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Built for Generations: Family Compounds Across New England & The Adirondacks05.12.2026

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Some properties are purchased for a moment in time. Others are held for generations.  Across New England and the Adirondacks, family compounds have long represented a distinct kind of ownership — properties designed not simply as homes, but as places to return to year after year. With [...]

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Timeless Appeal of Maine's Dark Harbor

"One Summer in Dark Harbor is Worth a Dozen Summers Abroad"

- Charles Dana Gibson, America's most famous turn-of-the-century illustrator

  Dark Harbor, located on the southern end of Islesboro, is home to a majority of the islands impressive cottages. Overlooking the Dark Harbor itself, Dark Harbor House is the gateway to this enclave of turn-of-the-century homes, and is viewed by many as one of its most beautiful.

Back yard view of Dark HarborThe Dark Harbor summer community began in 1888, with the formation of the Islesboro Land and Improvement Company. This company was formed by the Boston real estate broker James Murray Howe, and James D. Winsor, a wealthy Philadelphia steamship owner. They fell in love with the beautiful island of Islesboro, with its varying contours and breathtaking views of Penobscot Bay and the Camden Hills. One of the first new cottages built was the lovely Dark Harbor House. While much has changed on Islesboro over the years, the essential ingredients that made Dark Harbor so desirable exist to this day.

A vibrant summer community consisting of people from the arts, science, literature, commerce, and more, come together each year to enjoy each others company. Many have become members of the Tarratine Club, founded by Dark Harbor residents in the early 1900s. This club offers tennis, yachting, and golf as well as lunches and dinners at their golf and yachting facilities. However, membership in the Club is not necessary for a full and active life on Islesboro. Dinners at various cottages are enhanced by the fine culinary skills of island residents. In addition, guest lectures, art and historical exhibits, and special musical programs make for an interesting and active social and cultural life.

DarkHarbor, Islesboro, Aerial_printIslesboro offers many amenities not often associated with a Maine island.

  • A beautiful Community Center with an extensive fitness center was built in 2009.
  • Hiking on many hundreds of acres of protected lands is offered by the Islesboro Island Trust.
  • Two, well-stocked markets offer a wide assortment of groceries including those essential for the gourmet cook. Fresh produce grown in the many island gardens is available at weekly Farmers' Markets.
  • A restored 100-year-old Cottage is home to Island Central School, an award-winning K-12 public school, which will soon be complemented by a birth-five pre-school/day care facility, currently under construction.
  • Regular ferry car service to the mainland is only a 20-minute trip and is augmented by a private passenger ferry. Many harbors, both private and public, offer docks and moorings, and a very popular sailing school so that all can enjoy boating this is, after all, an island!
  • Lastly, the Town of Islesboro has created the Islesboro Broadband Company which is building the most advanced internet infrastructure in Maine. Fiber is being strung to every home and business on the island and by summer of 2017 will offer gigabit speed connections.

Dark Harbor House, Islesboro, METhe graceful homes and traditions of the turn of the century have not kept Dark Harbor and the entire island from embracing the future, making this an exceptional place to live, work and summer.

For more information on this Isleboro property for sale, check out the Dark Harbor House on our website or contact Terry Sortwell or Joseph Sortwell in our Camden office for other waterfront homes in coastal Maine.

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