18 Back Shore Road, Chebeague Island.

18 Back Shore Road, Chebeague Island — $825,000
4 beds, 2 baths, 1,985 SF

High ceilings, hardwood floors, and heavy-duty original cabinetry fill this circa 1905 home that’s a 10-minute walk to the Chebeague Transportation Company landing that goes to Cousins Island, or a 10-minute drive to the Casco Bay Lines landing to Portland. Seasonal guest quarters with two more bedrooms and a sun porch are in the attached barn. The 2.5± acre property includes a chicken coop, gazebo, and outdoor shower. Follow paths right to some of the island’s beautiful beaches. Listed by Carrie Martine, Legacy Properties | Sotheby’s International Realty. See the full listing.

509 Main Street, East Machias.

509 Main Street, East Machias — $950,000
9 beds, 9 baths, 6,860 SF

Currently operating as The Talbot House Inn Bed & Breakfast with five ensuite guest rooms, this circa 1874 home had a big restoration in 2008 that preserved tin ceilings, marble fireplaces, maple floors with inlay, plaster medallions, and crown molding. It could be kept as a commercial business, converted to a single-family home, or perhaps be a bit of both. The home is on 3.46+ acres with a storage shed and 589± SF building used as a retail shop. Listed by Christy Kilton-Alley, Keller Williams Realty Greater Portland. See the full listing.

55 Sherman Street, Portland.

55 Sherman Street, Portland — $1.625 million
8 beds, 8 baths, 6,104 SF

This circa 1910 seven-unit in Portland’s Parkside neighborhood by Deering Oaks has been owner-occupied for two decades, and according to the listing, it’s been “maintained with care” during that time. Unit 1—the seller’s unit—has two bedrooms and two bathrooms, and the rest of the units are one bedrooms or studios. All units are occupied except the seller’s unit and a recently renovated second-floor unit, which looks like it got fresh paint, floors, cabinets, and new appliances. Listed by Katherine Murray, Coldwell Banker Realty. See the full listing.