Lee Gilliam is a first-generation landscaper from outside of the Boston area. With more than 35 years in landscaping, he is bringing his knowledge to This Old House as the show’s landscape contractor.
Gilliam graduated from Newton North High School. He worked full-time in assembly work, while starting his own landscaping company, driving around in a Toyota Corolla station wagon, learning by trial and error. Self-taught, Gilliam refers to his education and training as the “school of hard knocks.” He decided to go into business for himself, founding his landscaping business, Gilliam and Sons Landscaping.
When Kevin O’Connor introduced Gilliam to the Ask This Old House audience, he described the journey that led to his discovery: “As you may recall, we have been in search across the country for contractors who we believe are worth celebrating. And one of our finds happens to be right here in our backyard. His name is Lee Gilliam. He has been a landscape contractor in the Boston area for 30 years.” Gilliam’s reputation preceded him — as one colleague recalled, “Your name kept resurfacing at every nursery I’ve been to, and all good.”
Gilliam’s success is built not just on his own skill but on the loyalty and craftsmanship of his crew. As he told Ask This Old House: “I’ve had guys with me for 20 years so they know what I like and what our customers like. They have a lot of pride. My guys have a lot of pride in what they do and they’re great people… they’re family.” He also makes a point of mentoring the next generation: “I tell young people, especially people who look like me, don’t give up — if I can do it, you can do it.”
A self-described people person, Gilliam enjoys working with his hands and teaching others about the best care for their properties. “It’s nice to plant something and see what happens from it,” he says, “I live in a region where people take a lot of pride in their properties, and there’s nothing better than fresh grass.”
Gilliam’s attention to detail is evident in every aspect of his work. He favors cobblestone edgings, bluestone materials, and natural brick, and makes a point to re-edge beds at least twice a month. “It looks nice and sharp,” he says. “When you get your fresh cut line in the springtime and the edging’s nice — it’s like a nice fresh haircut.
Gilliam grew up learning the value of hands-on work from his father. As one of five boys, outdoor projects were a way of life. “In junior high school and high school, those were our chores,” he recalled. “And so we had a lot of projects to do. And then when I get out of school, I went to work for my dad.”
For Gilliam, the most rewarding part of the job is rolling up his sleeves alongside the crew. “There’s a lot of satisfaction that I take in working with my hands, tackling a task and getting it done,” he shared. “And when I can shift from the person who has to stand back and talk about it and get to be a small part of the people who do it — that’s what I enjoy the most.” At home, he’s passed that love of projects on to his kids, building everything from a tree house to a zip line in the backyard.
Gilliam is excited to join the This Old House team and looks forward to sharing his knowledge and expertise with viewers. He hopes to inspire people to get involved in landscaping and to make their properties more beautiful. Gilliam resides outside of Boston and has two sons and a daughter.
Gilliam brings a deep respect for both tradition and innovation to his work. “I was always taught that you pay attention to the way things were built years ago because they lasted for a long time and don’t be afraid to use something that’s new,” he said. “But don’t ever forget about the old ways.”

