Homes with a View for Sale in Deer Isle, ME

Home with View for sale in Deer Isle, ME:

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 crafts

Home with View for sale in Deer Isle, ME:

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 pr

Home with View for sale in Deer Isle, ME:

Quintessential Maine magic! This early 1900s seasonal cabin has been thoughtfully expanded over the years and is perched on rocky headlands overlooking Blue Hill Bay. The four-bedroom, one-and-a-half-bath main cabin offers extraordinary views and generous living space, including a gracious dining room and a newer section with electric radiant heat and a beautiful stone fireplace. Set on more than three acres, the property also includes four additional buildings. One is an insulated one-bedroom guesthouse with a bath and kitchen that could potentially be winterized. Another, known as the Tea House, is a versatile studio space with many possibilities. The two-car garage is set back near the

Home with View for sale in Deer Isle, ME:

Tucked into a private 20-acre setting on Caterpillar Hill, this contemporary home was designed to bring in natural light and capture views of the fields and Eggemoggin Reach. Built in 1990 by Michael Hewes, the property offers over 3,800 square feet of finished living space across three levels, including a spacious recreation room with walkout access. The first floor includes a large eat-in kitchen, open dining area, and adjoining living and family rooms, each with generous windows, wood floors, and fireplaces that add warmth and character. A first-floor bedroom and bath provide flexible living options. Upstairs, the primary suite includes a beautiful full bathroom and large walk-in closets

Home with View for sale in Deer Isle, ME:

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 f

Home with View for sale in Deer Isle, ME:

3 bed/2bath home on nearly 2 acres in a fishing community in Stonington. This home has a large, private yard with drive thru right of way. The house features a new kitchen, new appliances, and new windows. Needs some finish out of trim, etc. One of the few affordable homes on the Island.