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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

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
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Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
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Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

83 Main Street, Vineyard Haven, MA

Price$2,995,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 31942

  • Residential
  • Square Feet 2513
  • Bedrooms 3
  • Bathroom 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

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
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Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
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Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

5 Sea Mist Lane, Aquinnah, MA

Price$1,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 31788

  • Residential
  • Square Feet 2800
  • Bedrooms 4
  • Bathroom 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

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
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Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

3 Sengekontacket Road, Oak Bluffs, MA

Price$1,750,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 31646

  • Residential
  • Square Feet 3400
  • Bedrooms 5
  • Bathroom 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

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
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Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

115 Sea View Avenue, Oak Bluffs, MA

Price$1,495,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 25268

  • Residential
  • Square Feet 2047
  • Bedrooms 4
  • Bathroom 4
  • Acreage 0.09

On the water ! At the Beach! Walk to town ! Owner reports Rental income $70,000.00 (+ - ).This is what Location, location , location means. Spectacular and charming 1900s Oak Bluffs gem. Major, tastefully done renovations. New ( 2012) Title 5 septic system. Heat is propane on the 1st level and electric in the upstairs and all baths ( each bath has it, own heat/thermostat). Each bedroom has its own bath. Lots of private spaces. First floor bedroom. Wrap around porch and water views from 3 bedrooms and all living areas. Upstairs porches with views that could only be better if you were on a boat. Moon Rises and Sun Rises. The best swimming beach is at your door. View the Oak Bluffs Fireworks from your own house. Walk to town. July gets $7,000 to $8,000 weekly. August gets $8,000 plus weekly( listed on "weneedavacation.com). If you were to add in more weeks in the shoulder seasons ( who would not love to sit on that front porch in June, Sept or October) that could be rented you have a potential for additional income !

Listed by Jane Brown Assoc.

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
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Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

7 Clambelly Road, Chilmark, MA

Price$1,375,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 30825

  • Residential
  • Square Feet 1876
  • Bedrooms 4
  • Bathroom 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 two 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

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
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Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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$1,249,000The 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

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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

Homes On Martha's Vineyard Main Office
PO Box 74, Post Office Square
Edgartown MA, 02539
Office: (508) 627-0506

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.95% last updated on 2017-04-27

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