Scroll down to browse all Martha's Vineyard Up Island real estate for sale. You will find a variety of listings, including luxury homes, waterfront properties, summer rentals, and much more. Contact us if you have questions or would like to tour a listing.
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"Cliff Cottage" enjoys one of the most picturesque settings and water-views on Martha's Vineyard. Originally built in 1850 and painstakingly remodeled by the current owner's, along with one of the Islands finest builders to reflect today's life style and amenities. The recently constructed detached studio with over 1,400 sq' offers 2 additional bedrooms with water-views along with an office and a garage. An association stairway leads to your private sandy beach on the south shore, additionally, there is deeded access to Menemsha Pond a short walk away.
Endless Atlantic Ocean views, Squibnocket Pond, rolling hillsides, dramatic vistas, centuries old stone walls, gravel roads... these are just some of the features of this extraordinary property new to market for the first time in nearly fifty five years. This architect designed modern Cape Cod home with five bedrooms and two and one half baths on nearly three acres can be your summer place. Swim, kayak, row or clam in Nashaquitsa Pond, surf at Squibnocket or relax and enjoy the unspoiled, crowd free beach at Zacks in Aquinnah (with membership).
NEWLY Priced to Encourage a QUICK Sale - Waterfront on Thumb Cove/Tisbury Great Pond. Rare opportunity to purchase one of the last undeveloped parcels on the West Tisbury part of Tisbury Great Pond. Situated between Middle Point Cove and Thumb Cove, this lot is currently 9.6 acres. Build a house and guest house for you and your extended family to enjoy the endless activities this location provides. Enjoy your summers kayaking and canoeing out to South Beach for a day in the sun or fishing. Gather oysters in the off-season. Evening campfires on the beach. A magical place to create lifelong memories. This parcel of land could truly become your Island Paradise on Tisbury Great Pond.
Located on the edge of Quitsa Pond, this four bedroom home is perfect for summering on the Vineyard. Views from nearly every room of this home over Quitsa and Menemsha Pond. With extremely desirable dock space included, this property has two full private docks and one floating dock only steps from your door. First level of home is a large living area with kitchen all fronted by a large screened in porch. There is also another area that serves as bedroom or could also be used as a den or office space. Upper level has 3 bedrooms, large living room, full bathroom and loft space - great for the young ones. This home is great for entertaining and offers some of the most spectacular views in Chilmark. Enjoy sunset views over the pond...or swim off of the private sandy beach area on the pond which is great for young swimmers and for launching kayaks...All of this just within a short distance of Squibnocket Beach.
Once home to one of the Islands most renowned artists, this six bedroom expanded farmhouse has blended modern amenities with the charm of an historical home. A place where permanent conservation restrictions create a pastoral environment, expansive rooms with oversized fireplaces overlook surrounding fields dotted with grazing livestock, serene pond and ancient stone walls.
This private three acre lot enjoys North shore waterviews, substantial building envelope, privacy from abutting Waskosim's Rock Reservation, beautiful stonewalls, and pondviews. This is a rare offering of one of only a few lots in an area of pastoral & ecologically protected land in Chilmark. Fully engineered. Well and utilities on site. Property includes rights to the two tennis courts nearby on Old Farm Rd which are all weather sandy green carpet surface similar to har-tru.