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.

54 Lake Street

Price$779,000

Est. Mortgage: $/month

Rental ID 31972

  • Residential
  • Square Feet 2124
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 0.48

Updated centrally located colonial within easy walking distance to ferry, restaurants, shops, beach, Vineyard Haven school, and Lake Tashmoo. Recently renovated first floor with new wide plank oak floors. Featuring an open layout with eat-in kitchen that flows into the living room, a full bath, a master bedroom with walk-in closet and en suite master bath, as well as a second bedroom with access to a private covered porch. The spacious top floor has nine foot ceilings, a large bonus living room, two more bedrooms and another full bath. There is a full length farmers porch on the front of the house and a large level back yard with outdoor shower. Perfect as a year round home, family vacation retreat or proven income-producing property. Home is being sold almost completely furnished.

Listed by Martha's Vineyard Island-Wide Realty

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: 4.05% last updated on May 11, 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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83 Main Street

Price$2,995,000

Est. Mortgage: $/month

Rental ID 31942

  • Residential
  • Square Feet 2513
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.6709

Historic waterfront home, renovated in 1997, with spectacular views of extensive gardens and Vineyard Haven Harbor. This unique property offers the convenience and congeniality of an in-town location, as well as a private sanctuary, where almost an acre of land slopes gracefully to a private beach. A two bedroom home that "lives" like three, with more than 2500 sf of living space. A breezy open plan, renovated to provide all modern amenities, features a large eat-in kitchen, dining room and living room, all with harbor views. Both second floor bedrooms, one with a deck also offers expansive views of the harbor, dotted in season with anchored sailboats. Historic waterfront home, renovated in 1997, with spectacular views of extensive gardens and Vineyard Haven Harbor. This unique property offers the convenience and congeniality of an in-town location, as well as a private sanctuary, where almost an acre of land slopes gracefully to a private beach. A two bedroom home that "lives" like three, with more than 2500 sf of living space. A breezy open plan, renovated to provide all modern amenities, features a large eat-in kitchen, dining room and living room, all with harbor views. Both second floor bedrooms, one with a deck also offers expansive views of the harbor, dotted in season with anchored sailboats. The substantial Master Bedroom Suite, with two gable ends permits ample space for a king size bed, spacious sitting/TV area, built-in desk, ensuite bath and even a large ficus tree. Many windows, french doors and skylights provide beautiful light throughout the house. Relax on the large decks, upstairs and down, while enjoying great views and harbor activities before strolling to dinner or theater in town. All this and three private parking spaces. It's no wonder this property has enjoyed excellent vacation rental history. Note: This property has an approved 4-bedroom septic.Many windows, french doors and skylights provide beautiful light throughout the house. Relax on the large decks, upstairs and down, while enjoying great views and harbor activities before strolling to dinner or theatre in town. All this and three private parking spaces. It's no wonder this property has enjoyed excellent vacation rental history. Note: This property has an approved 4-bedroom septic.

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: 4.05% last updated on May 11, 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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5 Sea Mist Lane

Price$1,950,000

Est. Mortgage: $/month

Rental 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

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.05% last updated on May 11, 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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Sengekontacket Road

Price$1,750,000

Est. Mortgage: $/month

Rental ID 31646

  • Residential
  • Square Feet 3400
  • Bedrooms 5
  • Bathrooms 4
  • Acreage 1.86

OAK BLUFFS: BRAND NEW! Situated on almost 2 acres of land, gently South sloping, abutting conservation land, this sun-filled Vineyard design has all of the features for a gracious year round or vacation life style. The very special Sengekontacket Community offers a private salt water docking area with easy access to Vineyard Sound, tennis courts, and a spring fed fresh water beach for its residents and guests. The house design has a cheerfully engaging great room with lots of windows, granite and marble counters, a black granite gas fireplace highlights the built-in cabinetry, beautiful wide oak flooring, and access to a broad stone patio that scans a sweeping back yard meadow. Also on the first floor, is a convenient mud room with separate laundry room, a half bathroom, and at the other end is an en suite master with private deck. The second floor, with brilliant Caribbean Pine flooring, has 4 more spacious bedrooms serviced by 3 more gorgeous bathrooms. Assessed from the mudroom is a stairway to a 6th unfinished bedroom/full bath over the garage. With high end appliances, irrigation, central AC, and exquisite custom detail, this is a property of exceptional value.

Listed by Ocean Park Realty Inc

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: 4.05% last updated on May 11, 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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7 Duarte Circle

Price$785,000

Est. Mortgage: $/month

Rental ID 31614

  • Residential
  • Square Feet 1572
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.53

Located in the highly sought after Katama area of Edgartown - 3 bedroom 2 bath offers endless potential as a year round residence, vacation home or income property... Conveniently located among some of Edgartown's favorite destinations with easy access to bike paths and trails, it is approximately 1 mile to the four way stop sign, leading to the village shops and restaurants or the bike path to south beach, Katama General Store and the Right Fork Diner Restaurant. At the end of the day, the outdoor shower and hot tub beckon and the deck and large backyard are the perfect spot for a BBQ or gazing at the stars. Bright oak floors enhance all living spaces and bedrooms, tile in the bathrooms and a pellet stove in the living room. Two guest bedrooms with ample closet space and shared bath complete the first floor. The second floor has been finished as a "master suite" with a second tv area and office. Bathroom has tiled shower, with views of the backyard. The master bedroom features a jacuzzi tub and large closet.

Listed by Point B Realty LLC

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: 4.05% last updated on May 11, 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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65 Winemack Street

Price$1,249,000

Est. Mortgage: $/month

Rental 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

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

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Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.05% last updated on May 11, 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

Rental 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

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: 4.05% last updated on May 11, 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

Rental 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

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: 4.05% last updated on May 11, 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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7 Clambelly Road

Price$1,375,000

Est. Mortgage: $/month

Rental ID 30825

  • Residential
  • Square Feet 1876
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 3.5

The true meaning of R&R is embodied at this fabulous property. Rustic, in tune with nature, comfortably big enough but not too big, easy to live in without much fuss. When you are engaged in your daily tasks the vision of this property is the carrot that gets you to the end of the week. The open living space with stone fireplace and expansive deck looks out to the tree tops and water view beyond. Two bedrooms and two baths on the same level makes it easy to retire after drowsing off with a good book. The adjacent bedrooms over the garage provide great overflow. Open the house in the spring and close it in late fall, taking advantage of the changing seasonal vistas and the worries of a year round house; the ultimate vacation retreat. If you are looking for year round use it has been estimated that at a cost of approximately $50,000 the space could be insulated and a heating and air conditioning system installed. A six bedroom septic system allows for expansion on the large parcel of land. Access to some of the finest beaches on the Island enhance the property even more.

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: 4.05% last updated on May 11, 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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4 Hye Lane

Price$869,000

Est. Mortgage: $/month

Rental ID 30535

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

Investment Opportunity!! House and Guest House with Garage and fully finished basement. Seller is offering a $10K credit at closing toward town sewer hookup. This will allow 6 bedrooms All beautifully renovated - Central 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... 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.

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: 4.05% last updated on May 11, 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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