Waterfront homes for sale & real estate in Islesboro, ME

Waterfront Home for sale in Islesboro, ME:

Escape to an island, down a wooded road to this secluded seasonal cabin retreat, set on over 10 acres with sunset views. View our video for a more immersive experience!

Waterfront Home for sale in Islesboro, ME:

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

Waterfront Home for sale in Islesboro, 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

Waterfront Home for sale in Islesboro, ME:

East Bay is a lovely coastal estate, an ideal summer retreat and a serene sanctuary for year-round living. Privately sited on 5 plus acres with 430 feet of accessible, pristine waterfront, the property is gracefully perched above a scenic pristine shoreline, where lush gardens and thoughtful landscaping frame cinematic views of Penobscot Bay and the islands. The residence unfolds along a gently sloping bluff, capturing sweeping vistas from nearly every room and outdoor space. Originally constructed as a post-and-beam home circa 2000, East Bay has since undergone a series of thoughtful transformations. Its final form, guided by the timeless coastal architecture of Royal Barry Wills, seamless