Islesboro Homes with Waterfront

Welcome to Islesboro, a picturesque island town located in Waldo County, Maine. Known for its stunning waterfront properties, Islesboro offers a unique blend of natural beauty and small-town charm.

Homes with waterfront views are abundant in Islesboro, making it a dream destination for those seeking a serene and idyllic lifestyle. Imagine waking up to the sound of waves gently lapping against the shore, with panoramic views of the sparkling ocean right from your window.

Whether you're looking for a cozy cottage overlooking the bay or a luxurious estate with a private beach, Islesboro has a diverse range of waterfront properties to suit every taste and budget. From historic homes with character to modern residences with all the amenities, there's something for everyone in this waterfront paradise.

In addition to its stunning real estate offerings, Islesboro boasts a tight-knit community, excellent schools, and a thriving arts and culture scene. Outdoor enthusiasts will appreciate the island's hiking trails, beaches, and opportunities for boating and fishing.

If you're in search of a peaceful retreat where you can unwind and reconnect with nature, look no further than Islesboro. With its charming homes, breathtaking waterfront views, and welcoming community, this island town offers a truly one-of-a-kind living experience.

Newest Islesboro Homes with Waterfront

$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.

$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..

$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.

$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.

$995,000

4 Beds ⋅ 4 Baths

Welcome to 239 Mill Creek Rd - A classic island Cape overlooking Mill Creek and Broad Cove, featuring 3 bedrooms, 2 full baths, and 2 half baths in a setting that captures the essence of coastal Maine living. Open living, kitchen, and dining spaces are filled with natural light and ocean breezes, flowing seamlessly onto a screened porch with water views. Wood floors run throughout the home, while the kitchen showcases warm wood countertops and a beautiful Monson slate sink handcrafted in Maine. The first-floor primary suite offers direct deck access, a wall of closets, and a private bath with a stall shower. A second full bath on the main floor includes a soaking tub with distinctive brick surround and convenient laundry area. Upstairs, a waterside guest bedroom enjoys creek views, while a charming half bath and separate clawfoot tub room add character. A second guest bedroom, accessed by the rear staircase, features built-ins and abundant natural light. Outside, discover a private duck pond with its own viewing deck, a firepit gathering area overlooking the pond, an artist studio with power, storage, and loft space, and a seasonal sleeping cottage with full bath complete with a screened porch overlooking the creek. Stairs lead to the shoreline along Mill Creek, while fenced gardening spaces, water views, and thoughtfully designed outdoor living areas create a truly special island retreat and an ideal family getaway.

239 Mill Creek Rd, Islesboro

Listing courtesy of Legacy Properties Sotheby's International Realty.

$549,000

2 Beds ⋅ 1 Baths

Experience the magic of coastal living at this seasonal camp, set on 7 acres of level land and offering 1,400 feet of accessible shoreline and beach. Whether you choose to enjoy the camp as it is or build your dream retreat, this property provides the ideal setting to enjoy island life. Imagine long summer days filled with swimming, boating, and beach combing, capped off by breathtaking sunsets over the water. When you're ready to explore, take a stroll up the beach to Islesboro Island Trust's Turtle Head Preserve, where rocky cliffs, panoramic views, and fascinating geological history await. Or head out to explore all the island has to offer. The property is being offered as is.

1446 Meadow Pond Rd, Islesboro

Listing courtesy of Legacy Properties Sotheby's International Realty.

$975,000

1 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 1,288 feet of shore front and beach.

1317 Trim Ln Unit -1, Islesboro

Listing courtesy of Legacy Properties Sotheby's International Realty.

$950,000

3 Beds ⋅ 3 Baths

North End Cottage, located in the coveted Turtle Head subdivision, is a charming chalet-style waterfront retreat set on 4.31+/- mostly wooded acres. Flowering gardens, vegetable beds, and stone paths leading to the covered front porch create a warm and welcoming first impression. Built in 2000, the home features large windows with sweeping views over East Penobscot Bay and offers convenient one-level living with two bedrooms, two bathrooms, and laundry on the main floor. The open floor plan includes a spacious chef's kitchen, dining area, and living room, all thoughtfully positioned to take advantage of the water views. A spiral staircase leads to a loft that can serve as an additional living room or office with elevated views of the bay. This year-round home is heated by radiant floors and a wood stove. Outside, a waterside deck with a hot tub provides the perfect place to relax and enjoy the coastal setting. The property includes a two-car garage with a workshop and well-appointed guest quarters above, complete with a living room, kitchen, bunk room, and full bath. An additional fenced garden and garden shed add to the property's appeal. With stair access to 311+/- feet of waterfront consisting of a beautiful stone beach, this property offers a rare opportunity to enjoy privacy, comfort, and the very best of Maine waterfront living. Located just a short distance from the nature trails of Turtle Head Conservation Land. The majority of the furnishings can be negotiated. The hot tub has a new cover.

1591 Turtle Head Rd, Islesboro

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

$8,950,000

6 Beds ⋅ 8 Baths

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 for larger gatherings while others are designated for intimate family settings. Six well-appointed bedrooms, including a main-floor primary bedroom suite, provide comfortable and private accommodations. There is also a three-car garage with a two-bedroom caretaker's apartment above it. The property's landscape features manicured lawns, mature gardens, gently rolling fields, wooded areas, and a historic pastoral lane that winds through the land. 2,695± feet of shorefront varies from sheltered coves, pebble beaches, granite outcroppings, and there is a deep-water dock with a ramp and float for direct access to the bay and the mainland. The property is subject to a Conservation Easement held by the Islesboro Islands Trust to protect the land's natural beauty.

230 Keller Point Rd, Islesboro

Listing courtesy of LandVest, Inc..

$595,000

Located just moments from the Islesboro ferry terminal, this 4.43± acre undeveloped land parcel offers the opportunity to pursue your creative vision. The mostly wooded lot features an identified and partially cleared building site and sweeping water views. With approximately 1,064± feet of diverse shoreline—including stretches of sand and pebble beach mixed with gentle tidal pools—this property combines natural beauty with accessibility and potential.

Lot 4D Ferry, Islesboro

Listing courtesy of LandVest, Inc..

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