Ilseboro, Maine Real Estate

Islesboro is a town in Waldo County, Maine, United States. The population was 566 at the 2010 census. It is a summer colony accessible by ferry from Lincolnville Beach 3 miles to the west, or by air taxi service. Home to Warren Island State Park, Islesboro includes the villages of Dark Harbor, Pripet, and North Islesboro.

Scroll down to find current real estate for sale in Ilseboro, Maine. Look through a variety of listings to find your new property. Contact our team for more information and to schedule a showing. Don't forget to create an account with our site to save your favorite listings, and receive email notifications when new properties match your search criteria.

299 Drexel Lane Islesboro ME 04848

Islesboro, ME299 Drexel Lane

Price$5,000,000

Est. Mortgage: $/month

MLS Number 1482305

  • Residential
  • MLS Status Active
  • Address 299 Drexel Lane
  • Location Rural
  • Bedrooms 20

As featured in Architectural Digest, this classic 20+ bedroom shingle style home has been beautifully maintained and totally redecorated by the current owner. Set privately at the north end of Islesboro island, this remarkable home was built in 1903 and is made up of 4 lots and over 48 total acres of spectacular oceanfront land including a deep water dock on Sabbathday Harbor. The land, which is partially in conservation with the Islesboro Island Trust, includes wonderful open fields with ocean views, walking paths through the woods down to the shorefront, beach and open ocean access, garden areas, and a majestic approach up a tree covered winding gravel road. The house is perfectly designed to accommodate large groups of friends and family, but cozy enough for single family living. There are great entertaining spaces including a large fieldstone fireplace in the living room, a fantastic custom built bar area, a great dining room with a fireplace, a large and well equipped kitchen with a walk in refrigerator and fabulous pantry area. There is also an office and laundry room on the first floor. The second floor features the master bedroom suite with its own private sun porch, and full bathroom with a claw foot tub and separate shower, as well as 14 additional bedrooms and 4 additional full bathrooms. The entire third floor of the home is a magical children's space complete with four separate themed bedrooms and a full bathroom, a school house, a library, a diner, play equipment, and a built in stage with props for endless entertainment. There are two large sun porches, and a sunny back deck overlooking an in ground swimming pool. There is also a detached barn for car storage. This is a one of a kind property.

Listed by Legacy Properties Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Feb 18, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

267 Shore Drive Islesboro ME 04848

Islesboro, ME267 Shore Drive

Price$3,850,000

Est. Mortgage: $/month

MLS Number 1479290

  • Residential
  • MLS Status Active
  • Address 267 Shore Drive
  • Bedrooms 12
  • Bathroom 6

The Devereux Cottage is a historic waterfront property on Islesboro occupying 4.39+/- acres with 359+/- feet of shorefront and excellent western facing views over Gilkey Harbor to Penobscot Bay and the Camden Hills. Built in 1917, this seasonal residence exhibits many original details such as exposed wood beams, arched doorways, fireplace mantels and a unique staircase that all work together to create interesting and appealing historic character. The house has a total of twelve bedrooms - a master, six spacious guest bedrooms and five smaller bedrooms - and over 7,000+/- square feet of living space. Most of the rooms have excellent water views and there are seven wood-burning fireplaces throughout the home. The landscape includes well-maintained lawn with beautiful flowering gardens and stonework; and there is a brand new 150+/- foot deep-water pier with a ramp and float on Gilkey Harbor. The 4.39+/- acres includes 2.2+/- acres on the water with the house and 2.19+/- acres of undeveloped land on the other side of the road that promotes privacy.

Listed by LandVest, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Feb 18, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

117 Jetty Road Islesboro ME 04848

Islesboro, ME117 Jetty Road

Price$3,475,000

Est. Mortgage: $/month

MLS Number 1279536

  • Residential
  • MLS Status Active
  • Address 117 Jetty Road
  • Bedrooms 9
  • Bathroom 10

Prominently sited on a scenic knoll surrounded by a multitude of gardens, the centrally located Dark Harbor House is a stunning example of Colonial Revival architecture designed by Fred Savage and built in 1896. In 2011/12 the current owners commissioned a complete restoration / renovation starting with a new foundation and ending with top period furnishings and landscaping - an authentically restored 125-year old house that is built to the most modern standards with new electrical, plumbing, security, gigabit speed connections and more. The commanding historic residence features views of the iconic Dark Harbor to the north, and to the west 196 feet of waterfront on Ames Cove includes a gravel beach and a six-kayak storage rack with custom launch system providing access to excellent kayaking in the picturesque Gilkey Harbor.

Listed by LandVest, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Feb 18, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

134 Big Tree Lane Islesboro ME 04848

Islesboro, ME134 Big Tree Lane

Price$2,500,000

Est. Mortgage: $/month

MLS Number 1368551

  • Residential
  • MLS Status Active
  • Address 134 Big Tree Lane
  • Bedrooms 5
  • Bathroom 5

This picturesque, year-round waterfront home is nestled on the sought after island of Islesboro. It is privately set on 7+ acres, w/ 650 ft. of varied shorefront, a deep water dock in protected Seal Harbor, and thoughtful landscaping w/ views across Penobscot Bay to the Camden Hills. This home was custom-built to the highest standards, and exemplifies exquisite form and function, allowing for smooth transitions among the gracious formal and casual informal living and entertaining spaces, indoors and out. This home offers a generous master bedroom plus 4 additional bedrooms, some w/ windows seats, a sitting room w/ balcony, covered porch and screened porch, a greenhouse, sunroom, a library w/ wood burning fireplace and hand-built custom shelves and cabinets, living room w/ wood burning fireplace, a formal dining room w/ custom built-lighted shelving, and kitchen w/ an AGA stove. Additional amenities include home office, laundry room, radiant heat, whole-house generator and 2-car garage.

Listed by Legacy Properties Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Feb 18, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

1228 Main Road Islesboro ME 04848

Islesboro, ME1228 Main Road

Price$1,300,000

Est. Mortgage: $/month

MLS Number 1435709

  • Residential
  • MLS Status Active
  • Address 1228 Main Road
  • Bedrooms 3
  • Bathroom 2

Charming 150 year old 1 1/2 story Cape Farmhouse situated on a high level knoll overlooking the East Penobscot Bay, the entrance for all vessels sailing or motoring their way ''Down East''. With views of the many inlets, islands, Cape Rosier, Castine, and Hutchin's Island. Perfect glorious morning sunrises! Across the road is protected land owned by the Islesboro Islands Trust so your view will never be obscured as it has been designated as a blueberry farmland! The property has manicured fields full of blueberries, extensive vegetable and herb gardens with a waterfall, tunnel covered with grape vines, pergola, fruit trees mostly fenced. A 30 x 60 Pole Barn with large doors that open for equipment or any other storage. Workshop, heated exercise room, and 2-car garage.

Listed by Legacy Properties Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Feb 18, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

447 Ferry Road Islesboro ME 04848

Islesboro, ME447 Ferry Road

Price$765,000

Est. Mortgage: $/month

MLS Number 1471962

  • Residential
  • MLS Status Active
  • Address 447 Ferry Road
  • Location Rural
  • Site Features Well Landscaped

Do you enjoy hiking, biking, kayaking, boating or hanging out on the beach? How about just peaceful mornings soaking up views of the ocean or early evenings having a glass of wine while watching spectacular sunsets over the bay? Do you collect sea glass - how much better from your very own beach? Or, are you simply looking to get away from the city?? This privately situated, year-round home on the coast of Islesboro facing the Penobscot Bay with 3 spacious bedrooms, a potential 4th large bedroom, 3 full baths (one on each floor), first floor living, xlg windows throughout so you never miss views of the bay, over 200ft of direct waterfront, possibility of having your own deep water dock is just what you need to enjoy vacations with your family and friends or peaceful year-round living. Also makes a great investment property. Only 3 miles off the coast of Lincolnville, a 20-minute ferry ride makes it easy to visit Camden, Belfast, and Rockport, as well as access airports in Bangor and Portland. This might be an island, but it has everything you need: broadband internet, a highly-rated school, markets, cafe, fire/police depts, and a health center with on-call staff. Islesboro is a welcoming, caring community that it is easy to live on and work from. FaceTime and Zoom showings always available.

Listed by Berkshire Hathaway HomeServices Northeast Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Feb 18, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

1068 Ellis Lane Islesboro ME 04848

Islesboro, ME1068 Ellis Lane

Price$595,000

Est. Mortgage: $/month

Pending

MLS Number 1477346

  • Residential
  • MLS Status Pending
  • Address 1068 Ellis Lane
  • Site Features Wooded
  • Bedrooms 2

Privacy and serenity located just south of Meadow Pond. This house was lovingly designed and built by the current owners; one a master finish carpenter, the other an artist. Excellent craftsmanship and thoughtful details are found throughout this shingle style home that blends elegance with simplicity in a comfortable setting. Sunlight fills the open living concept on the first floor and the large screened-in porch extends this space during warmer months. The kitchen has beautiful mahogany countertops, bespoke hutches and high-end appliances. First floor bedroom, full bath along with a nook with bunkbeds. Sunlight pours through the skylights of the second floor onto a large studio space, plus a bedroom, full bath and plenty of storage. Efficient radiant heat on both floors is accompanied by a wood stove, wood fireplace and a gas fireplace. The property comes with an additional building, includes a full bath, monitor heater and woodstove, that could easily be converted into a guest house or art studio.A short walk, bike or drive from Meadow Pond, perfect for summer kayaking or winter ice fishing. Close-by conservation lands offer year around hiking trails. Stay connected while living on a coastal Maine island with 1 Gigabit speed connection.

Listed by LandVest, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Feb 18, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

112-118 Church Turn Road Road Islesboro ME 04848

MLS Number 1467325

  • Residential
  • MLS Status Active
  • Location Interior Lot, Rural
  • Bedrooms 4
  • Bathroom 2

This listing is for two houses! The main house is a four-bedroom, two-bathroom year-round home with many extras, including a 14KW diesel generator. Two recently rebuilt decks looking out over a large lawn and a view of the Meadow Pond. Three bedrooms and a bathroom upstairs, master bedroom and bath downstairs along with a mudroom, sun room, dining room, living room and kitchen. Full unfinished basement. House is set up with high speed fiber optic broadband.In addition to the main house, there is a 42X30 building on a separate driveway. This contains an over-sized two-car garage, full bath, and office on the first floor and expansive two-bedroom, one-bathroom apartment on the second floor - all with radiant heat. Great opportunity for a rental income property, guest house, or in-law apartment. Owner will consider sale of two houses together or separately, as they are on separate lots. The opportunities of this property are endless.

Listed by Warren Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Feb 18, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

949 Main Road Islesboro ME 04848

Islesboro, ME949 Main Road

Price$525,000

Est. Mortgage: $/month

MLS Number 1471123

  • Residential
  • MLS Status Active
  • Address 949 Main Road
  • Bedrooms 3
  • Bathroom 2

In recent history known as TLC Farm, this circa 1870 Greek Revival farmhouse, with some original details remaining, is in need of complete renovation. Meadows and woods, farm pond and easy access to the elevated house sites near the Ryder's Cove water frontage are accessed by existing Lois Lane. Lois Lane, the original woods road, continues through the woods of spruce and pine to the site of Mill Dam located on Mill Cove, which was used as saw and grist mill in the past, however no building remains. This one of a kind property is suitable for a sub-division with several potential house sites taking advantage of water views and access to both coves as well as numerous suitable uses for a year round use such as family compound, farming, horse farm etc., Or just simply enjoying island living away from it all, but only 20 minutes ferry ride to mainland. Come and see this property with a great potential.

Listed by RE/MAX JARET & COHN

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Feb 18, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

442 Pendleton Point Road Islesboro ME 04848
Pending

MLS Number 1445143

  • Residential
  • MLS Status Pending
  • Bedrooms 5
  • Bathroom 5
  • Rooms 12

On 6+/- acres of landscaped field, woods, and orchard, at the corner of Pendleton Point Road and Decker Road, sits this 11/2-story single-family winterized home with a detached studio, a detached garage, and a greenhouse and a gazebo. The interior contains 10 rooms (5 bedrooms and 41/2 baths) plus an enclosed porch and an open porch. The foundation has recently been rebuilt and the house is on the town sewer.$550,000

Listed by Warren Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Feb 18, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

523 Pendleton Point Road Islesboro ME 04848
Pending

MLS Number 1470482

  • Residential
  • MLS Status Pending
  • Bedrooms 6
  • Bathroom 3
  • Rooms 8

Conveniently located right in the heart of Dark Harbor Village, this 100+/- year-old Victorian house is in exceptionally good condition and very tastefully decorated. With six bedrooms, 21/2 baths and more sleeping space available on the third floor, the home has plenty of capacity for a large family or even a bed and breakfast. Amenities include two fireplaces, large living room, study and much more. Home is being offered partially furnished and ready to move into in time for next summer.

Listed by Warren Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Feb 18, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

503 Pendleton Point Road Islesboro ME 04848

MLS Number 1339257

  • Residential
  • MLS Status Active
  • Bedrooms 3
  • Bathroom 3
  • Rooms 8

Inviting yearround home, heart of Dark Harbor Village, just steps from summer shops. Built in 1920, completely renovated 1978. Open floor plan kitchen, new stainless steel appliances, dining room, two large living rooms, perfect for first floor bedroom with full bath, master bedroom and bath with jacuzzi, guest bedroom and bath. Gambrelled two story shop/barn. Delightful pond and ample acreage included behind the house for two homesites via neighboring right-of-way. Enjoy a glimpse of Dark Harbor Pool from your front porch wicker and life in a quaint historic island summer community. $335,000.

Listed by Island Property

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Feb 18, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

1326 Main Road Islesboro ME 04848

Islesboro, ME1326 Main Road

Price$227,000

Est. Mortgage: $/month

MLS Number 1458764

  • Residential
  • MLS Status Active
  • Address 1326 Main Road
  • Bedrooms 2
  • Bathroom 1

Historic Greek Revival Two-bedroom island home built in 1860. Situated on the less trafficked end of North Islesboro on 2. 23 acres of open lawn and meadow with hardwood and apple trees and even a small pond, you'll find yourself settling into a relaxed pace with comfortable space inside and out. Kitchen island, first floor full bath, dining and living rooms plus two bedrooms and office upstairs. Great starter home or island getaway.

Listed by Island Property

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Feb 18, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

Listing data is derived in whole or in part from the Maine IDX & is for consumers' personal, non commercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. ©2021 Maine Real Estate Information System, Inc. All Rights Reserved. equal opportunity housing logo   Privacy Policy

The New England Real Estate Company participates in ©2021 Maine Listings Internet Data Exchange program, allowing us to display other Maine IDX Participants' listings. This website does not display complete listings. Certain listings of other real estate brokerage firms have been excluded. Mortgage figures are estimates. Check with your bank or proposed mortgage company for actual interest rates. This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.