Updated on Sep 29, 2026
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Type
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Private vacation home
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Bedrooms
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5
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Bathrooms
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3
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House Rules
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Pets allowed
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Children allowed: ages 0-17
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Smoking is not permitted
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No events allowed
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Max Occupancy
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10
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Host Language
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English
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Property Id
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293730
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A storied property in Chilmark for almost 150 years, the hilltop Tower House combines current taste, comfort and elegance with its own special provenance -- as an authentic part of the Vineyard's remarkable historic character.*
Today, enjoy this welcoming home's timeless, well-cared-for Summer House vibe: its spacious and well-furnished interior rooms, its many places for family and friends to gather, and its expansive, sunlit lawns. It overlooks a dramatic view -- over bright fields and ponds, a far shoreline, then further islands, and the seas and mainland beyond -- a layered, 30-mile panorama rare for the Vineyard.
FIRST FLOOR
Sunrises, sunsets and day-long sunlight grace this property.
- The large eat-in kitchen with bay windows catches sun all day
- The spacious adjacent deck provides outdoor dining, with separate seating area for enjoying the panoramic view first-hand.
- The formal front hall leads to the well-furnished tower living room with its 6 wrap-around windows
- A traditional dining room is a 3rd place to gather for meals
- The bright and casual 2nd living room opens to a wicker-furnished outdoor porch overlooking the home's wide lawns.
- A Queen bedroom has its own large, wheelchair-accessible bathroom
- A small powder room serves the lower floor rooms
UPPER FLOOR
Each bedroom has ocean views, art, and comfortable beds.
- The large tower Primary bedroom is filled with all-day light.
- A second King bedroom has its own ensuite full bathroom
- A Queen bedroom overlooks Quitsa and Menemsha Ponds
- A 'kids' 2-Twins bedroom is closest to the Primary bedroom
- The upstairs main bathroom (with tub) serves 3 bedrooms
(Note: in summer, all bedrooms are cooled by AC units).
BEACHES
Adding to this property's special character: private access to two closely-held, unspoiled Chilmark beaches, accessible daily and detailed below. (Note: our guests can apply for access, also, to well-known Lucy Vincent Beach or Squibnocket Beach via Chilmark Town Hall).
1) Intimate SHORT BEACH (within 5 minutes by car) on Menemsha Pond is perfect for young and old (no surf), where you can also secure your kayak.
2) Access pristine HANCOCK BEACH (15 minutes by car, key entry) for Atlantic shoreline surf and long beachwalks. Children may enjoy the big adjacent inland pond.
NEARBY...
Plenty of enjoyments lie in close reach of the Tower House.
- Within 3 miles:
Chilmark Tavern
Chilmark General Store
Beetlebung Farm
Chilmark Town Hall, Post Office, Library, & Community Center Martha's Vineyard Bank
Congregational Church
- A bit farther:
Menemsha village's beach, gas station, charming shops, fishing charters, and just-caught seafood from the docks.
A short ride from the house takes you to Aquinnah's magnificent colored cliffs, tiny shops, and working lighthouse.
- Farmer's markets, art galleries, craft and antique fairs start at West Tisbury mid-island with North Tisbury's offerings nearby.
- Just beyond are 3 bustling towns with exceptional shopping boutiques, good live theater, bookstores and ever-changing movies. Nature walks and bike trails criss-cross the island, 3 golf courses offer tee-times, and history comes alive in charming byways and museums.
- Or simply relax at home, with ball games on the lawn, fast internet, good books, puzzles & games, shady nap-spots!
WEDDINGS.
During September, weekly rentals of the Tower House run Wed. to Wed., allowing for wedding event set-up/breakdown and a wonderful weekend celebration in-between! Up to 10 people may easily stay on-site for all or part of the wedding week. This Victorian-era summer house with its ample gathering rooms and decks is without central heat or central AC, so bedroom AC units or space heaters are provided for weather that's extra-hot or -cold.
The expansive and level field adjoining the Tower House accommodates large dining, dancing and kitchen tents as well as additional bar stations, lounge areas, etc. The marriage ceremony most often takes place overlooking the water-and-islands view, on a side lawn with ample space for guest seating. The property's vine-trimmed stone walls, planting beds, arched garden arbor and gingerbread-trimmed porches add further areas for exceptional family and wedding party photography.
Our guest book attests to our many wedding families' joyful memories made here!
*A stand-out home, with an exceptional history, the house is an up-island landmark for its yellow-painted Queen Anne main house with red roof, and ball-topped tower. The grounds include a meadow-sized lawn beyond the main house, perfect for active kids, active sports, and in September -- weddings' large, tented celebrations.
The Tower House estate property includes a barn, private garage, and a 2 BR guest house (a separate rental). This property has changed hands only once since beginning as a multi-acre farm in the early 1800's. It has been our family's summer home for over 50 years.
Our family's third generation now provides the property's responsive, active care.
Located in Chilmark, this vacation home is in a rural area and near the beach. Island Cove Miniature Golf and Island Cove Adventures are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Chilmark Chocolates and Fulling Mill Brook Preserve. The Grey Barn and Farm and Polly Hill Arboretum are also worth visiting. Water skiing and windsurfing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and horse riding nearby.
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