Islesboro, Maine listings for sale

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$6,500,000 - Islesboro, ME
399 Hermit's Point Road Islesboro, ME - 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. Enjoy these photos from sunnier times. $6,500,000.
1918 | 8 | 10 | 9,025 sqft.
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$1,500,000 - Islesboro, ME
863+867 Main Road Islesboro, ME - Own a part of Islesboro history! Durkee's General Store has been an integral part of island life serving the community for 70+ years. Currently run as a grocery store, Durkee's General Store offers groceries, meats, a deli section, a selection of prepared foods, produce, household and automobile items, beer, wine, hard alcohol, cigarettes, and lottery. The third and current owner has run a successful business for 35+ years and is ready to pass the torch to the next owner to continue to operate as a grocery store or whatever else your imagination can dream up! The store includes a full kitchen, for take out or options for a cafe and options for a seating area inside or outback of the store on the lawn. The large basement under the store offers storage. Included with the property is a house with a 3-bedroom 1-bath apartment with a large kitchen and living room that extends to a porch in the warmer months, all on the second floor. Plus a bonus room for an office, study or exercise room. Enjoy your coffee on the deck off the kitchen looking out over fields and forest. Below on the first floor is a two bay garage that historically was the home of the fire station. Keep them as a garage or convert them to more retail or living space. Next to the garage bays is what could be a 1 bedroom 1 bath apartment or the first floor/family room for the upstairs. The bathroom plumbing has been roughed in and partially completed. The two living spaces could be combined with a staircase or kept as separate units. Set on a combined 17.3± acres, there is parking on 1± acres on the west side of the road, which also includes a fire pond. The store and house sit on 16± acres on the east side of the road, which is a mixture of field and forest. Stay connected with 1-gigabyte connection speed internet. Endless possibilities await the next owner! Also listed as commercial, see mls: 1575437. International 4700 freight truck and store equipment included with sale.
1950 | 3 | 1 | 5,592 sqft.
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$975,000 - Islesboro, ME
101 & 107 Derby Road Islesboro, ME - Iconic and Historic Dark Harbor Village Prime Real Estate. Two lots, two buildings 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 living space upstairs, even a harbor view from the widow's walk and the former Blue Heron Restaurant with 3,000 sq ft retail or residential space up or down. Restaurant will need significant improvement. $975,000.
? | 5 | 2 | 7,500 sqft.
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$899,000 - Islesboro, ME
1159 Main Road Islesboro, ME - Oceanfront retreat includes 17 acres with incredible views and 700 feet of sandy beach! Seller approved special financing is available on what was once known as The Bluff House, a former Sea Captain's House. This 1800's, 4 bedroom, 3 bath property has many renovations and updates complete with new birch flooring, new structural support system under the kitchen, new lighting in the kitchen and bathrooms, and new plumbing stubbed and ready to go. Currently the kitchen and two of the bathrooms are ready for your own touch! The large two car detached garage is completely floored upstairs and could be finished to be used as an office, guest suite or artist's studio. Islesboro is a hop, skip and a jump from the mainland with just a 20 minute ferry ride. One can enjoy the serenity of island life yet still be connected to the coastal towns of Maine. The Sea Captains house is an absolute gem that sits on the north side of the island where life is quiet and peaceful. Morning walks along the trails to the shore and then a walk about on the adjoining Hutchins Island Preserve offers a certain kind of serenity. Blueberry Hill Preserve and Pripet Riding Club are only minutes away. Islesboro offers a way of life that takes one back in time while having excellent fiber optic internet, two local stores and public and private ferry services. Come enjoy amazing open water vistas, watching sailing regattas and spending time on your own private beach.
1830 | 3 | 1 | 2,680 sqft.
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$850,000 - Islesboro, ME
292 + 300 Main Road Islesboro, ME - 292 + 300 Main Road are comprised of an elaborate, historical, federal style, island home and the former island schoolhouse that is currently used as an art gallery. The main house has an updated kitchen, a large dining room with original built-ins, a family room that could be a first floor bedroom, a formal living room with an ornate fireplace surround with a wood stove insert, a grand front hall, a large primary bedroom on the second floor with room to expand into a primary suite, and four additional bedrooms. The front porch is over 54 feet long and provides a place for quintessential Maine summer living. The post and beam shed is just steps from the house and could be used for storage or finished for guests or a work from home space. The school house is made up of two very large rooms - 858 and 528 square feet respectively. Both rooms have extremely high ceilings and windows almost as high that afford seasonal Atlantic Ocean views on the North side. There is a half bath on the first floor and a studio apartment with a full bathroom on the second floor and room for expansion. Both buildings are set on just under four acres, each with its own well and septic tanks but a shared leach field. The property is a Maine masterpiece waiting for your creative vision. The house foundation needs repair. The property is sold furnished and AS IS.
1887 | 5 | 3 | 4,962 sqft.
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$660,000 - Islesboro, ME
138 Hewes Point Road Islesboro, ME - The Artist Cottage is nestled unseen from the road on 1.5± acres with 150+/- feet of tidal waterfront on Islesboro Harbor offering stunning views of Islesboro Harbor, Bounty Cove and the narrows. This charming seasonal cottage is located in the desirable and seldom available mid-island neighborhood of Hewes Point, near Maddie Dodge Field, with tennis and pickleball courts at your disposal and the town library just around the corner. The cottage features approximately 768± total square feet, including a waterside screened-in porch and open deck where you can enjoy watching the sunset. The first floor includes an entry, first floor bedroom, a full bath with washer/dryer. An open floor plan with living room and wood fire stove, wraps around to a cottage kitchen. A heat pump provides modern comfort. The second floor offers a versatile open space with beds and a sitting area for reading or watching TV. The elongated rectangular lot includes a 12' x 8' storage barn with electricity that offers the potential for additional living space. Move-in ready, the Artist Cottage exudes quintessential Maine charm and is ideal for those seeking a peaceful retreat. The sheltered cove location allows for easy kayaking, beachcombing, and wildlife viewing. The additional barn and land offer expansion possibilities. Stay connected with fiberoptic broadband internet with 1 gibibyte connection speeds. 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.
1990 | 2 | 1 | 768 sqft.
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$625,000 - Islesboro, ME
1052 Meadow Pond Road Islesboro, ME - Welcome to your idyllic retreat on Islesboro Island, where this exceptional Cape-style farmhouse awaits. Set on the shore of Meadow Pond with 165 feet of pristine frontage, this home offers 0.94 acres of beautifully maintained grounds. Enjoy tranquil and impeccable gardens, thoughtfully designed landscaping, lush fruit trees, and charming garden walkways inviting you to explore your property. Step inside this home, which seamlessly blends vintage craftsmanship with modern comfort and amenities (GWI broadband). Special features include the kitchen with granite countertops and a large functional kitchen pantry, a living room with a gas fireplace, a sitting room, a dining area, a breakfast room, a sunroom, and an office. The sunroom, boasting a wall of glass windows, overlooks the deck and meadow leading to the pond, providing a serene spot for relaxation. The primary bedroom with a vaulted ceiling overlooks the meadow, meandering down to the pond's edge. The home has been meticulously cared for, showcasing numerous upgrades, including newer windows, an efficient heating system, updated electrical, and a recently replaced roof. The spacious deck provides a wonderful view of Meadow Pond, complemented by a large automated awning for shade and comfort. A one-car garage ensures ample storage, while low-maintenance vinyl siding keeps upkeep to a minimum. A newly built shed is ideal for a workshop or landscaping tools. This is more than just a home; it's a serene sanctuary on one of Penobscot Bay's most beautiful islands.
1840 | 3 | 2 | 2,800 sqft.
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$499,000 - Islesboro, ME
292 Main Road Islesboro, ME - Welcome to 292 Main Road, Islesboro, ME—a large five-bedroom summer retreat perfect for those seeking a blend of comfort and charm. This spacious house boasts an elegant new kitchen equipped for culinary adventures, and electric baseboard heat to keep you cozy during the cooler months. Imagine sipping lemonade on the expansive front porch, watching the day unfold on your picturesque front lawn with a swing in an ancient maple tree. Only a short stroll from the property, enjoy the local amenities that Islesboro has to offer, including the town library, tennis courts, and a new playground for endless family fun. Hughes Point beckons with its inviting public beach, promising sun-soaked days by the water. A convenient one-mile drive takes you to the Island Market, the Islesboro Post Office, and a gas station, ensuring all your needs are within easy reach. The community center, featuring an indoor exercise gym and delightful luncheonette, adds to the island's allure. Don't miss the exciting farmers vegetable market during July and August, where you can indulge in the freshest local produce. Call today, your idyllic island home awaits! The property is sold furnished and AS IS.
1887 | 5 | 2 | 2,409 sqft.
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$499,000 - Islesboro, ME
108 Derby Road Islesboro, ME - IMPROVED PRICE. NOW $499,000. Charming Dark Harbor Village 1940's Four-Bedroom Home on sunny .66 acre lot with large landscaped lawn and grounds. Historically welcoming, nine rooms comprise approximately 2,300 square feet of living space with primary first floor bedroom and ensuite full bath three bedrooms and full bath upstairs. Handsome beam work, rich finish trim, hardwood flooring, tiled kitchen floor and breakfast nook. Step out onto the open deck and covered porch and convenient car port and handy sheds. Just a stroll to shops around the corner and minutes from other activities.
1940 | 4 | 2 | 2,300 sqft.
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$450,000 - Islesboro, ME
300 Main Road Islesboro, ME - 300 Main Rd is the former Island schoolhouse that is currently used as an art gallery. It is made up of two very large rooms - 858 and 528 square feet respectively. Both rooms have extremely high ceilings and windows almost as high that afford seasonal Atlantic Ocean views on the North side. There is a half bath on the first floor and a studio apartment with a full bathroom on the second floor and room for expansion. The school house is being separated from the Main House and will convey with 1 +/- acre, each with its own well and septic tanks but a shared leach field. The property is a piece of Maine history and waiting for your creative vision. The property is sold AS IS.
1887 | 1 | 2 | 2,553 sqft.