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4 Crooked Pine Rd, Boothbay Harbor
$525,000
2 Beds ⋅ 1 Baths ⋅ 1683458 MLS
Nestled within the desirable Sprucewold community, this charming seasonal cottage offers an inviting retreat just moments from the sparkling waters of Linekin Bay. Fully furnished and move-in ready, the 2-bedroom, 1-bath home blends classic rustic charm with relaxed coastal comfort. The welcoming living room features a beautiful stone fireplace, creating the perfect gathering space for cozy evenings, while the covered porch invites you to unwind and enjoy the peaceful surroundings. The nearby Crooked Pine dock offers convenient deep-water access—ideal for embracing the best of Maine's waterfront lifestyle. The property has an established history of successful rentals, offering added value for those seeking income potential. Just minutes from downtown Boothbay Harbor, you'll be close to charming shops, restaurants, galleries, and year-round events, with scenic Barrett's Park just down the road. Whether you're seeking a summer getaway, a place to create cherished family memories, or your own slice of the Maine coast, this delightful Sprucewold cottage is ready to welcome you.

4 Crooked Pine Rd, Boothbay Harbor

Listing courtesy of Newcastle Realty. 207-633-4433

160 Western Ave Unit Unit : #5C, Boothbay Harbor
$720,000
2 Beds ⋅ 2 Baths ⋅ 1682200 MLS
Experience the beauty of coastal Maine living from this inviting two-bedroom, two-bathroom upper-level condominium, perfectly situated along the picturesque shores of Boothbay Harbor. Offering spectacular views of the harbor's bustling marine activity, colorful mooring field, and beautifully maintained waterfront grounds, this residence captures the very essence of life along Maine's beloved coast. Located adjacent to the Boothbay Harbor Yacht Club, the condominium offers an exceptional combination of waterfront enjoyment and convenient, low-maintenance living. The thoughtfully designed layout features a primary bedroom with a private ensuite bathroom, a second bedroom, and an additional full bathroom. Enjoy access to the condominium association's deepwater dock and beautifully landscaped grounds, where the sights and sounds of the harbor provide an ever-changing coastal backdrop. Just over a mile from downtown Boothbay Harbor, you'll discover wonderful restaurants, charming boutiques, galleries, and waterfront attractions. Whether spending an afternoon exploring the harbor, enjoying a leisurely stroll into town, or simply watching the boats come and go, this location offers a wonderful opportunity to embrace the coastal Maine lifestyle.

160 Western Ave Unit Unit : #5C, Boothbay Harbor

Listing courtesy of Engel & Volkers Casco Bay.

43 Crooked Pine Rd, Boothbay Harbor
$735,000
5 Beds ⋅ 2 Baths ⋅ 1681542 MLS
Step back into the timeless charm of a Maine summer at this inviting seasonal cabin in Sprucewold, one of Boothbay Harbor's beloved historic cottage communities. Overlooking beautiful Linekin Bay, this five-bedroom, two-bath retreat captures the spirit of summers spent gathered with family and friends, where days unfold at an easy pace and evenings are made for lingering. Classic cabin character shines throughout, with custom built-ins, a welcoming fieldstone fireplace and warm, thoughtfully appointed spaces. The updated kitchen and baths provide modern comfort while complementing the home's original Maine-camp charm. Tastefully furnished and ready to enjoy, the five-bedroom layout offers plenty of room for family and friends. Two decks extend the living space outdoors—perfect for morning coffee, afternoon cocktails, summer dinners and taking in the peaceful views over Linekin Bay. The surrounding woods and water create a setting that feels wonderfully removed from the everyday, while Boothbay Harbor's shops, restaurants, galleries and waterfront are just minutes away. There is something wonderfully nostalgic about Sprucewold—its winding roads, distinctive cottages, wooded setting and enduring sense of community evoke a simpler era of Maine summers. Whether gathering around the fieldstone fireplace after a day on the water, enjoying dinner on the deck or settling into one of the cozy built-in spaces with a good book, this is a place made for creating memories. A special opportunity to own a beautifully cared-for piece of classic Maine summer life in one of Boothbay Harbor's most cherished seasonal communities.

43 Crooked Pine Rd, Boothbay Harbor

Listing courtesy of Blue Lobster Real Estate.

11 Weeks Rd, Boothbay Harbor
$629,000
5 Beds ⋅ 2 Baths ⋅ 1681198 MLS
Classic Coastal Maine Cottage Near Downtown Boothbay Harbor. Step back in time with this classically maintained early 1900 coastal Maine cottage, offering five bedrooms and two full baths and a wonderful sense of old fashioned cottage living. The home retains many of its original details, including the charming covered front porch, much of its original woodwork, and beautiful wavy glass windows that reflect the character and craftsmanship of its era. Warm, inviting, and full of history, this cottage offers a rare opportunity to enjoy the timeless appeal of a classic Boothbay Harbor home while being close to everything the region has to offer. Located just a short walk to downtown Boothbay Harbor, Barrett's Park and Boothbay Region Land Trust Trails, the property is ideally situated for enjoying shops, restaurants, waterfront activities, parks and the Beauty of Boothbay Harbor.

11 Weeks Rd, Boothbay Harbor

Listing courtesy of Harbor Realty.

15 Atlantic Ave Unit C, Boothbay Harbor
$679,000
2 Beds ⋅ 2 Baths ⋅ 1680507 MLS
Enjoy spectacular views of the footbridge, harbor, and downtown from this beautifully appointed second-story condominium. Nearly every room captures the scenery, with the spacious deck offering an ideal spot to relax. Inside, the open and contemporary floor plan features wood floors, solid-surface countertops, vaulted ceilings, and a comfortable primary bedroom suite. Designed for easy living and effortless entertaining, this inviting condominium combines style, views, and an exceptional location. Common area has a dock for temporary boat docking or launching your kayaks. Take a short walk to all of the quaint town shops and restaurants. The unit comes fully furnished and has been tastefully decorated. No rentals are allowed.

15 Atlantic Ave Unit C, Boothbay Harbor

Listing courtesy of Pine Tree Realty of Maine.

41 Summit Rd, Boothbay Harbor
$579,000
5 Beds ⋅ 3 Baths ⋅ 1679894 MLS
This five-bedroom, two-and-a-half-bathroom home is available for year-round living and features numerous recent updates, including a rebuilt double-sided fireplace, modern appliances, a new furnace, two mini-split units, updated flooring, a whole-house generator, and updated windows. The main level includes a large kitchen with a dining area and fireplace, as well as an adjacent office or sewing room, and a spacious living room with a fireplace. The second floor features three bedrooms, while the third floor offers two additional bedrooms and a family room, providing ample space for family or guests. The property is situated on approximately 0.27 acres with town water and sewer service. It is located in close proximity to Barrett's Park, East Side amenities, and the footbridge.

41 Summit Rd, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

8 Highland Park Rd, Boothbay Harbor
$299,000
3 Beds ⋅ 2 Baths ⋅ 1679503 MLS
LOCATION, LOCATION, LOCATION! Here's an opportunity that's all about where you are—and what surrounds you. Set on a combined .98 acres in desirable Boothbay Harbor, this property abuts the beautiful Lobster Cove Meadow Preserve, offering a remarkable natural backdrop just minutes from everything that makes the Boothbay region one of Maine's most sought-after coastal destinations. Step into a landscape of meadows, wetlands and forest, with miles of nearby walking trails and abundant wildlife, yet remain remarkably close to downtown Boothbay Harbor, the waterfront, restaurants, shops and boating. Lobster Cove Meadow itself encompasses nearly 47 acres and features 1.5 miles of trails, with connections into the larger Meadow Brook Conservation Area. The property consists of two parcels totaling approximately .98 acres, including the adjoining .23-acre parcel over which the existing right-of-way travels—creating a much more appealing overall package. A 3-bedroom, 2-bath manufactured home provides immediate use of the property, whether you're looking for a year-round residence, a Boothbay getaway, or a place to enjoy while considering what the future might hold. The real star here, though, is the setting: nature at your doorstep and the attractions of Boothbay Harbor just minutes away, including the acclaimed Coastal Maine Botanical Gardens, Carousel Music Theater and Boothbay Harbor's vibrant working waterfront. Nearly an acre in Boothbay Harbor, abutting conserved land and close to the heart of the region—this is the kind of location that's increasingly hard to find. Come for the property, but fall in love with the possibilities.

8 Highland Park Rd, Boothbay Harbor

Listing courtesy of Pooley Realty Group.

18 Crest Ave, Boothbay Harbor
$1,750,000
4 Beds ⋅ 4 Baths ⋅ 1677407 MLS
Contemporary five-bedroom, 3 ½-bath waterfront home located in Boothbay Harbor. This exceptional property offers stunning views of Linekin Bay and is within walking distance of the East Side of the Harbor, Barrett's Park, and downtown via the footbridge. The home features a private dock and access to the Sprucewold Beach Club. The main level includes a spacious living room with cathedral ceilings, a fireplace, and four skylights, as well as an open dining area perfect for entertaining. This level also houses three bedrooms, 2 ½ baths, and a versatile loft area. The finished lower level offers a large family room, access to a large deck from the sliding glass doors, a game room, two additional bedrooms, and a full bath with laundry. Modern amenities include a propane hot water baseboard heating, two mini-splits, municipal sewer, and a drilled well. This property also maintains a strong rental history, making it an excellent investment opportunity. Please no drive-bys, tenants in residence.

18 Crest Ave, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

336 Lakeside Dr, Boothbay Harbor
$850,000
3 Beds ⋅ 4 Baths ⋅ 1676894 MLS
This home is immaculately maintained and thoughtfully designed for comfortable, easy living. This three bedroom and three and a half bath home is situated on 1.82 private acres with a waterview of Hodgdon Cove and Townsend Gut in Boothbay Harbor with shared frontage on West Harbor Pond. The updated eat-in kitchen serves as the heart of the home and opens to a bright and adjoining sunroom filled with natural light. Just off the kitchen, is a spacious pantry and a convenient 1st floor laundry room. The adjacent dining room provides ample space for entertaining family and friends. The inviting living room features a recently installed gas fireplace and connects to a 1st floor office that could easily be converted into a primary bedroom, offering additional flexibility for one level living. Additional highlights include a jetted jacuzzii in a 2nd floor bathroom, 2-car drive in garage, a spacious walkout basement , three recently installed heat pumps that provide efficient heating and air conditioning and a home generator for added peace of mind. Perched atop a knoll, the property offers beautiful views of Hodgdon Cove, and enjoys the shared access to West Harbor Pond, where you can boat, swim and enjoy the water from your shared dock. This exceptional property combines comfort, convenience and access to some of the Boothbay Regions desirable waterfront amenities.

336 Lakeside Dr, Boothbay Harbor

Listing courtesy of Harbor Realty.

59 Ocean Point Rd Unit 23, Boothbay Harbor
$140,000
3 Beds ⋅ 2 Baths ⋅ 1676067 MLS
Affordable and well-maintained 3-bedroom, 2-bath home conveniently located in Boothbay Harbor! This move-in-ready property features a recently updated kitchen, fresh interior paint throughout, and a newer hot water heater. The spacious primary suite offers a private bath along with two large closets for ample storage. Enjoy a bright, comfortable living room and a welcoming eat-in kitchen, perfect for everyday living and entertaining. Step outside to relax on the freshly painted deck. Ideally situated within walking distance of downtown Boothbay Harbor, you'll have easy access to local shops, restaurants, and waterfront attractions. Combining affordability, convenience, and comfortable coastal living, this home is an exceptional opportunity you won't want to miss.

59 Ocean Point Rd Unit 23, Boothbay Harbor

Listing courtesy of Newcastle Realty. 207-633-4433

69 Western Ave, Boothbay Harbor
$899,000
6 Beds ⋅ 5 Baths ⋅ 1675802 MLS
OPEN HOUSE SUNDAY OCTOBER 4th FROM 11AM TO 1PM. Overlooking scenic Mill Cove and Boothbay Harbor, 69 Western Ave offers a unique opportunity to own a beautifully situated single family home coupled with a proven income-generating guest cottage above an oversized garage.. The main home offers 3BR and 1.5BA with both bathrooms completely updated in 2026. The kitchen has also undergone a significant upgrade (cabinets and countertop) in 2026 as well. Current owners have made significant heating/cooling improvements with floor to ceiling blown-in fiberglass insulation and a 50KBTU heat pump system, including a new 18000BTU heat pump that serves the front sunroom area. The cottage offers 3 BR, one full bath and 2 half baths. Possessing a beautifully appointed kitchen, pellet stove, and h/w floors, this additional property provides incredibly comfortable accommodations for either guests or Airbnb tenants. Just steps to Boothbay Harbor Yacht Club and minutes to downtown Boothbay Harbor. AN ABSOLUTE MUST SEE!

69 Western Ave, Boothbay Harbor

Listing courtesy of Portside Real Estate Group.

133 Western Ave, Boothbay Harbor
$1,800,000
6 Beds ⋅ 6 Baths ⋅ 1672838 MLS
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.

4 Townsend Ave, Boothbay Harbor
$880,000
5 Beds ⋅ 5 Baths ⋅ 1672362 MLS
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.

6 Abenaki Rd, Boothbay Harbor
$595,000
3 Beds ⋅ 3 Baths ⋅ 1672198 MLS
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.

16 Eastern Ave, Boothbay Harbor
$775,000
5 Beds ⋅ 3 Baths ⋅ 1672089 MLS
Step into the best of coastal New England living in this beautifully updated, iconic in-town Boothbay Harbor home. Set on a tree-lined residential street, this 2,480-square-foot, 5-6 bedroom, 3-bath property offers a highly desirable walkable lifestyle, just a short stroll to the harbor, shops, restaurants, and town amenities. Filled with natural light, the home blends timeless character with modern convenience, featuring rich woodwork, stunning hardwood floors, extensive updates, and a cozy Jotul wood stove. At the heart of the home is the spacious chef's kitchen, completely redesigned and expanded in 2026. Highlights include white cabinetry, extra-wide quartz countertops, a six-burner Thor gas range, farmhouse sink, LG Energy Star appliances, walk-in pantry, and bar counter opening to the family room. A first-floor full bath offers flexibility for guests or one-level living, while the oversized mudroom with laundry provides excellent storage and everyday functionality. 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. Public water and sewer add convenience. The bright third-floor attic, featuring oversized dormer windows and four solar-powered skylights, offers exciting potential for a future primary suite, office, studio, or bonus space. A detached shed provides additional storage. With a proven Airbnb history and consistent five-star guest reviews, this move-in-ready property is equally appealing as a year-round home, vacation retreat, or income-producing investment--all while preserving the historic character that makes Boothbay Harbor living so special.

16 Eastern Ave, Boothbay Harbor

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

87 Crest Ave, Boothbay Harbor
$475,000
1 Beds ⋅ 1 Baths ⋅ 1669450 MLS
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.

236 Lakeside Dr, Boothbay Harbor
$1,145,000
4 Beds ⋅ 3 Baths ⋅ 1664620 MLS
This exceptional waterfront estate in Boothbay Harbor pairs classic coastal Maine living with lucrative rental income potential or flexible multi-generational living. The property features a main residence designed for effortless, one-floor living with two bedrooms and two full bathrooms, including a newly renovated primary ensuite with a deep soaking tub. Directly below, a bright and fully independent lower-level suite equipped with a full kitchen, two additional bedrooms, and one bathroom presents an incredible opportunity to offset your mortgage or generate seasonal revenue right away. Rest easy knowing that all systems and infrastructure throughout the home have been recently updated, ensuring ultimate reliability and efficiency. The main living space is highlighted by vaulted ceilings and a massive, low-maintenance Trex wraparound deck that offers stunning water views without the hassle of annual upkeep. Set on 3.65 highly private acres boasting 240 feet of direct shoreline on West Harbor Pond, this turnkey home comes complete with central air, its own private dock, and a kayak launch--allowing you to live the ultimate coastal dream while letting your real estate asset work for you.

236 Lakeside Dr, Boothbay Harbor

Listing courtesy of Tindal & Callahan Real Estate.

78 West St, Boothbay Harbor
$950,000
2 Beds ⋅ 2 Baths ⋅ 1663839 MLS
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.

76 West St, Boothbay Harbor
$950,000
2 Beds ⋅ 2 Baths ⋅ 1663769 MLS
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.

96 Atlantic Ave Unit C4, Boothbay Harbor
$539,900
3 Beds ⋅ 3 Baths ⋅ 1661618 MLS
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.

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