Karen M. Overtoom Real Estate and Vacation Rentals
Martha's Vineyard Vacation Rentals


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Vineyard Haven, incorporated as the town of Tisbury, which is located at the Northwest end of the Island, combines the Island’s mercantile center, a working port, an early 20th-century main street, and the historic village of Holmes Hole. It has the Island’s second-best natural harbor and was founded by a group of Islanders who preferred not to live in Edgartown under its strict Puritanical rule. According to Island legend, it was the town of Tisbury that saw the most spectacular act of defiance to the British during the Revolutionary War. When a British captain tried to seize the local liberty (flag) pole to be used as a spar on a British warship, three young women crept out at night and blew it up. There is a plaque in their honor at the Old Schoolhouse Museum on Main Street, which now houses Sail Martha’s Vineyard and the Seamen’s Bethel, an organization whose mission is to help sailors.
The presence of the Bethel in Vineyard Haven reflects the 19th century changes in the town. It overtook Edgartown as the main working port because it had become a harbor of refuge for schooners going back and forth between Boston and New York and also because the early ferryboats preferred the shorter run from the mainland. Most of the coastwise shipping traveled through Vineyard Sound; in 1845 over 13,814 vessels were counted as passing through the port .
Unfortunately, much of Main Street burned in the late 19th century. William Street, the next street up the hill from Main Street, is a historic district filled with lovely houses from the whaling era. Off William Street, there is a historic cemetery with fascinating early 19th century gravestones. On the Spring Street side of the cemetery you can see the old Baptist and Congregational meetinghouses. The Baptist church building continues to fulfill its original purpose and is currently under renovation. The Congregational meetinghouse now houses both the Tisbury Town Hall and the Katherine Cornell Theatre, where the walls are decorated with wonderful murals by the late Island artist, Stanley Murphy. This building is one of the Island’s most handsome architectural legacies of whaling days. The Vineyard Playhouse building on Church Street was built in 1833 as a Methodist meetinghouse. Today it houses the Island’s only year-round professional theater company. Vineyard Haven’s Main Street continues to be a delightful mix of excellent shops and galleries and fine restaurants; while the harbor, Owen Park and West Chop Lighthouse stand out as scenic places much admired by photographers


Vineyard Haven
$3,000 - $5,000

Watch The Sun Rise Over Lake Tashmoo And The Sun Set Over The Vineyard Sound And Elizabeth Islands.

Vineyard Haven
$3,000 - $5,000

Wonderful Summer Rental In Vineyard Haven Overlooking The Golf Course At Mink Meadows.

Vineyard Haven
$5,000 - $8,000

Water Views Of Vineyard Sound & Lake Tashmoo In Every Bedroom Of This Vineyard Haven Rental.

Vineyard Haven
$5,000 - $8,000

Makonikey 4 Bedroom Home. Huge Yard, Walking Distance To Association Beach.

Karen M. Overtoom Real Estate
Scotchman's Bridge Lane, Box 841 West Tisbury, MA 02575
www.overtoommv.com | sales@overtoommv.com | 508-693-7832
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