Martha’s Vineyard Homes with Guest House

Find a variety of homes with a guest house on Martha’s Vineyard, whether you are looking for a seasonal home or year round residence. Martha’s Vineyard has beautiful oceanfront properties, homes with wooded acreage, Cape style homes, and much more. Browse homes on Martha’s Vineyard below. 

Houses for Sale with Guest House on Martha's Vineyard

Call Ocean Park Realty at 508-693-4210 if you have questions about any of these properties or would like to set up a private tour.

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21 Checamo Path West Tisbury MA

West Tisbury, MA21 Checamo Path

Price$1,350,000

Est. Mortgage: $/month

MLS Number 36997

  • Residential
  • Square Feet 3816
  • Bedrooms 5
  • Bathroom 3
  • Acreage 4.4

A HOME IN THE WOODS - You will enjoy abundant privacy at this large property with main house, guest house and large barn/shop building on 4.4 acres. The property abuts 365 acres of land owned by the town of West Tisbury that has miles of trails and connects to the state forest. Peace and quiet abounds at this oasis that provides the feeling of being in the country, while just ten minutes from all the down Island towns. The first floor of the main house has two living areas plus a sunken solarium. There is access to the large deck form one of the living rooms, as well as the first floor bedroom. There is a full bathroom on the first floor as well. The spacious and sunny kitchen is open to the dining area. On the second level there is a large open living area with steps up to the next level where you will find three large bedrooms, a full bathroom, as well as a laundry room. There is a wonderful third level loft living area that feels like a peaceful sanctuary with a private deck that looks out into the treetops. The charming guest house is 672 square feet and was built in 2015. It features a lovely covered front porch and fenced in back yard. It is set on the opposite side of the lot, allowing for privacy for both the main house and guest house. A 1,584 square foot outbuilding is currently being used as a wood shop, but could easily be converted into a barn or garage. There is also an open front structure that is currently being used to protect the owners boat and tractor. Bring your horses, home business or plans for upgrades - many possibilities exist here.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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8 Tuthill Lane and 27 Braleys Way Edgartown MA

MLS Number 36831

  • Residential
  • Square Feet 10398
  • Bedrooms 9
  • Bathroom 9
  • Half Bath 2

This incredibly private waterfront compound, uniquely located just minutes from historic Downtown Edgartown, is being offered for the first time in more than 30 years. This classic Martha's Vineyard retreat offers it all: a private sandy beach, boat access, more than 10,000-sq. ft. of living space in two homes, pool, barn, and endless sunsets. This unique combination would typically only be found in remote locations up island, yet here you can feel completely out of town while being a short stroll or bike ride into Edgartown and all it has to offer. Sited on three meticulously landscaped acres overlooking Eel Pond and Edgartown Harbor, nearly every room from the five-bedroom main house and four-bedroom guest house enjoys unobstructed water views. A sophisticated yet comfortable setting, this Island compound offers unmatched privacy. The main residence features multiple living areas and a restful primary bedroom suite with sun deck, spacious bathroom and a private office with fireplace. Other features include a gourmet kitchen with sitting area, home office, study, pool room, four guest bedroom suites, and an oversized screened porch, perfect for summer entertaining. The guest house is equally inviting and offers welcoming living and dining area, a screened porch, family room, playful bunkroom, two additional guest bedrooms, oversized primary bedroom suite with private deck, and a three-car garage. The gunite pool and spa provide panoramic water views are surrounded by a bluestone patio, classic stonewalls, and lush plantings of colorful roses and hydrangeas. The expansive lawn leads to the water's edge on Eel pond where you can enjoy easy access to Edgartown Harbor and beyond from your private beach where the owners can keep a boat. This desirable private waterfrontage allows you to spend summers clamming, kayaking, paddle boarding, swimming and boating. A truly remarkable Island escape in Edgartown that epitomizes the best of Martha's Vineyard in one of its most coveted locations.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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31 New York Avenue Oak Bluffs MA

Oak Bluffs, MA31 New York Avenue

Price$1,195,000

Est. Mortgage: $/month

MLS Number 37020

  • Residential
  • Square Feet 2390
  • Bedrooms 5
  • Bathroom 3
  • Acreage 0.1733

This East Chop home is a true example of New England's classic shingle style architecture. This 1920's Craftsman style home offers the charm and sophistication of its time with impeccably preserved wainscoting, a traditional foyer and high ceilings throughout the entire first floor. The sun-filled living and dining area share one side of the first floor and is a perfect space for entertaining especially around the beach stone fireplace. The kitchen is at the center of the home and, renovated in 2009, offers a warm and inviting space with top of the line appliances, concrete countertops, custom cabinetry and with many of the same aesthetics of wainscoting and high ceilings. This 4-br home has one bedroom on the first floor, plus a laundry room/office space, mudroom, with three more bedrooms on the second floor. The signature front porch overlooks thoughtfully planned perennial gardens, lawn space and mature plantings. There's also a 1-br guest house and it's equally charming! Built in 2013, its wood walls, high ceilings, concrete floor and en suite bedroom with balcony make this 720 sf dwelling perfect for family overflow, guests wanting privacy or can be used as an income-generating property. The fenced in yard is surrounded by tall privet hedge and offers a private, courtyard feeling among the gardens, dogwoods, and other mature plantings. There's a bluestone patio and firepit for summer and winter evening gatherings alike. Only a short walk to East Chop beach, harbor and downtown shops, this one set up for Vineyard living!

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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100 Watcha Club Road West Tisbury MA

West Tisbury, MA100 Watcha Club Road

Price$8,500,000

Est. Mortgage: $/month

MLS Number 36565

  • Residential
  • Square Feet 4380
  • Bedrooms 8
  • Bathroom 5
  • Half Bath 1

WATERFRONT ESTATE ON THE SOUTH SHORE. With over 12 acres of land and a large parcel of conservation land directly to the north, this property offers the ultimate in seclusion. There are stunning first floor water views of Watcha Pond and the Atlantic Ocean from the main house and the guesthouse also enjoys water views of Watcha Pond. The 4 members of the Watcha Club Road Association are part owners of a private beach on the Atlantic Ocean half a mile away which you may reach via a quiet dirt road, or simply by traveling the two- tenths of a mile across the pond to the barrier beach from the boat landing at either the main house or guesthouse. Owners also have deeded access to an additional 500+ ft of sandy ocean beach adjoining the east end of the association beach. Ancient moss-covered paths wind their way from both properties down to the pond. The 4-bedroom, 3,000+sq. ft. main house built in 1982 may be used while a future owner designs a new home that takes full advantage of the stunning setting. These cleared views would not be possible if this were an undeveloped building site. The 1,100-sq. ft. guesthouse with 3 bedrooms was designed by architect Joseph Dick and completed in 2013. It has been lightly used and feels brand new. NOTE: A subdivision plan has been drafted and sellers would consider selling the main house on 7.15 acres (guest house would be permitted).

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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30 Pondview Drive Oak Bluffs MA

Oak Bluffs, MA30 Pondview Drive

Price$1,279,000

Est. Mortgage: $/month

MLS Number 36606

  • Residential
  • Square Feet 2016
  • Bedrooms 5
  • Bathroom 3
  • Acreage 0.6322

Do not miss out on this LOWEST PRICED NEW CONSTRUCTION ON THE VINEYARD. Located in beautiful Vineyard Hills Association with deeded Lagoon beach access boasts this custom built 5 bedroom 3 bathroom NEW CONSTRUCTION. The colonial style home flares its character and curb appeal with its large farmers porch, beautiful 3rd floor dormers, and circular driveway. More than 2,000 sq. ft. of living space that was custom designed with an open floor plan to the Living, Dining and Kitchen on the first floor and a first floor bedroom and bath. There are 4 additional bedrooms on the second floor with a master suite with another full bathroom. The 3rd floor has an additional 500 plus sq. ft of unfinished living space that can be finished off for the entertainment/media/game room. The HVAC system is propane FHA and central AC with blown open cell insulation. Site plan includes future site for guest house and full size swimming pool. The property has a 6 bedroom septic system . The custom kitchen cabinets are a white shaker style of solid maple with a gorgeous Silestone Quartz counter top. Beautiful stainless steel appliances with an island bar in the center of the kitchen. 5 inch plank solid oak flooring and tile throughout the entire home with Andersen windows (400 series) and Jeld-Wen doors. All mahogany decking throughout the farmers porch, sun deck and the outdoor shower complete this home to enjoy many Vineyard memories. Easy to show.

Listed by Dockside Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 2020
* 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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