This story is part of the BDN’s Home Buying series that shares stories of Mainers who became homeowners despite the state’s volatile real estate market. Want to share your experience buying a home in Maine? Email kobrien@bangordailynews.com.
A 34-year-old who spent her adult life sailing around New England and the Caribbean has bought her first home in coastal Maine.
Originally from Cape Cod, Annie Kelly spent the past decade in Rhode Island after moving there for school. She bought a three-bedroom, one-bathroom cottage in St. George in August, ending a years-long search for a home base for her nomadic career.
For years she has worked as a boat captain in the charter and yachting industry, which means she travels for work and usually lives on whatever vessel she’s on rather than returning home at the end of each day.
“About three years ago I got tired of not having a mailing address or not knowing where to register my car,” Kelly said.
Kelly’s years-long housing search illustrates how overwhelming looking for a home to buy can be, especially for first-time home buyers with somewhat unconventional careers. Her experience also highlights how challenging it can be when a prospective buyer’s search spans multiple states.
“You can read about the process, but actually being in it is so different and I was really overwhelmed and confused for a lot of it,” Kelly said. “The learning curve you have to do to even understand what’s going on in the process was outrageous.”
She previously rented a small, one-bedroom apartment in Newport for $2,400 a month but otherwise kept most of her belongings, from furniture to souvenirs from her travels, in a storage unit.
“Over the last eight or nine years I didn’t pay rent anywhere, I would just bounce from boat to boat,” Kelly said. “I had a storage unit in Newport for a while that was like my house. I would go there, change out what’s in my duffel bag, then get on the next boat and go wherever the boat was going.”
While this career allowed her to save money for a down payment, as she didn’t pay for housing or food while on board, she lacked a place to call home, she said.
Kelly began looking for a home roughly two years ago. She didn’t look exclusively in Maine at first, but dreamed of living along coastal Maine since 2019 when she began visiting the state during summer sailing expeditions.
“Maine is stunning, beautiful and feels very far away from everything, almost like a retreat,” Kelly said. “It felt like a mythical, magical place and we were always sad to leave.”
However, Kelly wondered if Maine winters would be too dark and cold for her to bear, and whether the midcoast region she loved would be too far from Massachusetts and Rhode Island, where most of her jobs were based.
To test this, Kelly spent last winter in Rockport, where she managed projects on a client’s boat while it was in storage. This was a stark contrast to the many winters Kelly spent on sailing trips to the Caribbean, she said.
At that point, Kelly had looked for a home in Massachusetts or Rhode Island for roughly a year, but shifted her house hunt to Maine in October 2025. She lived in an apartment in Warren that a friend owned while touring at least 20 houses in Maine, she said.
“Before being in Maine, I probably looked at 80 to 100 houses,” Kelly said.
When comparing the housing markets of southern New England and Maine, Kelly said she noticed far fewer open houses in Maine and the buying process in Maine moved slower. However, Kelly’s money stretched farther in Maine than elsewhere, which allowed her to buy more with less.
She wanted a home with at least two bedrooms and a barn or garage while staying under her $350,000 maximum budget, Kelly said. Ideally, Kelly wanted a home within a 30-minute drive to Camden or Rockland and had a preference for older homes with “spooky basements.”
“In my mind, if they’ve been here for 100 years, they’re going to be here for 100 more,” Kelly said. “I think it’s a sign of a good, strong house.”
She found her 1,200-square-foot home this past summer and was drawn to the house’s large backyard and age, as it was built in 1918. The three-bedroom, one-bathroom home sits on 3.5 acres with a barn and spacious back deck.
“It’s the right amount of updated without being flipped,” Kelly said. “As soon as I walked in I knew it was the right one for me.”
The home is also close to the town’s dock and is roughly 20 minutes from downtown Rockland.
Kelly’s $290,000 offer, submitted in July, was accepted and she closed on Aug. 31.
The lower monthly payments allow Kelly to save for larger projects that will be needed in the coming years, such as a new roof. But, Kelly noted she had to spend at least $2,000 on a series of inspections due to the house’s age.
“The biggest relief for me is just having somewhere to be based,” Kelly said. “It’s really nice to just have somewhere to have all my things and to come home in between trips.”
With a place to call home, Kelly said she’s looking forward to advancing her captaining career in a state with a “thriving working waterfront” and “rich history of boatbuilding.”
“Anywhere I’ve sailed into Maine, everyone has been welcoming and lovely,” Kelly said. “It felt like a wholesome place to be where I can come as a young person and continue building a career.”