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The Island at Winter Harbor
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​PLAN YOUR OWN ISLAND GETAWAY
​

Welcome to
The Island At Winter Harbor
Mathews County, Virginia

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"A Step Back in Time"
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​During the last decades of the Great Steamboat Era of the Chesapeake Bay, The Beach House on what is now The Island at Winter Harbor, surely witnessed The Old Bay Lines three magnificent ships, The City of Norfolk and The City of Richmond which travelled from Baltimore to Norfolk, one in each direction, and The District of Columbia which travelled from Washington to Norfolk and back, passing in the night.

The Beach House was originally built in 1933 as a small 8 room hotel on a thin strip of land that was the Eastern most point in Mathews County, Virginia.   For decades, it served vacationers and patrons from the many steamboats that plied the waters of the Chesapeake Bay.  In the mid 20th century, during a strong Nor’Easter, the upper part of the peninsula was breached by the storm and The Island at Winter Harbor was born.

"I would rather sit on a pumpkin and have it all to myself, than be crowded on a velvet cushion."    Henry David Thoreau

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​Vacationers have cherished the beauty of the private and pristine 2+ mile long white sand beach and the back waters of Winter Harbor for decades.   From the screen porch one looks East across broad views of the Chesapeake and to the West there are breathtaking sunsets over the grass marshes of Winter Harbor, which has some of Virginia’s best fishing and crabbing.  

The simple and rustic “lowcountry” style home has been updated with heat and air conditioning and it’s eight bedrooms, and two baths can accommodate up to 16 people.  There is a large gathering room with several seating areas and dining room tables and there is a full kitchen with all amenities except a dishwasher.  The island is reached by your own boat or by a 19 foot skiff that can be rented for the week.  Boating experience operating a tiller controlled motor is necessary to rent the island skiff (please look at a picture of the boat in the photo gallery) .

This exceptional property is now available to you and your family.  A limited number of weeks are available.

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