Martha's Vineyard Luxury Waterfront Homes

Browse all luxury waterfront homes for sale on Martha's Vineyard below. Contact us to ask questions or schedule a tour.

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8 Tuthill Lane and 27 Braleys Way Edgartown MA 02539

MLS Number 36831

  • Residential
  • Mls Status Active
  • Village Downtown
  • Bedrooms 9
  • Bathroom 10

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: 2.88% last updated on Sep 23, 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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81 Oyster Pond Road Edgartown MA 02539

Edgartown, MA81 Oyster Pond Road

Price$12,500,000

Est. Mortgage: $/month

MLS Number 38572

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 4.5
  • Acreage 3

Private Oyster Pond waterfront residence on 3-acres with a private dock, manicured lawn, and beautiful gardens. This contemporary 5 bedroom, 4.5 bath home boasts a unique design flooded with natural light. The home features a living room with a cathedral ceiling with exposed beams and a stone fireplace, a gourmet kitchen with top-of-the-line stainless appliances all with incredible views of Oyster Pond. The dining area offers access to the spacious mahogany sundeck overlooking the private heated pool, and gardens. The first-floor primary bedroom includes a home office and views of Oyster Pond. The guest bedrooms and baths are on the lower level with private access to the pool area. The spacious mudroom entryway provides convenient access to the two-car garage. The guest apartment is located above the garage with an elegant kitchen, and spacious living room offering privacy and incredible views. The expansive lawn stretches to the edge of Oyster Pond and a private dock where you can enjoy clamming, kayaking, paddle boarding, swimming, and boating. The residents of Oyster Pond enjoy access to the Pond and the barrier beach on the ocean. A truly special Martha’s Vineyard escape in one of the Island's most coveted locations.

Listed by Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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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 Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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1115 Main Street Vineyard Haven MA 02568

Vineyard Haven, MA1115 Main Street

Price$11,950,000

Est. Mortgage: $/month

MLS Number 38728

  • 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.

Listed by Viewpoints

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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14 & 22 Cataumet Avenue Vineyard Haven MA 02568

MLS Number 38212

  • Residential
  • Mls Status Active
  • Bedrooms 11
  • Bathroom 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 Landvest MV

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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44 Green Hollow Road Edgartown MA 02539

Edgartown, MA44 Green Hollow Road

Price$10,900,000

Est. Mortgage: $/month

MLS Number 38325

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 3
  • Acreage 1.14

Edgartown Water Front Opportunity – The Minnow, an existing 1925 vintage “camp” cottage has been re-imagined by the thoughtful eye of esteemed architect, Patrick Ahearn. The following have been approved: 6 bedroom septic and a house/carriage house. The total net SQ FT of the proposed home is 6,230 SF (including the basement at 1,713 SF). The detached guest floor above the garage is 766 net SF. Perfectly sited to enjoy the views of Katama Bay, the property includes a deep water dock and sandy beach. Property and plans are easy to show. The plans and approvals are included with the land listing price of $10,900,000.

Listed by eXp Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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68 North Water Street Edgartown MA 02539

Edgartown, MA68 North Water Street

Price$9,989,000

Est. Mortgage: $/month

Pending

MLS Number 35647

  • Residential
  • Mls Status Pending
  • Bedrooms 6
  • Bathroom 6
  • Acreage 0.31

An expansive compound in the heart of Edgartown village does not come to the market very often. A stunning renovation by Stern McCafferty Architecture + Interiors has yielded a home that seamlessly blends the old and new, the historic with the contemporary. Light, bright, and with the highest levels of finished detail, the home is filled with details to remind you that you are in one of the most richly historic communities in all of New England. Just look out the front windows and watch the yachts pass between the beautiful waterfront homes and it calls to mind that only a few generations ago it was whaling vessels that dominated the water views and the homes themselves belonged to successful ship’s captains. The 4,100 s.f. main house and 660 s.f. guest house with sweeping lawn, lovely manicured gardens and oversized swimming pool is an oasis in bustling North Water Street with its brick sidewalks, traditional streetlights, and signature Greek Revival homes. Step inside and you enter a sophisticated home with a contemporary sensibility. Sleek modern furniture and furnishings are juxtaposed with traditional architectural details. In keeping with the modern desire for an open plan living there is lots of space for gatherings of friends and family. There are four large bedrooms with three baths – one of which is a master ensuite with office, and on the third level, a large sleeping and play space for younger kids, also with a full bath. The swimming pool is set within the beautiful gardens and is one of the largest pools in the village at 42’ x 18’. At the far end of the property is a charming two-bedroom cottage and garage. A parking court is accessed off a private lane on Morse Street which is large enough to park an abundance of cars. The property is a gem in the crown of historic North Water Street.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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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 Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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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 Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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20 Eliot Avenue Chilmark MA 02535

Chilmark, MA20 Eliot Avenue

Price$7,900,000

Est. Mortgage: $/month

MLS Number 38217

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 0.6

Surrounded by nature, this is a South Shore waterfront sanctuary. The presence of the peaceful placid pond combined with the power of the ocean and the sound of the waves is part of the special experience of living here. It has a particular sense of privacy and peacefulness. Hidden away on a quiet road of lilacs and summer cottages, the yard is defined by stone walls, lush gardens, natural art objects and several outdoor patios. Just beyond the lawn is a sandy path for easy access to the ocean and pond. The feeling inside the tasteful home is one of understated pleasing ambience. There are three bedroom suites and the ability to create a fourth. Each of the bedrooms has a connection to an outside space, two have pond and ocean views and one bedroom includes a sleeping loft space. The large and open kitchen which was recently renovated has a vaulted ceiling and an expansive dining space. Natural light and views of the pond fill the room and glass doors lead to the outdoor patios. The library with fireplace and a wall of windows to the water also serves as a formal dining room. In the living room, the dramatic height and spectacular views of the ocean and pond give you an expansive sense of water. The views from the adjacent sunroom have an intimacy and this room is currently used as an office and sitting room. The primary bedroom suite has extraordinary panoramic views and is a retreat that includes an open sitting room and fireplace as well as a private balcony and bathroom. The character of this property, its authenticity, vistas and connection to the natural landscape all combine to create a truly unique experience.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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69 Kanomika Road Edgartown MA 02539

Edgartown, MA69 Kanomika Road

Price$6,595,000

Est. Mortgage: $/month

MLS Number 38770

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 4.5
  • Acreage 5.7

EDGARTOWN GREAT POND retreat with 6 bedrooms, 5.7 acres, over 400’ of waterfront, and boating access to the Atlantic barrier beach. Look no further than this beautiful residence designed by Sherman & Associates for a move-in ready option on the coveted shores of 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 all guests, 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 gorgeous boardwalk out to the waterfront provides a sublime connection between the house, land, and water, and the experience of boating, paddleboarding, kayaking, and swimming on the pond. Access by boat to the Atlantic barrier beach provides an experience that is second to none on Martha’s Vineyard.

Listed by Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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41 Naushon Road West Tisbury MA 02575

West Tisbury, MA41 Naushon Road

Price$5,695,000

Est. Mortgage: $/month

MLS Number 38639

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 6.5
  • Acreage 1.5

Spectacular waterfront property in Upper Makonikey with sweeping water views, private sandy beach right in front of the house, and more. Perched with a front row seat of Vineyard Sound, with active boating and soothing waters, this sprawling home is a choice destination with a variety of amenities and custom features. Water views abound and there is room for a multitude of guests. Truly a rare offering on the island’s north shore.

Listed by Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 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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"Based on information submitted to MA_LINKMV as of September 24, 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."