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. $6,500,000.
1918 | 8 | 10 | 9,025 sqft.
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$3,950,000 - Islesboro, ME
118 E East Shore Drive Islesboro, ME - 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.
1972 | 5 | 4 | 2,400 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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$1,400,000 - Islesboro, ME
219 Willis Lane Islesboro, ME - Meadow Pond Road A-Frame with approximately 500 feet of waterfront on 20 acres of gently sloping hard and soft wood forest. Fabulous gravel beach, sweeping westerly Penobscot Bay ocean views. Gorgeous sunsets and vistas. Private gravel drive in excellent condition. Lush ferns abound. 2500 square feet living space in A-frame and two-story addition will need finishing. Natural openings looking to the bay provide additional attractive building site possibilities. A-Frame opened up back to the studs. $1,400,000.
1964 | 3 | 1 | 2,690 sqft.
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$884,000 - Islesboro, ME
1159 Main Road Islesboro, ME - Oceanfront retreat includes 17 acres with incredible views and 700 feet of sandy beach! 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 | 4 | 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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$760,000 - 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 (101 Derby Road) 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 (107 Derby Road) with 3,000 sq ft retail or residential space up or down. Restaurant will need significant improvement. $760,000 together or $525,000 for 101 Derby; $265,000 for 107 Derby.
? | 5 | 2 | 7,500 sqft.
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$595,000 - 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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$525,000 - Islesboro, ME
101 Derby Road Islesboro, ME - 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 loft with full bath, even a harbor view from the widow's walk. Cedar shingles, apple and cherry trees, pleasant side yard. $525,000.
? | 4 | 2 | 4,500 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.