Islesboro, ME homes for sale & real estate

Islesboro, ME Homes for Sale

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

Islesboro, ME Homes for Sale

Tucked away on two serene acres along Islesboro's northeast shore, this beautifully reimagined coastal cottage captures the essence of Maine island living. With sweeping views over East Penobscot Bay, the property blends timeless charm with modern comfort in a way that feels effortless. Originally built as a simple ''Maine camp, '' the home has been expanded and refined into a warm, year-round retreat. Inside, the single-level layout flows easily from the open central living area to the glass-walled entryway and out to a covered porch overlooking the water. There are four comfortable bedrooms—including a cheerful bunkroom with built-in bunks—two full baths, and thoughtful touche

Islesboro, ME Homes for Sale

Quintessential coastal Maine island cottage with salt water views and beach access. Cozy year-round living with open concept kitchen and living room. Two bedrooms and 1½ baths. Many new improvements including new septic system, new south roof shingles, and exterior up-dates. Tax shown is for entire property. Tax for parcel to be conveyed will be far less, to be determined by assessor.

Islesboro, ME Homes for Sale

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