Homes for Sale on The Maine Islands

Encompassing 8.8± acres on Keller Point, this historic estate enjoys spectacular views to the south down the bay, west to the Camden Hills, and east over Seal Harbor and Islesboro. The iconic 1918 Renaissance Revival stucco 'cottage' is a stately residence characterized by attractive arched doorways and windows, porches and loggia. Spacious living and dining areas, with eight en-suite bedrooms, accommodate large groups, while more intimate areas—indoors and outside—invite quiet conversation or time with a good book. The property's grounds are those of a classic Maine summer estate, artfully landscaped with lawns, flowering shrubs and specimen trees. The property also includes a lovely saltwater swimming pool, a stone guest house in need of renovation, a paddle tennis court, and additional estate-style outbuildings. Located at the end of a private peninsula, the property has 3,570± feet of shorefront with granite ledge, sand and pebble beaches, and a substantial deep-water dock.

399 Hermit's Point Road, Islesboro

Listing courtesy of LandVest, Inc..

$8,500,000

3 Beds ⋅ 1 Baths

Stone Cove Farm is a classic saltwater farm with historic buildings, 267± acres of fields and woods, and spectacular views over the eastern end of the Fox Islands Thorofare, the ''Sparkplug'' lighthouse, Stimpson Island, and across East Penobscot Bay to Isle au Haut. Sited on a knoll with southerly views over the fields to the water, the house is a mid-nineteenth century extended Cape farmhouse with charming period details. The seasonal home has three bedrooms, a bunk room; and two historic barns complement the residence. Approximately 3,400± feet of varied and accessible ocean frontage includes a grassy point of land, dramatic rocky shore, and a pebble beach. A small island, ideal for picnics and children's exploration, is also included. The property offers the potential for additional residential development, a deep-water dock, and/or a return to agricultural pursuits. Extensive due diligence available.

377 S Shore Road, North Haven

Listing courtesy of LandVest, Inc..

$4,995,000

5 Beds ⋅ 5 Baths

Bluff Point is a spectacular waterfront estate on Islesboro occupying a 37.9± acre peninsula with stunning views of Penobscot Bay and the islands to the south and east and overlooking the more intimate Ryder Cove and Sabbathday Harbor to the west. Originally part of the George W.C. Drexel Estate, the property features a winding, scenic approach through forest, open meadow and blueberry fields. The architect-designed main residence, built in 2001, is an aesthetically pleasing contemporary representation of the Arts & Crafts movement that is in perfect keeping with its surrounding natural environment. Two bedrooms and comfortable living spaces are enhanced by custom interior woodwork, large windows and elegant light fixtures that combine to create an informal and sophisticated interior. Historic outbuildings set within the estate-style grounds complete the property including a three-bedroom guest house, a charming tea house, a small barn, a water's edge boathouse and a recently constructed two-level studio/workshop. The private peninsula includes 3,700± feet of dramatic rocky shorefront with stretches of pebble beach and a deep-water dock with ramp, floats and mooring on the protected Ryder Cove. Islesboro, located three miles off the coast in Maine's Penobscot Bay, is readily accessed by car ferry, or by private aircraft landing on the island's 2,400-foot airstrip.

383 & 362 Drexel Lane, Islesboro

Listing courtesy of LandVest, Inc..

$3,500,000

Kents Wharf is primarily a wholesale seafood business buying and selling lobsters but it has endless possibilities for a commercial pier hosting any number of types of waterfront businesses. The property consists of two wharf properties and a house. The main dock at 31 Steamboat Hill Road that has a large completely updated dock area that also has gas, boat diesel and new bait freezer. 29 steamboat is the smaller wharf to the east that is tenant occupied. Multiple floats and dock spaces along with 15 harbor moorings make this a very rare offering on the coast for business or personal use. The house at 313 Atlantic Road has been recently renovated and currently used for employee housing but could be sold off separately. Turnkey operation and current manager can stay on if needed

31 Steamboat Road, Swans Island

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group. steveshelton@masiello.com

$1,850,000

7 Beds ⋅ 7 Baths

Darling Circa 1895 Home in Quaint Dark Harbor Village. Easy stroll to shops. Handy to private club facilities. An ideal and centrally located and air conditioned home with luxurious room for family and guests and entertaining. Meticulous attention to interior detail and landscaping. Delightful paver patio and covered porch. Six bedrooms, 5.5 baths. New roof and eat-in kitchen, butler's pantry, two fireplaces in living and dining rooms, Detached post and beam playhouse with vaulted great room, custom kitchen, full bath and loft over the two-bay garage and private balcony. One of a kind opportunity. S1.85m.

119 Derby Road, Islesboro

Listing courtesy of Island Property.

$1,525,000

4 Beds ⋅ 2 Baths

Make your dream of living on one of Maine's picturesque islands a reality with this one-of-a-kind waterfront property overlooking Bartlett's Harbor and Penobscot Bay. With stunning views of the Camden Hills and incredible sunsets, this property has it all! A short walk to your own private beach, 1,000 +/- feet of private shoreline, potential for a deep-water dock, all on 4.85+/- sun drenched acres. The 4-bedroom home and an 'Island Camp' can be renovated or use one of the other beautiful building sites on the property to build your dream home from the ground up as there is an additional 5-bedroom septic design available. The potential is limitless! Arrival on North Haven Island is made easy by the frequent daily ferries from Rockland, Maine. Please be my guest and allow me to show you this beautiful property and its spectacular opportunities.

14 Thomas Road, North Haven

Listing courtesy of William Raveis Real Estate.

$1,350,000

5 Beds ⋅ 2 Baths

This classic home and guest cottage are set on over six acres, toward the end of a private road on the western shore of Islesboro, boasting spectacular sunsets and 355 feet of shore frontage. The property is a perfect island getaway! The main home features an open concept living area opening up to an expansive porch and deck, with retractable awning, overlooking established perennial gardens out to the bay. On the first floor is the living room with fireplace, dining room, kitchen, and breakfast area. There are two bedrooms with potential for a third bedroom in a room that is currently set up as an office and craft room. There is a full bath and laundry closet. The first floor is approximately 1,566 sf. There is also an attached 2-car garage with unfinished storage space above. The second floor has approximately 1,292 sf of unfinished space with insulation and electricity, and is ready for your finishing! Across the lawn, there is a self-sufficient two story guest cottage which has a deck overlooking the water. It's just right for guest overflow or rental income. 2 bedrooms, 1 full bath. Enjoy this property's sprawling lawn, or head off over a little bridge over the creek and explore the woods. The beach is perfect for strolling, beach combing, wading. Boaters will love this home as it is an ideal spot for sailors and motor boaters. Bay Shore Lane is a private road with almost no traffic. This property has 1GB fiber optic broadband internet with booster for good coverage in both home and cottage, wired for phone (land line), TV antenna for local channels and Direct TV dish. Some accessibility features too.

246 Bay Shore Lane, Islesboro

Listing courtesy of Legacy Properties Sotheby's International Realty.

$1,275,000

3 Beds ⋅ 4 Baths

Conceptualized by a renowned ship builder, this true post and beam home was crafted from timbers that were felled and milled from the property. The beams have chamfered edges and are one example of the care that was taken in every detail of the house. Set on 1.52± acres with 150 ft± of waterfront, with protected views of west Penobscot Bay, the protected lands of Turtle Head and Sears Island, this 3-bedroom, 3.5 bath home has space and elegance and comfort. The open floor plan includes a chef's kitchen, large hearth and chimney built from local island stones and offers multiple sitting areas all with water views. Radiant heat throughout the house warms the Brazilian slate floors on the first floor and wood floors of the second floor. The large deck is perfect for entertaining and offers the opportunity to watch both the sunrise and sunset. The garden level with a private entrance, offers a separate space for guests, staff or renters to have their own full bath, second kitchen, dining space, bedroom and enjoy the water views. Plenty of storage in the mechanical room and the attic. The grounds have been cared for and there is a walking path that leads you down to a pebble and stone beach. Plenty of privacy is offered by the up-island location and the thoughtfully crafted protective easements for view and vegetation. The northern side of the property abuts 24 acres of conservation land. The private dirt roads that lead you to the property are well maintained. Stay connected with fiber optic broadband internet with 1 gibibyte connection speeds. Used as a successful seasonal and year round rental in previous years, consider the opportunities with this year round home. Islesboro is a 20-minute ride from the mainland town of Lincolnville, accessed by a public car ferry, water taxi or private boat or small airplane. No drive by please.

195 Beach Drive, Islesboro

Listing courtesy of Cates Real Estate. ginnie@catesre.com

$1,200,000

Introducing a unique opportunity to buy a successful turnkey business, the property it's situated on, and to do what you love! The pet industry is booming, and you have the chance to own this outstanding doggy daycare, spa, store, and boarding facility in Southern Maine. The business has been a labor of love for the owners over the last 20 plus years, and it's evidenced by how much their clients love this place. It has knowledgeable and loyal staff who would love to stay on to help you run this business of your dreams. If you love dogs, are ready to be your own boss, and are looking for work you are truly passionate about, this is for you.

99 Confidential Road, Confidential

Listing courtesy of Maine Realty Advisors.

$1,160,000

4 Beds ⋅ 2 Baths

With only 15 properties sold in the last 10 years, this is a ONE in a lifetime opportunity to own your own cottage on Monhegan Island! Long known as a destination for artists and art lovers, when you hop on the ferry in Port Clyde stress just leaves your body as you know what is on the other end of your trip! This 3-4 bedroom cottage is perfect for the buyer that is looking for a place to unwind, log off, and decompress. The ocean view overlooking Lobster Cove is romantic and the sunsets are breathtaking. Enjoy the 9 miles of hiking trails, or spend your afternoons enjoying the local shops. Taking a snooze listening to the birds and sounds of passing boats is always on the menu. Cottage does come furnished for your immediate enjoyment!

142 lobster cove Road, Monhegan Island Plt

Listing courtesy of Maine Homes and Camps.

$1,000,000

2 Beds ⋅ 1 Baths

Nestled on Cousins Island in Yarmouth Maine is 59 Seth's Landing. This property is an exceptional opportunity for anyone looking to invest in prime oceanfront real estate. The property offers stunning panoramic views of Casco Bay, making it an ideal location for anyone seeking a peaceful and relaxing environment. Situated on over 2 acres there is ample space to build a dream home or upgrade the current camp to fit your specific requirements. This flexibility opens up a range of possibilities, whether they are looking for a vacation home or a permanent residence. Cousins Island also offers a unique opportunity to explore the area's natural beauty, with its rugged coastline and pristine waters. The island is known for its trails and nature preserves, providing plenty of outdoor activities to enjoy. 59 Seth's Landing offers breathtaking ocean views and ample space to create one's perfect coastal retreat. Come see for yourself you won't want to leave!

59 Seth's Landing, Yarmouth

Listing courtesy of RE/MAX Oceanside.

$995,000

2 Beds ⋅ 1 Baths

Seth's Landing holds a wonderful position on the western shore of Cousins Island. Accessed by a permanent bridge and less than 4 miles from the historic Village of Yarmouth, this quaint year-round cottage offers 2 bedrooms, one full bath and an open living room, breakfast area, and sunroom. The waterside deck overlooking 136'+ of shorefront on Casco Bay allows for complete enjoyment of the sights and sounds waterfront living provides. The home faces the Northwest with magnificent sunsets across to Whites Cove and the mouth of the Royal River and is close in proximity to Madeline Point, a public boat landing with a mooring field and a deepwater dock. Sandy Point Beach, and the Katherine Tinker Preserve all offer bikes racks for your summer visits. Cousins Island is a convenient 15 miles from Maine's largest city, Portland, recently named Best Restaurant City in the US while holding #8 in Best places to live in the US. The city also offers an International Jetport, world class hospital, a thriving symphony, and several museums.

55 Seths Landing, Yarmouth

Listing courtesy of LandVest, Inc..

$950,000

3 Beds ⋅ 2 Baths

On the Island of Monhegan, surrounded by high cliffs, sea, and natural space, sits the Chadwick House, a quintessential, off-center chimney cape in the heart of the village. This house has been well looked after for many years and now is a fully-equipped, year-round home with a rich and durable history. If you want to get away to explore the miles of well-cared-for trails, geographic diversity, and a variety of food, crafts, and art, this is the place. This 3 bedroom, 2 bath house is surrounded by a fenced-in yard with extensive plantings and enjoys views of the harbor and Manana Island. Beach access is across the street on Fish Beach Ln.

240 Monhegan Avenue, Monhegan Island Plt

Listing courtesy of Legacy Properties Sotheby's International Realty.

$950,000

On an island in Maine sits this sweet cottage with room to expand or build on the elevated point looking West over Penobscot Bay. Explore 14 acres and approximately 1,300 feet of shore front and beach. Additional land available. Additionally listed as MLS #1552457 (Residential)

1317 Trim Lane, Islesboro

Listing courtesy of Legacy Properties Sotheby's International Realty.

$950,000

2 Beds ⋅ 1 Baths

On an island in Maine sits this sweet cottage with room to expand or build on the elevated point looking West over Penobscot Bay. Explore 14 acres and approximately 1,300 feet of shore front and beach. Additional land available. Additionally listed as MLS # 1552458 (land)

1317 Trim Lane, Islesboro

Listing courtesy of Legacy Properties Sotheby's International Realty.

$949,000

2 Beds ⋅ 2 Baths

Beautifully constructed year-round home on Dyer's Island with expansive ocean views of Hurricane Sound. Built in 2000 by Shelter Institute and meticulously finished off by the owners, this post and beam home has a flexible floor plan with timeless details. 2021 white kitchen with soapstone countertops, wood floors, exposed beams, cherry staircase, and south facing windows and doors which capture the expansive ocean views. The first level includes an entry area, kitchen, dining room, living room with office area, 4-season sunroom, and full bath with laundry. Upstairs are two bedrooms and a shared bath. The sunroom could easily be converted into a first floor bedroom, making this one level living. Easy access to the oceanside Douglas Fir deck which expands the length of the house and has steps to the beautifully landscaped granite gardens below. Attached two-car garage has a workbench and stairs to an unfinished second level that could be converted into a studio space or separate living quarters. Shared ownership in a deepwater dock system on Dyer's Harbor may be included. This is a lovingly cared for property minutes from Vinalhaven's village center.

7 Blair Road, Vinalhaven

Listing courtesy of Davidson Realty.

$875,000

4 Beds ⋅ 3 Baths

This well maintained and very tasteful shingled home includes 8 acres and almost 2000' of cove frontage on Mill River, a protected salt water inlet just off the Fox Islands Thorofare. The residence was architect designed and built in two phases, offering flexibility for various living styles as well the option to live comfortably off season. The larger primary section includes a great room with vaulted ceiling and fireplace, dining area with doors onto the waterside deck, crisp white kitchen, two first floor bedrooms, full bath/laundry, and ensuite bedroom above with small balcony. The attached guest quarters has a full basement and includes a small kitchen, living room with wood stove, 2nd floor ensuite bedroom and living room/studio area. Wood floors, soft white walls and abundant natural light throughout, with most rooms having water views. Enjoy relaxed summer living outside under the pergola covered patio, waterside deck, or in various outside seating areas including the large sections of granite that slide into the ocean. Plenty of shoreline and acreage to explore, and enough land to possibly build a guesthouse. This is a well appointed and comfortable waterfront home in a quiet setting that is as enjoyable for a couple as it is for a family. Ramp and float transfer as do all appliances. Many furnishings can be purchased outside of closing. Occupancy can occur after September 8, 2023.

75 Boy Scout Point Road, Vinalhaven

Listing courtesy of Davidson Realty.

$799,000

2 Beds ⋅ 1 Baths

Welcome to Long Island, Maine, just a scenic 30 minute ferry ride from Portland's Old Port. This seaside year round home offers stunning waterfront views of Casco Bay and its islands, with your own private stairway down to the quaint and quiet East End public beach. Put your paddle board and/or kayaks in just steps away. This is a 1400 SF 2 bedroom, 1 bath cottage with a 1 car garage (an island rarity) and garden shed. Garage has been used as sleeping quarters when hosting family and friends. Sitting on almost 1/2 an acre, this property lends itself to yard games, bbqs, and endless gatherings. Not one, but two decks to relax on while looking out at Casco Bay. Walk inside through a large mudroom to kick off the sand and sun from the day...step into the kitchen with tons of cabinet and counter space, dining area flows to a large open living area. Water views from every window! Upstairs are two bedrooms, and a large bath with laundry. Wake up to the sound of the waves crashing on the beach right out your window and watch as the lobster boats, ferry, and sailboats cruise right by. Boat mooring possibilities are here. A brand new generator has been recently installed. An amazing opportunity to enjoy a beautiful island location in Maine with a million dollar view. This property is being sold AS IS. Book your private showing today!

74 Eastern Avenue, Long Island

Listing courtesy of Portside Real Estate Group.

$799,000

2 Beds ⋅ 1 Baths

This idyllic property feels like a magical escape from reality, as if it were lifted straight from the pages of a cherished storybook Nestled beneath a magnificent chestnut tree and overlooking the peaceful waters of Crocketts Cove, this 2 bedroom cottage and boathouse is a true gem. Built in the late 1800s, the cottage has been thoughtfully restored and updated while retaining its original charm and character. Resting on 1.8 acres of land bordering conservation land, this property offers a secluded and tranquil setting, perfect for those seeking a rejuvenating retreat. The boathouse, situated on the water's edge, provides a secure storage spot for kayaks, canoes, or a small boat, and easy access to the water. Along with the boathouse, the property has 350 feet of tidal shorefront and its own private island named Two Bush. In the cove, remnants of a granite pier still exist, which could be restored to reach deeper waters. Nature lovers will also appreciate the 40-acre Tip Toe Mountain Preserve, which is just a short walk away. The preserve offers multiple well-maintained trails and hikes leading to breathtaking sunset viewpoints that are locally renowned. This unique and captivating property is a dream come true for those seeking a truly special retreat in a serene and natural setting.

238 Tip Toe Mountain Road, Vinalhaven

Listing courtesy of Vinalhaven Realty.

$770,000

4 Baths

Investment opportunity on the beautiful island of Islesboro. Set back from the road between Pendleton Point Road and West Shore Drive are two separate homes that are ready for your creative use. 313 Pendleton Point is a solid 3 BR 2 BA ranch built by a local craftsman. Offering efficient one floor living, a spacious basement/workshop area, as well as a large, two-story shingled barn. 315 Pendleton Point is an energy efficient cape with 3 BR and 1.5 BA with beautiful views of the Camden Hills and West Penobscot Bay. Also included on the lot are two large garages, perfect for an art studio space or large enough to use an a workshop. Sitting on a combined 3.13+/- acres, these properties provide many opportunities for your next move. Consider the investment possibilities to rent one or both homes, use for multi-generational living, or the opportunity to live and work on the same property. Stay connected with fiberoptic broadband internet with 1 gibibyte connection speeds. Located just three miles off the coast in Penobscot Bay, Islesboro is a 20 minute ride from the mainland town of Lincolnville, access by a public car ferry, water taxi, private boat or small airplane. Reach out to learn about possible opportunities.

315 & 313 Pendleton Point Road, Islesboro

Listing courtesy of Cates Real Estate. ginnie@catesre.com

$770,000

6 Beds ⋅ 4 Baths

Investment opportunity on the beautiful island of Islesboro. Set back from the road between Pendleton Point Road and West Shore Drive are two separate homes that are ready for your creative use. 313 Pendleton Point is a solid 3 BR 2 BA ranch built by a local craftsman. Offering efficient one floor living, a spacious basement/workshop area, as well as a large, two-story shingled barn. 315 Pendleton Point is an energy efficient cape with 3 BR and 1.5 BA with beautiful views of the Camden Hills and West Penobscot Bay. Also included on the lot are two large garages, perfect for an art studio space or large enough to use an a workshop. Sitting on a combined 3.13+/- acres, these properties provide many opportunities for your next move. Consider the investment possibilities to rent one or both homes, use for multi-generational living, or the opportunity to live and work on the same property. Stay connected with fiberoptic broadband internet with 1 gibibyte connection speeds. Located just three miles off the coast in Penobscot Bay, Islesboro is a 20 minute ride from the mainland town of Lincolnville, access by a public car ferry, water taxi, private boat or small airplane.

315 & 313 Pendleton Point Road, Islesboro

Listing courtesy of Cates Real Estate. ginnie@catesre.com

$689,000

3 Beds ⋅ 1 Baths

Custom built year-round home on Carvers Cove. Architect designed, this 3 bedroom/1 bathroom home is situated on 8.5 acres with 297 ft of tidal shorefront. The property is a mix of mature trees, ferns and fruit trees, providing a serene and peaceful environment. The shoreline is easily navigable and perfect for putting in a kayak or swimming at high tide. **Update 1/25/22*- tree work in front of the home has been done to improve view from house. Come check it out!** The house was fully renovated with a new roof, well, heat pump system, all new plumbing, electrical, septic system and appliances in 2019. The first floor has an open concept with combined kitchen, living and dining room, bathroom and a large multi-use room that could be converted into a first floor bedroom or family room. Upstairs there are 3 large bedrooms, all with cathedral ceilings. A cleared orchard, closer to the water, was to be the site of a matching larger home. The architect design along with 4 additional soil tests are available to a new buyer. Close to town, yet very private. This house and property has many possibilities and is ready for your personal touches!

17 Pequot Road, Vinalhaven

Listing courtesy of Vinalhaven Realty.

$598,500

3 Beds ⋅ 2 Baths

Beautifully renovated main house and barn with studio apartment . Classic 1880's island home brought up to todays desires. Chef's kitchen, Granite countertops, commercial grade stainless appliances, new lighting and cabinetry. New bathroom. New heating and cooling. Year-round barn with studio above provide rental income. Cupola lookout with views of the Harbor and out the Eastern Way. Hot tub and expansive deck to entertain all your family and friends. Walking distance to the lighthouse. This property is a must see!

237 Harbor Road, Swans Island

Listing courtesy of The Knowles Company. 207 276-3322

$525,000

Stunning private large building lot on Combs Neck with expansive open ocean views of East Penobscot Bay and Isle Au Haut, Acadia National Park. The 3.3 acre lot enjoys a large, never to be developed, conservation area and a deeded shared deep water dock reaching into Seal Bay. This property is a rare find for those who love the beauty of the open ocean while enjoying the peacefulness of a quiet bay and an undeveloped conserved natural landscape. The property has been surveyed, soil tested and approved for your 3BR dream home.

131 Coombs Neck Road, Vinalhaven

Listing courtesy of www.HomeZu.com.

$500,000

3 Beds ⋅ 1 Baths

As named '' The Precipice'' was sited on the top of a ledge ..... perched and turned for ultimate views up and down Burnt Coat Harbor. This incredibly unique cottage is shaped by the contours of its site with multiple tiers each designed to capture the view. The kitchen and bath are on the entrance level with the living room and a bedroom dropping down a few steps to capture views and light from north to south. Distant views of the mountains of Mount Desert Island to the north and island studded views down through the harbor's entrance to the Atlantic Ocean beyond. Extended views from an office at the top of the stairs and then stepping down to the primary waterfront bedroom with private deck . Burnt Coat Harbor on the south side of Swans Island is known as one of the best protected harbors in Eastern Maine. It is over a mile long and a half mile broad with enough water for even deep drafted boats. In summer the harbor is a favorite spot for the Maine Windjammers to drop anchor for the night. Maine at its best

6 Deer Run Lane, Swans Island

Listing courtesy of The Knowles Company. 207 276-3322

The Maine Islands

Newest Homes for Sale on the Maine Islands