Boothbay Homes for Sale

Privately situated above the picturesque Damariscotta River, this custom-built Post & Beam coastal home offers a serene and secluded setting, breathtaking, ever-changing waterfront views, and the best of Maine living in one of the region's most coveted seaside communities. Thoughtfully designed for comfort and effortless living, this three-bedroom residence offers spacious, versatile interiors and a welcoming blend of classic coastal character and functionality. At the heart of the home, a sun-filled great room frames panoramic eastern views and features a dramatic floor-to-ceiling stone gas fireplace, creating an inviting gathering space in every season. The adjoining dining room and well-appointed kitchen offer generous counter space and an ideal layout for entertaining family and friends. The main level also features a bedroom with a full bath and direct access to an expansive deck, where refreshing coastal breezes and spectacular sunrise views set the scene for relaxed mornings and outdoor enjoyment. Upstairs, two additional bedrooms, each with a private full bath, provide comfortable accommodations for family and guests. A dedicated laundry area adds convenience, while elevated vantage points offer a captivating perspective of the river and its ever-changing activity. A detached two-car garage provides ample space for vehicles, storage, hobbies, and projects. Residents enjoy shared access to two deep-water docks, opening the door to boating, kayaking, and the quintessential Maine waterfront lifestyle. Ownership of a mooring is also available. Ideally situated just minutes from the charm of Boothbay Harbor, the exceptional amenities of Boothbay Harbor Country Club, and the renowned Coastal Maine Botanical Gardens, this special property offers a rare balance of privacy, natural beauty, and convenient access to the very best of the Boothbay Peninsula.

25 Belhaven Way, Boothbay

Listing courtesy of Newcastle Realty. 207-633-4433

$945,000

Experience classic Maine waterfront living in this 2,300-square-foot, three-bedroom, two-bath post-and-beam home, privately set along a quiet side road in Little River. With 342 feet of peaceful shorefront on Glen Cove, the property invites you to kayak, swim, or simply unwind on the waterfront deck while taking in a landscape of calm tidal coves, or nearby rugged rocky shoreline, and open-water views. Membership provides access to the nearby community dock on Little River, offering convenient dinghy tie-up and a direct connection to the Damariscotta River and beyond. The home's wood-shingle exterior lends timeless New England character, while exposed beams and warm wood finishes create an inviting interior. Designed for comfortable main-level living, the open kitchen, dining, and living area flows into a cozy sunroom with southerly exposure. A home office with built-in bookcases and cathedral ceilings provides a quiet retreat, while two upstairs guest rooms and a full bath offer welcoming accommodations for family and friends. The spacious basement provides ample room for a workshop, storage, or other uses. Glen Cove Dam, Ocean Point, and East Boothbay Village are all nearby, with Boothbay Harbor just a few miles farther.

32 Hiawatha Trl, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$295,000

3 Beds ⋅ 1 Baths

This affordable, year-round, three-bedroom, one-bathroom home features one-floor living, with an eat-in kitchen which is open to the living room. This home has a level backyard, and a new roof installed in 2026. It is conveniently located in close proximity to Boothbay Center for an easy commute, as well as a short distance from downtown Boothbay Harbor.

193 Country Club Rd, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$789,000

This post-and-beam, three-bedroom, two-bath home sits on 1.58 acres and offers southeasterly views of the Back River from nearly every room. Recent improvements include a full-bath and bedroom addition, two new interior staircases, a reconfigured deck and entry steps, extensive landscaping, a hillside fire-pit area, and significant woodland clearing. The full daylight basement is ideal for a workshop or future living space, with plumbing in place for future bathroom. All systems have been serviced for an easy, welcoming move-in. Freshly painted inside, the home features wood floors, a wood-burning fireplace with a stone hearth, and inviting spaces that showcase the expansive view. Relax on the deck and enjoy the waterfront and surrounding nature. Deeded right-of-way and easement provide water access and protects the beautiful water view. Barters Island offers a welcoming community 0.5 mile from Coastal Maine Botanical Gardens, public boat launch, Porters Preserve BRLT hiking trails, Trevett Store, and is just a short drive to Boothbay Harbor.

353 East, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$3,495,000

6 Beds ⋅ 6 Baths

Set on a private 5-acre peninsula with 740 feet of deepwater frontage on the Back River, this masterfully crafted coastal estate offers an exceptional Maine waterfront retreat. Substantially updated by the current owners, enhancements include a stunning new kitchen, updated bathrooms, new decking, fresh paint, refined flooring, and revitalized landscaping. Blending timeless post and beam craftsmanship with modern luxury, the residence offers 6 bedrooms, 5.5 bathrooms, and over 5,000 square feet of finished living space across three levels. From the moment you enter, the home captivates with soaring cathedral ceilings, exposed timbers, skylights, and walls of glass framing beautiful water views. The dramatic great room is anchored by a floor-to-ceiling fieldstone fireplace and custom wide-pine floors with an inlaid nautical compass rose. The newly renovated chef's kitchen features premium finishes, custom cabinetry, a center island, and an adjoining dining area. Multiple sets of French doors open to an expansive screened porch and open-air decks overlooking the river, ideal for morning coffee, summer dinners, or sunset cocktails. The main level features a private primary suite with its own fireplace, spa-like bath, and direct access to the screened porch. Upstairs, multiple guest bedrooms, a den, and an airy loft overlooking the great room provide flexible accommodations. The fully finished daylight walkout lower level adds an expansive family and game room, additional guest suites, and direct access to the outdoors. Outside, a private path leads to the deepwater dock, float, and two private moorings, providing direct boating access to the Sheepscot River and open ocean. Complete with an attached two-car garage, custom laundry room, whole-house automatic generator, and peaceful end-of-lane privacy, this turnkey coastal estate is just minutes from Boothbay Harbor and the renowned Country Club, and just over an hour from Portland International Jetport.

38 Higbee Ln, Boothbay

Listing courtesy of Legacy Properties Sotheby's International Realty.

$399,000

2 Beds ⋅ 3 Baths

This versatile property offers the rare combination of residential living, flexible additional spaces, and established income-producing potential in a highly visible Route 27 location. Conveniently located just minutes from the harbor waterfront, marinas, restaurants, shopping, and year-round attractions, this property provides both everyday convenience and the opportunity to enjoy the coastal lifestyle of the Boothbay Peninsula. The well-maintained residential component features 2 bedrooms, 1.5 baths, updated flooring, modern appliances, and a three-season sunroom. A separate spa/office suite with its own private entrance and half bath provides exceptional flexibility for a home office, wellness space, studio, guest area, or other permitted use while maintaining separation from the main living area. Additional space is available in the heated garage/showroom, previously used as a flooring showroom. The expansive area offers potential for storage, a workshop, studio space, or other permitted uses. A circular driveway and generous parking provide convenient access for residents, clients, or guests. Currently operated as a short-term rental, the property offers an established rental history with future reservations already scheduled. Rental history, reservation calendar, and additional operating information are available upon request. Any existing reservations, rental agreements, credits, or other obligations shall be subject to terms negotiated between the parties. Whether envisioned as a year-round home, a flexible live/work property, or an opportunity to generate rental income, 494 Wiscassett Road offers an uncommon combination of residential comfort, flexibility, visibility, and investment potential in the Boothbay market. Prospective purchasers should independently verify zoning, permitted uses, licensing requirements, rental regulations, and suitability for intended use with the Town of Boothbay and applicable authorities.

494 Wiscasset Rd, Boothbay

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group.

$549,000

A home that feels pleasantly removed from the hustle and bustle while keeping the villages, waterfront, recreation and attractions of the Boothbay region within easy reach. Surrounded by mature trees, established gardens and thoughtfully landscaped grounds, this solid and well-maintained Boothbay home gives a warm farmhouse feel in a peaceful setting close to everything the peninsula has to offer. A metal roof, classic shutters and warm wood accents add to the inviting exterior, while the outdoor spaces have been designed to make the most of Maine's natural beauty. Inside, the open kitchen, dining and living area forms the heart of the home. The kitchen features a butcher-block-topped island, stainless steel appliances, open shelving and farmhouse-inspired finishes, flowing easily into the dining and living spaces. A cozy stove, abundant natural light and comfortable bedrooms continue the home's relaxed character. Outdoor living is a highlight, with a screened porch and spacious deck overlooking the surrounding greenery, plus an above-ground pool, vegetable and perennial gardens, and a tucked-away fire pit area. A large workshop with additional covered storage provides excellent space for projects and equipment, while a dedicated RV parking pad with shore power adds even more versatility. The location makes it easy to enjoy everything the Boothbay region has to offer. Downtown Boothbay is just under three miles away, Boothbay Harbor Country Club is less than 10 minutes away, and downtown Boothbay Harbor is only a few minutes farther. Coastal Maine Botanical Gardens and the Maine State Aquarium nearby, while Saunders Preserve is within walking distance. Boothbay Region Land Trust preserves, trails and many of the peninsula's other attractions are also close by. Comfortable, inviting and clearly cared for, this property offers the space to garden, entertain, relax, work on projects and enjoy the outdoors. Recently appraised over asking price.

12 Butler Rd, Boothbay

Listing courtesy of RE/MAX Shoreline.

$525,000

22 Triple Leaf Ln, Boothbay

Listing courtesy of Newcastle Realty. 207-633-4433

$697,000

Well maintained and in move into condition is this 3 bedroom plus, 2 1/2 bath home with extensive upgrades. Stroll down the hill to the Association waterfront for picnics or get to your own private boat. Short walk into East Boothbay village and the general store. Very conveniently located to town as well. And don't forget the outbuilding bunkhouse for the kids!

114 Presley Dr, Boothbay

Listing courtesy of Newcastle Realty. 207-633-4433

$925,000

3 Beds ⋅ 4 Baths

Welcome to a beautifully constructed coastal retreat in the heart of East Boothbay, tucked into a private setting with peaceful water views and an inviting sense of Maine charm. Thoughtfully positioned to capture warm southerly light, this three-bedroom home features en suite accommodations throughout, including a spacious first-floor primary suite for easy living. Floor-to-ceiling windows, wood floors, and a dramatic cathedral ceiling create an airy, sun-filled gathering space anchored by a massive stone fireplace—perfect for cozy evenings after a day by the water. Offered furnished, the home is ready to enjoy from the moment you arrive. Located close to the local store and boat launch, and surrounded by an idyllic enclave of well-built homes, this is a special East Boothbay setting where comfort, craftsmanship, and coastal living come together beautifully.

27 Stone Cove Rd, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$795,000

Situated on a private 2.65 acre lot, with 417' of tidal frontage on Sherman Cove, this 3 bedroom, 2 bath Cape has many amenities to offer. Natural light floods the house, with many large windows and doors; open living/dining/kitchen with hardwood flooring, woodstove and access to a full length waterside deck; the front to back family room has a gorgeous stone fireplace, cathedral ceiling and access to the deck and gardens; the full daylight basement provides garage space for 3+ cars and plenty of storage. The property is beautifully landscaped and is located halfway between Boothbay Harbor and Route 1, providing easy access into town or off the peninsula.

29 Wiscasset Rd, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$595,000

3 Beds ⋅ 1 Baths

Located at Murray Hill in East Boothbay. This classic, well-restored 1890s cottage, perched on a forested hillside offers a fantastic opportunity to spend your summer overlooking Linekin Bay. It comes with convenient access to a town dock and a boat launching ramp which are just a short walk from this cottage, perfect for enjoying the water. One of the highlights of this property is its large, enclosed sunporch, a perfect spot to relax and take in the beautiful sights of the bay. The cottage features three bedrooms, one bathroom, and a living room with a cozy fireplace. New 3-bdroom septic system has been installed as well as a new parking area. Additionally, you'll be able to enjoy a short walk to the East Boothbay General Store for your morning coffee.

5 Massachusetts Ave, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$2,500,000

Set in the historic village of East Boothbay, on the scenic and sought-after Murray Hill Road, this exceptional estate combines historic New England character, modern comfort, and remarkable versatility. At its heart is a beautifully restored 1769 Georgian residence, featuring five working fireplaces—including the original cooking fireplace with beehive oven—thoughtfully updated for contemporary living. Sun-filled rooms overlook Mill Pond, where the property enjoys its own private beach and opportunities for kayaking and swimming. A substantial multi-purpose barn offers three parking bays, including space capable of accommodating a 36-foot yacht for winter storage, plus a workshop, generous storage, and an artist's studio or private office. A nearby boat launch & pier, approximately 350-yards away, provides convenient access to Linekin Bay. The distinctive guest cottage provide exceptional accommodations. A charming two-story waterfront cottage on Mill Pond, it features a large waterside deck, kitchen, laundry, and private living quarters. The grounds are equally impressive, with fruit trees, gardens, and sweeping lawns. An idyllic setting for recreation, entertaining, and memorable gatherings. Offering privacy, history, water access, and guest accommodations, this is a rare opportunity to enjoy classic coastal Maine living in one of the Boothbay Region's most desirable settings. To enjoy a special, estate-like experience, additional acreage is available, including the 11+ acre conserved meadow, vegetable plot & blueberry patch, and Marsh pond with private island. To complete the package, the renovated, elegant 1-bedroom carriage house is also available--see MLS #1671005.

29 & 39 Murray Hill Rd, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$289,000

2 Beds ⋅ 1 Baths

368 Dover Rd, Boothbay

Listing courtesy of Harbor Realty.

$445,000

2 Beds ⋅ 1 Baths

Set in a quiet and private Boothbay neighborhood, 23 Nichols Road offers the simple pleasures of Maine living with an especially appealing natural setting. This inviting one-level home is tucked away on a private dead-end road and enjoys a wooded landscape, a level yard, and common access to the water. The home itself offers comfortable one-floor living with 2 bedrooms, and office/den, one full bath with laundry, a sunny living area, kitchen and dining space, and an attached one-car garage. Two decks and level yard provide an easy place to enjoy the outdoors, while the wooded surroundings create a peaceful sense of privacy. With close proximity to some of the Boothbay region's treasured conserved lands, the nearby Pine Tree Preserve of 144 acres of forest, provides access to trails for walking and exploring. The Linekin and Burley Preserves add another 138 acres of protected woodland and nearly three miles of trails, extending from Route 96 toward the Damariscotta River. Conveniently located for enjoying all that the Boothbay region has to offer, with downtown Boothbay Harbor, Ocean Point, golfing, boating, and coastal trails all within easy reach. A special opportunity to own a comfortable, turn-key home in a wonderful neighborhood.

23 Nichols Rd, Boothbay

Listing courtesy of Vitalius Real Estate Group, LLC.

$1,895,000

4 Beds ⋅ 5 Baths

Situated on over 9 acres of mature pastoral grounds with more than 400 feet of tidal water frontage on the Back River, this estate offers endless possibilities. The property features a beautifully renovated late-1700s original cape seamlessly integrated with well-designed high end quality finished additions, totaling over 4,000 square feet of living space. Key features of the home include: 4 to 5 updated bedrooms and 4.5 updated bathrooms, a dedicated in-law/guest wing, a modern kitchen with cathedral beamed ceilings, Bosch appliances, and a tiled backsplash, multiple living areas and dedicated office spaces, stunning west-facing water views and an original two-story barn, perfect for a workshop, studio, or hobbies. Conveniently located just 3 miles from the Boothbay Harbor Country Club and Coastal Maine Botanical Gardens.

586 Back River Rd, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$1,850,000

Experience the beauty of waterfront living in this classic shingle-style home overlooking Linekin Bay. Spectacular westerly views provide unforgettable sunsets, while the changing tides reveal a pebble beach perfect for exploring and play. At high tide, the protected waters invite swimming just steps from your door. Inside, a dramatic wall of windows frames the ever-changing views, creating the feeling of living aboard a boat while filling the home with natural light. Custom high-paneled wainscoting and thoughtful architectural details add timeless elegance throughout. The home offers a first-floor primary suite with a private sunroom overlooking the bay, an updated kitchen that opens seamlessly to the living and dining areas, and two additional bedrooms with a full bath on the second floor. A separate family room, featuring a vaulted ceiling and a stone fireplace provides room for gathering with family and friends. Completing the property is a detached garage with a studio space, ideal for creative pursuits or a home office. Plus, a shared deepwater dock is just a short walk away. This exceptional waterfront property captures the very best of the Maine coast.

749 Ocean Point Rd, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$399,000

1 Beds ⋅ 1 Baths

This newly constructed home on 6.2 private wooded acres in Boothbay is an ideal setting for a year-round or summer get away. Located just a few miles from Boothbay Harbor's stores, waterfront, and dining, this unique setting is tucked off a country woods road that allows for privacy, nature, and relaxation. Currently configured with one bedroom, the floor plan offers easy expansion into two bedrooms. The cathedral ceiling and open layout for the living, dining, and kitchen areas has southerly exposure and plenty of sunlight. Wood floors and walls add warmth throughout, while the spacious private deck extends the living space outdoors. Heat with the hot-air furnace or unwind by the pellet stove. A generous attached 32' x 26' garage provides added convenience. With no restrictive covenants, the property can be enjoyed as one large parcel, a future house site, or expand the current use.

48 Matthews Rd, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$1,800,000

4 Beds ⋅ 2 Baths

Winterized cottage with seasonal guest cottage is sited on the front of Ocean Point where Ocean Point got its name. Absolutely stunning views from this location of crashing surf, rolling waves lulling you to sleep at night, 4 lighthouses, lots of boating traffic to watch all day long and skies so clear at night you can see all the stars. The main cottage was originally built in 1878 and has had many updates over the years. This cottage consists of 4 bedrooms, 2 baths, living room/dining area, renovated kitchen, sunroom and a 2nd floor deck. The guest cottage is a studio with bathroom, small kitchen with enclosed porch and small deck. The guest cottage has a great rental history. Ocean Point is also known for its vibrant summer community, which includes a ''casino building'' that hosts a variety of activities for all ages throughout the summer months, a beach at Grimes Cove and dingy shares are available to buy if you want to have a boat on a mooring in Card Cove.

113 Shore Rd, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$389,900

4 +/- acres. Welcome to 332 Back River Road. A peaceful, relaxing place to call home. A flexible floor plan that blends classic Maine style with modern function-inside and out. The main level offers easy one-floor living. An open kitchen with an island and a breakfast bar flows nicely into the living room, making it perfect for entertaining. It's rounded out with 2 bedrooms, master with access to a full bath, and a laundry room with storage. The upstairs surprises and delivers with a sun-filled sprawling loft and a cozy reading nook. Flex space for a home office, studio or guest room, plus a bonus room and a second full bath. Outside, you're private oasis awaits with room to roam, spread out, and stake your claim. It has a bright and level backyard for games and gardens. The detached 2-car garage comes with untapped space above and below, ready for a workshop or an ADU, to earn extra income. A 5 minute ride to Knickercane Boat Launch and Park, and 6 minutes to Trevett's Store or Coastal Maine Botanical Gardens. All within an amazing community and great schools. Classic Maine character, modern flexibility, and space to grow. Schedule your showing today.

332 Back River Rd, Boothbay

Listing courtesy of EXP Realty.

$3,995,000

3 Beds ⋅ 4 Baths

Distinctive opportunity to live at the renowned Boothbay Harbor Country Club, recognized as the best golf and country club experience in Maine. This exceptionally designed and appointed home will be built with supreme quality and luxury, including a ground floor ensuite bedroom, and a spectacular primary bedroom suite upstairs with his & hers bathrooms, closets, and a study that could serve as an extra bedroom. The open concept kitchen and great room makes for satisfying everyday use, as does the abundanta outdoor living space, be it the screened porch, veranda, open deck, and granite patios. Sumptuously comfortable, the home offers owners an effortless club lifestyle, with golf cart access to Club amenities that feature the 18-hole course, lavish spa, family pool, fitness center, tennis & pickleball courts, dining facilities, and more. Club-maintained gardens & landscaping, municipal water & sewer, and other attributes make for ''lock and leave'' convenience, just up the hill from downtown Boothbay Harbor.

Lot 7 Whispering Pines, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$2,995,000

2 Beds ⋅ 3 Baths

Distinctive opportunity to live at the renowned Boothbay Harbor Country Club, recognized as the best golf and country club experience in Maine. This exceptionally designed and appointed home will be built with supreme quality and luxury, including one-floor living with two ensuite bedrooms, an open concept kitchen & great room, and abundant outdoor living spaces. Sumptuously comfortable, the home offers owners an effortless club lifestyle, with golf cart access to Club amenities that include the award-winning 18-hole course, lavish spa, family pool, fitness center, tennis & pickleball courts, dining facilities, and more. Club-maintained gardens & landscaping, municipal water & sewer, and other features make for ''lock and leave'' convenience, just up the hill from downtown Boothbay Harbor.

Lot 10 Whispering Pines, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$989,000

1 Beds ⋅ 1 Baths

Imagine the charm of Old World with all the modern conveniences of today. This amazing Carriage House was totally renovated in 2021 without giving up its soul. Drenching light, from sunrise to sunset, through immense french doors with views of a five acre Marsh Pond and Island across ten acres of open meadow protected by a conservation trust. The open floor plan encompasses a custom kitchen, dining and living area before entering a stylish bedroom and master bath. What is presently a one car garage and storage area could be developed into an additional bedroom and a garage. Sited on nearly a half acre, it is just steps away from Linekin Bay and boat launch and looks across to Mill Pond which draws and releases water from the Damariscotta River. You are just minutes away from the beautiful village of Boothbay Harbor and the luxurious Boothbay Harbor Country Club voted the number one club and golf course in New England. As you awaken each day, the morning sun seems to push you towards the famed East Boothbay General Store at the end of the road where delightful coffees, breakfast foods and freshly baked delights welcome you each morning.

32 Murray Hill Rd, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$558,000

3 Beds ⋅ 4 Baths

Discover the perfect blend of privacy, comfort, and creativity on 6.48 picturesque acres. This charming three-bedroom, log-sided home offers plenty of room to gather with family and friends, pursue your favorite hobbies, or simply enjoy the beauty of the outdoors with gardens, open space, and peaceful surroundings. Take in distant views of the Damariscotta River, especially from the second-floor office--a serene setting for working from home. The welcoming kitchen is designed for everyday living, featuring a center island with breakfast seating, a spacious pantry, and a sunny box bay window above the sink that's perfect for growing fresh herbs year-round. The walkout lower level includes a versatile room with its own private deck. Formerly a pottery studio, it's ready to become your art studio, workshop, home office, fitness room, or whatever inspires you. Outside, you'll find a detached garage/workshop with storage above, a garden shed, and endless opportunities to enjoy the expansive property. If you've been looking for a home that offers space, character, and room to create the lifestyle you've always wanted, this is one you won't want to miss--all for $558,000.

82 Back Narrows Rd, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$750,000

5 Beds ⋅ 4 Baths

Welcome to 39 Shackleton's Way in Boothbay, an extensively renovated 3,300 square foot residence offering an exceptional blend of modern craftsmanship, thoughtful design, and everyday comfort. Set on 1.2 private acres and reimagined down to the studs since 2022, the home has undergone a complete renovation with extensive updates throughout. The spacious floor plan features five bedrooms, one of which is currently used as a home office, three full bathrooms, one half bath, and an attached two-car garage. At the heart of the home is a beautifully appointed kitchen with commercial-grade appliances and an oversized island designed for gathering and entertaining. Hardwood floors, custom built-ins, and carefully curated finishes create a warm yet sophisticated atmosphere throughout. The primary suite serves as a private retreat, featuring cathedral ceilings and a luxurious spa-inspired bathroom. Additional living spaces include a dedicated office with built-in cabinetry, a beautifully finished wet bar, and a well-designed in-law apartment complete with its own living space, offering exceptional flexibility for guests, extended family, or multigenerational living. Recent improvements include new heat pumps, radiant heat flooring, new decks, and extensive interior and exterior enhancements completed as part of the home's comprehensive renovation. Thoughtful details throughout, including designer wallpaper accents and custom millwork, contribute to the home's distinctive character and quality. Surrounded by mature trees and offering a peaceful, private setting, the property is ideally located just 3 minutes from Boothbay Harbor Country Club and only 7 minutes from downtown Boothbay Harbor's restaurants, shops, marinas, and waterfront attractions. Offering the space, quality, and flexibility rarely found in today's market, 39 Shackleton's Way presents a unique opportunity to enjoy coastal Maine living in one of the region's most desirable locations.

39 Shackletons Way, Boothbay

Listing courtesy of Legacy Properties Sotheby's International Realty.

$674,000

Presenting the charming home of Sweet Windruff Farm on East Side Road, Barters Island -- a timeless 1860s New England Cape offering warmth, character, and waterfront living on The Back River. Whether you're seeking a summer retreat or a year-round coastal home, this beautifully maintained property captures the essence of Maine living. Enter through the gate into a welcoming mudroom-style entryway featuring original brick flooring and classic built-ins. Beyond, the heart of the home opens into a warm dining and kitchen area centered around a cozy woodstove, with peaceful views stretching toward the cove and your waterfront frontage on The Back River. Rich in old-style charm and thoughtfully designed living space, the home offers two bedrooms and two baths, including a first-floor primary bedroom suite and laundry room for convenient one-level living. Upstairs provides additional privacy with flexible space ideal for guests, a sewing room, studio, or home office. The inviting living room and den feature built-in bookcases and a beautiful fireplace -- perfect for gathering with friends or simply taking the chill off a cool coastal evening. Every room reflects the care and personality of its current owners, blending comfort, craftsmanship, and timeless New England character. Outside, the property continues to impress. Set back from the road, the home enjoys a fenced yard with mature fruit and maple trees, sitting areas, a greenhouse, and a charming potter's shed. A lovely screened front porch offers the perfect place to relax and enjoy water views after a day exploring the Maine coast. The two-story barn, built in 1999 by a local craftsman along with the kitchen addition, provides exceptional versatility with garage space for vehicles or boats, a workshop, and an attached separate work area ideal for hobbies, storage, or a home-based business. This special waterfront property offers comfort, privacy, and authentic coastal charm in one of Maine's island communities.

367 East, Boothbay

Listing courtesy of Legacy Properties Sotheby's International Realty.

$865,000

7 Beds ⋅ 6 Baths

Freshly updated multi-family, comprised of two 2-bedroom apartments and three efficiency units. Recent improvements include interior finishes, rock wool insulation, siding, roofing, and more. An income property, it has been popular for short-term rentals, but would also lend well to mixed use, employee housing, and/or owner occupancy with the ability to expand and contract space based on family need. Positioned opposite the Boothbay Harbor Country Club, the property is centrally located and benefits from municipal water and sewer services.

8 Country Club Rd, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$425,000

This two-level condominium offers a spacious and comfortable layout featuring three bedrooms and 2.5 bathrooms. The custom kitchen is appointed with cherry cabinetry, granite countertops, and a vaulted ceiling with skylights that provide abundant natural light. Adjacent to the kitchen is a welcoming dining area and a large living room that offers scenic views of Beaver Pond. The second floor includes a dedicated office space, ideal for working from home or creative use. The unit is well-lit throughout the day, benefiting from both morning and afternoon sun. For added convenience, the property includes a one-car garage with extra storage. Its central location also ensures an easy commute to Boothbay Harbor, Damariscotta and Wiscasset.

5 Hillside Pl Unit 2, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$435,000

On 1.25-acres at the gateway to the Boothbay Region, this two-unit New Englander offers many possibilities in a mixed-use zoning district. Both units were recently updated, including the kitchens, bathrooms, flooring, and more. The first floor features a spacious 1-bedroom, 2-bath apartment, with vaulted ceilings and a propane heat stove in the living room, a cheerful kitchen with adjacent laundry, and an ensuite bedroom and bath. At the south end, there is a storage room that could be converted to a second bedroom. Upstairs, an open concept kitchen/living/dining includes cathedral ceilings and a propane heat stove, with two bedrooms and a bathroom beyond. Outside, the property includes a private back yard with storage shed, long front porch, and extensive road frontage. Served by public utilities and roads, this property is easy to manage and provides convenient access to major roads for commuters.

934 Wiscasset Rd, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$865,000

6 Baths

Freshly updated multi-family, comprised of two 2-bedroom apartments and three efficiency units. Recent improvements include interior finishes, rock wool insulation, siding, roofing, and more. An income property, it has been popular for short-term rentals, but would also lend well to mixed use, employee housing, and/or owner occupancy with the ability to expand and contract space based on family need. Positioned opposite the Boothbay Harbor Country Club, the property is centrally located and benefits from municipal water and sewer services.

8 Country Club Rd, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$725,000

This classic farmhouse is sited on an exceptional 8 acre parcel with approximately 400' of tidal waterfront on Back River. This sizeable parcel is rare and lends itself to a private estate or future division. The farmhouse is solid and has classic lines and although it was cared for, it awaits updates. 3 bedrooms and 1.5 baths, an attached barn and a 2 car garage are intriguing to any old house enthusiast. The land allows for a gentle walk to the shore through a beautiful forest of mostly hardwoods and rolling terrain. This unique parcel has ample opportunities and is truly a quintessential Maine property.

576 Back River Rd, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$649,000

This custom ranch offers refined one-floor living with three bedrooms and two and a half bathrooms, blending comfort, privacy, and understated elegance. Thoughtfully designed, the layout places the owners' suite on one end of the home, creating a peaceful retreat, while separate accommodations on the opposite side welcome family and guests with ease. Wood floors extend throughout, and a cathedral ceiling paired with an open-concept design fill the home with natural light and a wonderful sense of warmth and openness. Designed for effortless living, the property also features an attached two-car garage, a dedicated workshop in the basement, and a serene 1.19-acre setting that invites both relaxation and quiet enjoyment. Just minutes away, a public boat launch makes it easy to spend the day boating or kayaking, while the Trevett Store offers the simple pleasure of a classic coastal Maine lobster roll. With Coastal Maine Botanical Gardens and Boothbay Land Trust nearby, this home places you close to the natural beauty, charm, and coastal lifestyle that make the Boothbay Region so special.

23 Sunny Acres Ln, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$321,500

Locate along the Gateway to Boothbay Harbor! This could end up being your primary residence or use as current owner has found fabulous- rental with a home base while they explore the coast of Maine and use as their Maine get-away. Recently vacated by long term tenants the 2 bedroom first floor needs some cosmetics (paint etc) . It features a gas fireplace, laundry in bathroom and open concept style. The walkout finished basement offers the owners unit of 1 bedroom , full bath, living room / dining room / sitting area . New shed at the rear of the property allows for gardening equipment or sporting items.

24 Jason Cir, Boothbay

Listing courtesy of Cromwell Coastal Properties. (207)208-9311

$435,000

3 Baths

On 1.25-acres at the gateway to the Boothbay Region, this two-unit New Englander offers many possibilities in a mixed-use zoning district. Both units were recently updated, including the kitchens, bathrooms, flooring, and more. The first floor features a spacious 1-bedroom, 2-bath apartment, with vaulted ceilings and a propane heat stove in the living room, a cheerful kitchen with adjacent laundry, and an ensuite bedroom and bath. At the south end, there is a storage room that could be converted to a second bedroom. Upstairs, an open concept kitchen/living/dining includes cathedral ceilings and a propane heat stove, with two bedrooms and a bathroom beyond. Outside, the property includes a private back yard with storage shed, long front porch, and extensive road frontage. Served by public utilities and roads, this property is easy to manage and provides convenient access to major roads for commuters.

934 Wiscasset Rd, Boothbay

Listing courtesy of Tindal & Callahan Real Estate.

$375,000

NEW PRICE FOR NEW CONSTRUCTION. Now offered at a reduced price, these brand-new townhome condominiums developed by the Boothbay Regional Development Corporation make homeownership more attainable than ever. With down pymt assistance available to qualified buyers, this is a rare chance to own new construction in the heart of the Boothbay Peninsula. Each thoughtfully designed 2-bedroom, 1.5-bath home features an open-concept living, dining, and kitchen area, private outdoor space & easy access to surrounding natural areas, and parking in a shared lot. Built for energy efficiency and low maintenance, these move-in-ready homes are ideal for buyers seeking a starter home with comfort, quality, and long-term value. Priced on a sliding scale depending on income. Available to income-eligible buyers up to 120o|o of Area Median Income (106,680 for a household of three). Reduced price. Down pymt assistance available. Contact today for qualification details and to schedule a showing.

3 Cedar Bnd Unit 3, Boothbay

Listing courtesy of Vitalius Real Estate Group, LLC.

$299,500