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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14 & 22 Cataumet Avenue

MLS ID 38212

  • Residential
  • Mls Status Active
  • Bedrooms 11
  • Bathrooms 8
  • Acreage 1.55

This magical beachfront estate is located in the heart of the exclusive West Chop community on a double lot with 200 feet of beach dune frontage. There are four classic shingle style structures complimenting the property of which all enjoy enchanting views across the expansive rolling lawns and gardens to the beach and breathtaking sunset views over the Vineyard Sound. There are two, turn of the century, five-bedrooms homes, each with extraordinary character including wrap-around porches and 2nd floor balconies. Additionally, there is a charming 1-bedroom/1-bath guest house with cathedral ceiling living room and fireplace, and a studio building offering a fitness area and sauna. This unique compound, set within mature vegetation offering complete privacy, beautiful gardens and specimen trees is just a short walk to the West Chop Club with Mink Meadows Golf Club and downtown Vineyard Haven just minutes away. This is a very special Vineyard property that must be seen if considering the best waterfront offerings.

Listed by Gerrett Conover of Landvest MV

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$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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10 Quampache Lane

Edgartown, MA10 Quampache Lane

Price$3,595,000

Est. Mortgage: $/month

MLS ID 38144

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathrooms 3.5
  • Acreage 8.32

With properties rarely coming to market in this special location, enjoy the peace and serenity of this charming estate setting in the Oyster Pond neighborhood. Built in 1988, the home sits on 8 acres, abutting the state forest. Several updates throughout including a new kitchen, new roof and chimney, central AC, new well pump and outdoor shower. This contemporary 4 bedroom / 4 bath home is flooded with natural light with floor to ceiling windows in the living room, vaulted ceilings and a gas fireplace. The gourmet kitchen features top of the line stainless appliances (including Wolf range), marble countertops, a breakfast bar, and an adjacent dining area for 10 people. There is a spacious den, which can double as a home office, a first-floor guest room and a full hallway bathroom. The second floor overlooks the floor below and features three large bedrooms, all with en-suite baths. The primary bedroom at the end of hall has a private, attached sunporch that overlooks the expansive lawn. The screened porch, deck, and outdoor shower add to the list of features. With acres of land, opportunity abounds for an additional guest house, pool and tennis court with proper approvals. Only 500 yards from the house is the Association Pond access where you can launch a kayak/canoe/skiff and explore the stunning 208-acre Pond with swans, turtles and oysters around every turn. To cap it all, this particular property is one of the few that has deeded rights to the southern barrier beach offering sought-after private beach access.

Listed by Gerrett Conover of Landvest MV

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$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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64 Road to the Plains

Edgartown, MA64 Road to the Plains

Price$1,250,000

Est. Mortgage: $/month

MLS ID 38201

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.5

Cozy Contemporary in Katama! A sunny open concept with vaulted ceilings, large windows and glass doors leading out to a spacious wrap-around deck, the home offers great gathering areas whether inside or out. Comfortable accommodations include two guest bedrooms on the first floor and the primary bedroom with a private balcony on the second. Town sewer is available and would allow for future expansion to six bedrooms and a guest house with proper permitting - lots of options! Located within 2 miles to all Edgartown offers – swimming at popular South Beach and shopping and dining in the Village. And for kayaking and paddleboarding, the Edgartown Great Pond is only 1 mile away! Offered turnkey and with a solid rental history.

Listed by Lesley Heidt of Sandpiper Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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15 South Street

Edgartown, MA15 South Street

Price$6,900,000

Est. Mortgage: $/month

MLS ID 37954

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathrooms 5.5
  • Acreage 0.55

This Edgartown Village compound is a crowd pleaser renters pay up to $35,000 per week to enjoy. It's your chance to have it all, for your own use or to use as an investment rental. Composed of 3 structures, a 4 bedroom 3.5 bathroom Main house (3,702 sq. ft.), a 2 bedroom, 2 bath Guest house (1,054 sq. ft.), and a pool house (416 sq. ft.) for lounging. The "walk-to-town" location is minutes away to restaurants, shopping areas, and the harbor. South Beach is a short distance away by car or bike. Enjoy the 16' x 34' Gunite Pebble Tec heated pool surrounded by a bluestone patio and lawn area. In total there is 5,168 sq. ft. of living space in the structures. Older family members will appreciate 3 of the bedrooms are ground level. The well designed main house has a cathedral ceiling great room with a gas fireplace flanked by custom built-in cabinets. On the pool side there is a wall of glass 27 ft. long composed of Pella sliders and fixed windows. In the chefs kitchen there are cabinets galore, spacious quartz counters and enough seating at the counter for 7 upholstered stools. All within a working grid is a Wolf 6 burner gas range, wall oven, Subzero refrigerator, beverage refrigerator, microwave oven, dishwasher, and 2 stainless steel sinks. The adjacent dining area currently seats 6 however it can be adjusted to seat 12. Also on the main level is a powder room, mud room, spacious foyer, and separate Den/TV room. Rounding it out, is a large Primary suite complete with a fireplace, vaulted ceiling, walk-in closet, linen closet, granite bathroom, and sliding doors leading out to the pool and patio. Upstairs is another Primary suite and 2 other bedrooms with a shared bathroom and a TV/Den area. All floors are random width knotty oak. Main house, guest house, and Pool house are air conditioned. The well equipped Guest house features granite counters, stainless steel appliances, and all oak floors. All structures are fully furnished and sold "turn-key" except for personal items and artwork. A closing in mid-August would likely allow the new owner to assume $70,000 in a 2 week rental, all possibly tax-free per current codes - verify this with a tax professional. Easy to show now but will be more difficult as summer approaches.

Listed by Frank M. Markwica of Sandpiper Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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 Calebs Common Circle

Edgartown, MA4 Calebs Common Circle

Price$2,550,000

Est. Mortgage: $/month

MLS ID 38141

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathrooms 4.5
  • Acreage 1

CHAPPY COMPOUND - Two distinct beach houses, beautifully renovated with bright interiors, lofted ceilings and unique character. Both are privately sited – rent one and enjoy the other - with separate pea stone driveways and amenities. A charming studio/office, post & peg built garage, a firepit, picnic grove, and treehouse with slide and twinkling lights, complete the compound. Each house features many custom finishes, professional grade stainless appliances and soapstone counters in the kitchens, hardwood floors, marble and tile baths, mahogany decking and outdoor showers with changing areas. The 1,854 s/f main house enjoys a first floor owners suite, a distinctive screened porch and sunporch on the second floor from the two bedrooms, one with a very special bedroom with bunkhouse loft. The 1,146 s/f guest house features charming hand-painted floors in the first floor bedrooms and a second floor bedroom suite-a private oasis with tile bath and lounge or office area at the landing. Enjoy the quiet sandy Sheriffs Meadow beach at the end of the road. Showing May - June 13th, Seller prefers to close after Labor Day.

Listed by Dawn Bellante Holand, 508.524.1601 of Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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346 Edgartown Vineyard Haven Road

MLS ID 38147

  • Residential
  • Mls Status Active
  • Bedrooms 2
  • Bathrooms 1
  • Acreage 0.8699

EXPANSION POTENTIAL - WALK TO THE TRIANGLE - BIKE TO BEACH! Cute two bedroom, one bath cottage, within walking distance of the Triangle in Edgartown. Excellent floor plan for its size including a wood burning fireplace and oil heat. Nice level wooded lot with EXPANSION POSSIBILITIES. Lot size can accommodate a second full size home and existing cottage can become a one bedroom guest house, which can also be expanded up to 900sq.ft. Property is in the Lily Pond District and is subject to the restrictions of that district. Currently a two bedroom lot with the possibility of a third bedroom with an enhanced treatment system which should be confirmed with the Edgartown Board of Health. Seasonal Tenants in place until October 31, 2021. 24 hour noticed required.

Listed by Alisan Lohan-Conway of Alisan Lohan-Conway Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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212 Tashmoo Avenue

Vineyard Haven, MA212 Tashmoo Avenue

Price$1,500,000

Est. Mortgage: $/month

MLS ID 38111

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 0.318

Charm and Sunshine await you in this quality built, custom designed contemporary Vineyard home. Offered fully furnished with rentals in place for summer 2021...IMMEDIATE INCOME! Seller has 2 prime weeks set aside for personal use, so you can choose to use the house or rent out for more income. Home and grounds are in perfect condition, so all you have to do is unpack your suitcase. Home is a "reverse style" layout with the upper floor being an open great room concept with soaring ceilings and numerous sliders that access the (partially covered) wrap around deck. There is also a small patio off the main level entry and the "essential" outdoor shower. Lot size allows for a guest house...please check town regulations. Close to Lake Tashmoo Beach, Grove St Beach, Land Bank Beach of Herring Creek Rd. and all things that are Vineyard Haven.

Listed by Doug Reece of RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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33 Llewellyn Way

Edgartown, MA33 Llewellyn Way

Price$4,150,000

Est. Mortgage: $/month

Pending

MLS ID 38133

  • Residential
  • Mls Status Pending
  • Bedrooms 6
  • Bathrooms 5.5
  • Acreage 1.03

This wonderful property is located less than 1 mile to downtown Edgartown yet offers a private and beautiful setting with open fields and mature trees. This 1-acre parcel abuts over 5 acres of conservation land with walking trails and ponds. The 5-bedroom / 4.5-bath main house features a large tray ceiling living room with fireplace, which is open to the dining room and kitchen. There is also a ground floor office and an attached 2-car garage. There is a large, second floor master suite with a luxurious bathroom and all rooms have large windows offering an abundance of light. There is a finished 3rd floor as well as a lower level, with media room, exercise room and recreational area. Complimenting the property is a one-bedroom guest house, expansive decks, and grill areas surrounded by beautiful landscaping and an amazing pool with jacuzzi and natural waterfall feature.

Listed by Gerrett Conover of Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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27 Oyster Lane

Chilmark, MA27 Oyster Lane

Price$2,700,000

Est. Mortgage: $/month

Active With Contract

MLS ID 37903

  • Residential
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 9.87

Four bedroom home designed by Hugh Weisman on 6.86 acres with adjacent lot already subdivided to be kept for future use or sold as wanted. One guest house can be built on one of the lots approved by the MV Commission. Large beautiful pond and natural matured landscaping all add to the appeal of this up-island offering.

Listed by Brenda Codding of Up Island Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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18 Renear Street

Vineyard Haven, MA18 Renear Street

Price$985,000

Est. Mortgage: $/month

Active With Contract

MLS ID 38128

  • Residential
  • Bedrooms 4
  • Bathrooms 2
  • Acreage 0.4821

This is truly a special in town property. Perfectly set on a beautiful 21000 sqft double lot is this wonderful 1917 square foot 3 bedroom 1 bath main house and 600 square foot studio guest house above the two car garage. Home has under gone a great deal of remodeling with the majority of it completed circa 2007. Main house features single floor living, bright and open living room with high ceilings, beautiful kitchen with pecan wood cabinets, granite counter top and upgraded appliances. The cozy dinning area and adjacent family room with mini split heating and cooling is a bonus. You'll enjoy lounging in the expansive master bedroom with sitting area and California style walk in closet. Although at this time there is no en-suite master bath, the space for it is there and ready to go. The two additional bedrooms are more than adequate in size. Full dry basement with tons of storage. Now to the privately situated legal studio apartment, the spacious 600 sqft floor plan features kitchen, full bath, sleeping and sitting area, mini split unit for heating and cooling. The two car garage currently used as a workshop. Condominiumizing this property maybe a possibility. September Closing

Listed by Roy Cutrer Jr of Laer Realty Partners

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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

"Based on information submitted to MA_LINKMV as of May 16, 2021 . All data is obtained from various sources and has not been, and will not be, verified by broker or MA_LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing."