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.

655 Herring Creek Road

MLS ID 33187

  • Residential
  • Square Feet 928
  • Bedrooms 2
  • Bathrooms 1
  • Acreage 1.26

It's all about the beach, stunning sunrises, epic sunsets and the sound of the waves lapping on the shore. Live the Island life in this classic style summer house perched waterfront between Lake Tashmoo and Vineyard Sound. Kayaking, paddle boarding sailing just steps away. Designed for casual vacation living, it's a perfect summer home for generations to come.

Listed by Conroy & Company R.E., Inc.

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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: 4.32% last updated on Feb 8, 2018
* 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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24 Fitchburg Avenue

Price$699,000

Est. Mortgage: $/month

MLS ID 33117

  • Residential
  • Square Feet 1428
  • Bedrooms 3
  • Bathrooms 3
  • Acreage 0.23

The perfect vacation house on Martha's Vineyard! Don't miss this one! LIKE NEW condition, no mess no fuss, centrally located to take in all down-island activities. Just a few blocks away from the Lagoon where you can launch a kayak or just hang out. The property is designed for minimal upkeep and maximum fun. There are 2 bedrooms downstairs and 1 master bedroom privately located upstairs plus a total of 3 full bathrooms in the house. The bright open floor plan includes, a chef's kitchen, dining area, large granite island, cathedral ceilings, large finished basement with a "bonus room" for an office, study, or hobby room. The level grassy yard is enough for some lawn games and working on your tan. An oversized shed is ample space for bikes and kayaks. An outdoor shower completes the package. This is a very successful rental at $2,500/week with 5 weeks currently booked for 2018. Buy now and take the rental money or wait until renters leave to move in. Easy to show.

Listed by Sandpiper Realty

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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: 4.32% last updated on Feb 8, 2018
* 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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212 Skiff Avenue

Price$1,270,000

Est. Mortgage: $/month

MLS ID 32798

  • Residential
  • Square Feet 2552
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.12

Looking for an upscale vacation home that is easily maintained and within close proximity to the ferry and all that Vineyard Haven offers? Look no further. This maintenance free home, built in 2011 with newly finished lower level, is the answer. With a well designed open floor plan that accommodates today's casual and active lifestyle, the main level---consisting of chef's kitchen, living and dining area with views and a great room with fireplace---flows freely to the porch and patio with views to the Lagoon. The second floor features a very private and spacious Master bedroom with fireplace and bath as well as 2 guest bedrooms: one with queen bed and the other with 2 double beds. The finished lower level allows for additional gathering space and privacy for overflow guests. When ready to venture out, it is but a short distance to the Black Dog, the Net Result for fresh seafood, Beach Road Restaurant for a fresh farm to table tapas menu and the Film Center. Kids will love the 10+ acre Memorial Park a few streets away providing a soccer field, softball field, basketball court, swings, slides, and bathrooms. All that before you even get to Main Street and its shops and offerings! Eastville Beach is just a mile away for a quick dip or taking in a sunset. Best of all, if you are a boater, an active marina is in sight at the bottom of the hill. The property is perfect as either a vacation rental income property or a second home and is being offered furnished and essentially "turnkey". Summer rental rates are $5,500/wk to $6,500/wk. Come and explore your options.

Listed by Sandpiper Realty

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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: 4.32% last updated on Feb 8, 2018
* 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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6 Mourning Dove Way

Price$975,000

Est. Mortgage: $/month

MLS ID 32529

  • Residential
  • Square Feet 1312
  • Bedrooms 4
  • Bathrooms 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.

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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: 4.32% last updated on Feb 8, 2018
* 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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227 Buddys Drive

Price$1,070,000

Est. Mortgage: $/month

MLS ID 32174

  • Residential
  • Square Feet 2762
  • Bedrooms 6
  • Bathrooms 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. AND Just UPDATED! NEW Granite counter tops and cabinet hardware in the kitchen. NEW Central AC through out the home. Newly painted house trim. Power washed and oiled the large deck. Full yard cleanup Please watch the VIDEO of the property below. BRING YOUR BUYERS OR PREVIEW FOR YOURSELF....

Listed by Coldwell Banker Landmarks

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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: 4.32% last updated on Feb 8, 2018
* 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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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

{$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: 4.32% last updated on Feb 8, 2018
* 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: 4.32% last updated on Feb 8, 2018
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details