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LINK ID: 34015 $379,000


Town: Aquinnah
Type: Land

Stone walls, old oaks, grape vines, ferns, boulders and a stream are just some of the features of this hidden parcel of land on Jeffers Place in Aquinnah. A two bedroom (possible three) septic system is in place. A well has been drilled but may need work or replacement. Some survey work has been done.

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LINK ID: 34012 $1,149,000


Town: Vineyard Haven
Type: Single Family

OPPORTUNITIES ABOUND. Set behind a handsome stone wall, this beautifully appointed craftsman-style home has been uniquely designed with two separate living areas and two kitchens, making it perfect for multi-generational living, an Airbnb/vacation rental property -- or a highly visible live-work setup. Built in 2008, this custom-crafted home integrates reclaimed architectural details with modern, state-of-the-art construction features including energy efficient insulation, multi-zoned heating and air conditioning, Lutron® lighting as well as superior quality details such as custom milled wood paneling, built-ins, crown molding and wainscoting. In addition, the current owners have made further upgrades to the property (see attached summary). Tisbury zoning bylaws allow for an in-home office/business for a professional services business, tradesperson or artisan -- with visible on-street signage. There is a detached, heated 800-square-foot garage/office/workshop with separate driveway entrance off Martin Road-Foster Road, providing nice separation and privacy from the house. This gorgeous property is currently being used as a successful rental property, with a solid rental history. The property is ideally located within a 10-minute walk to Vineyard Haven village and ferries. Tasteful furnishings and contents are available for separate purchase/negotiation for a TURNKEY OPPORTUNITY. Come and see firsthand how this property can be a smart move toward your personal, business or investment goals!

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LINK ID: 33975 $859,900

Guest Bedroom
Guest BedroomHeading up to the second floor- notice the wood floorsFull basement with laundryHuge exterior mahogany deck ! Plenty of room for entertaining!
Town: Edgartown
Type: Single Family

This home lives large SURPRISE inside~ Edgartown in Majors Cove, a private community with protective covenants, offers easy access to the Shores of Sengekontacket and Nantucket Sound for boating, kayaking and fishing! Colonial Style home with SOARING CEILINGS and an OPEN floor plan that truly is SPECTACULAR for entertaining, relaxing and family gatherings! Complementing all of the intimate spaces is an OVER SIZED SCREEN PORCH, accommodating both casual relaxation and dining, that flows to a substantial exterior MAHOGANY DECK. Other features include a wood burning fireplace hardwood flooring, CENTRAL AC and a NEWER FURNACE! There are 3 bedrooms and 2 full bathrooms along with a full basement with plenty of storage space! TREMENDOUS INVESTMENT OPPORTUNITY for SUMMER RENTALS! Association includes tennis courts and potential for a boat mooring.

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LINK ID: 33963 $4,375,000

Squibnocket Beach
Squibnocket BeachChilmark house 1Squibnocket PondGuest bath
Town: Chilmark
Type: Single Family

Perched above and just steps from beloved Squibnocket Beach and Pond, this idyllic beach house has amazing views of the Atlantic and shoreline out to Squibnocket Point. It has been fully renovated with many tasteful, modern enhancements and sustainably-sourced materials, and yet retains some of the most charming elements of its past. The airy floor plan offers a family-friendly open kitchen, living and dining area, a master bedroom, and a guest wing with three more bedrooms. The lower level is finished, adding about 1350 square feet of space including a spacious 30' x 20' recreation room and laundry room. The property is surrounded by stone walls, a bluestone patio facing the Atlantic, and a path to the Pond (with rights to build an elevated walkway and kayak rack). Originally known as the Hilly Mayhew House, this property was for over 80 years the haven for the international modernist painter Vaclav Vytlacil and his family. He created hundreds of seascapes and harbor scenes of the Vineyard, many of which can still be found on the island and around the world. Walk to the beach, kayak in the pond, or just sit out on your patio watching the day unfold, osprey fish and surfers ride the waves.

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LINK ID: 33959 $775,000


Town: Chilmark
Type: Single Family

Cozy, cottage with lots of windows and light set in a very quiet area far off North Road abutting Seven Gates. Lot offers a lovely back and side yard perfect for entertaining. Stone wall border creates a wonderful, rural Chilmark feel yet the lot is just minutes back down to West Tisbury and still offers access to Lucy Vincent Beach. Home has a new septic system, updated bathroom, hot water heater and well installed in 2013. There is a spacious 500 sq ft wrap around mahogany deck with seating that provides ample room for your summer guests while entertaining. You could perhaps increase the living space by adding a second floor with town approval. Home is insulated, has monitor heat and has been used year round in the past. Several weeks are already booked late July thru August for $12,000. Check out the 3D video on sidebar.

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LINK ID: 33954 $11,750,000

The pristine beach, just steps from the home
The pristine beach, just steps from the homeFront elevation of the house from the beachThe expansive porch is perfect for entertaining1153 Main Street Vineyard Haven, MA 02568
Town: Vineyard Haven
Type: Single Family

Located on a winding private road, this original 1896 West Chop waterfront home was completely renovated to exacting standards in 1992. With 8 bedrooms and 6 and a half bathrooms, and a classical layout with formal and informal areas in which to relax and pass the time, this home encompasses all that this desirable location provides for multi-generational family gatherings and summer memories at West Chop. A stately front entrance leads to the formal living room with adjoining separate sitting room, with fireplace, that opens to the expansive water facing porch providing active views of the Vineyard Sound and additional entertaining space to while away a lazy summer afternoon. The home offers an exceptional combination of elegant charm and modern amenities including the large gourmet kitchen breakfast room, with Wolf and Sub Zero appliances, bespoke cabinetry and a butler’s pantry that leads through to the formal dining room. The staircase leads to a large master suite with full bath, office and balcony overlooking the water. Three further bedrooms and 2 additional bathrooms occupy the remainder of the second floor with 4 further bedrooms and 3 baths on the third floor. The huge walk out basement was created during the renovation, and could be finished to create living space for wine cellar, family room or gym. Air Conditioning has been installed throughout for 2019. Walk from the house through established perennial gardens to the beautiful sandy beach for easy swimming, tide rides to the pier and docks and enjoyment of the water. This is a rare opportunity to buy in the heart of the West Chop community. Contact us for more information about this special North Shore private setting with opportunities for beaches, tennis, golf, and more.

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LINK ID: 33942 $3,950,000


Town: Oak Bluffs
Type: Single Family

Top of the Chop ~ A stunning contemporary with dramatic sweeping views of Vineyard Sound. A complete transformation by South Mountain & Company of the former residence resulted in a masterpiece of modern living and superb style. Upon entering you are immediately greeted with water views and the breathtaking landscape and it continues to unfold as you go through the home. The single story home was designed with the living and entertaining area at the core with the master wing tucked privately away and a two bedroom guest wing down its own corridor. The baths are luxurious, the kitchen a work of art and the finishes throughout are simply exquisite. East Chop is an upscale summer community, a most ideal location with the beach, harbor and town just a short distance away.

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LINK ID: 33936 $1,900,000


Town: Vineyard Haven
Type: Single Family

Downtown Vineyard Haven home with harbor views. This historic 3-bedroom home is perfectly located on the outskirts of Downtown Vineyard Haven, next to Owen Park. The outside is well maintained and the two-story deck allows for unobstructed views of Vineyard Haven Harbor, while the inside is just waiting for a buyer to make it their own.

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LINK ID: 33922 $2,495,000


Town: West Tisbury
Type: Single Family

Country Sophistication - Located at the end of a winding driveway that sweeps through expansive grounds, you will find this gorgeous country estate. The mudroom entrance opens to the well appointed chef's kitchen, with granite counters, top of the line appliances and sitting area with beach stone fireplace. The combined great room and dining room with limestone fireplace, is filled with natural light from oversized windows, transoms and french doors leading to the exterior on both front and rear of the house. The 1st floor offers a master suite that boasts a Jacuzzi tub with a guest bedroom and bath. Upstairs are 2 additional bedrooms with shared bath and a second staircase leading to a large sitting room above the kitchen. The outside is perfect for entertaining on a grand scale with an expansive lawn, as well as a 20 x 40 gunite pool, all nestled in the beautifully landscaped gardens. Completing this tranquil setting is a 2 car garage with brick flooring, a potting shed and upstairs bedroom, sitting room and bath. The 8 acre parcel allows for a full second structure if desired.

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LINK ID: 33918 $2,495,000

Upstairs guest bedroom 1
Upstairs guest bedroom 1First floor guest bed/second master facing the poolUpstairs guest bedroom 2South facing front of the house
Town: West Tisbury
Type: Single Family

Immaculate 6 bedroom home with heated pool in beloved Indian Hill area of West Tisbury. Smart decisions throughout ensuring an easy fit for any buyer. Two master bedrooms on the first floor with separation from the additional two bedrooms upstairs. The chefs kitchen is set up nicely with quality appliances, counter top work space, loads of cabinetry and storage and a large pantry. Open to the kitchen is a cozy living room with a fireplace making a great sociable family living space.The great room has vaulted ceilings and French doors to decks on the front and back of the home. At one end of the great room is a fireplace with dining area and the other end houses custom built-ins with entertainment center. The whole space offers various easy options for summer/winter change of use. In addition to the 4 bedrooms there's an additional bedroom/office/ storage room in the main house, plus guest suite comprising of large bedroom/bathroom above the two car garage (with brick flooring) . The property has a tasteful in ground 20x40 gunite pool that fits organically into the landscape with easy access from different areas of the home. The land allows for an additional home to be built as well as generous accessory structures. Excellent rental history makes this property a great investment or a wonderful year round family home.

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LINK ID: 33881 $2,690,000


Town: Edgartown
Type: Single Family

Green Pastures- A private, residential enclave offering shared access to an association dock and waterfront on the calm waters of Katama Bay. Prominently positioned, amongst the large homesites and 18 acres of open community owned property, you’ll find this delightful four bedroom, year round, home. A sizeable two-story garage, with plenty of storage for boats, beach and boating gear below and a detached bedroom with half-bath and deck above, is the perfect complement to this Chappaquiddick retreat. Plenty of space for a guest house and swimming pool -A fantastic offering in one of Chappy’s loveliest communities!

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LINK ID: 33871 $199,999


Town: Edgartown
Type: Condo

Exceptionally rare opportunity to purchase a waterfront condo/hotel room at the Harborside Inn located on Historic Edgartown Harbor. One of only two known units with FULL 30/30th deeded ownership rights which represents the entire season that this facility is open. Amenities include boat dock, parking, maid service, heated outdoor pool and spa. Pied-a-terre, nanny's quarters, guest quarters, home away from home, weekend getaway...endless possibilities and uses. The Harborside is a member of RCI and Interval International. Moments from the finest shopping, restaurants, art galleries, and beaches on Martha's Vineyard. Don't miss out on this once in a lifetime investment opportunity!! Please call for more details!

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265 - 276 of 415 Listings