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$1,100,000
3 Beds ⋅ 3 Baths ⋅ 1654210 MLS
This historic property was formerly the Green Shutters Inn and now includes a completely renovated New England style home with 3 bedrooms and 2.5 baths. Additionally, there are 4 seasonal cabins that provide rental income or a fun spot for family or friends. The home was rebuilt in 2013 from the foundation up, keeping many old features like the classic wood shingled siding, a spacious south facing porch to enjoy all day long and an incredible screened porch for more privacy on the back- all with composite decking. Birch floors throughout with a great room with high ceilings and many windows with lots of light, is a perfect gathering place all year. Double glass doors lead to the outside to the cabins but you can create a patio area that is private and quiet. Private well and quasi public sewer. Located within walking distance to Boothbay Harbor and Barrett's Park this location is private but convenient. Sited on 1.25 acres with potential to divide or keep as is to enjoy the unique setting in Boothbay Harbor.

74 & 76 Bay St, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$395,000
1645874 MLS
Once a community schoolhouse, this 1880s building exudes historical character and charm. Located in downtown Boothbay Harbor, the property has been used as a place of worship since the 1960s. Each floor features a large hall, two half bathrooms, and ancillary office or meeting rooms. The spaces are flooded with natural light, with large banks of windows along the south side. Downtown Business zoning, public water and sewer, and high visibility add to the appeal.

25 Oak St, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$986,000
1659741 MLS
Own a signature piece of Boothbay Harbor--an iconic 1920 building in the very heart of downtown with approximately 5,500 square feet, offering exceptional exposure and flexibility for a variety of commercial and residential possibilities. Thoughtfully improved and meticulously maintained, this property is positioned to perform today and inspire what's next for the future. Presently the building has 3 distinct rental units with street level retail and two high-end office spaces. Present zoning supports multiple commercial and residential uses. Recent upgrades include roof, boiler, hot-water heater, air conditioning, window upgrades, interior layout and design improvements. The ''Our Port'' office space comes furnished and turn key. The building is already equipped with sprinklers for peace of mind. Whether you're looking for a flagship storefront, an elevated office presence, or a mixed-use opportunity in one of Maine's most beloved coastal destinations, this downtown cornerstone delivers. Schedule your private showing and explore the potential of this remarkable property.

4 Townsend Ave, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$849,000
9 Beds ⋅ 6 Baths ⋅ 1640418 MLS
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.

53 Commercial St, Boothbay Harbor

Listing courtesy of Tim Dunham Realty. 207-729-7297

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