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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8 Tuthill Lane and 27 Braleys Way

MLS ID 36831

  • Residential
  • Square Feet 10398
  • Bedrooms 9
  • Bathrooms 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

$
$
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$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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, MA31 New York Avenue

Price$1,195,000

Est. Mortgage: $/month

MLS ID 37020

  • Residential
  • Square Feet 2390
  • Bedrooms 5
  • Bathrooms 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: 2.99% last updated on Jul 30, 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, MA100 Watcha Club Road

Price$8,500,000

Est. Mortgage: $/month

MLS ID 36565

  • Residential
  • Square Feet 4380
  • Bedrooms 8
  • Bathrooms 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: 2.99% last updated on Jul 30, 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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40 Pankhanne Street

Oak Bluffs, MA40 Pankhanne Street

Price$1,469,000

Est. Mortgage: $/month

MLS ID 35812

  • Residential
  • Square Feet 2624
  • Bedrooms 4
  • Bathrooms 4
  • Half Bath 1

THIS HOUSE IS IMMACULATE - It has never been lived in. Energy Saving and Environmentally Friendly! Beautifully Built, Outstanding Quality and Wonderfully stylish, 4 Bedroom (5 Bedroom Septic), 4.5 Bathroom home with tremendous attention to detail and energy saving. Huge open plan living room with a fabulous white, streamlined kitchen with custom cabinets, quartz countertops and stainless steel Bosch appliances. Large island with gorgeous wood, handmade counter top, storage and plenty of room for seating. Wood burning fireplace in very bright living room with an abundance of Anderson Architectural Series windows throughout and 5" wide solid White Oak flooring throughout. Ground floor Bedroom with Full Bathroom with radiant heat and private screened porch, outdoor shower and patio. There's also half bath and a separate laundry room on this floor. Upstairs - A SECOND Bedroom Suite with Full Bathroom, two guest bedrooms and a guest bathroom. All bathrooms have ceramic tiles with radiant heat in the floors. 5" wide sold white oak floors throughout. Central Air plus and RenewAir whole house Energy Recovery ventilator system! As much as R40 in the walls. All interior walls are insulated and as much as R65 in the roof! Copper gutters and downspouts. Front porch with Douglas Fir and tension wires for balusters. Impressive Three car garage with full bathroom on lower level. Use as a garage, Use as a giant entertainment area, or use part for a 5th Bedroom. There's already a Fifth Full bath in place! This house has been meticulously finished with unique attention to detail both aesthetically and in the construction of this home. Please see attached list for details. Easy to Show! Adjacent 10,000sq.ft. lot may be purchased separately. Preference to person who purchases the house. Create a compound with second house, a pool or a future guest house!

Listed by Alisan Lohan-Conway Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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, MA30 Pondview Drive

Price$1,279,000

Est. Mortgage: $/month

MLS ID 36606

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

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: 2.99% last updated on Jul 30, 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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69 Kanomika Road

Edgartown, MA69 Kanomika Road

Price$5,650,000

Est. Mortgage: $/month

MLS ID 36839

  • Residential
  • Square Feet 3958
  • Bedrooms 6
  • Bathrooms 4
  • Half Bath 1

Edgartown Great Pond waterfront home with 6 bedrooms, 5.7 acres, over 400' of pond frontage, and boating access to the Atlantic barrier beach. Look no further than this beautiful home designed by Sherman & Associates if looking for a move-in ready option on the great pond. Set privately in Kanomika, a hidden enclave that occupies one of the few true peninsulas on Edgartown Great Pond, this property offers room for family and friends, with options available for pool and guest house. The interior features brilliant light and volume, with huge windows and high ceilings throughout. Fabulous views of the water from many rooms. All of the bedrooms and living spaces offer generous proportions. A brand new boardwalk out to the waterfront provides a sublime connection between the house, land, and water, and the experience of boating, paddleboarding, kayaking, swimming and beach-going on the pond to the Atlantic is second to none on Martha's Vineyard. Built in 2000 and enjoyed by one family for the past 20 years, this property is ready to help create your island memories.

Listed by Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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26 Louis Field Road

Edgartown, MA26 Louis Field Road

Price$1,900,000

Est. Mortgage: $/month

MLS ID 36958

  • Residential
  • Square Feet 900
  • Bedrooms 1
  • Bathrooms 2
  • Acreage 2.6

OVERLOOKING BUCOLIC SWEETENED WATER FARM, EDG. - A 2.6 Acre Lot has an existing private 900 sq. ft. luxury Guest House with air conditioning, heat , a fireplace and a separate Home Office in the finished lower level for year-round living. Then you build your 5 bedroom Main House on the last of the pasture lots in this planned farm community with views of scenic open meadows and horses grazing. Located off the paved bike path that leads to to Edgartown downtown and Morning Glory Farm. Fully landscaped yard with garage and two separate driveways for the Guest House and Main House. * Furnishings available for a quick Closing !

Listed by Suzanne Lanzone & Associates LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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34 Bijahs Way

Chilmark, MA34 Bijahs Way

Price$1,049,000

Est. Mortgage: $/month

MLS ID 36934

  • Residential
  • Square Feet 2293
  • Bedrooms 4
  • Bathrooms 2
  • Half Bath 1

Well designed for low maintenance this 4 bedroom home located off Tea Lane in Chilmark has plenty to offer. With over 4 acres and access from 2 different roads a guest house could be added with it's own entrance for total privacy. The open kitchen living floor plan with sliders to a large 25 ft deck offers great entertaining space. Built in bookcases and window seat add to the charm of the room and tie in nicely with the hardwood floors. The kitchen has nice lighting with a lot of counter space and large pantry. There are 2 floors of outside decks overlooking the garden area and the walkout basement adds additional living space or studio. Spacious entryway leads to first floor master bedroom with private bath and 2 additional bedrooms that share a bath. This home is in excellent condition and ready for immediate enjoyment. Many possibilities on this 4+ acre Lot! Easy to show!

Listed by Carroll & Vincent R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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71 Davis Lane, 14 Pent Lane, 7 Peases Point Way

MLS ID 36792

  • Residential
  • Square Feet 8935
  • Bedrooms 13
  • Bathrooms 9
  • Half Bath 3

Edgartown Village Compound. Rare opportunity to own an exceptional, one-of-a-kind, family compound in the heart of Downtown Edgartown. Comprised of three distinct properties, located on Davis Lane, Pease's Point Way and Pent Lane, this sprawling estate sits on roughly .87 acres, and encompasses over 8,500 square feet of interior living space that includes the historic 6-bedroom main residence, an elegant 4-bedroom residence along with a guest house, and a charming 3-bedroom cottage. The three properties, each with its own private street access, are perfectly positioned to create this remarkable compound, with abutting property lines that border an expansive yard complete with pristine lawns and mature landscaping. Enjoy your own unparalleled private oasis in one of the most coveted neighborhoods in the village, within close proximity to downtown shops and restaurants, Edgartown Harbor and some of the Vineyard's best beaches. This is one of very few properties with contiguous parcels available in Downtown Edgartown, and this newly created offering represents a unique opportunity for a buyer to fully realize their own vision of the perfect family compound to be enjoyed over generations. With the capacity for expansion, using existing structures as well as the adjacent open land, the possibilities are endless. It's important to disclose that the seller is an Estate and in Massachusetts any contract will reflect "Estate Rules". Please inquire for greater detail if needed.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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138 & 138B State Road

Chilmark, MA138 & 138B State Road

Price$4,950,000

Est. Mortgage: $/month

MLS ID 36861

  • Residential
  • Square Feet 2558
  • Bedrooms 5
  • Bathrooms 4
  • Acreage 4

This is an amazing Chilmark waterfront property that sits between Stonewall and Nashaquitsa ponds just past Hariffs Bridge. A 3 bedroom main house and 2 bedroom guest house occupy 4 acres of private natural land, and include access to Stonewall pond and Stonewall beach. The "Lenom" property has been in the same family since the 1970's and is being offered for the first time in over 50 years. The year-round main home has been lovingly maintained over the years and AC was added in 2017, the whole house interior was painted in 2020 which has transformed the space and emphasizes the cathedral height living room and the impressive central stone fireplace. Glass doors and three large picture windows surround the dining area to maximize the water views and summer indoor/outdoor living and entertaining. There's also a lovely patio directly off from the dining area to enjoy the outdoor space. The open kitchen has views over to 'Quitsa pond and was fully renovated in 2013 and painted in 2020. Upstairs there's a loft/TV space and also a great viewing roof deck to enjoy sunrises and sunsets and 360 degree water views all day long. The master bedroom is nicely separated from the other 2 guest bedrooms and there are three bathrooms in total, plus an outdoor shower. The guest cottage was converted from the original boathouse to a comfy one bed plus loft bedroom escape right at the water's edge. The upstairs living room with deck that overlooks the pond, bathroom, (with a second water view outdoor shower), and compact open kitchen/dining make this a great space for extra guests or extended family to stay. A new 2 bed septic has been designed and approved for this building. The property has been a popular rental with many repeat families enjoying the homes for generations.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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