Courtesy: Cates Real Estate
207-701-5600
Make summer memories at this seasonal cottage overlooking an expansive 1000+/- feet of waterfront along the East Penobscot Bay and with views extending towards Castine and Cape Rosier. The property includes a main cottage and a guest cottage that can also function as a boathouse. As if taken right off a sailing yacht, the open timber frame main cottage is efficient, comfortable, tastefully finished, and has the charm of being on a ship moored in a harbor. The galley kitchen offers ample storage and essential appliances for a summer feast. This sweet cottage also includes a living area, a bedroom with a closet, and a surprisingly roomy bathroom with a portable toilet. The waterside of the main cottage has floor-to-ceiling sliding glass doors to maximize the view, no matter the forecast. The sleeping loft features a porthole window and a banister reminiscent of a ship's stern rail. The deck has plenty of space for outdoor living and storage for small watercraft, and it is accompanied by an outdoor shower with on-demand hot water. The guest cottage/boat house has a king-size Murphy-style bed, its own bathroom with a composting toilet, and a sliding barn door for launching and storing small boats. The kitchen sink and both bathroom sinks have manual foot pumps to provide water. The property is mostly rocky coastline, inviting you to explore and beachcomb. A place to relax and enjoy the Maine summer with simplicity. Nearby public walking trails extend the outdoor space for exploring nature.
Courtesy: Warren Realty
207-734-8857
Welcome to 228 Gooseberry Point Road on the picturesque island of Islesboro. Located on over 5 private acres with 743 feet of frontage on West Penobscot Bay, the 4-bedroom house is in excellent condition with many recent upgrades including newly landscaped, whole-house generator, hot tub, delightful patio just 75± feet from the beach. Water view from every bedroom! Fully winterized, this home is move-in ready now and is a delightful home which will last for many years. Come and see it and imagine your own slice of out beautiful island.
Courtesy: The New England Real Estate Company, LLC
207-236-7000
Set on the peaceful north end of Islesboro, this exceptional waterfront property offers a rare combination of privacy, modern construction, and effortless access to the shore. With 5.77 acres and 262 feet of open shoreline, you can enjoy one of the island's most sought-after features: direct, stair-free access to the water, allowing you to walk right from your yard to the beach. Built in 2025, this beautifully crafted log-style home offers 2,200 square feet of thoughtfully designed living space. Cathedral ceilings and a dramatic wall of windows fill the open-concept kitchen and living area with natural light, creating a bright, welcoming atmosphere that brings the outdoors in, and opens to a covered back porch facing the shoreline. The first floor features two spacious bedrooms, including a primary suite with a walk-in closet and sliding doors that open to a screened-in porch, the ideal spot to relax and take in the coastal air. Upstairs, a large third bedroom with its own bathroom offers a private retreat for guests or family. Tucked at the end of a long private road, the setting is both quiet and secluded. A newly built detached two-car garage adds practicality and convenience, completing this turnkey island retreat. Offered at 1.7M USD, this property is a rare opportunity to own a newly constructed waterfront home in one of Islesboro's most peaceful and private locations. For those seeking additional space or a multi-generational compound, there is also the option to purchase the full 13-acre offering, which includes a separate, well-maintained 4-bedroom, year-round home, creating a truly unique and versatile coastal estate.
Courtesy: The New England Real Estate Company, LLC
207-236-7000
Set on the serene north end of Islesboro, this rare coastal compound offers the kind of privacy, flexibility, and natural beauty that's increasingly hard to find. With 13 acres, 525 feet of open shoreline, and direct, stair-free access to the water, this property stands apart from nearly every other waterfront offering on the island. The centerpiece is a stunning 2025 built log style home, thoughtfully designed with over 2,200 square feet of warm, inviting living space. Cathedral ceilings and a wall of windows flood the open kitchen and living area with natural light, creating an airy yet cozy gathering space. The first floor features two spacious bedrooms, including a primary suite with a walk-in closet and sliding doors leading to a screened-in porch, perfect for quiet mornings or summer evenings. Upstairs, a large third bedroom with its own bath provides a private retreat for guests or family. A detached two-car garage adds convenience and storage. The second home, built in 1968, is a well-maintained, year-round residence offering four bedrooms and two baths, all on one level. Full of character and functionality, it includes a charming bunk room with built-in beds and clever storage, making it ideal for hosting. A covered porch and waterside fire pit create easy spaces for relaxation and entertaining. Included are 10 fruit young trees and a new greenhouse, perfect for those looking to embrace a more self sufficient or garden focused lifestyle. Both homes enjoy fenced backyards with gated access to the beach. The setting is exceptionally private, tucked at the end of a long drive and bordered by conservation land. Whether you're seeking a multi-generational retreat, an income-producing opportunity, or a private island escape, this property delivers unmatched versatility. Offered as a complete compound or the 2025 home with 5.77 acres, (See separate listing )
Courtesy: Realty of Maine
207-338-6800
Set along the shore of Meadow Pond on Islesboro, this well-maintained Cape-style farmhouse offers 165 feet of frontage and 0.94 acres of beautifully landscaped grounds. The property features established gardens, fruit trees, and winding paths that create a peaceful, private setting. Inside, the home blends classic charm with modern updates, including state-of-the-art fiber broadband internet. The kitchen offers granite countertops and a spacious pantry, with multiple living areas including a living room with a gas fireplace, sitting room, dining area, sunroom, and a dedicated office. The sunroom is a standout space, with a wall of windows overlooking the deck, meadow, and pond. The primary bedroom features a vaulted ceiling and enjoys similar views of the landscape leading to the water. The home has been thoughtfully updated over time, with improvements including newer windows, an efficient heating system, updated electrical, and a recently replaced roof. Outside, a spacious deck with an automated awning provides a comfortable place to take in views of Meadow Pond. Additional features include a one-car garage, low-maintenance vinyl siding, and a shed ideal for storage or workshop space. Life on Islesboro is defined by its strong sense of community and natural beauty. This 14-mile-long island in Penobscot Bay offers a mix of year-round and seasonal living, with amenities including a community center, health center, K-12 school, and local businesses. Residents enjoy boating, kayaking, scenic walks, and seasonal events, all while remaining connected to the mainland via ferry from Lincolnville. A rare opportunity to enjoy waterfront living in one of Midcoast Maine's most distinctive island communities.
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.
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: 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. 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 1656320
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.
Courtesy: Cates Real Estate
207-701-5600
Built in 2004, ''Seabox Cottage'' is a graceful 3-bedroom, 3-full-bath home that offers elevated views of Islesboro Harbor and East Penobscot Bay. The home's Shingle and Colonial Revival design is based on 1894 plans by Fred L. Savage and Milton W. Stratton and intentionally echoes the design praised in 1895 as ''one of the prettiest cottages in town,'' nodding to the elegant turn-of-the-century cottages of Dark Harbor. When you arrive, the circular driveway, manicured gardens, and lawns complement the architecture. The home combines luxury and comfort, with radiant floors throughout, an impressive fieldstone fireplace in the first-floor living room, and a propane stove in the second-floor common room. The large chef's kitchen boasts soapstone countertops and sinks as well as a Viking range. The sunroom, perfect for dining, relaxing, or an office with a view, blends indoor and outdoor life as it flows out to the wrap-around, columned porch. The primary bedroom suite is a private sanctuary with a large ensuite bathroom featuring a luxurious soaking tub with a view and a spacious floor-to-ceiling tile shower. The suite includes an adjacent flexible space, ideal for a dressing room, workout room, or other use. Off the kitchen is a combined mudroom, laundry, and pantry. The property includes a garden shed with an electric car charger next to a dedicated space for an RV or camper. Comprised of 2 lots, it is served by 2 wells and 2 septic systems and boasts a proven rental history.
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: 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: Cates Real Estate
207-701-5600
Discover Mill Creek Cottage: Watch the Mill Creek rise and fall from this private 1.92± acre property with 200'± of waterfront on Mill Creek, offering stunning views of Broad Cove and Gilkey Harbor. This year-round, 3-bedroom, 2-full-bath, cedar-shingled, cape-style cottage is elevated above Mill Creek, with a commanding view over the water. The property welcomes you with a long driveway that leads your eyes to a scenic waterfront. Conservation land frames the right side of the view, protecting it in perpetuity. The western exposure provides stunning sunsets. Interior highlights include a spacious first-floor primary bedroom with an adjacent full bathroom and a comfortable living room with a wood-burning stove. Outside, an open deck and a covered porch are ideal for seasonal enjoyment, and a detached garage is off the driveway. There is a new storm door, and most of the rooms have freshly primed or painted walls and ceilings. The property is close to the ferry and downtown Islesboro activities. Stay connected with fiber-optic broadband internet with 1 gigabit connection speeds. Islesboro is a 20-minute ride from the mainland town of Lincolnville, accessed by a public car ferry, water taxi, private boat, or small airplane. Open house Friday May 8th 3pm- 4:30pm
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
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. Lease in place from June 15- September 15 2026.
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: 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: 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: LandVest, Inc.
207-236-3543
Located on 22.21± secluded acres up-island on Islesboro, Longmeadow Farm is an exceptional waterfront estate with southwesterly views across Seal Harbor and Penobscot Bay towards the Camden Hills. Custom-designed by the current owners in collaboration with top professionals, the main residence blends the understated elegance of Shingle-style architecture with meticulous, modern craftsmanship. Showcasing refined coastal living, the home features impeccable attention to detail, from luxurious natural materials to seamless indoor-outdoor transitions—all intended to blend with the surrounding landscape. An open main floor plan combines comfort and elegance, with rooms appropriate for larger gatherings while others are designated for intimate family settings. Six well-appointed bedrooms, including a main-floor primary bedroom suite, provide comfortable and private accommodations. There is also a three-car garage with a two-bedroom caretaker's apartment above it. The property's landscape features manicured lawns, mature gardens, gently rolling fields, wooded areas, and a historic pastoral lane that winds through the land. 2,695± feet of shorefront varies from sheltered coves, pebble beaches, granite outcroppings, and there is a deep-water dock with a ramp and float for direct access to the bay and the mainland. The property is subject to a Conservation Easement held by the Islesboro Islands Trust to protect the land's natural beauty.
Courtesy: LandVest, Inc.
207-236-3543
1588 Turtle Head Road is a premier waterfront retreat with stunning western views across Turtle Head Cove and Penobscot Bay, back towards Belfast and the Camden Hills. The property includes a beautifully renovated mid-century modern home with two bedrooms and a spacious, open floor plan designed to capture natural light and maximize the water views. There is also a versatile garage/barn with a fully redone one-bedroom guest apartment above, perfect for hosting extended family and friends. Recent improvements can be found throughout the property, including a new sauna, and it has been very well-landscaped with lawn and gardens, professional stonework, and 328± feet of shorefront with a sand and pebble beach area. An all-new, granite deep-water pier with three moorings - a two ton, a four ton, and a six ton appropriate for a 100-foot sailboat - make this an ideal island retreat with convenient access to the mainland and the excellent boating in Penobscot Bay.
Courtesy: Island Property
207-734-8809
Iconic and Historic Dark Harbor Village Prime Real Estate in the heart of summer community and activity. Peg's Giftshop with 1,700 sq ft of retail space and 2,800 sq ft of residential space upstairs with three bedrooms, kitchen, living/dining room, full bath and third level apartment with full bath, even a harbor view from the widow's walk. Cedar shingles, apple and cherry trees, pleasant side yard. Will need attention so roll up your sleeves for an excellent housing and business opportunity. $495,000.
Courtesy: Island Property
207-734-8809
The Grace Cottage, Hermit's Point. This magnificent stuccoed Renaissance Revival cottage built in 1918 designed by noted Philadelphia architect, Wilson Eyre commands unsurpassed views from its 8.8 acre peninsular location and 3,570 feet of shore line. Eight bedrooms, seven fireplaces. Replete with all the requisite amenities for an elegant summer's stay including pool, dock and stone lodge. $6,500,000.
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.
