Luxury Real Estate

View Luxury Homes For Sale on Martha's Vineyard

Please contact us for a showing or if you need assistance in searching for a luxury home. Create an account to save favorite listings and to receive email notifications when similar listings become available. 

104 and 111 Old Herring Creek Road West Tisbury MA 02575

MLS Number 39574

  • Residential
  • Mls Status Active
  • Bedrooms 7
  • Bathroom 5.5
  • Acreage 9.49

Private waterfront estate comprised of two parcels in the prestigious North Shore neighborhood. This beautiful compound is spread over 9.5 acres of pristine land and includes over 600 feet of private Vineyard Sound beach.  The elegantly refurbished beach house has all the modern conveniences and features spectacular water views from almost every room.  There is a breakfast eating area off the gourmet kitchen which is adjacent to the porch allowing you to eat with the feeling of being outdoors. The primary ensuite bedroom features your own private deck overlooking the ocean giving you the luxury of enjoying a cup of coffee while watching the sunset.  Additional guest bedrooms include immaculate views throughout. This unique retreat includes a guest cottage on a second separate waterfront lot. The guest cottage includes a roof deck overlooking the property, Vineyard Sound and the Elizabeth Islands. Enjoy a magical walk from both homes to your own private beach.  The residences and grounds offer one of the most stunning private compounds on Martha's Vineyard.

Listed by Thomas C. Wallace of Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

12 and 10 Boldwater Road Edgartown MA 02539

Edgartown, MA12 and 10 Boldwater Road

Price$18,000,000

Est. Mortgage: $/month

MLS Number 39172

  • Residential
  • Mls Status Active
  • Bedrooms 9
  • Bathroom 9
  • Acreage 22

Every square inch of this Robert A. M. Stern ten thousand foot estate was lovingly scrutinized and optimized for stately comfort , proper flow and a magnanimous feeling of what an extremely significant estate should be comprised of. We believe it to be "one of one" homes on the Vineyard. It's memorable great room with its thirty foot ceiling, reclaimed oak beams and custom crafted six foot by nine foot doors and windows creates an atmosphere that is second to none! This estate has six fireplaces each unique and perfectly matched to it’s location! The seven plus bedroom suites are designed with comfortable privacy and flow; the master bedroom suite is designed with its own private level of living with an open sitting area with a custom fireplace, his and hers private baths and a stately deck overlooking the private grounds. Three private offices, an au-pair suite,exercise room and a five hundred plus bottle Wine cellar are are but a few of the other touches that finish this one of a kind estate. One has to mention the laundry facility with its four commercial washers and dryers, folding tables, commercial irons and steam table as it equals a professional laundry. The landscaping was lovingly designed for the 22 acre grounds by a team of high end landscape architects. The principal estate blends perfectly with a plethora of plantings that bring happiness to the surroundings as they all take their sequential scheduled moments of boasting their wonderful colors and unique designs in a year round symphony of sophisticated beauty. The grounds behind the estate reveals a great span of natural privacy containing old growth vineyard oaks and a wall of private woods. Contained inside the back yard is an Olympic size gunite pool ,which is encased by a massive slate patio with room for all for private sunbathing, outdoor dining and living. Behind the pool is an in ground hot tub and a one thousand foot exercise facility with a massage room, en suite with full bath and sauna, weight room and large screened in heated porch , also with a custom fireplace. "Next stop, there isn't one"!

Listed by Fred Mascolo of Jane Brown Assoc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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

2 Squibnocket Road Chilmark MA 02535

Chilmark, MA2 Squibnocket Road

Price$15,000,000

Est. Mortgage: $/month

MLS Number 39331

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 5.5
  • Acreage 4.5

Sited on 4.5 acres and nestled at the top of the hill you will find this commanding residence flanked with views of the Atlantic Ocean, Menemsha Pond and the Vineyard Sound. Living is seamless both indoors and out at this light, bright and tranquil abode. Sophisticated summer living at its finest, no detail is overlooked in this pristine four-bedroom, three and a half bathroom residence with a two-bedroom, two bath guest house. This Up-Island retreat offers a spacious layout, lap pool, very private guest house and deeded access to Menemsha Pond. Start or end your days doing laps in the pool or venture down to Squibnocket beach, for a swim or surf, just a short distance away. A highly coveted setting with a beach amenity only available to Chilmark residents. This is truly a one of a kind offering that should not be overlooked!

Listed by Madelyn Silvia of Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

17 Boldwater Road Edgartown MA 02539

Edgartown, MA17 Boldwater Road

Price$14,900,000

Est. Mortgage: $/month

MLS Number 38502

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 6.5
  • Acreage 8.1

One of the better water front locations in the Bold Water association. Enhanced by a newly and completely renovated Post and Beam home by one of the islands most sought after designer architects. This is a compound, including, full guest house, Pool, Beautiful grounds, detached garage and game area. The appeal of this unique property is to be seen. Although perfectly suitable , year round, it was designed with a light and airy summer feeling. The frontage on the Great Pond is very suitable for boating, both power and sail ; very easy deeded access to one of the most spectacular beaches on the entire south shore barrier. And, private to Bold Water Association.

Listed by Dick Binder of Metes & Bounds

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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

12 Boldwater Road Edgartown MA 02539

Edgartown, MA12 Boldwater Road

Price$12,000,000

Est. Mortgage: $/month

MLS Number 39586

  • Residential
  • Mls Status Active
  • Bedrooms 9
  • Bathroom 10
  • Acreage 10

Every square inch of this Robert A. M. Stern ten thousand foot estate was lovingly scrutinized and optimized for stately comfort , proper flow and a magnanimous feeling of what an extremely significant estate should be comprised of. We believe it to be "one of one" homes on the Vineyard. It's memorable great room with its thirty foot ceiling, reclaimed oak beams and custom crafted six foot by nine foot doors and windows creates an atmosphere that is second to none! This estate has five fireplaces each unique and perfectly matched to it’s location! The seven plus bedroom suites are designed with comfortable privacy and flow; the master bedroom suite is designed with its own private level of living with an open sitting area with a custom fireplace, his and hers private baths and a stately deck overlooking the private grounds. Three private offices, an au-pair suite,exercise room and a five hundred plus bottle Wine cellar are are but a few of the other touches that finish this one of a kind estate. One has to mention the laundry facility with its four commercial washers and dryers, folding tables, commercial irons and steam table as it equals a professional laundry. The landscaping was lovingly designed for the 10 acre grounds by a team of high end landscape architects. The principal estate blends perfectly with a plethora of plantings that bring happiness to the surroundings as they all take their sequential scheduled moments of boasting their wonderful colors and unique designs in a year round symphony of sophisticated beauty. The grounds behind the estate reveals a great span of natural privacy containing old growth vineyard oaks and a wall of private woods. Contained inside the back yard is an Olympic size gunite pool ,which is encased by a massive slate patio with room for all for private sunbathing, outdoor dining and living. Behind the pool is an in ground hot tub and a one thousand five hundred foot exercise facility with a massage room, en suite with full bath and sauna, weight room and large screened in heated porch , also with a custom fireplace. "Next stop, there isn't one"!

Listed by Fred Mascolo of Jane Brown Assoc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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

8 Jethro Lane Chilmark MA 02535

Chilmark, MA8 Jethro Lane

Price$11,995,000

Est. Mortgage: $/month

MLS Number 35593

  • Residential
  • Mls Status Active
  • Village North
  • Bedrooms 8
  • Bathroom 6.5

Stunning Chilmark north shore 4 acre waterfront paradise with wonderful sunsets and unique privacy nestled between a large wooded hill and a 200 acre private estate. The 5 bedroom 4 1/2 bath TWO kitchen main house and 2 bedroom (with 2 dormers) 2 bath guest house enjoy dramatic views of the Elizabeth Islands from the Gay Head Lighthouse to Woods Hole from every room. The property is beautifully manicured with an enchanting contour stretching to the bluff overlooking a dreamy private cove and sandy beach. Four cleared acres are very rare on the heavily wooded north shore. Waterfront values on the rugged, elevated and protected Vineyard north shore are attracting more interest after Hurricane Sandy damaged the low elevation fragile south shore NY, NJ and New England coast line. The property is in the highly desirable 335 acre Spring Point community with 38 home sites with 135 acres of common land, 3/4 mile of private beach, 2 tennis courts and endless dirt roads and trails.

Listed by Robert Kenney of Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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

1115 Main Street Vineyard Haven MA 02568

Vineyard Haven, MA1115 Main Street

Price$11,950,000

Est. Mortgage: $/month

MLS Number 39443

  • Residential
  • Mls Status Active
  • Bedrooms 11
  • Bathroom 8.5
  • Acreage 0.3145

Step back in time as you explore the old-world charm of this West Chop waterfront grande dame overlooking Vineyard Sound, the Elizabeth Islands, and Woods Hole. Built in 1893 and meticulously maintained and updated over the past century, the much-loved 7,026-sf Victorian home includes many original hand-crafted architectural details. The expansive great room with exposed beams and windows on three sides offers panoramic water views with truly magnificent sunsets, and the adjacent reading room faces a cozy wood-burning fireplace with a door to the covered porch. Flooded with morning light, the kitchen – convenient to the entry mudroom and butler’s pantry/laundry room – features a six-burner Wolf stove, soapstone counters, and sunny breakfast area. Each of the three floors includes a spacious main bedroom with an en-suite bath and expansive water views, for a total of three primary bedroom suites. The fully renovated basement addition – with an underground hallway and door leading to the beach path – also includes two bedrooms, totaling eleven throughout the house. Two bedrooms have fireplaces, and custom built-ins provide plenty of storage. Outside, beautifully crafted stone walls, a south-facing stone terrace, and mature perennial landscaping create a tranquil seaside retreat on .31 acres, with convenient proximity to the West Chop Club and Mink Meadows Golf Club. There’s no shortage of nearby things to do, from tennis and golf to swimming and sailing, but perhaps this property’s greatest appeal is its sense of timelessness, the charm and allure of a bygone era. With only a handful of owners over the generations, now is the rare opportunity to make summers at “Pierside” a part of your family’s history. *Stone Pagoda not included in sale of property*

Listed by Emily Flake of Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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

1005 Main Street Vineyard Haven MA 02568

Vineyard Haven, MA1005 Main Street

Price$11,600,000

Est. Mortgage: $/month

MLS Number 38460

  • Residential
  • Mls Status Active
  • Bedrooms 9
  • Bathroom 7
  • Acreage 0.8333

Welcome to 1005 Main St! Located at the northern tip of Martha's Vineyard comes one of the most beautiful oceanfront properties on the entire island. A 5,050 square foot estate with an incredible deck, private beach, lovely painted floors and a ton of space for entertainment is now on the market. A feeling of privacy and peace surrounds this property due to the amazing landscaping, views, and unique character that this home brings. Come watch the sunset from the very spacious and freshly painted deck and be taken away into the immersive environment of the immaculate surroundings. Call and set up an appointment today!

Listed by Ryan Knoechelman of Rovi Homes

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

18 & 28 Hillbrook Lane West Tisbury MA 02575

West Tisbury, MA18 & 28 Hillbrook Lane

Price$10,750,000

Est. Mortgage: $/month

MLS Number 39615

  • Residential
  • Mls Status Active
  • Bedrooms 7
  • Bathroom 6.5
  • Acreage 9.65

Located off of beautiful Indian Hill Road, lies these two wonderful properties, totaling nearly 10 acres. The driveway winds past weathered stone walls, mature trees and down gently sloped terrain to the various improvements that exists. The main 4-bedroom / 4.5-bath residence offers over 4,000 sq ft of living space on three levels with an attached garage. There is an open floor plan on the 1st floor with all rooms enjoying water views, across the open pastures and surrounding treescapes to the Elizabeth Islands. There is a 60’ swimming pool, a jacuzzi, pool house, one-bedroom guest cottage and tennis court, all complimenting the property. There is a fork in the driveway as well as a walking path, connecting the second property which offers a small pond and a beautifully restored 3-bedroom Cape, built in the 1700’s. This property also enjoys water views. The overall setting of these two properties is magical and feels incredibly private. Cedar Tree Neck Preserve is within short walking distance and this property must be seen by anyone searching for a quintessential up-island property.

Listed by Gerrett Conover of Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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

29 Slough Cove Road Edgartown MA 02539

Edgartown, MA29 Slough Cove Road

Price$10,495,000

Est. Mortgage: $/month

MLS Number 39347

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 4
  • Acreage 1.53

NEW FOR SPRING 2023: ELEGANT COUNTRY ESTATE WITH POOL IN KATAMA. Sited at the end of a long private drive, amid a bucolic 1.5-acre meadow setting with stone retaining walls and lush perennial gardens, this elegant country estate, designed by noted architect Patrick Ahearn, offers the epitome of luxurious living in Katama. The home’s timeless and charming character is highlighted by thoughtful, top-notch architectural details and styling throughout -- like custom millwork and paneling, antique rough hewn beams, and more. In addition, the well-designed floor plan features multiple living areas that open out to a central courtyard with bluestone terrace, an outdoor wood-burning fireplace and an 18'x36' gunite swimming pool with built-in whirlpool spa. The property is ideally located near South Beach, with the sounds of the ocean nearby. There is time to customize colors and finishes to create your very own signature island residence. Detailed construction specifications are available upon request. Construction is already in-progress and the property is slated for completion by Spring, 2023.

Listed by Wendy Harman of Compass | Point B

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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

1153 Main Street Vineyard Haven MA 02568

Vineyard Haven, MA1153 Main Street

Price$9,500,000

Est. Mortgage: $/month

MLS Number 38206

  • Residential
  • Mls Status Active
  • Bedrooms 8
  • Bathroom 6.5
  • Acreage 0.59

Beautifully sited on a winding, private lane and overlooking pristine North Shore West Chop, conservation trust protected beach, this elegant seaside home flawlessly combines the refined lifestyle of its 1896 origins with a modern style. Meticulously maintained and completely renovated, it is move-in ready for you to enjoy wide, panoramic views of Vineyard Sound and the Elizabeth Islands, dramatic sunsets, natural light, and a fine, sandy beach made for memorable summer days and nights. The house features a first floor that openly flows from an eloquent entrance foyer through dining, living and kitchen areas, and ending up on the most incredible spacious covered porch taking in the magical views of always entertaining boating and fishing activity lawn, gardens, and the Sound. Coastal living has never been easier with its 8 BRs and 6.5 BAs that will make filling this open and airy waterfront home with the happy sounds of summer vacations and family gatherings a breeze. The property is wonderfully landscaped with many specimen trees, nicely framing the lawn and gardens and there is potential to add a swimming pool. Mink Meadows Golf Course and downtown Vineyard Haven are only minutes away. A truly amazing Vineyard property in one of the few remaining N. Shore Martha’s Vineyard private communities!

Listed by Gerrett Conover of Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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

13 Boldwater Road Edgartown MA 02539

Edgartown, MA13 Boldwater Road

Price$9,495,000

Est. Mortgage: $/month

MLS Number 38730

  • Residential
  • Mls Status Active
  • Bedrooms 7
  • Bathroom 5.5
  • Acreage 5.4

A truly exceptional waterfront home on Jane's Cove in the distinguished Boldwater neighborhood on Martha's Vineyard. This beautiful compound is spread over 5+ acres of pristine land and includes a sprawling 5 bedroom/5 bathroom main house and 2 bedroom guest suite with views of the pond from almost every room. A winding drive leads from the road to the main residence. The recently renovated main house features a generous first floor plan, detailed woodwork, modern finishes, and splashes of color throughout. This home was clearly designed to take full advantage of its beautiful surroundings. The first floor contains, a large living room and a family room each with a fireplace, a dining room, gourmet kitchen, and a beautiful screened in porch. This home features a bedroom suite on the first floor and a primary bedroom suite on the second floor with water views off the private balcony. Three additional guest bedrooms complete the second floor. The property offers a separate guest quarters located above the spacious 3-car garage featuring two bedrooms, tile bath, kitchenette and a sun-filled living room that opens to a welcoming deck overlooking the pond. A path meanders down to the water’s edge where you can enjoy kayaking, paddling and boating. The Boldwater Association offers tennis, private boat landing and a South Shore sandy beach. This is a rare opportunity to call a serene piece of Martha’s Vineyard “home.”

Listed by Alyssa Halisky of Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

"Based on information submitted to MA_LINKMV as of May 27, 2022 . 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."