Vacation Homes on the Vineyard

Browse all residential listings below that will make for the perfect vacation home. Close to downtown, shops, restaurants, and of course, beaches. Enjoy all that these beautiful homes have to offer.

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Whether you're moving locally or seeking a vacation home, let Coldwell Banker Landmarks Real Estate help you find your next home on the Island. Please contact us to visit any of the Martha's Vineyard properties below, or call 508-693-6866.

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65 Winemack Street

Price$1,149,900

Est. Mortgage: $/month

MLS ID 31438

  • Residential
  • Square Feet 3828
  • Bedrooms 5
  • Bathrooms 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

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Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

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$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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35A North Neck Road

Price$5,500,000

Est. Mortgage: $/month

MLS ID 31324

  • Residential
  • Square Feet 2486
  • Bedrooms 5
  • Bathrooms 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

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Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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496 County Road

Price$1,195,000

Est. Mortgage: $/month

MLS ID 30940

  • Residential
  • Square Feet 2000
  • Bedrooms 3
  • Bathrooms 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

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Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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11 Plantingfield Wood Circle

MLS ID 30336

  • Residential
  • Square Feet 3600
  • Bedrooms 4
  • Bathrooms 4
  • Acreage 0.72

EDGARTOWN VILLAGE: STYLISH AND CHIC IN-TOWN LIVING. Set in a private, desirable enclave on the north side of Edgartown Village, and just a short stroll to Sheriff's Pond and its beautiful nature trails, this stylish and chic, newly-built colonial perfectly blends the convenience of in-town living with a private and beautiful setting abutting conservation land. Thoughtfully designed and meticulously crafted, this stunning retreat features 9-foot ceilings, gleaming hardwood floors, central air, custom tile and stone/granite work, hand-selected light fixtures and designer details throughout. The open-designed living areas are generously proportioned to complement casual island living and entertaining. The spacious dining area can easily accommodate both small or large gatherings and the handsome gourmet cook's kitchen features stone/granite countertops, high-end stainless appliances and easy access to the private bluestone terrace, which is perfect for alfresco dining and outdoor enjoyment. There are a total of four bedrooms, each with beautifully appointed en suite baths -- including two master bedrooms suites (one is located on the first floor; the other is located on the second floor). Add to all of this, a professionally landscaped yard with privacy fence, irrigation system and a detached two-car garage with ample storage. You will feel worlds away from the hustle and bustle, yet all the best of Edgartown Village -- including restaurants, shops, beaches, the harbor and more -- is just a short stroll away. This property is ideal for a year-round or seasonal home -- AND it would also make a fantastic vacation rental property (estimated rental income $10,000-$12,000/week in peak season!).

Listed by Point B Realty LLC

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Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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15 Maqua Way

Price$2,999,000

Est. Mortgage: $/month

MLS ID 29277

  • Residential
  • Square Feet 2920
  • Bedrooms 7
  • Bathrooms 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}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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40 Norton Farm Road

Price$2,395,000

Est. Mortgage: $/month

MLS ID 19207

  • Residential
  • Square Feet 3984
  • Bedrooms 4
  • Bathrooms 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}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.78% last updated on Sep 14, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details