Luxury homes for sale & real estate in Deer Isle, ME

Luxury Home for sale in Deer Isle, ME:

Discover a unique opportunity in Mid-Island Islesboro, where history and potential converge in two remarkable buildings on one property. The Schoolhouse (300 Main Road): This was formerly the Pendleton School, Islesboro's main elementary school until the early 1950s. Currently operating as the Double Door Gallery during the summer, it features two large open rooms on the first floor with curved walls, bead board, wood paneling, and a half bath. The second floor offers a studio apartment with expansion potential, providing immediate income through gallery rentals and apartment leasing. This property is a piece of history with a bright future, ready for its next chapter as a vibrant art galle

Luxury Home 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

Luxury Home 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

Luxury Home for sale in Deer Isle, ME:

Slip away to Seabox Cottage, your ideal summer retreat or year-round haven. Reminiscent of the gracious turn-of-the-century summer homes of Dark Harbor, Seabox blends timeless craftsmanship with modern comfort. A long gravel drive winds through the wooded property and opens to sunny, landscaped gardens, arriving at a circular turnaround that welcomes you to the home's charming wraparound covered porches. Inside, the home offers elevated views of East Penobscot Bay from both levels. At the heart of the first floor is an open-concept living space anchored by a stunning stone fireplace. The well-appointed cook's kitchen with pantry flows seamlessly into the dining and living areas, all opening

Luxury Home for sale in Deer Isle, ME:

Located on 5.45± private acres along the picturesque Fox Island Thorofare, this exceptional waterfront property offers 368± feet of shorefront and spectacular views of the Thorofare and the Camden Hills in the distance. The classic main house epitomizes island charm while signature Shingle-style architectural details anchor the home in its natural setting. Three-bedrooms, single floor living, and water views from every room, contribute to the comfortable and appealing character. An open great room offers living / dining space accented by timeless, white-painted walls and ceiling, and doors that open to a wraparound deck. A recently renovated gourmet kitchen includes custom cab

Luxury Home for sale in Deer Isle, 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