Rooms to Grow: A supremely long lot stretches behind the 1899 Tradd Street house that Susan and Gene Massamillo purchased six years ago. The Connecticut transplants called upon landscape designer Sheila Wertimer to transform the overgrown backyard—including a back portion fenced-off and forgotten decades prior—into a series of three unique “rooms.” Susan has since added plenty of her own touches, including containers full of succulents inspired by those she saw in England’s Sissinghurst Castle Garden.
Susan and Gene Massamillo
High Impact: “The Massamillos’ house is elevated above the garden—not so high that it’s intimidating, but just enough that one gets a lovely, long perspective to the back garden from many rooms in the house,” says Wertimer. A bluestone patio steps down into a French parterre, where Susan plays with a changing array of white annuals. Last year, she combined impatiens and artemisia, then trained sweet peas to climb up tuteurs, with gaura popping up here and there.
Scenic Overlook: Shaded by palm trees and sheer white curtains, the back porch is outfitted for year-round living with a whirring ceiling fan, a quartet of comfy wicker chairs, and a galvanized tub for icing drinks. “We’re out here constantly,” says Susan.
British Accents: To give Susan the perennial garden she’d been dreaming of, Wertimer created beds of ‘Royal Blue’ plumbago, pink Knock Out roses, and ‘Lemon Drop’ lantana on either side of a lawn that serves as play space for pups Max and Zoe.
Susan added ‘Amistad’ salvia to conceal a shed, then began developing an English-garden aesthetic by planting annuals like cleome, coleus, and angelonia in drifts.
A staghorn fern in one of the crepe myrtles that toss pink confetti each summer (this one was growing over an old millstone that the Massamillos dug up and set into a walkway).
Patience Rewarded: Wertimer’s design called for a single-stem olive tree to mark each corner of the perennial garden. “It took a year to find four with straight stems that were the same height, but it was worth the wait—they’re spectacular,” says Susan.
Calm & Cool: The garden’s final room conjures the Mediterranean with an all-green landscape that mingles Italian cypress trees, Confederate jasmine, variegated flax lily, sago palms, and banana trees.
A Step Up: For a striking focal point, Susan fills an urn with foliage in shades of burgundy, purple, and chartreuse. Last year, she allowed one bloom—that of purple passionflower—to sneak into the planter, which is displayed on a centuries-old carriage step (or “upping stone”) they found buried by weeds.
Secret Retreat: Lawn chairs tuck into a nook enveloped by papyrus and Chinese fan palms.
Susan and Gene Massamillo’s downtown garden was designed to transport them—and their many guests—to lush landscapes around the globe