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$150,000
3 Beds ⋅ 1 Baths
Set on 3.8 acres, this New England Farmhouse house offers both charm and potential. With deferred maintenance to address, the house presents an opportunity to restore a traditional Maine home--or take advantage of the improved lot and build or place something new. This home offers a dug well and older septic system. While home is being sold as-is a new furnace and hot water heater have been installed within the past 10 years. The barn, currently being used as a studio, is in need of significant structural repair. For buyers with vision, this is the quintessential New England farmhouse waiting to be brought back to life.

441 N Deer Isle Rd, Deer Isle

Listing courtesy of The Island Agency.

$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..

$339,000
2 Beds ⋅ 1 Baths
This mid-island saltbox sits on a sunny, open lot just off a quiet dirt road that winds past ponds and meadows, with only a neighbor or two beyond. Spacious lawns, open fields, and surrounding woods give the 5.67 acres a real sense of privacy and space. There is room for a garage, guest house, or separate building site to the west. Built in 2005, the home has wood floors and warm interiors throughout. The main level opens to a great room with lofted ceilings, skylights, and ceiling fans; the kitchen has shaker cabinets and a peninsula with seating for four. Two bedrooms and a full bath are upstairs. A covered porch wraps two sides of the home, a good spot in any weather. Solid, newer construction and easy access off the main road.

27 Spofford Dr, Deer Isle

Listing courtesy of The Island Agency.

$248,000
4 Beds ⋅ 1 Baths
Classic circa-1900 Cape offering the perfect blend of coastal convenience, timeless character, and the opportunity to restore and personalize a true piece of Maine Island charm in highly sought-after Deer Isle. Set just moments from the serene waters of the Inner Harbor, this property is a short scenic drive to the charming galleries and shops of Deer Isle Village, as well as the vibrant working waterfront, restaurants, and boating community of Stonington. The home features a spacious traditional layout awaiting your personal vision and updates. The main level consists of a kitchen, dining room, living room, primary bedroom, and full bath. The upper level features three additional bedrooms, including a flexible space ready to adapt to your changing needs--whether as a second bathroom, home office, study, or creative retreat.'' Step onto the screened covered porch to relax and enjoy peaceful views of the Inner Harbor. Surrounding the home, abundant mature perennial gardens filled with generations of established plantings, colorful seasonal blooms, just waiting to be lovingly revived. Lilacs, flowering perennials, and lush garden beds, a beautiful canvas for gardeners and nature lovers alike. Whether you envision a summer retreat, vacation rental, artist's escape, or full-time residence, this special property presents an opportunity to create something truly memorable in one of Maine's most scenic and treasured island communities.

510 S Deer Isle Rd, Deer Isle

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group.

$395,000
3 Beds ⋅ 3 Baths
Your opportunity to own two homes on one 5.7 acre parcel in the Sunset area of Deer Isle. The main house includes two bedrooms, many updates, a beautiful deck overlooking the back of the property, as well as energy efficient, on demand gas fired HWBB heat and a heat pump. The one bedroom apartment with a one car garage on the first floor would be ideal for a weekly or long term rental or as a private space for those overflow summer visitors. The property is a ten minute walk from a public beach and less than a mile from the Island Country Club, a popular golf course with tennis courts and soon to come pickleball courts.

282 Sunset Rd, Deer Isle

Listing courtesy of The Island Agency.

$399,000
3 Beds ⋅ 2 Baths
Renovated open concept modern farm house post & beam. Features new appliances, bamboo flooring & granite counter top. First floor primary bedroom, 16x24 addition with cathedral ceiling & full bathroom ensuite, high end features, including large jacuzzi tub & carrara vanity. This 3 bedroom 2 full bath home is designed for entertaining, with a large deck & outdoor kitchen. It is beautifully landscaped with perennial gardens & mature trees. This home has been completely insulated & has new roof, under ground electricity, new plumbing and automatic generator. It is nestled in Greenlaw Cove, 5 mins to Eggemoggin Reach Beach. It is close to Deer Isle Village, also a short drive to Haystack Mountain School & downtown Stonington.

36 Greenlaw District Rd, Deer Isle

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group.

$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.

$349,900
3 Beds ⋅ 3 Baths
278 Sunset Road, Deer Isle- Single-level living with a fully remodeled, income-producing lower-level apartment with separate entrance-- this updated mid-century ranch offers flexibility for a range of buyers. The main level provides comfortable everyday living, anchored by a sunny living room centered around the fireplace. The kitchen features quality appliances and fresh white shaker cabinetry. The primary bedroom includes an attached second bath, while the second bedroom sits adjacent to the full bath on the main floor. An attached garage adds convenience. The lower-level apartment has its own private entrance, full kitchen, generous open living space, full bath, and fireplace -- creating a warm and welcoming space in its own right. The apartment can also be accessed directly from the main level, allowing the property to function as a larger 3-bedroom, 2.5-bath home with approximately 2,117 square feet of living space. The space works well for family, guests, or rental income, and it has recently operated as a successful vacation rental with proven income potential. Set on 1.10 acres, the property offers a lovely front yard, private backyard, paved driveway, and ample storage throughout. A small deck sits off the back of the home, and the setting would lend itself well to a larger deck to better take advantage of the quiet backyard. Situated on the western side of Deer Isle, the location offers easy access to many of the island's favorite outdoor spots. The Dunham Point loop, community garden, and Sylvester's Cove Beach are all close by, and the Island Country Club -- a public golf course with tennis courts and pickleball courts coming soon -- is just down the road. A versatile property in a convenient location with income potential built right in.

278 Sunset Rd, Deer Isle

Listing courtesy of The Island Agency.

$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..

$750,000
4 Beds ⋅ 3 Baths
This log home offers partial ocean views with plenty of living space inside and out all located on a 1.77 acre parcel on a dead end road. This property is eligible under the First Look Initiative. All Owner Occupant offers will be responded to after 7 days on the market and Investor offers will be responded to after 30 days. However, all offers can be submitted during the First Look period.

70 Owens Way, Deer Isle

Listing courtesy of Crescent Realty Group.

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