Islesboro Real Estate

Welcome to Islesboro, a picturesque island town nestled in Waldo County, Maine. Known for its stunning natural beauty and charming coastal atmosphere, Islesboro offers a peaceful retreat from the hustle and bustle of everyday life.

With a rich history dating back to the 18th century, Islesboro is home to a close-knit community that values tradition and connection to the land and sea. The island's pristine beaches, lush forests, and scenic hiking trails provide endless opportunities for outdoor exploration and relaxation.

In addition to its natural attractions, Islesboro boasts a vibrant arts and culture scene, with local galleries, studios, and events showcasing the talents of the island's creative community. Residents and visitors alike can enjoy shopping at unique boutiques, dining at delicious restaurants, and experiencing the warm hospitality that Islesboro is known for.

Whether you're looking for a peaceful retreat, a vacation getaway, or a place to call home, Islesboro offers a unique blend of natural beauty, community spirit, and coastal charm. Come discover the magic of Islesboro and experience island living at its finest.

Newest Listings in Islesboro

$95,000

1.8 acres ready to be built on with a well in place, soil test, septic design, temporary driveway and partially cleared. Islesboro has markets, a health center, community center, gym, a highly rated school, and broadband. Only 3 miles from the mainland, it is only a 15-minute ferry ride to the island. Close to Camden and Belfast, Bangor Airport is only 1hr away and Portland Jetport is less than 2hrs away.

1236 Meadow Pond Rd, Islesboro

Listing courtesy of Berkshire Hathaway HomeServices Northeast Real Estate.

$1,950,000

7 Beds ⋅ 6 Baths

Welcome to 130 Big Tree Lane, located on the picturesque island of Islesboro. This home is truly a family compound, with 6 bedrooms, 5 full baths, and 2 half baths across three structures. The design of the living spaces is ideal, offering privacy for the homeowners and their guests. The home is located on 5 well manicured acres on protected Seal Harbor, a mid-island location that is quiet, and yet not far from everywhere you want to go. The views are spectacular; across the harbor, all the way to the Camden Hills. Enjoy watching young sailors making loops in their 420s while you have your morning coffee, and enjoy the sunset while you have supper on the deck. From the deck you can also appreciate the large dock, which affords deep water for your boat, even at low tide. The dock's float was recently replaced. The cape style house has classic Maine charm: Post and beam architecture with warm pine finishes. The open plan kitchen stretches to the family room, then out to the large deck, offering a fantastic set up both for families and also graciously entertaining larger groups. The structure and indoor finishes have been beautifully maintained. The first floor of the main house also includes a full bath, an office, a convenient mudroom, and a full size laundry. Upstairs in the main house, you'll find three bedrooms and two full baths. From the main house, it's a short walk over to the cheerful guest house, which has a great kitchen, 2 bedrooms, 1 full bath, and 1 half bath. The property boasts two garages: One attached to the main house, and one at guest house; perfect storage for cars, boats, and gear. Above the main house garage, you'll find another bedroom and full bath. This comfortable apartment has its own entrance. Use for guests, or live-in staff. All of the living structures are winterized for your year round use. The main house offers a stately fireplace, and there is a charming wood shed off the drive. Come tour this home, and fall in love!

130 Big Tree Ln, Islesboro

Listing courtesy of Warren Realty.

$435,000

5 Beds ⋅ 1 Baths

Woody Point. Cherished Ryder Cove Enclave Classic 1890's Clapboard Five-Bedroom Waterfront Home. It's seen glorious days from the covered porch on Sabbathday Harbor. Newer roof. Well worth the work to restore. 141 feet of beach and ledge. Large apple trees. Entry, kitchen, dining room with stamped tin ceiling, living room, bedroom down, four up and full bath, utility room. Great family home at water's edge.

877 Ryder Cove Ln, Islesboro

Listing courtesy of Island Property.

$1,200,000

3 Beds ⋅ 3 Baths

Welcome to Flying Without Wings Farm, a rare opportunity to own a beautifully renovated horse farm on the scenic coastal island of Islesboro, Maine. Set on 21.68 picturesque acres, this exceptional property combines historic New England charm with modern comfort and thoughtfully designed equestrian amenities. The tastefully remodeled 1800s farmhouse offers 3 bedrooms and 2.5 bathrooms, blending timeless character with updated finishes. Warm and inviting living spaces feature wood stoves, energy-efficient heat pumps, and a full solar array, providing year-round comfort and sustainability. Equestrians will appreciate the impressive post-and-beam barn complete with horse stalls and a spacious hay loft, a 150' x 50' indoor riding arena, three large fenced pastures, and a peaceful farm pond. A detached two-car garage provides additional storage and convenience. Whether you're an avid horse enthusiast, looking for a working farm, or simply dreaming of a private island retreat with room to roam, Flying Without Wings Farm offers an extraordinary lifestyle in one of Maine's most beautiful coastal communities. This is a truly unique opportunity to own a turnkey equestrian property where history, nature, and modern living come together.

1141 Main Rd, Islesboro

Listing courtesy of Keller Williams Realty.

$3,495,000

5 Beds ⋅ 4 Baths

Perched above the shores of Charlotte's Cove on Islesboro's east shore, this exceptional waterfront property offers 15± acres, 770± feet of shorefront, and spectacular views over East Penobscot Bay to the islands beyond. The setting is bucolic and pristine, with rolling meadows full of wildflowers, old stone walls, walking paths, lawn and gardens, and a small pond filled with trout. Fully renovated two years ago, the year-round contemporary cottage offers five bedrooms, a relaxed open floor plan, and wraparound decks on two levels that invite easy indoor-outdoor living. A new deep-water dock with ramp, float, and two moorings provides outstanding access to boating throughout Penobscot Bay, with convenient access to the mainland by water. Several excellent building sites create the opportunity to establish a significant family compound or waterfront estate, while a portion of the property is protected by a conservation easement that helps preserve the natural character, views, and privacy of the setting. Just minutes from Dark Harbor and the Island Market, this is a rare island offering with exceptional privacy, natural beauty, waterfront access, and development potential.

118 E Shore Dr, Islesboro

Listing courtesy of LandVest, Inc..

$375,000

3 Beds ⋅ 1 Baths

Island Living with Room to Grow! Set on 5.85± acres along Main Road, this classic red New England home offers the perfect blend of comfort, character, and future potential. Surrounded by mature trees, established landscaping, and a recently added raised bed garden ready for your next growing season. Plenty of open space, the property enjoys wonderful curb appeal and a peaceful setting in one of Maine's most treasured island communities. Originally the homestead of Jason W. Ladd, this inviting red home has been part of the Islesboro landscape for well over a century. The original 1900 residence, with its hand-hewn beams and fieldstone foundation, was expanded and renovated in 1968, creating the single floor three-bedroom, one-bath home enjoyed today. A detached two-story barn/garage provides abundant storage, workshop space, or room for hobbies. The value of this property extends beyond the home. With approximately 5.85 acres, there is potential for subdivision, subject to local and state approvals, making this an attractive opportunity for buyers looking to invest in Islesboro's future while enjoying the property today. Just a scenic ferry ride from the mainland, Islesboro offers a rare coastal lifestyle with miles of shoreline, quiet roads, a close knit year-round community, and easy access to boating, hiking, and the natural beauty of Penobscot Bay. Whether you're searching for a year round residence, a seasonal retreat, or a property with long term investment potential, 804 Main Road is ready for its next chapter. Showings by appointment with 24-hour notice required.

804 Main Rd, Islesboro

Listing courtesy of The New England Real Estate Company, LLC. lisadg@thenewenglandreco.com

$50,000

This level lot is just a short walk from the charm and amenities of Dark Harbor Village, Gilkey Harbor, and scenic Kissel Point. Located close to many of the island's year-round activities, including community center, gym, and school. Owner financing may be available. In addition to this property offering, if you are looking for a larger property or guest accommodations, consider the abutting property at 115 Babbidge Road MLS 1669761

Lot 23 Map 39 Babbidge, Islesboro

Listing courtesy of Legacy Properties Sotheby's International Realty.

$350,000

5 Beds ⋅ 2 Baths

This property offering includes an historic Arts and Craftsman-style Foursquare house - thought to be one of the first houses built in Dark Harbor - set on a sunny and open lot, as well as an additional vacant wooded lot both, just a short walk from the charm and amenities of Dark Harbor Village, Gilkey Harbor, and scenic Kissel Point. Brimming with original character and island warmth, the residence offers the best of both community connection and personal retreat. Ascend granite steps and enter through the welcoming formal front door beneath a gracious covered porch, perfect for waving to neighbors or enjoying a quiet cup of coffee. Inside, a central hall anchors the home, with a lovely parlor and dining room on one side, and a cozy study, powder room, and laundry area on the other. The kitchen, complete with pantry, is located to the center rear of the house, adjacent to a small sunlit room which leads out to a back deck, an ideal spot for relaxed outdoor dining. There is also a mudroom that opens to the covered back porch. The second floor includes three bedrooms and a full bath. An additional flexible use room has a staircase to a spacious, unfinished attic which offers expansion potential and includes glimpses of the water. The detached barn is closely adjacent to the house and is suitable for storing outdoor furniture. Located close to many of the island's year-round activities, including community center, gym, and school. Offered partially furnished. Owner financing may be available.

115 Babbidge Rd, Islesboro

Listing courtesy of Legacy Properties Sotheby's International Realty.

$299,000

Deep Cove Lane. Southwesterly water views from this four acre wooded hillside parcel, 365 feet of gravel beach on Sabbathday Harbor. Soils tested. End of the private lane. You'll want to check the price twice.

M26, L5 Deep Cove Ln, Islesboro

Listing courtesy of Island Property.

$450,000

3 Beds ⋅ 1 Baths

Sterling View Farm. Cunning Three-Bedroom Cedar Shingle Home located mid-island handy to town and ferry. Many fine finishing details, wainscoting, exposed beams, wood flooring and widow's walk. Guest cottage all on idyllic 2.3 acre meadow with sunsets and waterview.

114 Tehan Ln, Islesboro

Listing courtesy of Island Property.

$799,000

4 Beds ⋅ 3 Baths

The Bluff House is a gracious 19th Century Greek Revival ship captain's house, set high on the north end of the island with inviting views over its nearly 18 private and mostly wooded acres with trails leading to over 700 feet of sandy beach on the eastern shore of Islesboro. As the back of this stately home opens to a sprawling lawn with the views over tree tops east to Penobscot Bay, the Bluff House's privacy, quiet neighborhood, and bucolic feel beckon a time long ago. Set up island, this home is in close proximity to the island's community center, places of interest, and activities. This 1800's, 4 bedroom, 3 bath property has many renovations and updates complete with new engineered European White Oak flooring, new structural support system under the kitchen, new lighting in the kitchen and bathrooms, and new plumbing stubbed and ready to go. Currently the kitchen and two of the bathrooms are ready for your own touch and completion! There are generous yet comfortable spaces to enjoy - family room, living room, dining room, library/study - at the Bluff House with its architectural elements echoing an age of simplicity and elegance, while its systems and structures have been updated during thoughtful and meticulous renovation creating a distinguished, historic home of notable character with modern convenience, including a two car garage - with sub flooring in place and could be finished as an office, studio, or other space -, 10kw generator, and high speed internet. A perfect island home ready for year round living or seasonal retreat.

1159 Main Rd, Islesboro

Listing courtesy of Legacy Properties Sotheby's International Realty.

$5,750,000

6 Beds ⋅ 9 Baths

East Bay is an exceptional coastal estate offering the perfect blend of a private summer retreat and a tranquil year-round residence. Set on more than five secluded acres with 430 feet of pristine, accessible waterfront, the property enjoys an elevated position above the scenic shoreline, where beautifully curated gardens and mature landscaping frame sweeping views across Penobscot Bay and its islands. The residence unfolds along a gently sloping bluff, capturing spectacular water vistas from nearly every room and outdoor living space. Originally built as a post-and-beam home around 2000, East Bay has been thoughtfully transformed over time. Its current design, inspired by the timeless coastal architecture of Royal Barry Wills, combines classic New England character with understated sophistication. Designed for both elegant entertaining and comfortable everyday living, the home offers a seamless balance of formal and informal spaces. Highlights include a first-floor primary suite with a private sitting room and office, multiple guest suites, inviting sitting rooms, a library, additional office spaces, a wine cellar, exercise room, updated mechanical systems, air conditioning, a generator, and a carport. The outdoor amenities are equally impressive. A heated swimming pool, hot tub, and sauna are perfectly positioned to maximize the breathtaking waterfront setting and views, while a custom-built staircase provides direct access to the property's private beach. Evoking the charm and grandeur of Islesboro's historic summer cottages, East Bay is a rare legacy property--an extraordinary expression of Maine's rugged coastal beauty, enduring craftsmanship, and timeless elegance. Explore the 3D tour and floor plans for a fully immersive experience of this remarkable estate.

866 Pendleton Point Rd, Islesboro

Listing courtesy of Legacy Properties Sotheby's International Realty.

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