and narrow your search. If you have fewer than 200 results, you can save your search.

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. Contact us with any questions or to schedule a tour. Register to save your favorite listings and get notified when similar properties become available.

 

Eastern Parcel at South Shore Estates, West Tisbury, MA

MLS Number 31685

  • Residential
  • Square Feet 3500
  • Bedrooms 4
  • Bathroom 2
  • Acreage 29

This 29.1+/- acre oceanfront property features two lots and 300' of frontage on the Atlantic Ocean. The 16.6 +/- acre front lot contains a four-bedroom residence with salt-water swimming pool, hot tub, Har-Tru tennis court, and an impressive underground 12,000 bottle-capacity wine cellar. The home was designed by Gary Graham of Graham Meus, Inc. to highlight the home's proximity to the beach. The owner of this parcel has exclusive rights to use 300' of private beach. This sandy shoreline is within walking distance from the house and is nestled in between two private beaches of neighboring properties. The main outdoor deck is the perfect place to entertain or to relax by the pool. Enjoy a peaceful morning reading the newspaper and sipping coffee poolside, or host an elegant luncheon for close friends or business contacts after a tennis match. The brilliant colors of sunset over the Atlantic Ocean make a perfect backdrop to a cocktail party or al fresco dining on the deck. Each bedroom and living space has wonderful views of the ocean. The residence features a media room, exercise room, office, two sitting rooms, three full bathrooms, two half bathrooms (one with adjacent steam bath and a separate cedar sauna), two outdoor showers, and five replaces. The home is divided into three wings, which are connected by decks on both the first and second floors. This thoughtful layout provides the owner and his or her guests with ample privacy and the opportunity for solitude, if desired. The 12.5 +/- rear lot can host an additional residence or guest home. The most attractive building site on this lot offers peaceful views down Jennie's Cove. The owner of this property has rights to use, along with the owner of The Western Parcel and one other owner, the 141 +/- acres of conservation land northwest of the property for hiking, trail running, and nature walks.

Listed by South Light Property LLC

{$agent->Name}

Ocean Park Realty
69 Circuit Avenue
PO Box 182
Oak Bluffs MA, 02557
Office: 508-693-4210

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 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 & 6 Red Gate Farm Road, Aquinnah, MA

Price$22,500,000

Est. Mortgage: $/month

MLS Number 33264

  • Land
  • Village South
  • Acreage 97.63

Offering priceless peace and privacy on the Aquinnah coastline, this rare and pristine 97.63±-acre oceanfront haven sprawls across 1,060± feet of exquisite dune-fringed sandy beachfront and also fronts another 1,100± feet on picturesque Squibnocket Pond. Held by the same family for nearly 40 years as part of Red Gate Farm, the vast acreage gives the sense of a world apart in an idyllic landscape which has remained virtually unchanged over the centuries. Perched atop various ridges, the potential homesites command glorious views to the ocean's brilliant blue waters and sunsets, also seen from across the pond, in the midst of this sublime seaside paradise of pastoral coastal heathlands and high dunes. Trails meander through the lush age-old landscape of iconic beetlebung, oak, and beech trees in the splendid solitude of this truly extraordinary property, a natural habitat for abundant wildlife. The pond offers a water sports oasis for kayaking, canoeing, sailing, and fishing.

Listed by Wallace & Co. Sotheby's

{$agent->Name}

Ocean Park Realty
69 Circuit Avenue
PO Box 182
Oak Bluffs MA, 02557
Office: 508-693-4210

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 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

Western Parcel at South Shore Estates, West Tisbury, MA

MLS Number 31690

  • Residential
  • Village South Shore
  • Square Feet 700
  • Bedrooms 1
  • Bathroom 1

This 30.3 +/- acre oceanfront parcel contains two lots. It features a one- bedroom beach house perched on stilts with direct ocean views and exclusive use of 300' of private beach within walking distance from the beach house. The 17.6 +/- acre front lot contains the beach house and a building site for a two-story main residence north of the beach house. A home built here will have breathtaking southwest views of the Atlantic Ocean, the beautiful ponds that line the South Shore, and the Squibnocket Cliffs beyond. ? The 12.7 +/- acre northern lot can host an additional residence or guest home, making this property an ideal purchase for an individual looking to build multiple homes. ? The owner of this parcel shares rights to the 141 +/- acres of conservation land northwest of the property with the owner of The Eastern Parcel and the owner of the property to the west of the parcel.

Listed by South Light Property LLC

{$agent->Name}

Ocean Park Realty
69 Circuit Avenue
PO Box 182
Oak Bluffs MA, 02557
Office: 508-693-4210

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 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

22 Lelands Path, Edgartown, MA

Price$15,900,000

Est. Mortgage: $/month

MLS Number 33189

  • Residential
  • Village Chappy
  • Square Feet 9441
  • Bedrooms 8
  • Bathroom 8

You cannot find a more complete package! This home has covered all the bases for comfort and elegance. Each of the rooms is designed to capture the strong views from the land looking over Edgartown Harbor and the Atlantic Ocean. The house is designed to allow guest and family to be together on the multiple porches or sharing meals as well as relaxing or watching a movie together. The home has several wings for everyone to spread out and have privacy and quiet time as well. Each bedroom has a bathroom and each wing has a private laundry. The views are really outstanding from all points of the house. Patrick Ahearn was able to capture the natural beauty of this property and what it overlooks by designing a home that embraced the land completely with the home design. If you like privacy and easy access to secluded sandy beaches, you should see this home. Conservation land abuts the property securing what is so special about the natural aesthetic of Chappaquiddick open meadows, water views and sandy long beaches.

Listed by Tea Lane Associates

{$agent->Name}

Ocean Park Realty
69 Circuit Avenue
PO Box 182
Oak Bluffs MA, 02557
Office: 508-693-4210

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 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

22 Lelands Path, Edgartown, MA

Price$15,900,000

Est. Mortgage: $/month

MLS Number 33391

  • Residential
  • Village Chappy
  • Square Feet 10099
  • Bedrooms 8
  • Bathroom 9

Magnificent Chappy estate overlooking Katama Bay and surrounded by conservation land. Designed by Patrick Ahearn, this custom residence is perched high on a hill on 5.95 acres with over 180 degrees of unobstructed water views. Built for today's lifestyle and technology, the property has numerous amenities which include, an expansive living room for large family gatherings, 4 fireplaces, screened porch, wine cellar, gym, sauna, steam shower, roof top deck, custom woodwork, arched ceilings, 3 car garage and a top of the line gourmet kitchen with adjacent morning room. Offering over 10,000 square feet of luxurious living space, this home features 8 bedrooms and 11 baths. Truly a rare and unique opportunity to own and enjoy a generational quality estate.

Listed by Wallace & Co. Sotheby's

{$agent->Name}

Ocean Park Realty
69 Circuit Avenue
PO Box 182
Oak Bluffs MA, 02557
Office: 508-693-4210

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 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