Courtesy: Tim Dunham Realty
207-729-7297
Prime downtown Boothbay Harbor (between Captain Sawyer's B&B and Ports of Italy Restaurant) with ocean/harbor views from multiple vantage points, on-site parking, and excellent foot/vehicle traffic. The classic New Englander (approx. 2,900± SF) is now configured entirely for lodging—with the former street-level retail/antique space converted into a 5th short-term rental—plus two upper apartments; a detached Carriage House adds ~1,000± SF with 2 bedrooms/1 bath, for ~4,400± SF total across both buildings. In 2025, three of the five VRBO-style guest spaces were operated as short-term rentals, producing ~$70,000 in rental income. Substantial improvements since the 2022 purchase position this as a flexible live-work or investment opportunity—owner-occupied lodging, boutique hospitality, or an expanded STR portfolio. Enjoy year-round harbor living steps to shops and dining, with captivating water views, versatile layouts, and valuable in-town parking.
Courtesy: Tindal & Callahan Real Estate
207-633-6711
An in-town gem, this luxurious two-unit property has been recently renovated with high quality finishes, systems, and all attention paid to its owned frontage on Boothbay Harbor. Each unit has two ensuite bedrooms, open concept living, extensive decking, air conditioning, and off-street, paved parking. Enjoy an easy stroll to downtown restaurants, shops, and activities, and retreat home to satisfying living spaces and a private waterfront lawn. A turn-key offering, this property needs nothing and is ready for your vision and enjoyment.
Courtesy: Harbor Realty
207-633-4803
Enjoy water views of Boothbay Harbor from this beautifully renovated duplex, ideally located just steps away from the historic footbridge and with easy reach of local shops, restaurants, yacht clubs and the country club. The first floor apartment, the only unit that has been used as a rental, has 2 bedrooms and a 1 bath, featuring comfortable living spaces and harbor views. The second unit spans two levels with 3 bedrooms and 1 bath and has been exclusively used for extended family but additional rental income or owner occupancy are great options for this large space. Thoughtfully updated over the past 10 years, this property blends modern conveniences with a classic coastal charm. Whether you are seeking an investment, a multigenerational living option, or a year round home in one of Maine's most beloved seaside communities, this is a great opportunity.
Courtesy: Tindal & Callahan Real Estate
207-633-6711
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.
Courtesy: Tindal & Callahan Real Estate
207-633-6711
This versatile Boothbay Harbor property has been nicely renovated and used for short-term rentals. The main unit features two bedrooms, one bathroom, laundry, and open concept living. Next door is a 464sf+/- seasonal one bedroom, one-and-a-half bath guest efficiency, which has been rented separately or as an add-on to the main unit. Both units are in great shape, ready for immediate use or rental. Owners and guests enjoy nice touches, such as high-end window treatments, extensive decking, and easy access to downtown amenities. With nearly a half acre of land, this property has been additionally leveraged for parking revenue.
Courtesy: Tindal & Callahan Real Estate
207-633-6711
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 have a heat pump for air conditioning. Next door to Boothbay Harbor's historic Opera House, the property is walking distance to all downtown activities and attractions, and comes with ample off-street parking for residents and visitors.
Boothbay Harbor is located in Maine. Boothbay Harbor, Maine has a population of 2,073. Boothbay Harbor is less family-centric than the surrounding county with 18.18% of the households containing married families with children. The county average for households married with children is 23.29%.
The median household income in Boothbay Harbor, Maine is $57,917. The median household income for the surrounding county is $62,121 compared to the national median of $69,021. The median age of people living in Boothbay Harbor is 58.6 years.
The average high temperature in July is 77.7 degrees, with an average low temperature in January of 10.6 degrees. The average rainfall is approximately 48.2 inches per year, with 65.4 inches of snow per year.
