Legacy Properties Sotheby’s International Realty specializes in curating extraordinary coastal living experiences. Some are accessible via a bridge from the mainland, others are only accessible by boat or ferry including a 13-bedroom estate on Clapboard Island, a 29-bedroom estate on Islesboro and a beautifully renovated cottage on picturesque Monhegan Island. Explore our exclusive island homes for sale and discover the island home that’s perfect for you.
188 Aldrich Road, Islesboro, Maine
Offered at $8,500,000
Represented by Michael Lynch & Cindy Lang
This prestigious oceanfront Islesboro estate overlooking Penobscot Bay features an incredible 29 bedrooms and 16.5 bathrooms. Extraordinary amenities include 800+ feet of shore frontage, a private west-facing deep water dock, a beach, a heated in-ground pool, a carriage house with a 1-bedroom year-round apartment, a greenhouse, cultivated gardens, and a 3-car garage. Learn more about this luxury island property for sale here.
Clapboard Island, Falmouth, Maine
Offered at $7,500,000
Represented by Kristina Keaney & Carrie Martin
Welcome to Clapboard Island, a luxurious 22-acre private island estate in Casco Bay just off the coast from Falmouth Foreside and Portland. Amenities include a furnished 13-bedroom stunning main house, plus a guest cottage, charming barn, boathouse, playhouse, private beaches, deep-water dock, and convenient designated mainland parking. This exceptional island property is a true coastal paradise and Maine life at its finest. Learn more about this luxury island property for sale here.
168 Seguinland Road, Georgetown, Maine
Offered at $3,300,000
Represented by Colin Harvey
Welcome to 168 Seguinland Road, an extraordinary oceanfront residence located in Georgetown, Maine. This property spans 4,700 square feet and features 4 bedrooms and 4.5 bathrooms, all set on a 3.4-acre private lot. The lot boasts nearly 400 feet of coastline and stunning southeasterly views. Inside, discover exceptional craftsmanship and luxury finishes throughout the home. The main level features a secluded bedroom wing, a spacious great room with a custom stone fireplace, an ocean-facing sunroom, and a gourmet kitchen with rare granite countertops and hand-crafted stained-glass lighting. Upstairs, find two bedrooms, including a primary suite with a spa-style bathroom and serene sitting area. Outside, enjoy a deep-water dock for easy water access. Plus, a two-story heated barn offers an artist’s studio, workshop, and ample storage. With its unparalleled oceanfront setting, this property is a rare find and an idyllic place to call home. Learn more about this luxury island property for sale here.
30 Pleasant Cove Lane, Portland, Maine
Offered at $2,350,000
Represented by Amy Farrell
An icon in the Diamond Cove community, & offered to the market for the first time, this impeccably maintained island property on Great Diamond Island, provides a sense of warmth & place. Perched above Pleasant Cove Beach, this coastal-style home offers 4 bedrooms, 3.5 bathrooms, and stunning views of Casco Bay. Enjoy the open-concept living areas, custom kitchen, and waterfront porch. Retreat to the primary suite with an updated bathroom and walk-in closet. Outside, relax on the stone patio with an outdoor fireplace and hot tub. Plus, enjoy exclusive access to DCHA amenities like a pool, tennis courts, and private beaches, making this the ultimate Maine island retreat. Learn more about this luxury island property for sale here.
30 Sand Beach Road, Stonington, Maine
Offered at $2,250,000
Represented by Laura Farr
Nestled into the rugged coastline of Maine, this fully restored classic 1850s farmhouse offers historic character and unparalleled views of Mark Island Lighthouse, Penobscot Bay and Vinalhaven. Preserving its original charm, this landmark home boasts carefully sourced fixtures and modern amenities for comfort. With ocean views from every room, 5 bedrooms, and 4.5 bathrooms, relaxation is effortless. Outside, enjoy stone firepits and granite steps amidst native wildflowers and forested areas. The shoreline and cove provide water access and opportunities for exploration. Embrace the legacy of this iconic Downeast home and create your own story. Learn more about this luxury island property for sale here.
30 & 33 Taylor Road, Westport Island,Maine
Offered at $1,800,000
Represented by Randy Miller and Charlie Richardson
Perched on historic Westport Island, this 4.5-acre property offers great views of the Sheepscot River. Inside, an open floor plan, wood-burning fireplace, and updated kitchen await. Thoughtfully landscaped grounds invite you into the yard where you will find a bocce court, a firepit and a multitude of magnificent shrubs and flowers, blooming throughout the spring, summer, and fall. A dock and float offer waterfront access for swimming and boating. Just a short drive to Wiscasset’s renowned eateries and shops. Learn more about this luxury island property for sale here.
1101 1105 & 1107 State Highway 3, Bar Harbor, Maine
Offered at $1,500,000
Represented by Susan Allen and Carroll Fernald
Enjoy scenic views of Thomas Bay from the comfort of this shoreland property. There are three residences on site, including a charming 1900s farmhouse, a one bedroom ranch and a seaside cottage. Two of the houses have lovely screened-in porches overlooking the water. There is tidal water access to both Thomas Bay and Northeast Creek for boating and birding enthusiasts, and the property sits in close proximity to the towns of Bar Harbor and Ellsworth. Most furnishings included. Room and bathroom count includes all three houses. Learn more about this luxury island property for sale here.
9 Sterling Cove Road, Monhegan, Maine
Offered at $1,395,000
Represented by Brian Wickenden
This extraordinary Monhegan island gem features a stunning wall of windows, a floor-to-ceiling fireplace, and beautiful furnishings, all included in the rare offering. The shingle-style 3-bedroom seasonal home is in a great location by the island’s postcard-worthy harbor, and the 1.97-acre property includes a small pond that was once the historic ice pond for the community. Monhegan is an iconic Maine island 12 miles off the coast in the Atlantic Ocean, and a destination for artists, art lovers, hikers, and nature enthusiasts. Learn more about this luxury island property for sale here.
119 Derby Road, Islesboro, Maine
Offered at $1,150,000
Represented by Michael Lynch
This home is a classic piece of Islesboro’s history, offering both tranquility and convenience. Originally built circa 1895, the well-maintained home boasts 5 bedrooms, 4.5 baths, and classic architectural elements. Modern upgrades include air conditioning, a generator, and high-speed internet. One of property’s distinguishing features is its freestanding post and beam barn and garage, which has been transformed into a luxury guest-and-party space utterly unique on the island. Surrounded by trees, gardens, and a picket fence, and event a sweet little playhouse nestled between the home and barn, the property is the perfect place to call home. Learn more about this luxury island property for sale here.
