Jen Stephens is a New England Home 5 Under 40 Winner

August 25, 2025

Text by Maria LaPiana

A passion for preservation and a wealth of horticultural knowledge define Jen Stephens—the person and the accomplished landscape designer. Stephens, who’ll be forty in November, is a principal at Matthew Cunningham Landscape Design, with offices in Stoneham and Vineyard Haven, both in Massachusetts, and Portland, Maine.

She grew up on a Christmas tree farm in rural Massachusetts, where she discovered a love of plants and landscapes from an early age. She also became attuned to the idea of renewability. “Every April we’d be out there planting hundreds of bare-root seedlings to replace the trees we cut,” she remembers. “And then we’d watch them grow to full-size trees in ten years.” It stayed with her. “Subconsciously, I learned just how much of an influence Mother Nature has on the rhythm of growth,” she says.

As a child, Stephens loved both science and art. “I always thought I’d go to art school,” she says, but instead she fell in love with the campus at the University of Massachusetts Amherst. “When I found landscape architecture among its majors, I just knew,” she says. “It flexes both sides of my brain.”

While earning her bachelor’s in landscape architecture, she spent summers working at Bigelow Nurseries in Northborough, where she became a Massachusetts Certified Horticulturist. Her first post-grad job was at Copley Wolff Design Group, focusing on public spaces. She liked the work, she says, but designing for people she didn’t know? Not so much.

When Stephens was offered an opportunity to join former 5 Under 40 winner Matthew Cunningham—his first hire, by the way—she jumped at it. She’s been integral to many of the firm’s notable projects from day one. Stephens says she’s inspired by “good food, music, and old things.” She lives in a 200-year-old house in Acton, Massachusetts, with her husband, Peter (also a landscape architect), and their young daughter.

What’s next? “I want to mentor some of our emerging professionals,” she says. “I’d like to inspire their curiosity and give back to the community I love.”

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