Vintage homes for sale & real estate in Boothbay, ME

Vintage Home for sale in Boothbay, ME:

Cross over one of the few remaining swing bridges in Maine to enter into the charming community of Southport Island. Just a few minutes later, you'll arrive at 461 Hendricks Hill Road, a 1914 bungalow-style home perched on the hill above Cozy Harbor. This home, originally built as the parsonage to the local Methodist Church, is conveniently located just minutes from the Hendricks Head beach and lighthouse and steps from the Southport General Store and Barn; also nearby is the Southport Yacht Club, and not far is the larger town of Boothbay Harbor with other Midcoast waterfront towns within an easy drive. With three bedrooms and one bath, this home is graced with period woodwork throughout a

Vintage Home for sale in Boothbay, ME:

Welcome to the heart of Boothbay Harbor! This beautifully renovated 3-bedroom New Englander perfectly blends timeless charm with modern comfort. Set on a corner lot with gorgeous landscaping, this home offers water views and an unbeatable in-town location—just a short stroll to shops, restaurants, and the harbor. Inside, you'll find thoughtfully preserved period details paired with tasteful updates, including a beautifully renovated kitchen, energy-efficient spray foam insulation, a modern solar system, and a cozy woodstove for extra warmth during colder months. With its prime location and blend of comfort and efficiency, this property would make an excellent primary home, seasonal re

Vintage Home for sale in Boothbay, ME:

Being offered individually or together, 43 Oak Street and 66 Townsend Avenue represent a unique opportunity to own multi-family properties in downtown Boothbay Harbor. With road frontage on both Oak Street and Townsend Avenue, owners have the option of keeping each property distinctly separate, or borrowing from each other to maximize utility and value. All units have been recently updated and improved, and boast excellent reviews on short-term rental sites.

Vintage Home for sale in Boothbay, ME:

A rare chance to own a piece of waterfront on Southport's renowned Cape Newagen Harbor. This inviting cottage is all about the views, with windows lining the walls to bring the harbor, the Cuckolds Lighthouse, and open ocean right into your living space. The open floor plan makes it easy to relax with family or gather with friends. Upstairs, the bedrooms capture sweeping harbor views and beyond and each room opens onto their own outdoor spaces allowing for additional space to relax and take in the surrounding views. The detached garage includes a finished living space above—an ideal spot for guests, a quiet studio, or a cozy hideaway. Equipped with an additional full bathroom, use of

Vintage Home for sale in Boothbay, ME:

Escape to this charming Midcoast Maine cottage nestled along the banks of the beautiful Sheepscot River. It's the perfect place to slow down and savor the area's natural coastal beauty and abundant wildlife. Enjoy your morning coffee on the screened-in porch as you watch lobstermen haul their catch. Whether you're seeking a seasonal retreat or, with a little work, a year-round haven, this property is a true riverside gem.

Vintage Home for sale in Boothbay, ME:

Boothbay Harbor's first gas-lit home, this 1880s Victorian 3-unit has been freshly renovated and enjoyed by vacationers as a short-term rental. The ''Captain's Quarters'' features two bedrooms, one-and-a-half baths, and is loaded with period charm, such as its stunning tin ceilings, leaded glass windows, and an original gas-lit finial. The building's ell, ''First Mate'', is a two story unit with two bedrooms, one bath, and extensive decking. The main house's second and third floors comprise a to-be-finished third unit, with two bedrooms and one bath on the second floor, and extensive, partially finished space on the third floor, including a fun space in the cupola, above it all! All units h