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For the Islesboro Ferry Schedule: Click here 

Create a custom search and view detailed information for properties for sale on the island of Islesoboro inMaine.  We offer dedicated personalized Service and are Client Focused. Our goal is to help you. 

Available homes for sale on Islesboro

299 Drexel Lane, Islesboro image
299 Drexel Lane, Islesboro $5,000,000

As featured in Architectural Digest, this classic 20+ bedroom shingle style home has been beautifully maintained and totally redecorated by the current owner. Set privat...

  • 20 Beds
  • 8 Baths
Courtesy of Legacy Properties Sotheby's International Realty

Listing courtesy of Legacy Properties Sotheby's International Realty.

267 Shore Drive, Islesboro image
267 Shore Drive, Islesboro $3,850,000

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 ...

  • 12 Beds
  • 6 Baths
Courtesy of LandVest, Inc.

Listing courtesy of LandVest, Inc..

447 Ferry Road, Islesboro image
447 Ferry Road, Islesboro $765,000

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 glas...

  • 3 Beds
  • 3 Baths
Courtesy of Berkshire Hathaway HomeServices Northeast Real Estate

Listing courtesy of Berkshire Hathaway HomeServices Northeast Real Estate.

949 Main Road, Islesboro image
949 Main Road, Islesboro $525,000

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, ...

  • 3 Beds
  • 2 Baths
Courtesy of RE/MAX JARET & COHN

Listing courtesy of RE/MAX JARET & COHN.

112-118 Church Turn Road Road, Islesboro image
112-118 Church Turn Road Road, Islesboro $549,000

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 rebuil...

  • 4 Beds
  • 2 Baths
Courtesy of Warren Realty

Listing courtesy of Warren Realty.

1326 Main Road, Islesboro image
1326 Main Road, Islesboro $227,000

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...

  • 2 Beds
  • 1 Baths
Courtesy of Island Property

Listing courtesy of Island Property.

1228 Main Road, Islesboro image
1228 Main Road, Islesboro $1,300,000

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...

  • 3 Beds
  • 2 Baths
Courtesy of Legacy Properties Sotheby's International Realty

Listing courtesy of Legacy Properties Sotheby's International Realty.

134 Big Tree Lane, Islesboro image
134 Big Tree Lane, Islesboro $2,500,000

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 ...

  • 5 Beds
  • 5 Baths
Courtesy of Legacy Properties Sotheby's International Realty

Listing courtesy of Legacy Properties Sotheby's International Realty.

503 Pendleton Point Road, Islesboro image
503 Pendleton Point Road, Islesboro $335,000

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 stee...

  • 3 Beds
  • 3 Baths
Courtesy of Island Property

Listing courtesy of Island Property.

117 Jetty Road, Islesboro image
117 Jetty Road, Islesboro $3,475,000

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 d...

  • 9 Beds
  • 10 Baths
Courtesy of LandVest, Inc.

Listing courtesy of LandVest, Inc..

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

This information is provided exclusively for consumers' personal, non-commerical use and may not be used for any purpose other than to identify prospective properties consumers may be intrested in purchasing.

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Dwelling in Maine: Real Estate

We are creative, innovative, community centered, environmental minded, and people-oriented real estate brokerage in Maine. Dwelling in Maine maintains well-trained real estate professionals who continually strive to provide top quality service to our buyer and seller clients and customers. Our experienced real estate brokers live, love, shop, play, and dwell locally.   

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