If you’re looking to buy a business on Main Street in coastal Maine, you have plenty of options.
Many are historic buildings that include ground-floor businesses with residences above or behind them, often overlooking the waterfronts that were once economic drivers in larger downtowns. Some have been on the market for months.
Entering the county in Bucksport, the former home of the Bucksport Enterprise newspaper at 105 Main St., overlooking the Penobscot River, is for sale for $275,000. Mixed-use zoning on the street means it can be used commercially, as a residence or both, according to the listing. The 1832 Cape Cod-style building has 13 rooms, including three bedrooms.
Nearby, a brick professional building from 1860 at 151 Main St. is for sale for $319,000. Four offices are occupied on the first floor, and the second and third floors could add another 1,500 square feet of space with a full renovation after being untouched for “many years,” according to the listing.
Farther south, two commercial properties are for sale in downtown Castine.

Built in 1765, 3 Main St. can be had for $1.495 million. The 5,000 square foot building is home to three established businesses — a restaurant and variety store, a bookstore with a coffee shop inside and an art gallery. It also includes four apartments on the top two floors, according to the listing.
Just up the road, a multi-use building at 15 Main St. that’s home to a retail store on the first floor and a vinyl record shop on the second is listed for $649,000. The 1850 building could be used for a combination of a home and a business or just become a residence, according to the listing. It comes with three bedrooms and two full baths in the main house, with a 1-bedroom apartment in the back.
In Blue Hill, a restaurant with an upstairs apartment is for sale at 40 Main St. for $1.2 million. It was mostly recently home to Sandy’s Blue Hill Cafe until the owners retired within the last year, according to the business’ Facebook page. The 1796 building was renovated for $800,000 in 2018. It includes a kitchen, bar, patio and dining room and is being sold with equipment included and some seller financing available.
Down on Stonington’s Main Street, another former restaurant with upstairs apartments is for sale for more than a million dollars. Most recently home to Crybabies restaurant, 36 Main St. is listed for just under $1.2 million. The 8,000 square foot building with views of the water includes five apartments ranging from one to three bedrooms and restaurant space on the first floor. It was built in 1890.

In Surry, the Pugnuts ice cream shop in the village — including the ice cream and gelato business — is for sale for $1.1 million. The listing includes the shop, an apartment above it, a small former post office building and a 1900 farmhouse behind it with more than 2,000 square feet of living space
Approaching the other side of the county, historic Main Street structures for sale in Ellsworth include two in an 1837 group called the Peters Block at the corner of Main and State streets along the Union River. The four-story buildings span 9,425 square feet and are joined by a shared wall. They’re listed for $925,000.
The corner building was recently home to Serendib restaurant on the ground floor, which closed earlier this year. Additional floors include office space and storage areas. The State Street building also includes office space with tin walls and, on the third floor, an original ballroom with a domed tin ceiling.
Up the street at 108 Main, a 1932 brick building includes retail space on the ground floor and apartment upstairs for $998,000.


