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Martha's Vineyard Vacation Homes

Scroll down to browse all vacation homes for sale in Martha's Vineyard. Contact us if you have questions or would like to tour a listing.

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35A North Neck Road, Edgartown, MA

Price$5,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 31324

  • Residential
  • Square Feet 2486
  • Bedrooms 5
  • Bathroom 2
  • Acreage 4.679

Perched atop the most commanding rise on Chappaquiddick's coveted North Neck Road, “Hillhouse” is the ideal waterfront generational gathering place, with jaw-dropping views, private dock, and over 500 feet of sandy beachfront. Located on ~4.7 acres among the finest homes on Martha's Vineyard's Chappaquiddick Island, your new vacation destination awaits. Upon reaching the property's peak from a recently reconfigured drive, the inviting ca. 1967 summer home greets with a winged floor plan. The residence includes 5 bedrooms spread on either side of an open and airy central living room that features a beautiful fireplace, exposed wood beams, high ceilings and astounding water views. The views are seemingly endless and must be seen to appreciate fully, sweeping on one side of the home from Cape Pogue to Edgartown Harbor and on the other across Wasque to Nantucket on the horizon. From the back deck, descending down the bluff on a private stair reveals a pristine expanse of sand and water, perfect for relaxation, sun, swimming and many other forms of recreation. The private dock provides attractive options for boating, fishing and swimming enjoyment as well. While the present improvements on the property have provided the perfect setting for enjoyment for many seasons, the development opportunities here are exceptional - a dream setting for any architect - with the possibility of 9 bedrooms and a much larger home.

Listed by Wallace & Co. Sotheby's

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

15 Maqua Way, Edgartown, MA

Price$2,999,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 29277

  • Residential
  • Square Feet 2920
  • Bedrooms 7
  • Bathroom 3
  • Acreage 5.23

Enjoy private beachfront and stunning water views from this antique home with 7 bedrooms spread over 3000 square feet. The home is in immaculate condition and lives like a house more modern than its 300-year-old pedigree would suggest, with lots of privacy as well as expansive common space. This is the perfect home for a large extended family or those who like to entertain lots of guests. Above all, though, this is the ultimate Chappy vacation escape, perfectly located for you to enjoy the natural playground of sun, sand, and sea in your backyard, with extensive opportunities for fishing, clamming, swimming, boating, and watersports of all kinds. Note: Seller will discount property by $400,000 if buyer wishes to build a new home on the lot and agrees to let seller salvage the house. View a drone video of the property by pasting this URL into your browser: https://vimeo.com/174675397

Listed by Wallace & Co. Sotheby's

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

40 Norton Farm Road, West Tisbury, MA

Price$2,395,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 19207

  • Residential
  • Square Feet 3984
  • Bedrooms 4
  • Bathroom 4
  • Acreage 2.2

Classic, elegant country home with water views, private pool, and nearby beach. This beautiful architectural home features a cook's kitchen, private library, three bedrooms with en suite bathrooms plus a loft bedroom with bathroom. The second and third floor rooms have lovely water views and private balconies. The first floor master bedroom, breakfast room and elegant dining room all open up to the sprawling backyard and pool. Three fireplaces, wood floors, french doors, and custom wood detailing throughout the home add to the elegance inside and the manicured lawn, gardens, Gunite heated in-ground pool, and privacy of 2+ acres facing Vineyard Sound complete the package outside. Walk to two Makonikey beaches, less than 1/2 mile away. This property has all the elements of a perfect Vineyard vacation home.

Listed by Tea Lane Associates

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

65 Winemack Street, Oak Bluffs, MA

Price$1,199,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 31438

  • Residential
  • Square Feet 3828
  • Bedrooms 5
  • Bathroom 4
  • Acreage 0.35

Practical East Chop Vacation or Year-Round Home. This spacious, well maintained, 5-bedroom (septic was built for 6-bedrooms) traditional center hall New England Colonial was built in 2001. Located in East Chop, the 3,828 sq. ft. house sits on 0.35 acres. Convenient to tennis, beaches, the harbor, public transportation, the hospital and downtown! The house includes 4 full bathrooms, living room, dining room, kitchen with loads of cabinet space and large center island with counter seating, large family/media room, and full basement. House is being sold fully furnished. Outdoor shower, shed, ample parking and tasteful landscaping complete the property. Septic has been designed for 6 bedrooms so that a detached garage with sixth bedroom above can be constructed, but verify any such plans with appropriate town building and health departments. Strong rental history. Showings can be arranged Tuesdays, Thursdays and Saturdays at around 11:30, please allow for a minimum of 24-hour notice.

Listed by RE/MAX on Island

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

169 Greenwood Avenue, Vineyard Haven, MA

Price$1,195,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 31977

  • Residential
  • Square Feet 5359
  • Bedrooms 5
  • Bathroom 4
  • Acreage 0.59

169 Greenwood Avenue, an exceptionally grand Martha's Vineyard home, was carefully crafted in 2007 as a sanctuary for the island lifestyle to be enjoyed all year long. With a commanding presence, its .59 acres of sprawling lawn and blooming trees are the perfect backdrop for this spacious and welcoming home. The abundant Andersen windows and doors allow light in from every angle and show the quality and flow of the living spaces. With 3,500+ square feet on two levels, this enormously comfortable dwelling has an epic open floor plan layout, two master suites and three guestrooms. The 1,800+ square feet of finished living space on the lower level provide extra space for guests, a full bathroom, game room for rainy days, and a full patio for even more outdoor living. The exterior grounds are equally as important to life at this residence, access and views to which are found from the decks, and windows throughout. At ½ mile to Owen Park beach and ¾ mile to the ferry and all downtown amenities, it's no wonder that this property handles vacation rentals effortlessly, boasting $50,000 of rental income annually. This unforgettable offering is being sold fully furnished. Seasonal rentals are in place until October.

Listed by Sandpiper Realty

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

496 County Road, Oak Bluffs, MA

Price$1,195,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 30940

  • Residential
  • Square Feet 2000
  • Bedrooms 3
  • Bathroom 2
  • Acreage 2.65

STORYBOOK OAK BLUFFS CHALET: This enchanting chalet-style home is nicely sited on 2.6 acres in a lovely, lush countryside location yet is centrally located with direct access to bike paths and less than a mile from the all-time favorite Farm Neck Golf Club and Restaurant. The spacious living room, reminiscent of an old-world country lodge, is graced by high ceilings with exposed beams, wood paneling, decorative woodwork and mural, and a soaring brick fireplace. The open floor design flows into the dining room. A second living room or library/den accessed from the dining area provides additional entertaining space. There are 3 bedrooms, two on the first floor and one off the "Sound of Music" balcony. This is truly a charming home filled with character, ideal for year-round living and as a vacation home. The large parcel welcomes expansion and/or additions to the existing building and also offers deeded easement to Fresh Pond.

Listed by Kendall & Kendall

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

227 Buddys Drive, Oak Bluffs, MA

Price$1,099,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32174

  • Residential
  • Square Feet 2762
  • Bedrooms 6
  • Bathroom 3
  • Acreage 0.59

BEAUTY, SPACE, TRANQUILITY Nestled in a quiet neighborhood with only two streets, this handsome roomy, beautifully maintained colonial stands ready for your big family, lots of friends, or a bevy of summer tenants. Six- yes Six!- bedrooms including two master suites, one conveniently located on the main level. The open living/dining/kitchen area opens onto a large deck and spacious backyard-- perfect for outdoor entertaining or just relaxing with a cup of coffee in the morning sunshine. And there's more: A large, unfinished space over the two-bay garage awaits your imagination. Studio? Playroom? Teen hangout? Work shop? Man cave? Enjoy the protected sanctuary of the State Forest, abutting your landscaped, irrigated half acre lot. Or pedal to any of the down - island towns from the nearby bike trail. No wonder this property captures excellent vacation rental income. It's a special find! NOTICE: The home is finally free of tenants and is EASY to show. Please watch the VIDEO of the property below.

Listed by Coldwell Banker Landmarks

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

37 Edgartown Meadows Road, Edgartown, MA

Price$995,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 31469

  • Residential
  • Square Feet 1996
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.94

With town approvals, 7 Bedrooms are allowed on this property, inclusive of a Guest House, a pool, and a garage due to the oversized lot and existing connections to Town Water and Town Sewer lines. It's a well designed Contemporary home nestled atop a deep lot of nearly one acre. Only minutes to Morning Glory Farm, Edgartown Village and within a short drive to South Beach. An eclectic mix of casual sophistication, this stylish Vineyard hide-a-way won't disappoint. There is a unexpected cadence to the floor plan that offers you a delightful surprise around each corner. In addition to the main living areas there is a third floor room with a view and private deck. The finished lower level provides a bonus room plus a laundry room and utility center. Note, the bonus room could easily be the 4th bedroom with an addition of an egress window being added. Many custom designed features appear throughout the house and grounds including stained glass windows, an oversized fireplace, hammered copper sink, Douglas Fir paneled doors, private outdoor shower, stone patio with a covered dining area, stone walls, and a circular driveway. If you are interested in a true vacation house with future expansion options, this place is for you. Easy access to downtown Edgartown by bus, bike path, or island car down the Edgartown-West Tisbury Road. Easy to show. Furnishings available. Directions: West Tisbury Rd. to Codman Spring's Rd.(across from Meetinghouse Rd) follow to fork then bear RIGHT on Whalers Walk then a QUICK LEFT at sign pointing toward Fisherman's Knot. Take a LEFT onto Edgartown Meadows Rd. Property is on the right #37 on tree.

Listed by Sandpiper Realty

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Sengekontacket Association Beach House

6 Mourning Dove Way, Oak Bluffs, MA

Price$975,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 32529

  • Residential
  • Square Feet 1312
  • Bedrooms 4
  • Bathroom 1
  • Acreage 0.91

Sengekontacket Association: This is not your traditional mainland property. It's much more. When you enter this elevated beach house, you know you're on vacation. This property is located at the end of a quiet cul-de-sac and the nearly acre tree lined lot gives you a greater sense of privacy even though you are centrally located between Edgartown, Oak Bluffs and Vineyard Haven. As you ascend the entryway stairs, you come into a bright and open living/dining/kitchen area. Looking out from the 2 large decks, you get the feeling of being in the canopy of the trees. There are 4 bedrooms, 2 with half baths located within and a full bathroom centrally located in the living space. The window-lined cupola and vaulted ceiling add to the openness of the living area. The Sengekontacket Association provides many amenities that residents can enjoy. There are 2 tennis courts, a clubhouse, an association beach, a boat launch with kayak storage and dock. Bring your boat, a mooring on Sengekontacket Pond is included.

Listed by Martha's Vineyard R.E.

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

4 Hye Lane, Edgartown, MA

Price$819,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 30535

  • Residential
  • Square Feet 2468
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.6

Investment Opportunity!! House and Guest House with Garage and fully finished basement. All beautifully renovated - AC - Wood floors, beautiful tile work, Spacious kitchen with granite counters and living area - multi level decks - Home is ready for your carefree summer vacation!! Also a smart year round opportunity to live in one and rent the other... Hookup to town sewer will allow 6 bedrooms. All nestled just off the W Tisbury Road. So close to town and super convenient to bike path, bus stop and short walk to Morning Glory Farm,

Listed by Jane Brown Assoc.

{$agent->Name}

Martha's Vineyard Real Estate
PO Box 74
31 North Summer Street
Edgartown MA, 02539
Office: (508) 627-7890

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.