Martha's Vineyard Homes with Guest House

Below are current listings for homes with a guest house on Martha's Vineyard.

Homes with Guest House for Sale on Martha's Vineyard

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88 North Water Street

Edgartown, MA88 North Water Street

Price$6,450,000

Est. Mortgage: $/month

MLS ID 36728

  • Residential
  • Square Feet 5022
  • Bedrooms 7
  • Bathrooms 5
  • Half Bath 1

This classic captain's home lies in the middle of historic North Water Street and offers terrific views of Edgartown Harbor. The stately 1850's residence with its tall ceilings, grand staircase and many fireplaces have retained most of its original character. The ground floor offers gracious living areas and a kitchen with large bay window facing the rear yard while the 2nd floor offers 6 bedrooms. There are steps to the 3rd floor attic and the rooftop windows walk offering views from one of the highest points in town. There is a large rear yard with ample room for a pool if desired and a two bedroom guest house with living room and shared bath. A must see if desiring a fine in town Edgartown water view property.

Listed by Landvest MV

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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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191 Katama Road

Edgartown, MA191 Katama Road

Price$10,900,000

Est. Mortgage: $/month

MLS ID 36600

  • Residential
  • Square Feet 1632
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 5.89

Exciting Opportunity on Edgartown Harbor - A front-row seat from where to enjoy breathtaking and active waterviews out the inner harbor and down the bay. Ideally suited for those that wish to be within close proximity to all the Village offers. With 154' of sandy shoreline and a beach-side “boathouse” that awaits your imagination, this 5.8 acre property is one to explore. Renovate the existing 1970's contemporary or re-site for more options. The over-sized parcel allows for the addition of a guest house, pool and other accessory structures or the potential to develop a future multi-generational compound.

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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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70 Marthas Road

Edgartown, MA70 Marthas Road

Price$1,150,000

Est. Mortgage: $/month

MLS ID 36708

  • Residential
  • Square Feet 1875
  • Bedrooms 3
  • Bathrooms 2
  • Half Bath 1

From the welcoming front porch to the year round sun room overlooking the mature landscaped back yard this home has so much to offer...as you enter the gracious vaulted ceiling living room with brick fireplace you immediately feel at home. The kitchen, with a center island, gas stove, stainless appliances, a beautiful view from the picture window above the sink and dining area that opens to the sun room (heated and cooled with central air), makes this the center of the home. There's a first floor master suite with walk-in closet, full en-suite bath with access to the enclosed outdoor shower and patio. Completing the first floor is the powder room & laundry. Upstairs are 2 bedrooms, 1 with an open interior balcony, and the second full bath. The grassy yard features many specimen fruit and flowering trees surrounded by perennial gardens. There is an oversized storage shed which can easily become a pool house. There is room for a guest house when you tie into the sewer system allowing 6 bedrooms. The home backs up to newly paved Meetinghouse Way which also has a dedicated bike lane. Now it's a safe and easy bike ride to South Beach.

Listed by Point B Realty LLC

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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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52 Mill House Way

Vineyard Haven, MA52 Mill House Way

Price$11,500,000

Est. Mortgage: $/month

MLS ID 36702

  • Residential
  • Square Feet 7101
  • Bedrooms 6
  • Bathrooms 6
  • Half Bath 2

This gracious, impeccably detailed, three-story air conditioned home with guest house and garage overlooks Vineyard Haven harbor towards the East Chop lighthouse, steps away from its own sandy beach and an easy stroll to downtown Vineyard Haven. Thoughtfully sited and designed, the 5,787- sf house on 1.55 acres includes four bedrooms, an expansive living and dining room, and multiple porches with spectacular water views. A graceful gambrel designed house was built in 2004 which incorporates an abundance of windows, red cedar shingles, and copper gutters. The first floor boasts an open living room with a dramatic fieldstone fireplace and a wall of French doors with views of the harbor. The gourmet kitchen adjoins a screened in porch for that perfect sunset dinner. Enjoy multiple outside sitting areas including a porch, another screened in porch and an outside kitchen and dining table on a sunny bluestone terrace. The second floor has a breathtaking master suite with an enviable master bathroom. Completing the second floor are three more bedrooms en suite and two sitting rooms. A third floor with large open spaces and sweeping views, especially from the widow's walk, will entice you for that afternoon read. Additional amenities include a full walkout basement with wet bar, an exercise room, a media room, plus a state of the art wine cellar and an elevator. This is a very special offering!

Listed by Viewpoints

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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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21 Vickers Street

Edgartown, MA21 Vickers Street

Price$1,425,000

Est. Mortgage: $/month

MLS ID 36680

  • Residential
  • Square Feet 1962
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.5

KATAMA, KATAMA, KATAMA!! "Rare gem spacious home in perfect condition." Owning a Beach House one mile from South Beach and two miles from the village of Edgartown makes for an amazing vacation home! Over the last few years there have been major improvements in this property: redesigned kitchen layout, incorporating banquet seating area with custom cushions and pillows, entry bench in family room as well as the new kitchen island, granite counter tops, new plumbing and lighting fixtures and appliances. The bathrooms were upgraded with new cabinetry, granite counter tops, Jacuzzi tub in master bath, tiled shower/tub enclosures and new fixtures. A new furnace was installed, new well pump, new hot water tank. In 2020 the house was re-shingled, new roof and central air were installed. The sellers have paid the $5000 fee to contribute to installation expense and obtains the right to connect to the sewer line in the future. By hooking up, you are allowed to have 6 bedrooms with a guest house or a carriage house.The house comes mostly furnished, some furniture being custom designed, and a strong rental history. There are so many possibilities for this property in one of the most sought out neighborhoods in Edgartown.

Listed by C McManus Realty Group

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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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102 Pond View Drive

Oak Bluffs, MA102 Pond View Drive

Price$790,000

Est. Mortgage: $/month

MLS ID 36605

  • Residential
  • Square Feet 1310
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 0.589

LOCATION,LOCATION,LOCATION! BUYERS looking to be in Oak Bluffs close enough to town, yet far enough out of town to realize the country feel of what Oak Bluffs really has to offer. Shopping, schools, ferries, and harbor just a 2 minute drive and a very short walk to Lagoon Pond. What more can you ask for? Deeded rights to Lagoon Pond....directly across the street (Barnes Road) from this 4 bedroom two bath home located in the lovely Vineyard Hills Community. This established subdivision offers larger lots along with open space/common areas and has become a very popular go to location of Oak Bluffs. The 1310 square ft home is settled into a hill in the rear of the property thus creating a great opportunity to utilize the walk out basement. In the front yard there may be room enough for a potential guest house/garage with the proper permits and approvals from the town boards. Entering the home into the spacious unfinished mudroom gives you the chance to personalize your entry with your own ideas. The owner has done some renovations about 8 years ago adding new stainless steel appliances, new bathrooms, and A/C,. This is a must see. Yes, there are areas that could use sprucing up but just think 4 Bedrooms, 2 full baths and full walk out basement with oil forced hot air. Outside shower already in place. All this on just over a half acre of land. Tenants in place 24 hr NOTICE.

Listed by Ocean Park Realty Inc

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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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4 Windy Way

West Tisbury, MA4 Windy Way

Price$4,200,000

Est. Mortgage: $/month

MLS ID 36532

  • Residential
  • Square Feet 1714
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 3.3

Views, views and sunsets galore! One of the most dramatic and gorgeous seascapes on the Vineyard at over 100' above sea level, unobstructed views stretch from Aquinnah to Woods Hole. The 3.3 acre private setting is most picturesque with grassy lawn and rolling dunes and only a short stroll away is 3,000+ feet of sandy association beach. Nestled into the countryside is a comfortable and sunny four bedroom, 2,600+sf contemporary style home that was designed to achieve water views from many rooms. Also included is a detached artist's studio that may be transformed into a future guest house. Renovate the current home or build your dream home, expansion options are plenty with a 6 bedroom septic in place. Located in Upper Makonikey, an exclusive rural enclave that boasts the up-island lifestyle yet is an easy drive to town. Enjoy long days on the beach and savor the endless sunsets at this special place, where the rest of the world feels far away.

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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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14 Pine Street

Vineyard Haven, MA14 Pine Street

Price$2,975,000

Est. Mortgage: $/month

MLS ID 36490

  • Residential
  • Square Feet 3858
  • Bedrooms 5
  • Bathrooms 3
  • Half Bath 2

Proudly sited on a hill in Tisbury village, this beautiful and stately home was painstakingly restored to preserve historic features while creating a fresh, modern living environment. Original heart pine floors and grand staircase, original interior shutters and antique lighting fixtures add charm while all new electrical, plumbing, wiring, HVAC, in-floor heat, Sonos sound, and Ecobee smart thermostats make it relevant for living today. At the heart of the home you will find the gorgeous eat-in kitchen which is open to a cozy sitting room with fireplace. The formal dining room and living room are located off the foyer. There is a first-floor bedroom suite, privately situated past the back entry and mud room area. The upstairs master suite features a luxurious bathroom and an adjacent office or reading space. Four bedrooms plus media room (or fifth bedroom). The third floor is wide open and ready for whatever your family needs. From there you can access the widow's walk with views of the harbor. The outdoor space is expansive and features a large stone patio with privacy pergola and three outbuildings. Six-bedroom septic system. Guest house and pool are possible. Walk to Main Street and the ferry. This property is move-in ready for the buyer who appreciates old world beauty along with the ease and comfort of modern construction.

Listed by Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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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9 Peases Point Road

Edgartown, MA9 Peases Point Road

Price$2,385,000

Est. Mortgage: $/month

MLS ID 36506

  • Residential
  • Square Feet 4133
  • Bedrooms 5
  • Bathrooms 6
  • Acreage 0.75

Welcome to this Edgartown Family Compound which features a spacious colonial that was designed with an open floor plan for easy island living. The living room, with a gas fireplace, dining area and large gourmet kitchen lends itself to comfortable entertaining. The kitchen features expansive granite countertops, double ovens, a gas stove top, trash compactor and an additional sitting nook. The great room area leads to an outdoor deck for gathering and grilling. The spacious bedrooms and finished third floor bonus area provides ample sleeping space and areas to gather. The two bedroom guest house which was built in 2006 features a front farmers porch, an additional covered porch off the great room and a lower level blue stone patio for dining and grilling. This property is located close to Katama General Store, Edgartown Village and South Beach. Come experience all that this family compound has to offer.

Listed by Vineyard Village Realty

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$
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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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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41 Road to the Plains

Edgartown, MA41 Road to the Plains

Price$1,400,000

Est. Mortgage: $/month

MLS ID 36495

  • Residential
  • Square Feet 1800
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 0.97

Located in sought-after Katama, this inviting and sun filled four-bedroom, two full bath home is uniquely positioned on nearly 1-acre set well back from the main road. The first floor features an open kitchen with recently updated appliances and windows that let the natural light stream in, a wood-burning fireplace living room, a family room, and an office. Adjacent to the living room, with access from 2 sets of French doors, is the large, wraparound deck overlooking the private yard. The second floor offers four bedrooms, including a spacious master bedroom. Once connected to town water and sewer, the Board of Health will allow up to 7-bedrooms and potentially a guest house with special permit. Minutes to South Beach, Edgartown's shopping, and restaurants, this home is perfectly located for convenience and privacy. More photos coming soon!

Listed by Wallace & Co. Sotheby's

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$
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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details