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$1,950,000

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.

6 Beds ⋅ 5 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.

$995,000

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.

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

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.

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.

$950,000

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.

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

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.

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.

$1,250,000

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.

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

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!!

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

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.

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

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.

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

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.

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.

$695,000

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.

$379,000

Located in the heart of Boothbay Harbor's downtown, this commercial building has excellent exposure with prime sidewalk frontage along Mckown Street and an easy stroll to the waterfront and parking. Explore this rarely available opportunity to own a piece of commercial downtown and create your own business opportunity. Currently this is home to a retail shop with approximately 735 sq. ft. on one floor. Town water and sewer make many options available for use- at one time this was a successful pastry shop. If you have ever dreamed of your own gallery or business, this is a wonderful opportunity to create one.

10 Mckown St, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

$895,000

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.

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.

$395,000

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.