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.

Get updates on your favorite homes and alerts when similar properties hit the market by creating a free account with our site

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.

75 Dodgers Hole Road

Price$789,000

Est. Mortgage: $/month

MLS ID 32362

  • Residential
  • Square Feet 1729
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 0.51

That rare commodity in this price range - a true, 4-Bedroom home! These owners have done everything right. In 2011 they re-shingled the roof, replaced all of the doors and windows and updated the heating system to 3-zone propane hot water heat. In 2013 all of the floors were replaced with solid oak floors that have been kept in pristine condition. Now, to prepare for sale the house has had a new Title V. 4-bedroom septic installed, the very large deck and railings have been rebuilt, the house has been painted top to bottom, the fireplace re-faced with stone, the landscape tidied and the kitchen dramatically updated. The result is a move-in ready home that is perfect for both year-round and vacation living.

Listed by Karen M. Overtoom R.E.

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: 4.03% last updated on Jul 13, 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

63 Pond View Drive

Price$735,000

Est. Mortgage: $/month

MLS ID 32306

  • Residential
  • Square Feet 1440
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.6363

Let there be peace .... This lovingly maintained 1997 home on nearly two-thirds of an acre sits deep in the tranquil surroundings of Vineyard Hills. It's got all that you need in either a family home or vacation retreat: A bright and open common living area with hardwood floors. The convenience of a bedroom, full bath and washer/dryer on the main level. Two generously sized bedrooms upstairs. An oversized deck that begs for a happy gathering. A front porch that beckons you for sunrise coffee in your rocker. A walkout basement that awaits your imaginative finishes -- such as a fourth bedroom? (A 4BR Title 5 septic system is already at your disposal.) And lots of room between you and your (handsome) neighbors. To your own generous parcel, add a garage, studio and/or shed some day. A deep swath of association woodlands lies beyond, enhancing that sanctuary feel. And don't forget your kayak: Association access to Lagoon Pond is within walking distance. Downtown Oak Bluffs is but a ten-minute drive away. The homeowner puts it all best. See "What I Love About My Home" in Documents.

Listed by Coldwell Banker Landmarks

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: 4.03% last updated on Jul 13, 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

41 Crocker Drive

Price$1,199,000

Est. Mortgage: $/month

MLS ID 32198

  • Residential
  • Square Feet 1484
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 0.46

A delightful vacation home in Katama! With 4 bedrooms, including a master with en-suite, there is room for all. Open concept living, dining and kitchen with cathedral ceilings and glass doors out to the deck offer plenty of space indoors and out for gathering, dining and relaxing. The renovated kitchen is stylish with granite countertops and stainless appliances and the baths have also been updated with tile and new fixtures. Impeccably maintained and ready to be enjoyed by a new owner. An ideal getaway close to the beach.

Listed by Sandpiper Realty

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: 4.03% last updated on Jul 13, 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

5 Cormorant Circle

Price$835,000

Est. Mortgage: $/month

MLS ID 32188

  • Residential
  • Square Feet 1820
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.5

A delightful home in desirable Island Grove - The bright and open floor plan along with vaulted ceiling in the living room provide an airy and spacious atmosphere. New appliances, a fresh coat of paint and hardwood floors make this a terrific opportunity for the vacation home buyer! With sewer tie-in, the home can be expanded to 6 bedrooms.

Listed by Sandpiper Realty

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: 4.03% last updated on Jul 13, 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

227 Buddys Drive

Price$1,099,000

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 can only be shown on turn over days, (SATURDAYS) as there are tenants in place till September. Sellers would prefer a September or October closing.

Listed by Coldwell Banker Landmarks

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: 4.03% last updated on Jul 13, 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

15 Holly Tree Lane

MLS ID 32071

  • Residential
  • Square Feet 2076
  • Bedrooms 5
  • Bathrooms 3
  • Acreage 0.5068

This carefree contemporary offers a relaxed Vineyard experience for vacation or year round living. Set amidst mature ornamental plantings and perennial gardens privacy is ensured while providing a beautiful setting for outdoor living and entertaining. Your summer will be spent on the screen porch extending along the back of the house spilling onto the sunny deck. The "piece de resistance" is the charming guest cottage which is totally independent of the main house while providing all of the comforts of home. Walk to the neighborhood beach, the walking trails of the West Chop Woods or the Vineyard Haven Yacht Club. Town is a bike ride away. Live the life of an Islander. Offered turnkey less personal items and artwork. A list of exclusions will be provided.

Listed by Coldwell Banker Landmarks

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: 4.03% last updated on Jul 13, 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

169 Greenwood Avenue

Price$1,195,000

Est. Mortgage: $/month

MLS ID 31977

  • Residential
  • Square Feet 5359
  • Bedrooms 5
  • Bathrooms 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

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: 4.03% last updated on Jul 13, 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

37 Edgartown Meadows Road

Price$1,050,000

Est. Mortgage: $/month

MLS ID 31469

  • Residential
  • Square Feet 1996
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 0.94

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. Room enough for family and friends with expansion options to increase square footage by double if so inclined and add up to 3 more bedrooms plus a garage and pool with town permits. This property is already tied into town water and town sewer so no septic system worries. In addition to the two main living areas there is a third floor room with a view and private deck. The finished lower level provides the fourth bedroom or media room plus a laundry room and utility center. 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.

Listed by Sandpiper Realty

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: 4.03% last updated on Jul 13, 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

208 Irenes Way

Price$685,000

Est. Mortgage: $/month

MLS ID 31962

  • Residential
  • Square Feet 1660
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 0.23

Move right in: This 2005 home is smartly appointed and impeccably maintained, and your wish list is covered -- an open first floor layout, gleaming hardwood floors, quality kitchen, a sunroom opening to a large mahogany deck, a convenient first floor bedroom and bath, first floor laundry room, and a whole lot of windows and light throughout. Only the walkout basement awaits your finishing touches. All this, plus you're within walking distance of Tashmoo landing and public tennis from your backyard. It's no wonder that this four-bedroom home enjoys strong vacation rental income. Speaking of which: The home will not be available to be shown while tenants are in residence. Come see it this summer, close in September and enjoy! PLEASE NOTE: The quoted square footage from the assessors' data is inaccurate. Actual square footage is ~2094sf, not including the basement. See original building plans in the Documents.

Listed by Coldwell Banker Landmarks

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: 4.03% last updated on Jul 13, 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

5 Sea Mist Lane

Price$1,950,000

Est. Mortgage: $/month

MLS ID 31788

  • Residential
  • Square Feet 2800
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 2

Awake to the sounds of the waves crashing on the not too distance shore. Followed by a morning walk along the sandy shores of the deeded association beach and return home for some morning coffee on the deck with everlasting views. This dramatic contemporary home awaits your family for summer vacationing, or extended holiday time on the Vineyard or year round living. A home rich with lovely details from the double sided fireplace in the living room to the spacious master bedroom and bathroom with striking ocean and Noman's land views. A gracious open living/dining/kitchen floor plan is perfect for gatherings and entertaining. A home and beach to enjoy for years and years to come!

Listed by Flanders Real Estate

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: 4.03% last updated on Jul 13, 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