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$1,100,000
2 Beds 1 Baths
DEER ISLE: 99 Huckleberry Point Road: A magical waterfront retreat offering exceptional privacy at the end of a private lane, with more than 1100 feet of shoreline overlooking Southeast Harbor and Long Cove. Nestled at the water's edge, this charming cottage enjoys an idyllic setting where you can watch the seals swim by and lobster boats return with the day's catch from the stone patio just steps away from the shore. The thoughtfully designed floor plan features a waterside porch with Douglas fir floors, a welcoming living room with a wood burning fireplace with granite surround, a well- appointed kitchen with granite counter tops, a first floor primary bedroom with an en-suite bath and versatile sleeping loft or home office. Fiber optic high speed internet available. Cottage is insulated and heated for cozy 3-season use. Beautifully landscaped grounds include gardens, a green house and private swimming cove. A vintage airstream provides cozy guest quarters just a few steps away from the floating dock with ramp. Easy access to kayaking among neighboring islands, swimming, fishing, and boating. Mooring possibility close by. This remarkable property offers the perfect blend of tranquility and natural beauty. No drive-bys please. 1,100,000.

99 Huckleberry Point Dr, Deer Isle

Listing courtesy of Saltmeadow Properties, Inc..

$649,000
2 Beds 2 Baths
Motivated seller. 3 living spaces on one property. 2 bed 2 bath year-round home, 1 bed 1 bath seasonal cottage, and a year-round writer's studio with sleeping loft. Imagine the possibilities. More than just a waterfront property, this is an opportunity to create a lifestyle rooted in community, creativity, and connection to the Maine coast. For generations, this beloved property has been a place of gathering, growth, and inspiration -- and now it's ready for its next chapter. Whether you envision a cooperative living arrangement, a family compound, a creative retreat, or an investment shared among friends, the flexibility here invites big dreams and fresh ideas. Multiple living spaces, revenue opportunities, flourishing flower gardens, and mature peach trees create a setting that feels both abundant and welcoming. Launch kayaks from your own shoreline, gather for sunset dinners, or simply enjoy the peace and beauty of waterfront living together. Affordable Maine waterfront is still possible when approached with creativity and community in mind. Form a partnership. Build a collective. Create something meaningful together. A rare chance to live simply, beautifully, and connected -- all in one extraordinary coastal property.

104 S Deer Isle Rd, Deer Isle

Listing courtesy of The Christopher Group, LLC.

$1,295,000
3 Beds 4 Baths
Phenomenal view and owned frontage of over 350' on Eggemoggin Reach. HOUSE is characteristic of a traditional New England waterfront home. When your not sitting overlooking the ocean, you can welcome guest into the large sun room. Expansive living space with open kitchen, dining room, living room.. Kitchen is custom made, with plenty of cupboard space, off there is a laundry room/storage room. Fireplace makes for a cozy family room. Primary bedroom has an abundance of closets primary bath has jacuzzi tub/shower, double sinks, overlooking the ocean. 2nd bedroom is located on the main floor. Basement has a bedroom with full walk out access, and a large game room. Oversized one bay garage is located under the house. Craftsmanship for this property is immaculate. Little Deer Isle is an island in Penobscot Bay, lying just north of the town (and island) of Deer Isle, Maine, United States, of which it is a part. The island is served by Maine State Route 15 via the Deer Isle Bridge. The northern end of the island is called Eggemoggin and there is a small island with a lighthouse on it at the tip called Pumpkin Island. Little Deer is approximately four miles (6.4 km) long and connects to Deer Isle by way of a causeway. There are only about 300 year-round residents of Little Deer, but many more summer residents. There is abundant wildlife on the island including deer, fox, squirrels, wild turkeys, ospreys, and bald eagles.

36 Wiegand Pl, Deer Isle

Listing courtesy of Keller Williams Realty.

$7,975,000
5 Beds 4 Baths
Located just off Sylvester Cove and the village of Sunset, Sheephead Island offers the rare opportunity to own an idyllic Maine island in its entirety. Encompassing 65± pristine acres with two homes, the island is connected to the mainland at low tide offering a truly private island setting with the ease and accessibility of a mainland property. Buildings include a five-bedroom colonial-style main house, a four-bedroom contemporary guest home, a boathouse and an artist's studio. The island's extensive shorefront is spectacular with miles of interesting ledge, tidal pools, and broad sandy beaches. Walking paths meander through fields and forest with a special hidden swimming pond. There is a deep-water dock with a ramp, float and mooring tucked into the northeast lee of the island, providing ample space for yacht moorage and protection from most winds and prevailing seas.

001 Sheephead Is, Deer Isle

Listing courtesy of LandVest, Inc..

$95,000
If true seclusion is what you're after, this rare Deer Isle offering delivers. Spanning just over 17 acres, the property sits along Woods Road, connecting Reach Road to the end of Quaco Road in Deer Isle Village. The land slopes from the road to approximately 330 feet of frontage on scenic Torrey Pond, offering a serene waterfront setting. Moving away from Torrey Pond on the opposite side of the road, the terrain rises gradually to about 110 feet in elevation, featuring a natural landscape of mature woods, soft mosses, ferns, and granite outcroppings. This is ideal for an off-grid retreat where abundant wildlife, starlit skies, and the quietude of nature define the experience. Access is via Woods Road, primarily a wide ATV trail, making this a perfect escape for those seeking privacy, adventure, and a true connection to the Maine wilderness.

Lot 6&66 & Rd, Deer Isle

Listing courtesy of The Island Agency. Morgan@TheIslandAgency.com

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