$700,000
139 Oregon Rd, Islesboro, ME 04848
Set on 6.1+/- picturesque acres with approximately 458 feet of frontage on Meadow Pond, this 1865 farmhouse offers a rare blend of historic character, privacy, and natural beauty. The grounds gently slope toward the water, with established landscaping surrounding the home, a well-kept lawn near the residence, and a more natural landscape beyond creating a peaceful meadow setting. Located on
Virginia Hess Cates Real Estate
$280,000
2Q Hermit's Point Rd, Islesboro, ME 04848
Settle into a well-established subdivision, the former Grace Estate, on a four acre lot with deeded view easement to West Penobscot Bay. Magnificent hard and soft woods, dappled with lush ferns and ledge outcroppings. Access drive completed. Building site and view will need clearing once you've selected your preferred location. All this, on a quiet peninsula of Islesboro ensured with the
John Oldham Island Property
$325,000
1552 Turtle Head Rd, Islesboro, ME 04848
Westerly Horizon Turtle Head Waterfront Building Lot. Exceptional western water views of upper Penobscot Bay from 2.6 acres of mixed hard and soft wood and fern glades with 185 feet of bold water frontage and gravel beaches. Deep water access, suitable for a dock. Subdivision restrictions and green buffer easement assure quality, density, and privacy. Soils report available. Path to building site
John Oldham Island Property
$275,000
108 Colony Rd, Islesboro, ME 04848
This delightful cottage is set on a sunlit lot within walking distance of Dark Harbor Village, Gilkey Harbor, and scenic Kissel Point. Enjoy soaking up Summer days on the deck surrounded by honeysuckle, peonies, and mature rhododendrons and playing out on the lawn. Inside, are cozy living spaces with a bedroom tucked upstairs. A detached storage shed provides convenient space for garden tools and
Michael Lynch Legacy Properties Sotheby's International Realty
$95,000
1236 Meadow Pond Rd, Islesboro, ME 04848
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
Wendy Huntington Berkshire Hathaway HomeServices Northeast Real Estate
$1,950,000
130 Big Tree Ln, Islesboro, ME 04848
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
William Warren Warren Realty
$375,000
804 Main Rd, Islesboro, ME 04848
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
Lisa Decker Griffith
The New England Real Estate Company, LLC
$1,200,000
1141 Main Rd, Islesboro, ME 04848
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
Devin Fairfield
Keller Williams Realty
$49,900
Lots 1 & 2 Morgan Rd, Burnham, ME 04848
Burnham - 21.1 Acre lot in a quiet country setting. Tax Map 5 Lots 59 & 58. Lot 1 & 2 in Burnham Woods Subdivision Recorded in the W.C.R.D. Book 10 Page 57. Great spot for hunting. 20 miles to Waterville. 30 miles to Belfast and the Ocean. 38 miles from Bangor & Augusta.
Jim Nealey Eagle Real Estate
$3,495,000
118 E Shore Dr, Islesboro, ME 04848
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
Joseph Sortwell LandVest, Inc.
$350,000
115 Babbidge Rd, Islesboro, ME 04848
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
Michael Lynch Legacy Properties Sotheby's International Realty
$50,000
Lot 23 Map 39 Babbidge Rd, Islesboro, ME 04848
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
Michael Lynch Legacy Properties Sotheby's International Realty
$299,000
M26, L5 Deep Cove Ln, Islesboro, ME 04848
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.
John Oldham Island Property
$399,000
114 Tehan Ln, Islesboro, ME 04848
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.
John Oldham Island Property
$799,000
1159 Main Rd, Islesboro, ME 04848
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
Michael Lynch Legacy Properties Sotheby's International Realty
$5,750,000
866 Pendleton Point Rd, Islesboro, ME 04848
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
Michael Lynch Legacy Properties Sotheby's International Realty
$279,000
521 W Bay Rd, Islesboro, ME 04848
This is a terrific opportunity to own a corner lot with views of the ocean from two sides. Rent out the house as an ADU and build your primary, summer, or investment residence in an open field, surrounded by apples tree and sweeping views of the Penobscot Bay and Broad Cove. Islesboro is only a 20-minute ferry ride from Lincolnville, close to Camden and Belfast, has a highly rated school,
Wendy Huntington Berkshire Hathaway HomeServices Northeast Real Estate
$975,000
239 Mill Creek Rd, Islesboro, ME 04848
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
Kristin Heal Legacy Properties Sotheby's International Realty
$950,000
1591 Turtle Head Rd, Islesboro, ME 04848
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
Virginia Hess Cates Real Estate
$549,000
1446 Meadow Pond Rd, Islesboro, ME 04848
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
Michael Lynch Legacy Properties Sotheby's International Realty
$975,000
1317 Trim Ln Unit 1, Islesboro, ME 04848
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.
Michael Lynch Legacy Properties Sotheby's International Realty
$585,000
1145 Moosewood Ln, Islesboro, ME 04848
Privately set on nearly 7 acres is this inviting 3-bedroom, 2-bath Log Cabin, thoughtfully crafted with double tongue-and-groove snug walls, offering timeless appeal. The property offers a serene natural setting with mature, established gardens filled with a thoughtful variety of flowers, plants, and flowering trees. The gardens are intertwined with inviting outdoor living spaces, including a
Virginia Hess Cates Real Estate
$595,000
Lot 4D Ferry Rd, Islesboro, ME 04848
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
Joseph Sortwell LandVest, Inc.
$945,000
391 Main Rd, Islesboro, ME 04848
Plum Point Cottage: Contemporary Island Home set on a hill with ocean views designed by architect Christopher Glass. With 400+/- feet of rocky waterfront, this property offers stunning sunrises over Bounty Cove and Penobscot Bay. The first floor welcomes you with a small mud room and features an open-concept kitchen and dining area with new marble tile floors, a living room with built-ins, and a
Virginia Hess Cates Real Estate
$350,000
459 Main Rd, Islesboro, ME 04848
Make summer memories at this seasonal cottage overlooking an expansive 1000+/- feet of waterfront along the East Penobscot Bay and with views extending towards Castine and Cape Rosier. The property includes a main cottage and a guest cottage that can also function as a boathouse. As if taken right off a sailing yacht, the open timber frame main cottage is efficient, comfortable, tastefully
Virginia Hess Cates Real Estate
$895,000
135 Rebel Hill Rd, Islesboro, ME 04848
Built in 2004, ''Seabox Cottage'' is a graceful 3-bedroom, 3-full-bath home that offers elevated views of Islesboro Harbor and East Penobscot Bay. The home's Shingle and Colonial Revival design is based on 1894 plans by Fred L. Savage and Milton W. Stratton and intentionally echoes the design praised in 1895 as ''one of the prettiest cottages in town,'' nodding to the elegant turn-of-the-century
Virginia Hess Cates Real Estate
$310,000
Map 22 Lot 4b Big Tree Ln, Islesboro, ME 04848
Discover this beautiful 5.7+/-acre wooded lot on Seal Harbor, Islesboro. Enjoy 541+/- feet of waterfrontage with southern and southwestern views of the protected, public harbor with a public dock and float hosting sailing lessons, swimming, and fishing in warmer months. This unique property features numerous established Ash and Oak trees, a private gravel beach and a bubbling brook. Part of the
Virginia Hess Cates Real Estate
$1,495,000
228 Gooseberry Point Rd, Islesboro, ME 04848
Welcome to 228 Gooseberry Point Road on the picturesque island of Islesboro. Located on over 5 private acres with 743 feet of frontage on West Penobscot Bay, the 4-bedroom house is in excellent condition with many recent upgrades including newly landscaped, whole-house generator, hot tub, delightful patio just 75± feet from the beach. Water view from every bedroom! Fully winterized, this home is
William Warren Warren Realty
$630,000
1052 Meadow Pond Rd, Islesboro, ME 04848
Set along the shore of Meadow Pond on Islesboro, this well-maintained Cape-style farmhouse offers 165 feet of frontage and 0.94 acres of beautifully landscaped grounds. The property features established gardens, fruit trees, and winding paths that create a peaceful, private setting.Inside, the home blends classic charm with modern updates, including state-of-the-art fiber broadband internet.
Wendy Wiley Realty of Maine
$1,495,000
1590 Pripet Wood Ln, Islesboro, ME 04848
Set on the peaceful north end of Islesboro, this exceptional waterfront property offers a rare combination of privacy, modern construction, and effortless access to the shore. With 5.77 acres and 262 feet of open shoreline, you can enjoy one of the island's most sought-after features: direct, stair-free access to the water, allowing you to walk right from your yard to the beach. Built in 2025,
Lisa Decker Griffith
The New England Real Estate Company, LLC
$2,450,000
1578 &1590 Pripet Woods Rd, Islesboro, ME 04848
Oceanfront Family Compound! Set on the serene north end of Islesboro, this rare coastal compound offers the kind of privacy, flexibility, and natural beauty that's increasingly hard to find. With 13 acres, 525 feet of open shoreline, and direct, stair-free access to the water, this property stands apart from nearly every other waterfront offering on the island. The centerpiece is a stunning 2025
Lisa Decker Griffith
The New England Real Estate Company, LLC
$585,000
766 Billy Shore Dr, Islesboro, ME 04848
Rarely does a property like this become available in Islesboro's storied and much-loved summer colony, Sabbathday Harbor. Perfectly sited, up high on the shores of East Penobscot Bay, this classic cottage offers sweeping easterly water views extending to Cape Rosier and approximately 100 feet of bold, accessible shoreline. The first floor features a living room with a wood stove and doors that
Michael Lynch Legacy Properties Sotheby's International Realty
$895,000
232 Mill Creek Rd, Islesboro, ME 04848
Discover Mill Creek Cottage: Watch the Mill Creek rise and fall from this private 1.92± acre property with 200'± of waterfront on Mill Creek, offering stunning views of Broad Cove and Gilkey Harbor. This year-round, 3-bedroom, 2-full-bath, cedar-shingled, cape-style cottage is elevated above Mill Creek, with a commanding view over the water. The property welcomes you with a long driveway that
Virginia Hess Cates Real Estate
$499,000
115 Babbidge Rd, Islesboro, ME 04848
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
Michael Lynch Legacy Properties Sotheby's International Realty
$100,000
Lot 23 Map 39 Babbidge Rd, Islesboro, ME 04848
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 abutting
Michael Lynch Legacy Properties Sotheby's International Realty
$285,500
108 Colony Rd, Islesboro, ME 04848
This delightful cottage is set on a sunlit lot within walking distance of Dark Harbor Village, Gilkey Harbor, and scenic Kissel Point. Enjoy soaking up Summer days on the deck surrounded by honeysuckle, peonies, and mature rhododendrons and playing out on the lawn. Inside, are cozy living spaces with a bedroom tucked upstairs. A detached storage shed provides convenient space for garden tools and
Michael Lynch Legacy Properties Sotheby's International Realty
$785,000
M15L20-TBD Golf Club Rd, Islesboro, ME 04848
This rare and exceptional waterfront parcel is located on Golf Club Road, just a short stroll from the Tarrantine Club's golf course. Spanning 1.9 private acres, the property boasts stunning westerly views across the cove and bay, along with 320 feet of accessible shoreline. It is also ideally positioned up and outside of the flood zone.
Michael Lynch Legacy Properties Sotheby's International Realty
$84,000
M40 Lot28 Main Rd, Islesboro, ME 04848
Unique opportunity to nestle on the shore with your camper. .21 acres of lawn edged with light woods and steps to 100 feet of shorefront on Islesboro Harbor and a tidal beach. Exceptional uninterrupted views of East Penobscot Bay. Too small to build but just right for your visits and vacations. How can you put a price on truly a slice of heaven? $84,000.
John Oldham Island Property
$8,950,000
230 Keller Point Rd, Islesboro, ME 04848
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.
Joseph Sortwell LandVest, Inc.
$599,000
1446 Meadow Pond Rd, Islesboro, ME 04848
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
Michael Lynch Legacy Properties Sotheby's International Realty
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