Courtesy: Warren Realty
207-734-8857
Comfortable, cozy year-round home in a very convenient location. Large living room, open kitchen/dining area, great sun room. Simple, but lovely, landscaping Many extras such as whole-house generator, full basement, outbuilding suitable as guest bedroom or garden shed.
Courtesy: Legacy Properties Sotheby's International Realty
207-230-1003
Escape to an island, down a wooded road to this secluded seasonal cabin retreat, set on over 10 acres with sunset views. View our video for a more immersive experience!
Courtesy: Cates Real Estate
207-701-5600
Come explore this unique opportunity encompassing 11.5+/- acre and offering western views of West Penobscot Bay, Northport and Camden Hills giving you a sense of place and privacy. A gravel driveway leads you to the house in a forest setting with remnants of gardens behind the structure. There is a large sun deck at the front of the house designed to take advantage of the view and outdoor space. The house that has been renovated to serve as offices and a nature center equipped with a kitchen, 1.5 bath and plenty of storage. A solar array on the property helps to reduce utility costs. There is a small workshop/shed alongside the driveway. The house site is elevated and positioned to provide privacy from neighbors and limited exposure to road noise. The property conveys with 100 feet of waterfront on West Penobscot Bay, allowing an owner to control the view of the water. The location is mid-island, close to the ferry, the airport and downtown area. Islesboro is just a 20-minute ferry ride from the mainland town of Lincolnville and is easily accessible by private boat or plane, making it an ideal destination for those seeking both tranquility and convenience. High speed internet with 1 gigabit upload and download connection speeds.
Courtesy: LandVest, Inc.
207-236-3543
Discover a blend of history and modern comfort in this island farmhouse nestled on the picturesque island of Islesboro, Maine. Built in 1880, this home offers a unique opportunity to own a property steeped in local history with breathtaking views and modern comforts. Situated on 2.2 +/- acres, the property also includes a 2-car garage and multiple outbuildings, providing ample space for storage or creative endeavors. This home retains its original 1880s farmhouse charm, with stunning stained-glass windows, heart-pine flooring, and custom woodwork throughout. Surrounded by exquisite perennial gardens, the property offers a serene escape and overlooks the expansive fields of a saltwater farm with views of Ryder Cove. Each room in the house is bathed in sunlight from morning through afternoon, creating a warm and inviting atmosphere. Enjoy cozy evenings by the granite fireplace in the living room or the soapstone wood stove in the kitchen. While preserving its historical integrity, the home has been thoughtfully modernized and updated to meet today's living standards. Islesboro offers a close-knit community experience with essential amenities that make island living both comfortable and convenient. Residents have access to two grocery stores, a state-of-the-art health clinic, fiber optic internet, a library, a vibrant K-12 school, and a community center for engaging with neighbors and enjoying community events and resources. This property offers not only a home but a lifestyle, where history, natural beauty, and community come together. Don't miss your chance to own a piece of Maine's rich heritage.
Courtesy: Cates Real Estate
207-701-5600
Discover a unique opportunity in Mid-Island Islesboro, where history and potential converge in two remarkable buildings on one property. The Schoolhouse (300 Main Road): This was formerly the Pendleton School, Islesboro's main elementary school until the early 1950s. Currently operating as the Double Door Gallery during the summer, it features two large open rooms on the first floor with curved walls, bead board, wood paneling, and a half bath. The second floor offers a studio apartment with expansion potential, providing immediate income through gallery rentals and apartment leasing. This property is a piece of history with a bright future, ready for its next chapter as a vibrant art gallery, or unique retail space. The Main House (292 Main Road): The Winfield Scott Pendleton House. Step back in time and discover the rich history of this stately 1887 Federal-style home, once owned by Winfield Scott Pendleton, a prominent ship captain and influential figure in Islesboro. This grand home with its distinctive cupola and expansive wrap-around porch is perfect for enjoying the summer breeze and watching island life unfold. French doors off the porch invite you into this elegant old home and once inside the architectural details speak to a bygone era of detailed craftsmanship. Discover an elegant staircase, bespoke built-in closets, a breakfront in the dining room, six-over-six windows, a stained-glass window, and a bespoke carved wooden mantle. Original interior trim throughout the house, along with a claw-foot tub and natural stone vanity, evoke a sense of timeless charm. Beyond the main house, you'll find recently built post and beam two-story outbuildings, offering versatile space for a workshop, storage, or other possibilities. Both properties are prominently situated, offering a mid-island location close to the library, public park and playground, island market, and post office.
Courtesy: Cates Real Estate
207-701-5600
Step into history with this remarkable property, originally the Pendleton School, Islesboro's main elementary school during the 1800's until the early 1950s. This former schoolhouse has plenty of potential. Currently operating as the Double Door Gallery during the summer months, showcasing local and regional artists, the property boasts two large open rooms on the first floor, featuring curved walls, bead board, and wood paneling on the walls and ceiling, along with a convenient half bath. The second floor presents a studio apartment with room for expansion, offering an immediate income-producing opportunity through gallery rentals and potential apartment leasing. Its mid-island location provides easy access to the library, public park and playground, island market, and post office, making it an ideal spot for community engagement. Imagine the possibilities: continue its legacy as a vibrant art gallery or transform it into whatever your imagination can dream up. This property is not just a building; it's a piece of history with a bright future, ready for its next chapter.
Courtesy: Cates Real Estate
207-701-5600
Winfield Scott Pendleton House: A Historic Islesboro Gem. Step back in time and discover the rich history of this stately 1887 Federal-style home, once owned by Winfield Scott Pendleton, a prominent ship captain and influential figure in Islesboro. Built shortly after Pendleton acquired the property in 1876 from his parents, the house served as a summer retreat for the Pendleton family until 1959. This grand home with its distinctive cupola and expansive wrap-around porch is perfect for enjoying the summer breeze and watching island life unfold. French doors off the porch invite you into this elegant old home and once inside the architectural details speak to a bygone era of detailed craftsmanship. Discover an elegant staircase, bespoke built-in closets, a breakfront in the dining room, six-over-six windows, a stained-glass window, and a bespoke carved wooden mantle. Original interior trim throughout the house, along with a claw-foot tub and natural stone vanity, evoke a sense of timeless charm. While the kitchen has been thoughtfully modernized, the home retains its historical integrity. This 5-bedroom residence is prominently situated, offering a mid-island location close to the library, public park and playground, island market, and post office. Beyond the main house, you'll find recently built post and beam two-story outbuildings, offering versatile space for a workshop, storage, or other possibilities. This stately 1887 home is now seeking its next steward—someone who will appreciate its beautiful history, embrace its unique character, and continue to care for and enjoy this magnificent piece of Islesboro heritage.
Courtesy: The New England Real Estate Company, LLC
207-236-7000
Tucked away on two serene acres along Islesboro's northeast shore, this beautifully reimagined coastal cottage captures the essence of Maine island living. With sweeping views over East Penobscot Bay, the property blends timeless charm with modern comfort in a way that feels effortless. Originally built as a simple ''Maine camp,'' the home has been expanded and refined into a warm, year-round retreat. Inside, the single-level layout flows easily from the open central living area to the glass-walled entryway and out to a covered porch overlooking the water. There are four comfortable bedrooms—including a cheerful bunkroom with built-in bunks—two full baths, and thoughtful touches throughout such as a new washer and dryer and lightning-fast 1GB internet. Outdoors, every element is designed for relaxation and connection to the coast. The property's gentle slope to the shore makes launching a kayak or taking a dip simple and inviting. Gather around the stone patio and fire pit set above the 120-foot seawall to watch the changing tides or enjoy freshly caught lobster from the local boats that work the cove. A fenced yard allows both people and pets to explore freely. Across the drive, a spacious boathouse and workshop hold generous storage, complete with ceiling hoists for kayaks and small boats. Recent upgrades include a new survey and improved easement and driveway. Set along quiet Pripet Woods Lane, with no traffic and Islesboro Island Trust trails nearby, this is a place to truly unplug, unwind, and stay as long as you wish. A rare opportunity to own a piece of classic coastal Maine—private, peaceful, and perfectly suited for every season.
Courtesy: Warren Realty
207-734-8857
Quintessential coastal Maine island cottage with salt water views and beach access. Cozy year-round living with open concept kitchen and living room. Two bedrooms and 1½ baths. Many new improvements including new septic system, new south roof shingles, and exterior up-dates. Tax shown is for entire property. Tax for parcel to be conveyed will be far less, to be determined by assessor.
Courtesy: Legacy Properties Sotheby's International Realty
207-230-1003
This property offering includes an historic Arts and Craftsman-style Foursquare house - thought to be one of the first houses built in Dark Harbor - set on a sunny and open lot, as well as an additional vacant wooded lot both, just a short walk from the charm and amenities of Dark Harbor Village, Gilkey Harbor, and scenic Kissel Point. Brimming with original character and island warmth, the residence offers the best of both community connection and personal retreat. Ascend granite steps and enter through the welcoming formal front door beneath a gracious covered porch, perfect for waving to neighbors or enjoying a quiet cup of coffee. Inside, a central hall anchors the home, with a lovely parlor and dining room on one side, and a cozy study, powder room, and laundry area on the other. The kitchen, complete with pantry, is located to the center rear of the house, adjacent to a small sunlit room which leads out to a back deck, an ideal spot for relaxed outdoor dining. There is also a mudroom that opens to the covered back porch. The second floor includes three bedrooms and a full bath. An additional flexible use room has a staircase to a spacious, unfinished attic which offers expansion potential and includes glimpses of the water. The detached barn is closely adjacent to the house and is suitable for storing outdoor furniture. Located close to many of the island's year-round activities, including community center, gym, and school. Offered partially furnished. * Owner financing may be available. * Also available with less acreage see MLS 1639455. In addition to this property offering, if you are looking for a larger property or guest accommodations, consider an abutting property at 108 Colony Road which is also for sale. See MLS 1628467
Courtesy: Legacy Properties Sotheby's International Realty
207-230-1003
Tucked away on a quiet side street, this charming property is just a short stroll from the heart of Dark Harbor Village, and within easy reach of local shops, the town center, the community center, school, private club activities, and an abundance of public trails, beaches, and activities. The home's spacious main level welcomes you through a covered carport into a functional mudroom and laundry area. The kitchen, complete with a cozy breakfast nook and tiled finishes, flows seamlessly into the family room, formal dining room, and inviting living room. The thoughtful layout includes a first-floor bedroom with an adjoining bath, plus three additional bedrooms and a shared bath upstairs - alongside a large, versatile gathering room. Throughout the home, you'll find beautiful timber beams, detailed millwork, and classic hardwood floors that speak to its craftsmanship and heritage. Outdoor living is just as appealing, with a covered front porch, a generous deck, and spacious lawn ideal for entertaining or enjoying peaceful moments.
Courtesy: Legacy Properties Sotheby's International Realty
207-230-1003
Experience the magic of coastal living at this seasonal camp, set on 7 acres of level land and offering 1,400 feet of accessible shoreline and beach. Whether you choose to enjoy the camp as it is or build your dream retreat, this property provides the ideal setting to enjoy island life. Imagine long summer days filled with swimming, boating, and beach combing, capped off by breathtaking sunsets over the water. When you're ready to explore, take a stroll up the beach to Islesboro Island Trust's Turtle Head Preserve, where rocky cliffs, panoramic views, and fascinating geological history await. Or head out to explore all the island has to offer. The property is being offered as is.
Courtesy: Legacy Properties Sotheby's International Realty
207-230-1003
Slip away to Seabox Cottage, your ideal summer retreat or year-round haven. Reminiscent of the gracious turn-of-the-century summer homes of Dark Harbor, Seabox blends timeless craftsmanship with modern comfort. A long gravel drive winds through the wooded property and opens to sunny, landscaped gardens, arriving at a circular turnaround that welcomes you to the home's charming wraparound covered porches. Inside, the home offers elevated views of East Penobscot Bay from both levels. At the heart of the first floor is an open-concept living space anchored by a stunning stone fireplace. The well-appointed cook's kitchen with pantry flows seamlessly into the dining and living areas, all opening onto porches with water and garden views. A separate room currently serves as a library and office, also with porch access, along with a full bath, mudroom, and laundry. An elegant window-lined staircase leads to a second-floor family room, where a wood stove adds warmth and character. On one side lies the primary suite, featuring a walk-in dressing room, separate closet, and luxurious bath with walk-in shower and soaking tub. On the other side are two additional bedrooms and a full bath. The property spans two parcels and includes two wells, two septic systems, a storage shed with electric car charger, and a designated area for RV or camper parking with water and septic hookups. Seabox offers both lifestyle and flexibility, enjoy it yourself, and when you're away, take advantage of its proven rental appeal. Ideally located near island amenities, library, public courts and fields, town center, trails, and beaches, it's a special place to relax, recharge, and enjoy the best of island living.
Courtesy: Camden Coast Real Estate
207-236-1111
This traditional extended Maine Cape is beautifully located on the north end of idyllic Islesoro Island, just a twenty minute ferry ride from the mainland in the seaside town of Lincolnville. Sited on just over an acre of land this property offers quiet and privacy while being easily accessible. Once a crafter's home this property has multiple spaces to live and entertain in while also offering a first floor living option. Being the new Steward of this unique property means rolling up your sleeves and getting to work. The ceiling on the second floor is in need of repair including exposed sub-flooring in some rooms and other cosmetic work needed. The results of the work to be done here are well worth the effort to make this property your next year round home or summer retreat.
Courtesy: Legacy Properties Sotheby's International Realty
207-230-1003
Rarely does a property like this become available in Islesboro's storied and much-loved summer colony, Sabbathday Harbor. Perfectly sited, up high on the shores of East Penobscot Bay, this classic cottage offers sweeping easterly water views extending to Cape Rosier and approximately 100 feet of bold, accessible shoreline. The first floor features a living room with a wood stove and doors that open to a spacious water view deck, a functional galley kitchen, and a full bath. The generous wrap-around deck provides the perfect vantage point for sunrise coffee, afternoon reading, or evening gatherings with the bay as your backdrop. Upstairs, three charming bedrooms capture the light and sea breezes. A separate simple structure could make for a fun getaway space. Steeped in tradition and rich in natural beauty, this property invites you to create lasting memories for generations to come in one of Maine's most cherished summer enclaves.
Courtesy: Berkshire Hathaway HomeServices Northeast Real Estate
207-338-3381
Nearly 3 acres on the tranquil island of Islesboro are now available. Property conveys partially furnished with a 8X12 cabin, 30X8 camper, storage and porta potty. Structures sit on a large cleared, flat and dry field with forest behind them. Many uses allowed. Enjoy as is to get away from it all, or build a beautiful new home, farm or run a business. Easy to build on. Electricity is in place and under ground. Conduit in place for broadband, which is at the road. Lot 4B on Islesboro tax map 30 to convey. Soil test now available.
Courtesy: Legacy Properties Sotheby's International Realty
207-230-1003
On an island in Maine sits this sweet cottage perched up from the water's edge with stunning westerly views. There is room to expand or build another dwelling. Explore 50 plus acres and over 2,000 feet of shore front and accessible beach. A portion of land abuts Islesboro Island Trust land. This property is also available as 3 separate parcels. See MLS 1633636, 1633637 & 1633638 for other property offerings.
Courtesy: Legacy Properties Sotheby's International Realty
207-230-1003
On an island in Maine sits this sweet cottage with room to expand or build on the elevated point looking West over Penobscot Bay. Explore 14 acres and 1,288 feet of shore front and beach. Additional property available. See MLS 1633635, 1633637 & 1633638 for other property offerings.
Courtesy: Legacy Properties Sotheby's International Realty
207-230-1003
East Bay is a lovely coastal estate, an ideal summer retreat and a serene sanctuary for year-round living. Privately sited on 5 plus acres with 430 feet of accessible, pristine waterfront, the property is gracefully perched above a scenic pristine shoreline, where lush gardens and thoughtful landscaping frame cinematic views of Penobscot Bay and the islands. The residence unfolds along a gently sloping bluff, capturing sweeping vistas from nearly every room and outdoor space. Originally constructed as a post-and-beam home circa 2000, East Bay has since undergone a series of thoughtful transformations. Its final form, guided by the timeless coastal architecture of Royal Barry Wills, seamlessly blends classic character with understated luxury. Gracious indoor and outdoor living spaces are designed for both grand entertaining and intimate gatherings, offering a harmonious balance of formal and informal areas. Highlights include a first-floor primary suite with private sitting room and office, multiple guest suites, sitting rooms, library, offices, a wine cellar, exercise room, updated systems, air conditioning, generator, and carport. The grounds are equally compelling: a heated pool, hot tub, and wood-fired sauna are thoughtfully positioned to take full advantage of the views, while a custom-built staircase provides direct access to the private beachfront. The result is a property that evokes the spirit of Islesboro's historic Summer Cottages. Located just south of the island's storied Dark Harbor Village, East Bay is a true legacy estate, an extraordinary fusion of Maine's rugged coastal beauty and enduring craftsmanship. View our 3D Tour and Floor Plans for a fully immersive experience.
Courtesy: Cates Real Estate
207-701-5600
Plum Point Cottage: Contemporary Island Home set on a hill with Breathtaking Ocean Views. Wake up to island life at Plum Point Cottage, a coastal retreat designed by Architect Christopher Glass. With 400+/- feet of rocky waterfront, this contemporary island setting offers stunning sunrises over Bounty Cove and Penobscot Bay from your private deck. The first floor welcomes you with a small mud room and features an open-concept kitchen and dining area with new marble tile floors, a living room with built-ins, and a mechanical room with laundry. Enjoy more ocean views from the spacious second floor including a family room with more built-ins and a wet bar and two bedrooms with a full bath. Watch the moon rise though the 'moon window' during the winter solstice; the moon light will shine through and fill the foyer with light. Enjoy star gazing at night through the sky lights and Venus rising in the morning. The sun deck matches the roof line providing full shade during the summer solstice. A detached two-car garage with new garage doors provides ample space for cars, small boats or a workshop, with stairs leading to a large unfinished storage area above. Rest easy knowing that the roof on the house and garage was recently shingled, the exterior of both buildings was vapor blasted and painted, all new PDQ doors and Marvin windows have been recently installed along with 3 new insulated garage doors. The house is well insulated with walls that are 1 foot think. This 2.7+/- acre property has a natural landscape inner mixed with the remains of old cutting gardens above the rocky coastline and a private beach, offering your own island escape. Stay connected with 1 gibibyte upload and download speed fiber optic internet. The beautiful island of Islesboro is a 20-minute ride from the mainland town of Lincolnville, accessed by a public car ferry, water taxi or private boat or small airplane.
Courtesy: Legacy Properties Sotheby's International Realty
207-230-1003
This property offering includes an historic Arts and Craftsman-style Foursquare house - thought to be one of the first houses built in Dark Harbor - set on a sunny and open lot, as well as an additional vacant wooded lot both, just a short walk from the charm and amenities of Dark Harbor Village, Gilkey Harbor, and scenic Kissel Point. Brimming with original character and island warmth, the residence offers the best of both community connection and personal retreat. Ascend granite steps and enter through the welcoming formal front door beneath a gracious covered porch, perfect for waving to neighbors or enjoying a quiet cup of coffee. Inside, a central hall anchors the home, with a lovely parlor and dining room on one side, and a cozy study, powder room, and laundry area on the other. The kitchen, complete with pantry, is located to the center rear of the house, adjacent to a small sunlit room which leads out to a back deck, an ideal spot for relaxed outdoor dining. There is also a mudroom that opens to the covered back porch. The second floor includes three bedrooms and a full bath. An additional flexible use room has a staircase to a spacious, unfinished attic which offers expansion potential and includes glimpses of the water. The detached barn is closely adjacent to the house and is suitable for storing outdoor furniture. Located close to many of the island's year-round activities, including community center, gym, and school. Offered partially furnished. Also available with less acreage see MLS 1639455. In addition to this property offering, if you are looking for a larger property or guest accommodations, consider an abutting property at 108 Colony Road which is also for sale. See MLS 1628467
Courtesy: Legacy Properties Sotheby's International Realty
207-230-1003
This delightful cottage is set on a sunlit lot within walking distance of Dark Harbor Village, Gilkey Harbor, and scenic Kissel Point. Enjoy soaking up Summer days on the deck surrounded by honeysuckle, peonies, and mature rhododendrons and playing out on the lawn. Inside, are cozy living spaces with a bedroom tucked upstairs. A detached storage shed provides convenient space for garden tools and gear. Located close to many of the island's year-round activities, including community center, gym, and school. Offered mostly furnished. In addition to this property offering, if you are looking for a larger or compound-style property, consider the abutting property at 115 Babbidge Road Road which is also for sale. See MLS 1628468
Courtesy: Island Property
207-734-8809
Little Broad Cove, Guinea, Islesboro. Easterly water views like you read about. Three bedroom yearround home with guest shore cottage across the road. Beautifully landscaped grounds, raised beds and sunny open yard with 138 feet of shorefront. Large living room and primary bedroom. Generous open decks. Both structures will need attention. Being sold ''as is''. Walk to the Historical Society, town tennis courts, and library. Short drive to town with market, post office, garage, and community center. Central to all your needs and activities. This is a handy home in a cherished enclave. $675000.
Courtesy: Island Property
207-734-8809
East Shore Drive, Islesboro. Dark Harbor Village north along the shore dotted with grand waterfront summer cottages to your private haven. You will have your breath taken away as this stunning wildflower meadow reveals an unsurpassed view of the ocean and possibilities. 15 parkland acres edged with woods and 770 feet of bold shorefront and beach comprise commanding hillside building sites, deepwater dock, immaculate five-bedroom year-round primary or guest cottage ideal for entertaining with its expansive deck and meticulously landscaped grounds and thoughtful accents anchoring your environ to the highest expectation. Enjoy views of Charlotte's Cove with abundant wildlife activity. Watch eagles, osprey, otters, seals and fish from your porch perch. $3,950,000.
Courtesy: Berkshire Hathaway HomeServices Northeast Real Estate
207-338-3381
If waking up to the sunrise glimmering off of the Atlantic Ocean is how you want to start your days or are looking for a great investment, this waterfront property with elevated and easterly views of the Penobscot Bay located on the very desirable East Shore Dr. in Islesboro checks all the boxes! With a beautiful and modern Den Outpost cabin, this property is ready to put the final touches on. Electricity and 1-gigabit state-of-the-art fiber broadband Internet are available right at the road. Islesboro is just a short 20 minute ferry ride from Lincolville and has markets, a new health center, community center, beaches and much more. You and your guests will be able to work from home or enjoy your peaceful vacations soaking up the ocean views. This is an unfinished cabin. Approved septic design attached.
Islesboro is located in Maine. Islesboro, Maine has a population of 600. Islesboro is more family-centric than the surrounding county with 28.81% of the households containing married families with children. The county average for households married with children is 23.46%.
The median household income in Islesboro, Maine is $67,813. The median household income for the surrounding county is $59,880 compared to the national median of $69,021. The median age of people living in Islesboro is 62.3 years.
The average high temperature in July is 77 degrees, with an average low temperature in January of 7.7 degrees. The average rainfall is approximately 48.7 inches per year, with 59 inches of snow per year.
