In 2020, Caroline Keefe moved back to Camden, her hometown, after a stint in Southern Maine and was feeling adrift. But one phone call from a former co-worker changed everything.
“I was in a bad place in my life at the time, and when she asked how I was doing. I said, ‘You know, not that great,’ said Keefe, who was studying remotely for her degree in anthropology at the University of Southern Maine at the time. “And she was like, ‘Well, I’ve got this demolition job. If you want to blow off some steam and make some money.’ It felt like divine intervention.”
Today, Keefe is the owner of Painted Lady Home & Garden, a one-woman landscaping and interior/exterior painting business she launched in the summer of 2025. But her introduction to the trades came from that phone call, which was made by Sunshine Stewart.
“She called me by accident,” Keefe said, “she meant to call a different Caroline!”
Stewart, a contractor who was killed last summer in an alleged homicide on Hundred Acre Island in Union, took Keefe under her wing. That first job was tearing down a shed in Port Clyde — no easy task for Keefe, who had never swung a hammer before and who, at the time, described herself as “a toothpick.”
“We worked together that day, and then every single day following,” Keefe said. “She was a strong woman and a badass, and I did not want to make a fool of myself. I somehow got through that first day, and at the end of it, I felt like superwoman, just alive and turned on, and there was this sense of calm in my nervous system that I hadn’t felt in such a long time. I knew right then and there I was going to keep working with her and learn everything she had to teach me.”
For the next three years, Keefe was Stewart’s protege, learning everything from demolition to fine finish work while also finishing college.
“We refinished floors, we gutted houses, we got red squirrels under control,” Keefe said. “Whatever the call was, we did it. Sunny was so patient, and she had this belief in me that made me feel powerful and confident. And suddenly, I saw the pieces of my life start to come together.”
During that time, Keefe, who was minoring in studio art, began to envision a more concrete future for herself, one that combined her love of art with the practical skills she was learning under Stewart’s tutelage.
“I realized in my time working with Sunny, that painting was the thing that really turned me on. Growing up, I painted my bedroom obsessively and designed it nonstop. So, it felt natural to move in that direction.”
To expand her skills, Keefe took a job with a local painting company, where she deepened her knowledge of interior and exterior painting. But it was no longer just her and Stewart, and Keefe had her first experiences working mostly with men.
“The guys I worked with on the crew were lovely,” Keefe said, “but stuff happens, whether it’s with clients or with other contractors. There’s no dancing around the fact that there’s a lot of disrespect.”
Then, one beautiful summer day, stuck indoors working on a re-staining project, Keefe noticed an all-woman gardening crew at the same job site.
“I was stuck inside with these noxious fumes, and there were two or three women, working and laughing together and I was like, that’s what I want to be doing right now. The owner of the gardening company was also there, and I asked if they were hiring. That’s how I started working with Lee Schneller Fine Gardens.”
Keefe has worked for Lee Schneller, a Japanese-influenced landscaping business, for four summers now.
“They have a large client roster of really pristine gardens that have been well maintained for years,” she said.
Keefe and the crew at Lee Schneller spent a month last March in Kyoto, working on a crew, and studying Japanese gardens and carpentry.
“It very much inspires my work — carpentry there in general is in its own echelon. There are plenty of native Maine gardeners that have very strong philosophies about native species. And coming from the Japanese gardening lineage, that is all very important to me — as is the fact that I live and work in Maine. So, blending the two worlds is where I’m trying to find my sweet spot.”
Keefe began Painted Lady Home & Garden while still working with Stewart and the painting company. It felt like going out on her own was the best way for her to continue to advance in the trades. Stewart and Keefe had talked off and on for years about the possibility of starting a business, and in the summer of 2024 Keefe printed her first stack of business cards, though she didn’t send her first official invoice until the summer of 2025.
“Sunny’s big dream was that she wanted to see more women working with tools,” she said. “‘I’m so sick of being the only woman that knows how to do anything,’ she’d tell me.”
Keefe’s clients span from local families who live in the midcoast year-round, to wealthy, generational estates.
“I have people that are here two weeks out of the year,” Keefe said. “I have moms of people I grew up with here, too. I try to make sure that my services are accessible to a wide range of people.”
Her vision, as the company grows and evolves, is to eventually employ a crew of both young men and women.
“I want to be very clear in that it’s really important to have good young men, good men of all ages on job sites, too. You know, these are our colleagues,” she said. “I’m not trying to create a women-only world. Like men are an essential part of the equation, and it’s really important that we invite them into these spaces with us, so that they can, you know, learn and grow and show up and be better men.”
A former Rotary Club exchange student, Keefe often spends part of the Maine winter visiting her former host family in Brazil, where she focuses on her fine art painting and the novel she is writing, a project she hopes to finish in the next two years.
“I don’t really show my paintings and I don’t sell them either, though it’s something that I certainly have aspirations to do one day,” she said “But my art is really personal, and at this stage, that’s how it will remain.”
As her artistic pursuits evolve and transform, Keefe’s gardening work continues to evolve as well.
“There are choices I make that year where I’m like, oh my god, why did I pick this Chesapeake crab-like lily? It’s the most common, ugly lily. But you know, it’s how you grow as a gardener and as an artist. I reserve the right to change my mind and refine my style.”
Keefe’s time with Stewart continues to impact her work, and she hopes to continue helping other young women feel comfortable and capable in a male-dominated profession.
“I sit on the boards of the Tradeswomen of Maine, and the Sunshine Stewart Memorial Fund. Both nonprofits are aimed at creating opportunities for women,” Keefe said. “A huge focus of my life’s work is to continue to destigmatize this work, and advocate for women in the trades.”
This story appears through a media partnership with Midcoast Villager.