” where a swim follows rustic lunches. Several weathered Adirondack chairs rest below a mature Sugar Maple tree, providing a respite from the midday sun.

The swimming pool was existing when Glenn purchased the house. He left the coping, but removed the awkward patios to allow it to fit quietly into the backyard landscape as a reflecting pool. The property expands beyond the back gate for some distance before connecting to hundreds of acres of the Roxbury Land Trust’s many preserves.

The breakfast room has a simple round pedestal table paired with directors’ chairs. The tableau is comfortable and unassuming, inviting guests to enjoy coffee while watching the mist burn off the morning landscape, the birds visit the feeder, and a few chipmunks scamper about. The Russell Wright servicewear is part of an extensive collection that could serve an expansive buffet dinner.

In the entry hall, a pair of circa 1830 hall chairs rest atop a custom ‘falling block’ patterned hook rug, which Glenn designed for the space. Above the chairs, in what amounts to a mid-20th-century artistic dialog, are works by Alexander Calder (left) and Le Corbusier (right). The Calder is the first work inside the house, which Glenn chose because Calder’s homestead and studio–still maintained by the late artist’s family–are less than two miles away.

The library’s furnishings, woven together like a historical tapestry, tell the story of Glenn’s interest in 19th—and 20th-century design. Pieces include a coffee table by T.H. Robsjohn Gibbins for Widdcomb, a 1940s sloping-arm sofa draped in an antique Suzani, and a Greek temple model found at a yard sale perched atop a marble pedestal. Part of his collection of objects by late 19th-century designer Christopher Dresser is presented on the top shelf of the etageres. The ceiling is covered in Farrow & Ball bumblebee paper.

A large-scale painting on paper by Melinda Stickney-Gibson takes pride of place at one end of the dining room, which is furnished with a 10-foot antique table and a set of leather-covered Anglo-Colonial X-back chairs that have been in Glenn’s possession for more than thirty years. At left, an 18th-century English server rests beneath a large mirror that amplifies the glow of a chandelier that Glenn designed.

In this view of the living room, an unusual 19th-century Thebes chair fashioned from slender bamboo branches sits in front of a pair of cocktail tables by T.H. Robsjohn-Gibbings. Directly above the fireplace is Untitled (Dollar Bill) 2000 by Thomas Friedman; to its left is a portrait by the late Donald Baechler, which was Glenn’s first art purchase after arriving in New York.

With a flat-screen TV hanging on the adjacent wall, this armless corner sofa affords ample seating for movie viewing, especially on chilly winter evenings with a crackling fire. Chunky seagrass matting underfoot grounds the tableau.

A second custom-designed hook rug rests on the upstairs landing, which features the home’s original spindles and handrail. A pair of African masks adds a tribal note.

Maintaining a through line between the house’s past and present was paramount, so Glenn kept the existing mustard-yellow toile wallpaper in the primary bedroom to acknowledge the previous owners. By day, ample sunlight streams through the room’s large casement windows; in the evening, a pair of James Mont’s Open Helix Lamps from the 1950s illuminate the space.