Luxury Waterfront Real Estate on Martha’s Vineyard

Each waterfront property on Martha’s Vineyard is truly unique. Luxury waterfront homes on the island offer an alluring range of amenities, including boathouses, private docks, guest houses, private beaches, and spectacular views of Lake Tashmoo, Edgartown Harbor, the Lighthouse, and Katama Bay.

Martha’s Vineyard, the largest and one of the most picturesque islands in New England, has some of the most beautiful waterfront properties.

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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: 3.04% last updated on Apr 15, 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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103 Main Street Vineyard Haven MA 02568

Vineyard Haven, MA103 Main Street

Price$13,500,000

Est. Mortgage: $/month

MLS Number 37110

  • Residential
  • Mls Status Active
  • Village West Chop
  • Bedrooms 5
  • Bathroom 5

A luxurious in-town, waterfront estate overlooking Vineyard Haven Harbor - The Vineyard has always been the place to go for rest and relaxation; it is an oasis of beauty and tranquility in a vintage seaside setting. 103 Main Street offers an exquisitely designed home nestled on 1.7 acres with expansive views of the boats coming and going and yet it is right in the Village just steps from boutiques and coffee shops, restaurants and theaters. This shingle style coastal New England home, designed by respected architect Patrick Ahearn, has 6,500 sf of living space and is warm and friendly with space to accommodate everyone. The terraced pool and abundance of casual outdoor living space is private but takes full advantage of the spectacular setting. A must see!

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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$13,000,000

Est. Mortgage: $/month

MLS Number 35593

  • Residential
  • Mls Status Active
  • Village North
  • Bedrooms 7
  • 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

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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2 & 4 Morse Street Edgartown MA 02539

Edgartown, MA2 & 4 Morse Street

Price$12,950,000

Est. Mortgage: $/month

Pending

MLS Number 36643

  • MultiFamily
  • Mls Status Pending
  • Village Downtown
  • Bedrooms 7
  • Bathroom 7

SPECTACULAR WATERFRONT COMPOUND ON HISTORIC EDGARTOWN HARBOR. Located in the heart of historic Edgartown, with expansive views across to the Edgartown Lighthouse, Chappaquiddick and Vineyard Sound, this unique two-home harborfront residence was designed by Twanette Tharp, one of the Vineyard's leading designers and featured in Architectural Digest (see attached article). Anchored by a private cobblestone courtyard and surrounded by lush privet hedges, the two residences, named "The Captain Dexter House" and "The Ferry House" were lovingly designed and built in 2000 with unmatched craftsmanship and impeccable architectural detailing. Captivating interior details include custom millwork and tongue-and-groove paneling, antique heart pine flooring, handsome fieldstone fireplaces, gourmet cook's kitchens, marble tile bathrooms, top quality hardware, nautical accents and more. Designed for idyllic indoor-outdoor living and entertaining both homes feature dramatic, second-story Great Rooms with vaulted ceilings that open onto mahogany decks where you can dine, sunbathe or just watch boats go by on the harbor. On the dockside level, there is a large outdoor living space where you can lounge, dine and entertain family and friends around a deluxe built-in chef's grill. Rounding out this special waterfront offering is a private dock slip that will accommodate a power boat up to 17 feet, offering easy water access for boating, fishing and/or for accessing a larger boat moored in the harbor (a mooring may be secured through the Edgartown Harbormaster; please inquire on details). There is also a detached Office/Studio with vaulted ceilings located in the cobblestone courtyard, perfect as an at-home office or art/writing studio. This Edgartown Village residence is the ultimate in luxurious harborside living as a boater's paradise, family compound and/or rental property (rental history available on request).

Listed by Point B Realty LLC

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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9 Briggs Road Edgartown MA 02539

Edgartown, MA9 Briggs Road

Price$12,500,000

Est. Mortgage: $/month

MLS Number 37475

  • Residential
  • Mls Status Active
  • Village South Shore
  • Bedrooms 6
  • Bathroom 6.5

This amazing, newly built home lies on nearly 5-acres of beautifully landscaped grounds with 385 ft of private pond frontage. The attention to detail and elegant style of the house is abundant. The main residence features a spacious and open floor plan with entry hall, large living room with fireplace, gourmet kitchen and eat-in area, all of which have tall ceilings and oversized doors and windows facing the pool, gardens and waterviews. There is a large 1st floor master bedroom suite and 4 second floor bedrooms with private baths. The 2-car carriage house compliments the main house architecture and offers a large 2nd floor space that could be utilized for any number of uses including additional bedrooms. The in-ground pool, patios, retaining walls and gardens are meticulously designed and 2 different paths offer access to the ponds edge for boating and beach access. Too many features to mention in a peaceful and private setting yet located less than 10 minutes to downtown Edgartown.

Listed by Landvest MV

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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61 North Water Street Edgartown MA 02539

Edgartown, MA61 North Water Street

Price$12,500,000

Est. Mortgage: $/month

MLS Number 37971

  • Residential
  • Mls Status Active
  • Bedrooms 8
  • Bathroom 5.5
  • Acreage 0.4

Located in the heart of historic North Water Street lies this classic 8-bedroom home on an oversized lot with a deep-water pier. The largely original, 1860’s building represents one of the last untouched Edgartown harbor front homes. This home is ready to live in and enjoy for the summer of 2021 so that you can experience this extraordinary setting and plan the customizations you’d make for your family for generations to come. The first-floor features a water facing living room, dining room and wonderful wide covered porch, all with amazing views of Edgartown Harbor and Chappaquiddick. The second floor has two water facing master suites, four smaller bedrooms and the third floor has additional living space with two bedrooms, bath and storage. The formal street side landscaping offers a boxwood lined brick path to the front doorway. The water side offers gorgeous, formal gardens surrounding a patio, brick garden walls and an expansive lawn leading to the private pier and the ornamental boathouse. This is an amazing opportunity to acquire a significant harbor front home with boating access, located blocks away from the historic downtown area. Please call to view this very special Edgartown harbor front property.

Listed by Landvest MV

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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111 Little Homers Pond Road Lot 3A West Tisbury MA 02575

MLS Number 37319

  • Land
  • Mls Status Active
  • Village South Shore
  • Acreage 12.3

This is a very rare south shore offering with breathtaking views spreading across the open meadows, over the sandy dunes and the Atlantic Ocean. Two main houses are allowed on this extraordinary parcel with both sites offering impressive ocean views with a quick walk onto the beach. This is a wonderful opportunity for a compound which offers shared association private beach and pond access. No further subdivision allowed on this parcel. There is a total of 182.6 acres in conservation, of which 141.8 acres is common land shared between the owners allowing access to miles of trails and extreme privacy. This is a dynamic natural setting embodying heathlands, pristine pond views, miles of Atlantic Ocean coastline and sandy dunes. An additional 40.8 acres (Lot 7) is shared common land for only lots 3, 4 and 5 of which 16.9 acres are developable. All approvals from NHESP in place and shown on engineering maps

Listed by Tea Lane Associates

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$
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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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37 West Tisbury MA 02575

West Tisbury, MA37

Price$10,500,000

Est. Mortgage: $/month

MLS Number 34587

  • Residential
  • Mls Status Active
  • Village Central
  • Bedrooms 9
  • Bathroom 8

"Stillpoint", this stunning compound is reintroduced with a fresh perspective and price. Stillpoint is the feeling when you enter this tranquil estate in West Tisbury on beautiful Martha's Vineyard. Classical New England elegance is combined with European influences that immediately transport one to Tuscany or the Cotswold's whilst encompassing quintessential American style. This 50 acre country estate is comprised of three dwellings; the elegant main Federal style home dates from 1795 and was brought to the Vineyard in 1987 from it's original site in the Berkshires. Complete with swimming pool and pool house, gorgeous landscaping and views over Priester Pond. Classical proportions provide 4 comfortable en suite bedrooms, ample living and entertaining rooms, and a fabulous gourmet kitchen with double doors to an amazing brick floor conservatory/sun room with bar area and another set of French doors to the pool terrace and gardens. The home is surrounded by beautiful landscaping including an Italian inspired terrace complete with fountain and meadow views. At the opposite end of the pool is a studio/ pool house currently used as an art studio. Across the driveway is a contemporary barn, built by South Mountain Company in 2012. The 2700 square foot barn is currently used as an event space, workshop and art space, but the building could easily convert to additional living space. A bank of solar roof panels provide power for this structure plus the main house. There's a outdoor fire pit and established vegetable garden. Across the lawn from the main home is an equally immaculate second home, which has been restored with the most impeccable attention to detail and taste. The Luce Athearn House, dates to 1714 and has 5 bedrooms and 4 bathrooms. see full description under "2nd dwelling". The whole property has so many unique and interesting places to explore and just be at one with nature and the surrounding . 50 acres of meadow, woodland and frontage on two ponds.....and if that isn't enough, the property abuts Polly Hill arboretum and Land bank conservation land. A Stillpoint one feels like one could be anywhere in the world yet its just a 5 minute drive to West Tisbury center. A 10 minute drive to the airport or to the Vineyard Haven ferry. When it's time to finally leave one is left with a feeling of gratitude at being able to experience this jewel of a property. The peace and tranquility will draw you back.

Listed by Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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$9,999,500

Est. Mortgage: $/month

MLS Number 33535

  • Residential
  • Mls Status Active
  • Village West Chop
  • Bedrooms 8
  • Bathroom 6.5

Located directly on the water with a short walk to your beach, this three-story shingle-style air conditioned home on Vineyard Sound, is an easy walk to the West Chop Club, and epitomizes the relaxed elegance of late 19th-century seaside living. Beautifully restored and decorated, the 5,345-sf house ideally located on a peaceful private road, includes eight bedrooms, multiple formal and informal gathering areas, and wide porches with spectacular water views. A superb example of traditional coastal New England architecture with its cedar shingles and abundance of windows, gables, and gambrels, this meticulously maintained house was built in 1897 and renovated in the early 1990s, paying tribute to its historical detail while adding many amenities. A spacious gourmet kitchen, outfitted with high-end appliances, adjoins a casual dining/lounging area and connects through a butler’s pantry to the formal dining room. Two living rooms, one with a large fireplace, comfortably accommodate a large gathering. The expansive master suite includes a balcony with water views, brick fireplace, spacious master bath, and adjoining sitting room and office. The .59-acre property makes the most of its dramatic setting with graceful perennial gardens, open lawns, and most importantly multiple possible sites for a pool. A private path leads to the West Chop Trust’s north shore beach for lazy days in the sun, tide rides, and fishing. Just two miles from the center of Vineyard Haven, a West Chop classic similar to this home rarely comes on the market, and provides the perfect setting to create memories of your own for generations to come. This private community affords easy access to beaches, independence and activities for all members, and an appealing lifestyle away from the hustle and bustle of other parts of the island. We are happy to provide all the wonderful amenities available in the West Chop area.

Listed by Viewpoints

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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 West Chop Lane Vineyard Haven MA 02568

Vineyard Haven, MA20 West Chop Lane

Price$5,999,500

Est. Mortgage: $/month

Active With Contract

MLS Number 35038

  • Residential
  • Village West Chop
  • Bedrooms 7
  • Bathroom 5.5
  • Acreage 3.53

Panoramic views over Vineyard Sound and the Elizabeth Islands, frontage on Mink Meadows Pond, and a tranquil wooded setting with beautiful mature plantings make this 3.53-acre property feel like a secluded and serene island retreat. A relaxed gathering spot for family and friends, the 4,704-SF house includes seven bedrooms and four-and-a-half baths, separate guest quarters, screened porch, two-car garage, and nearly 2,000 SF of outdoor decking. The great room anchors the house with its soaring cathedral ceiling, brick fireplace, and a wall of windows framing the dramatic sunset water views. The light, airy kitchen is outfitted with a spacious white granite island and countertops, Gaggenau ovens and cooktop, and walk-in pantry. Custom built-in shelves and cupboards throughout provide lots of storage space. Enjoy easy access to the sandy Mink Meadows association beach, along with preferential member status at Mink Meadows golf course. Nearby are West Chop Woods 85-acre nature reserve, Lake Tashmoo, the West Chop community, and Vineyard Haven Yacht Club. Making the most of its peaceful, private location and panoramic views, this beautifully crafted home, with renovation design by renowned island architect Ben Moore, has room for everyone, inside and out.

Listed by Viewpoints

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$
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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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85 Little Homers Pond Road (3C) West Tisbury MA 02575
Active With Contract

MLS Number 37186

  • Land
  • Village South Shore
  • Acreage 23.8

Surrounded by water and nature, this 23-acre building parcel is a South Shore paradise. This sprawling lot supports two full size houses and includes a beautiful 1200' stretch of shared private ocean beach. Walk, bike or cruise your golf cart to the beach in minutes. The main building site features views over Big Homers Pond, the dunes, the Atlantic and westerly views up the south shore of the island. There is a short walking path to an access point on Big Homers Pond for paddle boarding, sailing, playing with little ones or just sitting and enjoying the sunset. The rest of the parcel has a lovely orchard-type setting and total privacy with shared interest in 141 acres of abutting conservation land and 40 acres of abutting commonland. New electric and fiber optics are available near the site. Note: parcel was recently redesigned - assessor map/lot and value is based on a different configuration of this parcel. See map included here.

Listed by Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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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26 Crackatuxet Cove Road Edgartown MA 02539

Edgartown, MA26 Crackatuxet Cove Road

Price$5,450,000

Est. Mortgage: $/month

Active With Contract

MLS Number 36535

  • Residential
  • Village Katama
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 3.95

The 4-acre waterfront property, with a wonderful 4-bedroom home, is located in the exclusive Herring Creek Farm Association. Herring Creek Farm is one of the island’s most desirable addresses offering 215 acres of majestic land, most of which is under conservation restrictions in perpetuity. This beautiful setting is discovered by a winding drive that leads through open fields, stables and grazing farm animals. The farm is limited to only a few lucky residences and comes with rare direct access to some 1,500 sq. ft. of private and pristine Atlantic beachfront. The 1990’s home is winterized and was constructed utilizing bio-climatic design principles and is in great condition. It offers an abundance of light with its cathedral ceilings and expansive decks which offer stunning views of the ocean and open farmlands. The land stretches to the pond’s edge offering boating access as well. This incredibly unique offering is special as it exists or will lend itself towards creating the next amazing family compound with all of the above amenities. It is located in the best area of Katama with less than a 10-minute drive to downtown Edgartown.

Listed by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 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 April 19, 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."