Islesboro, Maine Homes for Sale

MLS Number 1495138

• Residential
• MLS Status Active
• Address 135 Shore Drive
• Location Intown
• Bedrooms 9

Prominently sited on 18.5+/- acres with 955+/- feet of varied shorefront on Gilkey Harbor and stunning views to the west, the Sears Cottage is one of the grand historic Islesboro estates constructed at the turn of the 20th century. The nine-bedroom, nine-bath home also includes staff quarters, a carriage house / stable, reading room, and substantial deep-water dock with floats. The residence, characteristic of the Renaissance Revival Style, has been thoughtfully restored and retains many original details such as eleven wood-burning fireplaces and fine woodwork throughout. The grounds are those of a classic Maine summer estate: artfully landscaped with lawns, flowering shrubs, specimen trees, and both formal and informal gardens interspersed with natural Maine woods.

Listed by LandVest, Inc.

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 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 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 1489232

• Residential
• MLS Status Active
• Location Near Town
• Bedrooms 4
• Bathroom 4

A fantastic opportunity to own what was once called the most expensive home in Maine for a fraction of the cost to build! Previously featured in Portland Press Herald & Boston Globe, this masterpiece of architectural and landscape design is set on very private 16 acres with 1,000 feet of bold ocean frontage. Built with loving care and enthusiasm, the estate took over 10 years and a reported $17 million to complete, furnished with antiques and fine art from around the world.Set on a cliff with a 180 degree view of Penobscot Bay, you have unobstructed view of the islands off the coast. Even Cadillac Mountain on MDI can be seen to the East. The US Geodetic Survey set a marker here where they mapped the coastline.Inside the 4 bedroom, 4 bath post & beam home is a symphony of wood including Red & White Oak, Mahogany floors and accents of Brazilian Cherry, Purple Heart & Ebony. As you enter, your eyes are drawn up 3 floors to the curved upper floors, reminiscent of decks of the iconic 1930's ocean liners. The hand crafted stairs are outfitted with bronze posts, mahogany handrails & stainless steel safety lines like a classic yacht. Venture down the spiral staircase to the sitting room adjacent to the wine cellar. Or the granite encased stairway lit by an antique Fresnel lens which leads to submarine doors from Bath Iron Boatyard.Abrams Mountain is located on Islesboro, a renowned island off of the coast of Maine, and a retreat for various celebrities such as John Travolta and Kirstie Alley. A charming, historic place where you will feel at home and there are ample opportunities to walk or bike the area. Abrams is just 3 hours from Portland or 4 1/2 hours from Boston, including the enjoyable 20 minute ferry ride from Lincolnville! If you have access to a private plane there is even an airport for convenient access.The estate is being sold fully furnished and with an impressive assortment of fine art & antiques including 2 restored, antique Steinway pianos.

Listed by Acadia Cornerstone Real Estate, LLC

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 1493410

• Residential
• MLS Status Active
• Address 1317 Trim Lane
• Location Other Location
• Bedrooms 2

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 the nearly 50 private acres of woods, trails and easy access to over 2,100 feet of shore front and beach. A portion of land abuts Islesboro Island Trust land.

Listed by Legacy Properties Sotheby's International Realty

MLS Number 1496328

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

Year-round cottage overlooking Penobscot Bay. Located near Turtle Head Preserve this property has nearly 5 acres and over 300' of shoreline frontage with a panoramic view and breathtaking sunsets.The first floor has a master en suite with soaking tub. There are vaulted ceilings and ocean view windows in the master bedroom, library, dining and living room. The first floor also has an open kitchen, full bath and laundry area.The second floor has two bedrooms and a full bathroom. One bedroom feature's a queen size built-in ''Captain's Bed''. A spiral staircase will lead you to the third story ''Crow's Nest''. This popular room has a 345 degree view, a wet bar and is currently used as a fourth bedroom.The house has a FHW baseboard heating system plus a portion of the downstairs has a heat pump with air conditioning. Also included is a wood stove, automatic generator and 1GB fiber optic internet service.There is a separate garage with a loft and generous storage space. The large yard features a high bush blueberry grove, fenced in garden area and flowering bushes.The home is being offered furnished, giving you the opportunity to move in, relax then decide how to add your personal signature.Please see our Video, 3D Tour, and floor plans as well.

Listed by Legacy Properties Sotheby's International Realty

MLS Number 1496928

• Residential
• MLS Status Active
• Site Features Level,Open,Wooded
• Bedrooms 4
• Bathroom 2

This lovingly restored and expanded Maine cottage, situated on eight+ acres on the northeast shoulder of Islesboro, boasts a spectacular view across East Penobscot Bay. The house is a perfect island getaway--and because it's fully winterized, it's a charming year-round home. Recent updates of this 1950's ''Maine camp'' have retained the rustic charm of the original structure while adding modern features and living spaces to make it a place you'll never want to leave.The cottage has a central and open living space. There is an outdoor porch overlooking the bay. An enclosed potager garden is tucked behind the house, yielding herbs and vegetables. There is a master bedroom, two cozy bedrooms with wonderful views of the water, and a bunkroom with four built-in bunkbeds, ideal for children of any age. There are two bathrooms. There is an all-glass mudroom/entry foyer, and a washer/dryer. High-speed (1GB) internet. Pripet Woods Lane is a private road with almost no traffic. The beach is perfect for strolling, beach-combing, wading, and harvesting clams and mussels. A stone patio and fire pit on the bluff above the 120'-long seawall overlook the bay. Lovely flat rocks on Islesboro Island Trust property around the corner of the cove are a natural picnic spot.Boaters will love this home. Castine Harbor is 12 minutes from the mooring by motorboat and 30 minutes by kayak. Belfast is 20 minutes, Deer Isle is 30, and an hour away through Eggemoggin Reach lies Southwest Harbor and Mt. Desert Island. This home has one of the very few beaches suitable for launching boats, an ideal spot for sailors and motorboaters. You can paddle out to buy fresh lobster as local fisherman haul their catch from the several pots in the cove.The house is mirrored by a more recently constructed boathouse/workshop equipped with hoists to lift four kayaks and a canoe or small sailboat up to a high ceiling. The builder confirmed the boathouse could be converted to a Tiny House with a loft.

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 1490843

• Residential
• MLS Status Active
• Address 1058 Main Road
• Location Interior Lot, Rural
• Site Features Level,Open

Immaculate 4-season home with open concept. Perfect retirement home with plenty of room for guests or grandchildren. Very reasonably priced. Lots of room for expansion, gardening, etc. Very well-built by local contractor.

Listed by Warren Realty

MLS Number 1493131

• Residential
• MLS Status Active
• Address 112 Church Turn Road
• Bedrooms 4
• Bathroom 2

Four bedroom, two bathroom year-round home with many extras, including 14KW diesel generator. Two recently rebuilt decks looking out over a large lawn and a view of Meadow Pond. Three bedrooms and a bathroom upstairs and master bedroom and bath downstairs along with a mud room, sun room, dining room and kitchen. Full unfinished basement. House is set up with high speed fiber optic broadband internet connection.

Listed by Warren Realty

MLS Number 1493133

• Residential
• MLS Status Active
• Address 118 Church Turn Road
• Location Interior Lot, Rural
• Site Features Level,Open

First floor is over-sized 2-car garage, full bath, and office. Second floor is expansive 2-bedroom, 1-bath apartment - all with radiant heat. Great opportunity for a rental income property, guest house, or in-law apartment. Lots of opportunity here!

Listed by Warren Realty