Islesboro, Maine Homes for Sale

MLS Number 1482305

• Residential
• MLS Status Active
• Address 299 Drexel Lane
• Location Rural
• Bedrooms 20

As featured in Architectural Digest, this classic 20+ bedroom shingle style home has been beautifully maintained and totally redecorated by the current owner. Set privately at the north end of Islesboro island, this remarkable home was built in 1903 and is made up of 4 lots and over 48 total acres of spectacular oceanfront land including a deep water dock on Sabbathday Harbor. The land, which is partially in conservation with the Islesboro Island Trust, includes wonderful open fields with ocean views, walking paths through the woods down to the shorefront, beach and open ocean access, garden areas, and a majestic approach up a tree covered winding gravel road. The house is perfectly designed to accommodate large groups of friends and family, but cozy enough for single family living. There are great entertaining spaces including a large fieldstone fireplace in the living room, a fantastic custom built bar area, a great dining room with a fireplace, a large and well equipped kitchen with a walk in refrigerator and fabulous pantry area. There is also an office and laundry room on the first floor. The second floor features the master bedroom suite with its own private sun porch, and full bathroom with a claw foot tub and separate shower, as well as 14 additional bedrooms and 4 additional full bathrooms. The entire third floor of the home is a magical children's space complete with four separate themed bedrooms and a full bathroom, a school house, a library, a diner, play equipment, and a built in stage with props for endless entertainment. There are two large sun porches, and a sunny back deck overlooking an in ground swimming pool. There is also a detached barn for car storage. This is a one of a kind property.

Listed by Legacy Properties Sotheby's International Realty

MLS Number 1483182

• Residential
• MLS Status Active
• Location Other Location
• Site Features Open,Well Landscaped
• Bedrooms 6

Located south of Dark Harbor Village with stunning views over East Penobscot Bay, East Bay is a beautifully designed and skillfully crafted waterfront home built in the tradition of a grand coastal Maine estate. Privately sited on 4.2+/- acres with 390 +/- feet of shorefront, the residence was first built in 2000 as a large post-and-beam barn with an apartment. It was expanded two times, the final renovation and redesign based on the architecture of Royal Barry Wills, and the year-round house now features over 10,000+/- square feet of living space with six bedrooms, including a main floor master suite. The residence is open and inviting with elegant living spaces defined by high ceilings, multiple fireplaces and exposed-wood beams that capture the essence of a historic Islesboro summer cottage with contemporary amenities. The landscape combines formal gardens with fields of wildflowers and the broad views encompass the islands of the eastern Bay, North Haven and the open ocean to the south.

Listed by LandVest, Inc.

MLS Number 1479290

• Residential
• MLS Status Active
• Address 267 Shore Drive
• Bedrooms 12
• Bathroom 6

The Devereux Cottage is a historic waterfront property on Islesboro occupying 4.39+/- acres with 359+/- feet of shorefront and excellent western facing views over Gilkey Harbor to Penobscot Bay and the Camden Hills. Built in 1917, this seasonal residence exhibits many original details such as exposed wood beams, arched doorways, fireplace mantels and a unique staircase that all work together to create interesting and appealing historic character. The house has a total of twelve bedrooms - a master, six spacious guest bedrooms and five smaller bedrooms - and over 7,000+/- square feet of living space. Most of the rooms have excellent water views and there are seven wood-burning fireplaces throughout the home. The landscape includes well-maintained lawn with beautiful flowering gardens and stonework; and there is a brand new 150+/- foot deep-water pier with a ramp and float on Gilkey Harbor. The 4.39+/- acres includes 2.2+/- acres on the water with the house and 2.19+/- acres of undeveloped land on the other side of the road that promotes privacy.

Listed by LandVest, Inc.

MLS Number 1279536

• Residential
• MLS Status Active
• Address 117 Jetty Road
• Bedrooms 9
• Bathroom 10

Prominently sited on a scenic knoll surrounded by a multitude of gardens, the centrally located Dark Harbor House is a stunning example of Colonial Revival architecture designed by Fred Savage and built in 1896. In 2011/12 the current owners commissioned a complete restoration / renovation starting with a new foundation and ending with top period furnishings and landscaping - an authentically restored 125-year old house that is built to the most modern standards with new electrical, plumbing, security, gigabit internet and more. The commanding historic residence features views of the iconic Dark Harbor to the north, and to the west 196 feet of waterfront on Ames Cove includes a gravel beach and a six-kayak storage rack with custom launch system providing access to excellent kayaking in the picturesque Gilkey Harbor. In addition to some of the highest internet speeds in Maine, Dark Harbor House has access to an extensive on-island education system including the Islesboro Preschool (birth to 5) and the Islesboro Central School (K-12).

Listed by LandVest, Inc.

MLS Number 1368551

• Residential
• MLS Status Active
• Address 134 Big Tree Lane
• Bedrooms 5
• Bathroom 5

This picturesque, year-round waterfront home is nestled on the sought after island of Islesboro. It is privately set on 7+ acres, w/ 650 ft. of varied shorefront, a deep water dock in protected Seal Harbor, and thoughtful landscaping w/ views across Penobscot Bay to the Camden Hills. This home was custom-built to the highest standards, and exemplifies exquisite form and function, allowing for smooth transitions among the gracious formal and casual informal living and entertaining spaces, indoors and out. This home offers a generous master bedroom plus 4 additional bedrooms, some w/ windows seats, a sitting room w/ balcony, covered porch and screened porch, a greenhouse, sunroom, a library w/ wood burning fireplace and hand-built custom shelves and cabinets, living room w/ wood burning fireplace, a formal dining room w/ custom built-lighted shelving, and kitchen w/ an AGA stove. Additional amenities include home office, laundry room, radiant heat, whole-house generator and 2-car garage.

Listed by Legacy Properties Sotheby's International Realty

MLS Number 1471962

• Residential
• MLS Status Active
• Address 447 Ferry Road
• Location Rural
• Site Features Well Landscaped

Do you enjoy hiking, biking, kayaking, boating or hanging out on the beach? How about just peaceful mornings soaking up views of the ocean or early evenings having a glass of wine while watching spectacular sunsets over the bay? Do you collect sea glass - how much better from your very own beach? Or, are you simply looking to get away from the city?? This privately situated, year-round home on the coast of Islesboro facing the Penobscot Bay with 3 spacious bedrooms, a potential 4th large bedroom, 3 full baths (one on each floor), first floor living, xlg windows throughout so you never miss views of the bay, over 200ft of direct waterfront, possibility of having your own deep water dock is just what you need to enjoy vacations with your family and friends or peaceful year-round living. Also makes a great investment property. Only 3 miles off the coast of Lincolnville, a 20-minute ferry ride makes it easy to visit Camden, Belfast, and Rockport, as well as access airports in Bangor and Portland. This might be an island, but it has everything you need: broadband internet, a highly-rated school, markets, cafe, fire/police depts, and a health center with on-call staff. Islesboro is a welcoming, caring community that it is easy to live on and work from. FaceTime and Zoom showings always available.

Listed by Berkshire Hathaway HomeServices Northeast Real Estate

MLS Number 1486062

• Residential
• MLS Status Active
• Site Features Level,Open,Wooded
• Bedrooms 3
• Bathroom 2

Splendid Turtle Head sunsets from this three-bedroom year-round home on dramatic shore front and beach on the quiet end of Islesboro. Sited on double lot with two-car garage, and sugar shack. Open water views framed by mature oaks, lawn right to the shore. Massive fireplace and cathedral ceilings, hardwood flooring, window walls, two fullbaths. Well worth freshening.

Listed by Island Property

MLS Number 1467325

• Residential
• MLS Status Active
• Location Interior Lot, Rural
• Bedrooms 4
• Bathroom 2

This listing is for two houses! The main house is a four-bedroom, two-bathroom year-round home with many extras, including a 14KW diesel generator. Two recently rebuilt decks looking out over a large lawn and a view of the Meadow Pond. Three bedrooms and a bathroom upstairs, master bedroom and bath downstairs along with a mudroom, sun room, dining room, living room and kitchen. Full unfinished basement. House is set up with high speed fiber optic broadband.In addition to the main house, there is a 42X30 building on a separate driveway. This contains an over-sized two-car garage, full bath, and office on the first floor and expansive two-bedroom, one-bathroom apartment on the second floor - all with radiant heat. Great opportunity for a rental income property, guest house, or in-law apartment. Owner will consider sale of two houses together or separately, as they are on separate lots. The opportunities of this property are endless.

Listed by Warren Realty

MLS Number 1483968

• Residential
• MLS Status Active
• Bedrooms 2
• Bathroom 1
• Rooms 5

Crow's Nest is a delightful two-bedroom year-round home located in quiet north Islesboro and sited on two gentle hillside acres looking across to Meadow Pond. Large sunny open combination living-dining-kitchen area perfect for family enjoyment. Spacious master bedroom with cathedral ceiling and fan, cozy guest bedroom, and bright large bathroom finished with rustic pine paneling. 400 square foot cedar deck for relaxing and dining or morning coffee. The carefully restored and fully furnished cottage is wonderfully private with a sea of green around it and has high-speed state-of-the-arts fiber-optics Internet. Excellent seasonal and year-round rental income history.

Listed by Island Property