Boothbay Harbor ME Real Estate, Homes for Sale

The Chimes House, believed to be a design by Gustav Stickley during the American Arts and Crafts Movement, is a distinctive Staley year-round cottage that reflects the timeless appeal of early twentieth-century craftsmanship. One of the era's celebrated homes, it embodies Stickley's philosophy of simplicity, exceptional quality, and harmony with the natural surroundings. Designed with open floor plans and family-friendly living spaces, the home features original built-in benches, cabinetry, and bookcases. Many historic details remain intact, including the original light fixtures and hardwood floors that complement this four-bedroom, two-and-one- half-bath residence. The property enjoys stunning long-water views across Townsend Gut, with seasonal winter views extending farther up the Gut. Residents enjoy access to a deeded association dock, providing convenient boating access to Boothbay Harbor and beyond. Thoughtfully updated while preserving its historic character, the home was relocated to its present site and now rests on a new foundation with steel beams. Recent improvements include updated electrical systems, a new fire and security system, a new four-bedroom septic system, new roofs on both the house and garage, a new cedar fence, fourteen new windows, and a complete exterior repaint. Additional features include an oversized basement and garage, an expansive classic wraparound porch, and a massive entertainment deck adjoining the kitchen and dining areas. Located within the Chimes Association in the highly sought-after West Boothbay Harbor area, the property offers quick access by boat to Boothbay Harbor and all that Maine's coast has to offer during the summer season.

1 Chimes Ln, Boothbay Harbor

Listing courtesy of Benchmark Real Estate.

$189,000

4 Beds ⋅ 2 Baths

A work in progress, this 1994 manufactured double-wide home with 2005 stick-built addition is being offered ''as-is'', and presents new owners with opportunity to tailor its ultimate fit and finish. Located less than a mile from downtown Boothbay Harbor, the property is convenient to amenities, yet tucked away on a quiet side street. Its relationship to Mill Cove encourages southerly sea breezes up Williams Street and through the home, and there are distant peeks of Mill Cove and Boothbay Harbor, beyond. Current owners have used the property seasonally, as a home base for their RV, with nearby access to the waterfront for sailing and other marine recreation. 24-hour notice is required for showings.

34 Williams St, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$495,000

2 Beds ⋅ 1 Baths

Spend your summer in this 2 bedroom cottage with a private dock on Appalachee Pond in Boothbay Harbor. Situated on .15 +/- of an acre with 50' of frontage on the pond. Steps away from the beach to enjoy swimming or just watching the activity. There is also a common dock on Linekin Bay for access to boating, sailing or swimming in the ocean. Appalachee is a quiet community that is located on a dead-end road. Not far from the east side of the harbor and downtown amenities.

114 Appalachee Rd, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$1,950,000

6 Beds ⋅ 6 Baths

Set on more than three protected acres just steps from the Boothbay Harbor Yacht Club, this 4,900-square-foot home pairs its 1845 origin with the 1990 expansion designed by local architect Walter Hill- retaining the former farm's coastal Maine character. A granite wall and mature plantings screen the front porch from street noise, setting a tone of calm and privacy from the moment you arrive. Conifers, flowering trees, shrubs, and ground covers frame water views toward Boothbay Harbor and out to Fisherman's Island. Inside, the original 1845 home and the 1990 addition flow seamlessly together. A first-floor bedroom suite offers single-level living, while the primary suite occupies its own wing upstairs. Two full baths and a half bath serve the main level; upstairs are three more baths. A large, screened sunroom opens to a backyard deck overlooking the extensive lawn island gardens. Climb to the widow's walk for a sweeping vantage out to sea. A detached 1868 barn provides versatile space for storage, a studio, a workshop, or garage. The attached 1845 barn is a typical Maine artifact, full of antique (surely unsafe) ladders and early farm implements. Location is everything here: walk to town or simply step next door to the Yacht Club for tennis, sailing lessons, moorings, launch service, dining, and a full calendar of member activities. Boothbay Harbor's amenities are minutes away, including a nearby Urgent Care facility. The home has year-round town water and sewer. Truly, a once-in-a-generation offering for buyers seeking history, privacy, and true harbor-town living.

133 Western Ave, Boothbay Harbor

Listing courtesy of Legacy Properties Sotheby's International Realty.

$986,000

5 Beds ⋅ 5 Baths

Own a signature piece of Boothbay Harbor--an iconic 1920 building in the very heart of downtown with approximately 5000 square feet offers 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. • Three distinct units: street-level retail plus two high-end office suites • Zoning flexibility supports multiple commercial and residential uses • Recent upgrades include roof, boiler, hot-water heater, windows, and interior layout/design improvements • Harbor views from the second floor • Light-filled interiors with large windows throughout • Sprinklered building for added 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.

$595,000

3 Beds ⋅ 3 Baths

Nestled in the desirable Lobster Cove neighborhood of Boothbay Harbor, this beautifully maintained Gambrel-style home was thoughtfully crafted by a local boat builder, showcasing exceptional quality and timeless craftsmanship. Rich wood trim, exposed beams, and custom wood detailing throughout create a warm, inviting atmosphere. Filled with natural light, the home features an open-concept layout designed for comfortable everyday living and entertaining. The spacious eat-in kitchen flows effortlessly to a large deck complete with a hot tub, providing the perfect space to relax or host family and friends while enjoying the peaceful surroundings. Combining quality construction, coastal charm, and modern comfort, this exceptional home offers a rare opportunity to enjoy the best of Boothbay Harbor living.

6 Abenaki Rd, Boothbay Harbor

Listing courtesy of Brookewood Realty.

$775,000

5 Beds ⋅ 3 Baths

Step into the best of coastal New England living in this beautifully updated in-town Boothbay Harbor home. Set on a quiet, tree-lined residential street, this 5-bedroom, 3-bath property offers a highly walkable lifestyle, just a short stroll to the harbor, downtown shops, restaurants, and waterfront attractions, with Farm 23 Bakery and Hannaford conveniently nearby. Filled with natural light, the home features original woodwork, hardwood floors through much of the home, timeless character, and extensive modern updates. The chef's kitchen was completely redesigned and expanded in 2026 with a 6-burner Thor gas range, farmhouse sink, LG Energy Star dishwasher, LG refrigerator, walk-in pantry, and bar counter open to the family room. A first-floor full bath offers flexibility for guests or one-level living, while the oversized mudroom with laundry adds everyday function. Major improvements include a complete roof replacement with new plywood sheathing and ridge caps, restored front porch, freshly painted exterior, window upgrades, and extensive interior renovations. Bright third-floor attic space with oversized dormers offers future potential for a primary suite, office, studio, or bonus space. Public water and sewer. Detached shed. Proven Airbnb history with consistent 5-star guest reviews.

16 Eastern Ave, Boothbay Harbor

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

$475,000

1 Beds ⋅ 1 Baths

Located in the highly desirable Sprucewold Colony in Boothbay Harbor, this charming 1-bedroom ( a spacious sleeping loft), 1 bath cabin offers the perfect seasonal retreat. The expansive open floor plan and generous square footage provide the opportunity to easily converted into a two bedroom home if desired. Tastefully renovated, the inviting interior features whitwashed walls, an open concept living and dining area, and a bright , airy atmosphere that creates a warm and welcoming space to enjoy throughout the Spring, summer and fall seasons in the Boothbay Region. Situated on a large private lot with desirable westerly exposure, the property is the perfect place to relax and take in the beautiful sunset views. A detached one-car garage provides excellent space for parking, storage , or a workshop. Conveniently located just a short walk from Barrett's Park and downtown Boothbay Harbor, this property offers easy access to the restaurants, shops and all the attractions that make Boothbay Harbor one of Maine's most sought after coastal destinations.

87 Crest Ave, Boothbay Harbor

Listing courtesy of Harbor Realty.

$995,000

3 Beds ⋅ 4 Baths

Overlooking the harbor and marina, this rarely available Signal Point condominium is immaculate, move-in ready, and beautifully updated with custom finishes. Features include a marble kitchen, Wolf range, renovated bathrooms, gas fireplace, wood floors, and three bedrooms, each with an ensuite bath. The spacious ocean-side primary suite offers a luxurious bath and private harborside balcony with stunning water views. Enjoy the open first-floor layout, relax on the patio while watching boats and sunsets, and take advantage of the convenience of parking once and walking to town, shops, and dining.

52 Mcfarland Point Dr Unit 27, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$339,000

1 Beds ⋅ 1 Baths

This tasteful one-bedroom, one-bath condominium offers comfortable year-round living. Highlights include a beautifully renovated kitchen with granite countertops, wood floors throughout, a new hot water boiler, and town water and sewer. An additional overflow room is currently used as an office. Sold mostly furnished, the unit features patio doors that bring in abundant sunlight and harbor views. The seasonally awning-covered deck has southwest exposure, making it an inviting spot to relax and enjoy the scenery. This well-maintained six-unit complex also offers a shared waterfront tidal dock, ideal for kayaks or a dinghy, and is just a short walk from the footbridge, shops, and restaurants downtown.

15 Atlantic Ave Unit D, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$439,000

3 Beds ⋅ 2 Baths

This charming 1830's Cape features a delightful family room with a vaulted ceiling and plenty of windows letting in light, perfect for relaxing or entertaining. The cozy kitchen accesses the south facing deck overlooking the backyard. The remainder of the first floor includes a formal dining room, a primary bedroom and a bathroom. The second floor consists of two bedrooms and a bathroom, plus a den or office space with a back stairway leading to the kitchen. Property includes a spacious 2-car detached garage. Located close to town, it is perfect for year round living or a seasonal coastal retreat.

261 Ocean Point Rd, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$428,000

3 Beds ⋅ 2 Baths

Located only a few hundred yards from the shore of Boothbay Harbor, and with beaming southerly orientation, this 0.93-acre property enjoys sunshine and cool ocean breezes. The early 1900s home has received significant improvements during current ownership, including a new roof & copper gutters, high-efficiency furnace & ductwork, hardwood floors, exterior curtain drains, and an 8' extension of the ell, where the ground-floor bedroom features a roughed-in area for an en-suite bathroom. On a quiet dead-end road, the neighborhood offers quiet walks along West Harbor Pond and a one-mile walk to village attractions. Fundamentally improved, this charming property is well-suited for seasonal or year-round use in a convenient location.

15 Lakeview Rd, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$950,000

6 Baths

A great opportunity for rental income to help pay your mortgage. This combined waterfront property totals 3,384 sq. feet, with each unit offering 3 bedrooms and 2 ½ baths. The interior layout of each unit features an eat-in kitchen, a dining area that opens to the living room. From the living room, you can access a waterside deck and a primary bedroom with a bath. The second floor includes two bedrooms and a bath. For convenience, each unit also includes an attached 1-car garage. Situated on approximately .79 acres, the property features 89' of frontage on the eastern shore of West Harbor Pond. The westerly orientation is perfect for enjoying sunsets over the water from the large deck or private dock. West Harbor Pond offers abundant wildlife and seasonal activities including kayaking, canoeing, fishing, and swimming in the summer, as well as skating and skiing in the winter. This location is close to downtown Boothbay Harbor or a short walk to West Boothbay Harbor.

12 & 14 Maddocks Rd, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$950,000

6 Beds ⋅ 6 Baths

A great opportunity for rental income to help pay your mortgage. This combined waterfront property totals 3,384 sq. feet, with each unit offering 3 bedrooms and 2 ½ baths. The interior layout of each unit features an eat-in kitchen, a dining area that opens to the living room. From the living room, you can access a waterside deck and a primary bedroom with a bath. The second floor includes two bedrooms and a bath. For convenience, each unit also includes an attached 1-car garage. Situated on approximately .79 acres, the property features 89' of frontage on the eastern shore of West Harbor Pond. The westerly orientation is perfect for enjoying sunsets over the water from the large deck or private dock. West Harbor Pond offers abundant wildlife and seasonal activities including kayaking, canoeing, fishing, and swimming in the summer, as well as skating and skiing in the winter. This location is close to downtown Boothbay Harbor or a short walk to West Boothbay Harbor.

12 & 14 Maddocks Rd, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$550,000

4 Beds ⋅ 2 Baths

Elevated views of Meadow Brook and woods with much of the surrounding lands conserved by The Boothbay Region Land Trust. Only minutes away from the sights, restaurants and summer fun of in-town Boothbay Harbor. This open concept raised ranch is spacious with vaulted ceilings, wood & tile floors. There is a first level primary bedroom with ensuite bath. The exercise room could be converted to a fourth bedroom. There is a 4 bedroom septic system. There is a wrap around deck to take in the views. A 6 person hot tub just outside the door is convenient for year round use. The floor plan lends itself to a potential of a separate first level unit (town approval required) This home has been overbuilt with extra insulation in the roof cap (R-80) and heavier 5/8'' fire rated sheetrock. Taxes most likely will be less as the assessment is for the entire parcel. A surveyed 1.2+/- acres come with the house.

1 Echo Lake Rd, Boothbay Harbor

Listing courtesy of NextHome Premier Realty.

$1,250,000

4 Beds ⋅ 3 Baths

Discover this exceptional waterfront home in Boothbay Harbor with its own private in-law apartment. Designed for effortless one-floor living, the main-level ranch features vaulted ceilings throughout, oversized windows and three sliding glass doors leading directly onto an expansive wraparound deck overlooking beautiful West Harbor Pond--the perfect setting for relaxing and entertaining with breathtaking views. Two bedrooms and two full bathrooms, including a primary suite, provide comfort and convenience. The recently renovated ensuite bathroom is a true retreat with a deep soaking tub and an elegant tiled surround shower. The lower level boasts a fully independent in-law apartment with its own full kitchen, 2 bedrooms, 1 bathroom and laundry. Tall 5-foot windows fill the space with abundant natural light, creating a warm and welcoming atmosphere for guests or extended family. Set on 3.65 private acres with 240 feet of direct waterfront, this property includes a dock and kayak launch for easy water access. Meticulously maintained and complete with central air, this home is truly move-in ready, offering the perfect blend of comfort, privacy, and coastal Maine lifestyle.

236 Lakeside Dr, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$950,000

2 Beds ⋅ 2 Baths

Classic Maine waterfront cottage with breathtaking sunsets and sparkling ocean views. This beautiful setting offers 2 cottages on the water! The main cottage is bright and airy with a great room and master bedroom. The guest house is perched at the edge of the pier and offers sleeping for four more guests. Both have exceptional views for the quintessential Maine waterfront getaway! This retreat features an expansive south-facing deck perched directly over the water, offering front-row seats to passing tall ships and ever-changing harbor scenery. Launch from your private dock and explore the harbor, cruise through Townsend Gut, or venture onto the Sheepscot River and beyond. Thoughtfully renovated in 2021, this turnkey property is being offered fully furnished, providing an effortless opportunity to enjoy the very best of Maine waterfront living. Come stand on the deck, soak in the salt air and the view, you won't want to leave!!

78 West St, Boothbay Harbor

Listing courtesy of Vitalius Real Estate Group.

$1,050,000

2 Beds ⋅ 2 Baths

Experience the charm of a classic Maine waterfront cottage, where breathtaking sunsets and shimmering coastal views create an unforgettable setting. This beautifully updated two-bedroom retreat features an expansive south-facing deck perched directly over the water, offering front-row seats to passing tall ships and ever-changing harbor scenery. Launch from your private dock and explore the harbor, cruise through Townsend Gut, or venture onto the Sheepscot River and beyond. Nestled within a protected cove, enhanced by lush landscaping, vibrant gardens, and a secluded private beach that create your own peaceful coastal oasis. Thoughtfully renovated in 2021, this turnkey property is being offered fully furnished, providing an effortless opportunity to enjoy the very best of Maine waterfront living.

76 West St, Boothbay Harbor

Listing courtesy of Vitalius Real Estate Group.

$1,995,000

5 Baths

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.

63 Townsend Ave, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$1,995,000

4 Beds ⋅ 5 Baths

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.

63 Townsend Ave, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$565,000

3 Beds ⋅ 3 Baths

This Boothbay Harbor condominium, featuring two to three bedrooms and 2.5 bathrooms, has undergone a series of impressive upgrades, including quartz countertops in the kitchen, stainless steel appliances, custom cabinetry, and modern fixtures in all bathrooms. The unit comes with quality living room furniture, bedroom sets, and kitchen essentials, making it truly move-in ready for new owners. Enjoy breathtaking harbor views and spectacular sunsets from your private deck. Just minutes from the footbridge, you'll have easy access to Boothbay Harbor's renowned restaurants and shops. In addition, a swimming pool nestled behind the complex offers a perfect retreat to cool off on hot days or relax in a quiet, private setting. The kitchen and bathrooms have all been updated with premium materials, and new windows have been installed throughout. The finished basement provides flexible space, doubling as a third bedroom or den. A dedicated laundry room and workshop offer excellent storage options and a convenient space for hobbies. This well-maintained condominium is truly worth exploring.

96 Atlantic Ave Unit C4, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$769,000

3 Beds ⋅ 3 Baths

Supremely private 3BR/3BA home in the Mill Cove area of Boothbay Harbor, part of the Mill Cove Landing Association. The 2,380 sq ft house features a bedroom and bathroom on each floor, open concept living, central air conditioning for the top two floors. A bonus room can be used as a library, art studio, media room, office, and more. Many fine finishes, including main level wood flooring, custom crown molding, Hunter Douglas window treatments, and plantation shutters by Norman. Other amenities include a direct-entry garage, extensive closet space, recent stainless appliances, and a 24kW Generac whole-house generator with a custom sound-blocking enclosure. The home has a beautiful gas fireplace in the living room with decorative molding. The oversized L-shaped deck is perfectly positioned to capture prevailing sea breezes, and it overlooks gardens and the marsh at Penny Lake, ensuring privacy behind you on conserved lands. A low quarterly condo fee includes mowing, snow removal, road and common ground maintenance, and a reserve fund. For boaters, this house is minutes, by foot or car, to several marinas and the Boothbay Harbor Yacht Club. Within a well-kept community, this is a spacious and private retreat for the summer season, holidays, or all year round, and just steps from the Harbor! Furnishings negotiable.

30 Village Court, Unit 36, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$695,000

3 Beds ⋅ 1 Baths

One of Boothbay Harbor's most iconic commercial spaces is available for the first time since the 1950s. At 34 Townsend Avenue, the property formerly housed the stalwart ''Village Store'' retail business, which attracted walk-in and local patronage in the heart of downtown Boothbay Harbor. With classic style, an attractive 0.35-acre lot, and abundant pedestrian traffic, this property makes a great foundation for one of the many allowed uses in the Downtown Business district.

34 Townsend Ave, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$365,000

2 Beds ⋅ 1 Baths

Charming intown log home set on a level half acre lot. This home features two comfortable bedrooms and a full bath which offers a cozy yet functional layout. A bright sunroom provides the perfect spot to relax and enjoy natural light year-round. With its rustic character and convenient location close to downtown Boothbay Harbor, this home is an ideal blend of charm and accessibility.

11 Warren Ln, Boothbay Harbor

Listing courtesy of Harbor Realty.

$624,900

3 Beds ⋅ 2 Baths

Perfect setting! Quiet, get away from it all! Walk 10 minutes to the harbor, shopping, restaurants, boat rides and more! Come back home to water views from almost every room! Pull in to your garage and directly enter the big finished open space that can be used in multiple ways. Need and office? Want a family room? How about extra space for guests? Ready for your choices. The unit is appointed with 3 good size bedrooms with oversized closets, 2 full baths , each with double sinks and linen storage. Open concept kitchen and living room allows great space for relaxing and more than enough room for entertaining! Updated kitchen with newer stainless appliances, granite counters, hardwood flooring . Newer slider to big back deck viewing peaceful rock garden area. Plenty of room for outside furniture and plantings. The kitchen center island is perfect for putting out treats, having a little lunch or a quiet cup of coffee. Dining area allows lots of room for oversized table and extra chairs. Large living room plus a newer bow window that looks out directly at Mill Cove waterfront. Step out to the front deck and enjoy private space with even deeper ocean views. Main bedroom with private access to full bath and large closet, is tucked away just steps from the kitchen. 2 additional large bedrooms with views and a second full bath on 3rd level complete this thoughtful floor plan. Good, solid Condo Association in place. New pavement in 2025. Annual fee 4000 per unit , per year. Come for a day - stay for a lifetime!

15 Village Ct Unit 5, Boothbay Harbor

Listing courtesy of Moore-Tuttle & Co. LLC.

$849,000

7 Baths

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

$895,000

3 Beds ⋅ 3 Baths

Perched above the shores of iconic Linekin Bay, this three-season Maine-coast escape delivers stunning views of Fish Hawk island, refreshing sea breezes, and prime deepwater dockage for boaters. Ideal for entertaining, the house offers open concept living, high ceilings, big water views, and outdoor spaces that include a screened porch, decks & balcony, and a charming, waterside cabin. Bedrooms on the lower level are private and cool, including an ensuite primary bedroom overlooking the bay. The waterfront cabin is a dreamy work-from-home setting, with privacy, water & electric, and easy boating breaks to level the mind. The best of both worlds, the property's membership in the Appalachee community comes with access to a freshwater beach, in addition to its owned ocean frontage. Renowned for its boating appeal, and especially for sailors, Linekin Bay delivers steady breezes, excellent fishing, and some of the region's warmest waters for swimming. Tucked away on a private road, yet just one mile to Boothbay Harbor's footbridge and downtown amenities.

127 Appalachee Rd, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$1,375,000

4 Beds ⋅ 3 Baths

This unique property is being offered for sale to the public for the first time in 100 years. The first floor of this prime commercial location has housed a successful retail craft store for 50 years. The space is fully equipped with hardwood and glass display units. And it has storage, receiving and packaging areas. It offers a great opportunity. The second and top floor have been completely renovated to create a home with 4 bedrooms, 2 full baths and a laundry room. Or two, 2 level apartments. All levels of this in town building have spectacular panoramic water views of Boothbay Harbor, the inner harbor and out to the ocean and Cuckold's Light.

37 Townsend Ave, Boothbay Harbor

Listing courtesy of Harbor Realty.

$1,100,000

3 Beds ⋅ 3 Baths

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.

$849,000

9 Beds ⋅ 6 Baths

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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