Martha's Vineyard Estates & Multi Generation Homes

View the latest listings for estates & multi-generational homes on Martha's Vineyard below. 

Martha's Vineyard Estates & Multi-Generational Homes for Sale

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47 and 31 Hatch Road

Vineyard Haven, MA47 and 31 Hatch Road

Price$7,950,000

Est. Mortgage: $/month

MLS ID 37396

  • Residential
  • Square Feet 6476
  • Bedrooms 7
  • Bathrooms 5
  • Half Baths 2

Elegant and refined, this exceptional estate property is sited on 1.3 acres. Located in the coveted Hatch Road neighborhood, this 2 home property boasts incredible architectural detail with all the modern amenities. As you enter the property via a winding gravel drive past an expansive lawn, you come to a setting not found so close to downtown Vineyard Haven. The main house dates back to 1900 and has been meticulously renovated and features a gourmet kitchen open to a dining room with french doors looking out to a rose garden, a spacious first floor master bedroom suite, dramatic great room with 20 foot ceilings with wood detail, and an inviting screened-in porch leading out to a private brick patio. The home features 4 additional guest bedrooms on the second floor. The guest house was designed in 2008 and built by a prominent Martha's Vineyard builder. The wood detail includes aged lumber and the walls are warmly lined with recycled barnwood. Stunning museum quality terrazzo flooring inlaid with wood beams and terrazzo countertops are featured in the spacious great room, gourmet kitchen and dining room. Other guest house amenities include two bedrooms with en suite baths each with stunning wide plank flooring, and a spacious loft perfect for a home office. A home gym/pool house, outdoor kitchen, 2 car-garage and pool complete this rare offering.

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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556 Edgartown West Tisbury Road

MLS ID 37449

  • Residential
  • Square Feet 1428
  • Bedrooms 4
  • Bathrooms 1
  • Half Baths 1

If you are looking for a property with character, "The Suzie Scott House" has more than you can imagine. Built in circa 1850, the current owner purchased this well maintained home as part of a long time family owned Estate. This sweet Antique sits on 1.4 acres with several out buildings (including the original out house converted to a shed). This is a property to really make your own, while keeping the character of the era, and still putting your stamp on it. Enter through a screened porch which leads into the Main Living space. A large room at the front of the house, off the Living Room (now being used as a bedroom), with fireplace, could be easily converted into a Family room / Office. The cozy Kitchen with dishwasher, washing machine and extra large gas stove could be a beautiful restoration project. A dining, sitting room and 2 more bedrooms finish off the main level. A small staircase leads to 2 second Floor bedrooms and 1/2 bath complete this very special listing. When the current owner purchased this home, the community was thrilled to learn that he was keeping the house, with all its character, in tact. Notice newest work done, shingled sides and most of roof ...Any way you choose to go, this is a beautiful piece of property! There is something to be said for mixing some old with new to create a unique "Vineyard Home".

Listed by Martha's Vineyard Seacoast Properties

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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 Mill Hill Road

Edgartown, MA30 Mill Hill Road

Price$3,950,000

Est. Mortgage: $/month

MLS ID 37397

  • Residential
  • Square Feet 2748
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 13.93

MILL HILL FARM - Breathtaking pastoral estate less than a mile from Main St. - It is so rare that a property such as this comes available. Standing at the homestead, one has the feeling of stepping back in time to a simpler way of life. This 1800's farm has been lovingly maintained while stewarded by one family for three generations. The Farmhouse, bunkhouse and additional outbuildings are surrounded by nearly 14 protected acres of rolling, open fields filled with wildflowers and native wooded edge . During a recent subdivision of the family property, there was foresight to protect the remaining acreage and preserve the unspoiled magnificence of Mill Hill Farm. No further subdivision will be allowed for 300 years. The original three bedroom Farm house was moved to this location and served as the residence and office of a local Doctor. A more recent addition of a kitchen, dining area and 3-season porch grace the southern end of the home leading out to a large, level yard. A thoughtful renovation and expansion to at least five bedrooms or more could result in a superlative and rare estate this close to town. The existing bunkhouse has more recently served as a one bedroom guest house that could be easily renovated to suit or returned to its original use as a barn. The opportunity is endless for the savvy buyer who chooses to act decisively.

Listed by Point B Realty LLC

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$
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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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19 Llewllyn Way

Edgartown, MA19 Llewllyn Way

Price$2,250,000

Est. Mortgage: $/month

MLS ID 37351

  • Residential
  • Square Feet 3428
  • Bedrooms 4
  • Bathrooms 4
  • Half Baths 2

Serene location overlooking the fields of Morning Glory farm, with Land Bank walking trails and biking trails out your back door. House is a short bike path ride to downtown Edgartown and a quick walk to Morning Glory Farm or Sweetened Water Preserve. The main house has everything you need: open concept first floor with exposed timbers and stone fireplace, two car garage and full basement for that home gym. There is not only a first floor master bedroom with ensuite bath, sauna, and private deck, but there is a second floor master bedroom with en suite and walkout balcony. Second floor also has home office/den, third bedroom and another full bath. Then there is the guest house! Newly built craftsman timber frame 1+ bedroom, 1.5 bath with 3 decks, outdoor shower, central AC, boasting quality construction and attention to detail. This property has everything you need...multi generational living, rental income from one of the homes or just extra space for friends and family. Working from home? Plenty of options for office space, plenty of room for a future pool. Possibility to tie into town sewer for future bedroom expansion. Rare opportunity in a desirable neighborhood.

Listed by Martha's Vineyard Island-Wide Realty

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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17 High Mark

Chilmark, MA17 High Mark

Price$4,900,000

Est. Mortgage: $/month

MLS ID 37278

  • Residential
  • Square Feet 3883
  • Bedrooms 7
  • Bathrooms 5
  • Acreage 10.4289

17 High Mark, built in 1928, sits atop Highmark Hill near the center of Chilmark. There's a plaque on the wall in the kitchen commemorating the original owner, architect, builders and neighbors of this estate which reads 'High Mark House - Abode of Ennobling Vision'. This unique Chilmark property is now exclusively offered for the first time in 49 years. Spread across 10.4 acres, the property consists of two parcels. The first parcel is 6.7 acres in size and holds the living quarters. The second parcel is 3.7 acres in size and provides a wide buffer to the main homesite or a suitable lot for further development. Structures on the larger parcel include the main house, guest house, detached bedroom, artist studio or playhouse, in ground pool with outdoor shower and dressing room, tennis court, detached two car garage and long shed workshop. Water views to the Atlantic Ocean, Menemsha Pond, and Nomans Land are seen from many of the rooms of the main house and guest house. The grounds hold specimen plantings in a park like, private setting with wide and long front and rear yards. The main house has both primary and guest bedroom suites, living room with large fireplace, dining room with ample seating for ten, office and gallery, kitchen and laundry room. The lower level has a library/media room (or another bedroom), full bath, utility room, cedar closet and multiple storage rooms. The guest house is 800 square feet with 3 bedrooms, full bath, an eat in kitchen and laundry. The detached bedroom is the perfect bunk house with views to the Atlantic. It is rare to find an estate property in Chilmark that has the features of this compound already in place . Many of the existing amenities found on this property (guest house, pool, etc.) allow for immediate enjoyment without special zoning permits and years of in town residency. Ample acreage provides room for building expansion or relocation.

Listed by Russell Maloney Real Estate

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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56 North Neck Road

Edgartown, MA56 North Neck Road

Price$9,850,000

Est. Mortgage: $/month

MLS ID 37136

  • Residential
  • Square Feet 9686
  • Bedrooms 7
  • Bathrooms 6
  • Half Baths 1

PRIVACY & LUXURY ON MARTHA'S VINEYARD - this is a rare chance to own a sprawling 18.4-acre estate on Chappaquiddick as it has been in the same family for over 40 years. Surrounded by acres of conservation land, and next to the Royal & Ancient Chappaquiddick Links, this multi-generational estate offers an exquisite Main house (8335sqft), a second residence (1319sqft), Gunite pool with outdoor shower, tennis court, and 4 bay garage with finished space (708sqft) over the garage. The main house, remodeled in 2005, offers striking panoramic views of Cape Pogue Sound, gourmet kitchen with upgraded top-of-the-line stainless steel appliances including a wine fridge, 2 full Viking ovens, 2 Sub Zero fridges and granite countertops; multiple decks for outdoor living, a wet bar in the lower level adjacent to the pool & patio and an office perfect for working from home. The second residence has 3 bedrooms, a full kitchen, 2 full bathroom, an outdoor shower, multi-level deck and a screened-in porch. The Bunk House has 1 bedroom, kitchenette, living area & a full bathroom. This estate offers multiple land plots allowing for potential expansion opportunities. This property comes with deeded Beach Access

Listed by Martha's Vineyard Seacoast Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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129, 139 Old Farm Road

Chilmark, MA129, 139 Old Farm Road

Price$3,675,000

Est. Mortgage: $/month

MLS ID 37095

  • Residential
  • Square Feet 1550
  • Bedrooms 3
  • Bathrooms 3
  • Half Baths 1

Beauty, privacy and stunning imagination describe the 12 acre estate with 325 yards of ancient stone walls weaving through a meadow landscape with an extraordinary 2,800 sq ft architectural Greenhouse supported by a charming post and beam 925 sq ft guest house and a 600 sq ft beautiful comfortable living barn. Designed like a cross, this advanced high-tech contemporary Greenhouse may have other uses such as a personal residence. It resembles a cathedral with a soaring angular roof line in perfect symmetry. It was built by Rough Brothers, the preeminent and largest manufacturer of greenhouses world wide. Rough does extensive research and designs systems and controls for conservatories, public and private gardens, US Dept of Agriculture and Forestry, major universities, Projects completed for NY Botanical Gardens, National Botanical Gardens in Washington DC, MIT University and Huntington Garden and Museum. Equipped with the most advanced temperature control system, it houses dozens of exotic and rare plants, trees, grasses, vegetables and flowers. The 12 acres have beautiful meadows, endless trees, dense brush and hundreds of healthy mature heirloom blueberry bushes. The property abuts the 300+ acres of Roth Woodlands and Waskosim's Rock and Tiasquam Valley Reservations extending uninterrupted from North Road to Middle Road.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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37 Pasture Gate Road

Vineyard Haven, MA37 Pasture Gate Road

Price$5,250,000

Est. Mortgage: $/month

MLS ID 37071

  • Residential
  • Square Feet 7604
  • Bedrooms 5
  • Bathrooms 4
  • Half Baths 2

THE PERFECT VINEYARD RETREAT THAT HAS IT ALL! This property offers all the room you need for today's "stay-at-home" environment. There are wings, lofts, and a private guest suite above the garage, providing a myriad of independent locations and common areas to gather at the beginning and end of the day. The grand entrance sets the tone of this Vineyard estate located on 3.15 acres of land. The home overlooks pastoral fields with surrounding woodlands to create a peaceful setting to retreat amid the dynamics of today's world. The pool area and custom-designed pool house provide an expansive outdoor living space full of sun and fresh air. The owners chose the location in the Tashmoo Association because of the proximity to Vineyard Haven Village and the amenities of the community, which provides tennis, and a dock. An up-Island property in a down-Island location. A grand foyer invites you to the living room on the right with fireplace and French doors to the back patio. The dining room connects the living room to the kitchen, which is more than generous with a breakfast area overlooking the gardens and pool. Open from the kitchen is a custom family/sunroom with views over the fields and horse farm beyond. Behind the kitchen and powder room is a classic study that can convert from a workspace to a den for a social gathering or to watch the game. There are four bedrooms in the main house on the second floor and a third-floor loft. A guest suite is located above the two-car garage with private access. One of the dramatic additions is another living room with fireplace, vaulted, lighted ceiling, bar and powder room with French doors to the pool. The sale also includes a beach lot (32C/4 and 32D/4) just before the opening to Lake Tashmoo with beach access on the Lake and the Sound. Boating from the association dock to your private location, anchoring your boat for a picnic, or digging clams for dinner puts the frosting on the cake or the Vine in Vineyard. If 7,604 sf is not quite enough for your new "stay-at-home" lifestyle, the renovated 2 bedroom cottage at 19 Chappaquonsett is also available as is the horse farm at 67 Lamberts Cove Road.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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$7,500,000

Est. Mortgage: $/month

MLS ID 36565

  • Residential
  • Square Feet 4380
  • Bedrooms 8
  • Bathrooms 5
  • Half Baths 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: 2.8% last updated on Oct 22, 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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277 North Road

Chilmark, MA277 North Road

Price$8,950,000

Est. Mortgage: $/month

MLS ID 36813

  • Residential
  • Square Feet 2914
  • Bedrooms 6
  • Bathrooms 3
  • Half Baths 2

The James Cagney Estate - A vast 70-acre estate with multiple building sites on the north shore of Chilmark. This is possibly the last time a real estate asset of this scale ever becomes available on Martha's Vineyard. The property is a world unto itself offering so much of what Chilmark and Martha's Vineyard are rightly famous for - water views, beach access, sun-dappled meadows, shaded forests through which streams and brooks wend, and lichen-covered stone walls. Exploring this estate - actually made up of three contiguous pieces of property - is like traveling through time and offers a window into a Chilmark of days gone by. The property was at one time the summer retreat of movie star Jimmy Cagney whose affection for this place is legendary. The Cagney house dates from the 1700s and is still in its original location along with a second house, studio, and barn. The prime waterview building site is located a distance away and is completely private. Located on a ridge and surrounded by acres of meadows and stone walls, this site offers views of Vineyard Sound and the mainland in the distance. A third building site is situated in another area of wide open meadows. The opportunities to develop this estate are many and varied and are limited only by a buyer's vision. This rare property could be yours to be treasured now and for generations of your family to come - truly a refuge from the exigencies of modern city living.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 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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