Homes with Pools on Martha’s Vineyard

Find Martha’s Vineyard homes with pools in Aquinnah, Chilmark, Edgartown, West Tisbury, Oak Bluffs, and Vineyard Haven. Martha’s Vineyard offers a wonderful seaside experience with world-class beaches, beautiful conservation areas, and a laid back lifestyle. Whether you’re looking for a permanent residence or a vacation home, Hancock Real Estate can help you find your island dream home.

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8 Tuthill Lane and 27 Braleys Way Edgartown MA

MLS Number 36831

  • Residential
  • Square Feet 10398
  • Bedrooms 9
  • Bathroom 9
  • Half Baths 2

This incredibly private waterfront compound, uniquely located just minutes from historic Downtown Edgartown, is being offered for the first time in more than 30 years. This classic Martha's Vineyard retreat offers it all: a private sandy beach, boat access, more than 10,000-sq. ft. of living space in two homes, pool, barn, and endless sunsets. This unique combination would typically only be found in remote locations up island, yet here you can feel completely out of town while being a short stroll or bike ride into Edgartown and all it has to offer. Sited on three meticulously landscaped acres overlooking Eel Pond and Edgartown Harbor, nearly every room from the five-bedroom main house and four-bedroom guest house enjoys unobstructed water views. A sophisticated yet comfortable setting, this Island compound offers unmatched privacy. The main residence features multiple living areas and a restful primary bedroom suite with sun deck, spacious bathroom and a private office with fireplace. Other features include a gourmet kitchen with sitting area, home office, study, pool room, four guest bedroom suites, and an oversized screened porch, perfect for summer entertaining. The guest house is equally inviting and offers welcoming living and dining area, a screened porch, family room, playful bunkroom, two additional guest bedrooms, oversized primary bedroom suite with private deck, and a three-car garage. The gunite pool and spa provide panoramic water views are surrounded by a bluestone patio, classic stonewalls, and lush plantings of colorful roses and hydrangeas. The expansive lawn leads to the water's edge on Eel pond where you can enjoy easy access to Edgartown Harbor and beyond from your private beach where the owners can keep a boat. This desirable private waterfrontage allows you to spend summers clamming, kayaking, paddle boarding, swimming and boating. A truly remarkable Island escape in Edgartown that epitomizes the best of Martha's Vineyard in one of its most coveted locations.

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 2.8% 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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65 Butlers Cove Road Edgartown MA

Edgartown, MA65 Butlers Cove Road

Price$18,500,000

Est. Mortgage: $/month

MLS Number 34264

  • Residential
  • Square Feet 10000
  • Bedrooms 6
  • Bathroom 6
  • Half Baths 1

Located in the exclusive Herring Creek Farm Association and offering over 10,000 square feet of exquisitely appointed living area, lies this magnificent waterfront estate. The classic architecture is complimented by the well-executed floor plan. The ground floor offers wonderful living spaces including a grand entrance with dining room, gourmet kitchen, family room and screened porch to one side, and a living room, sunroom and den to the other. There is a ground floor suite plus 5 additional 2nd floor bedrooms including a luxurious master suite. The residence is complimented by an attached 3-car garage with parking courtyard, a large pool and patio area and a open porch with stone fireplace. The beautifully landscaped grounds offer sunset views across the pond and barrier beach as well as expansive views across the open fields and stable to the east. The common association land offers over 100 acres of open fields, a horse stable and over 1,500 feet of private Atlantic beach. Complete privacy, a luxurious turn-key house in a amazing setting, with private beach and all within a short drive to downtown Edgartown, makes this property one of the island's finest.

Listed by Landvest MV

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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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103 Main Street Vineyard Haven MA

Vineyard Haven, MA103 Main Street

Price$13,500,000

Est. Mortgage: $/month

MLS Number 37110

  • Residential
  • Square Feet 7046
  • Bedrooms 5
  • Bathroom 4
  • Half Baths 2

THE ULTIMATE WATERFRONT RETREAT - The Vineyard has always been the place to go for R&R, and if you needed it in the past, you certainly need it now. It is the oasis of beauty and tranquility in a vintage community. This property offers the best of the Island. Located on Vineyard Haven Harbor, the home sits on a large 1.7A parcel of land, which provides privacy, spectacular views of harbor activity, yet steps away from the Village for your morning coffee, afternoon shopping, and dinner and theater in the evening. A unique feature is proximity to the ferry to come to and leave the Island easily. Think of it - the kids who will probably be with you a lot more, Mom and Dad, who will visit, and the family workforce can easily use the Vineyard home as "operation center," adjusting to the new lifestyle perfectly. Designed by premier architect Patrick Ahearn, with 7,045 sf, the home is warm and friendly with space to accommodate everyone's needs. The large kitchen with sitting room and fireplace opens to a screened porch. A dramatic stone fireplace is the focal point of the sitting area on the porch with generous room for dining for twelve with views of Harbor activity. This space is the hub of the house. There is a large, quiet office on the first floor for serious work along with a smaller office space off the kitchen. A grand formal dining room with a fireplace and living room is designed for special occasions. Another all-season sun porch on the first floor provides additional space for a variety of activities. The informal and formal areas connect with an outdoor patio. The master bedroom suite with a sitting area occupies the south wing of the second floor and is cleverly separated from the activity of the household. Three more bedrooms are in the north wing of the house. Another expansive deck connects both wings. The views from the first floor are spectacular, and they become panoramic and magnificent on the second floor. There is a guest suite over the two car garage which can be accessed from the outside or the adjoining deck on the second floor. The piece de resistance is the widow's walk offering the most brilliant views. The terraced pool and built-in outside grill overlooking the Harbor complete this perfect Vineyard home.

Listed by Sandpiper 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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44 Forest Road West Tisbury MA

West Tisbury, MA44 Forest Road

Price$12,800,000

Est. Mortgage: $/month

MLS Number 34815

  • Residential
  • Square Feet 4436
  • Bedrooms 6
  • Bathroom 4
  • Acreage 4.2

Quintessential Seven Gates waterfront compound. Outstanding Martha's Vineyard retreat. Stunning views and immediate sandy beachfront. The property features a main residence and barn designed and built by South Mountain Company. Immaculately kept, the structures are virtually turn-key. The interiors offer rich details, displaying highest level craftsmanship, and elegant design, perfect for seaside relaxation. Views of the Sound and Elizabeth Islands are readily available from nearly every room, including from the guest suite above the barn. Just off the main house is an inviting pool area, complete with bluestone patio, extensive stone walls and hardscape, and separate hot-tub area. The property is set within one of the most incomparable private areas of the Island. Seven Gates Farm has a rich history, and comprises approximately 1600 acres. In addition to generous private lot sizes, nearly 1000 common acres are held in permanent conservation with The Trustees of Reservations. Many gorgeous open fields, woodlands, ponds and private trails abound. Properties in the farm enjoy access to miles of private beach, two piers and two tennis courts. This is a coveted opportunity to reside within a timeless community, originally a collection of large farms, that has been deeply focused on preservation and stewardship since the late 1800's when the Head of Geology for Harvard University first developed his vision for Seven Gates Farm as a 'civil wilderness' that should be enjoyed, cherished and protected. Note: 2% fee to Seven Gates Farm in addition to purchase price and Land Bank. See below for additional details.

Listed by Compass

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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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18 Spruce Gate Road Chilmark MA

Chilmark, MA18 Spruce Gate Road

Price$12,500,000

Est. Mortgage: $/month

MLS Number 34218

  • Residential
  • Square Feet 3700
  • Bedrooms 5
  • Bathroom 3
  • Half Baths 1

Squibnocket Farm Estate with expansive views of the Atlantic Ocean. Located in Martha's Vineyards' only exclusively gated private 450 + acre community which boasts over 1.5 miles of pond front, over 2 miles of ocean front, 300+ acres of conservation land and shared with only 12 other homes. This turnkey waterview offering melds modern construction and comfort with an idyllic farm-like setting and directly abuts 17 acres of conservation land. Stately and elegant, the property residence sprawls peacefully amid surrounding natural beauty. The home was designed and built by Soikkeli & Company, a well-known luxury contractor on the Island. The exterior design evokes traditional New England farmhouse style, with multiple gables and cedar shingles defining the facade. The living space centers on a gorgeous chef's kitchen - soapstone counters, custom farm sink, all new top of the line appliances and fixtures, and a charming pantry are just a few of the outstanding elements found within. Two living rooms flank the kitchen on either side, and the master suite is set perfectly on the first level at the home's southern end. Four additional bedrooms are found on a northerly wing, as is the two-car garage. Views of the ocean, Squibnocket Pond, Noman's Land, and open fields are readily available from many rooms. The house is wired for sound and includes smart home features such as Nest learning thermostats for the AC and heating systems, and sound controlled by HEOS. The organic landscape was thoughtfully designed, highlighting ancient stonewalls on the property borders, flower beds, and a new gunite pool overlooking a gracious lawn and the ocean beyond. The property offers nearly 3 acres of fenced pasture as well as permits for a Chilmark barn. Outdoor living areas to enjoy include an expansive back deck, a superb screened porch with outdoor fireplace, and an outdoor fire pit - ideal for summer evenings or nighttime star-gazing. Ownership in Squibnocket Farm provides access to miles of trails, multiple accesses to Squibnocket Pond, and access to the exquisite homeowners beach, which is home to some of the most stunning sandy beachfront and dunes on the Atlantic seaboard. Squibnocket Farm is a paradise that must be seen to fully experience - a rare enclave of privacy and calm.

Listed by Wallace & Co. Sotheby's

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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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9 Briggs Road Edgartown MA

Edgartown, MA9 Briggs Road

Price$12,500,000

Est. Mortgage: $/month

MLS Number 37475

  • Residential
  • Square Feet 6049
  • Bedrooms 6
  • Bathroom 6
  • Half Baths 1

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

$
$
%
$/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, 5 and 20 Stillpoint Meadows Road West Tisbury MA

MLS Number 34587

  • Residential
  • Square Feet 6726
  • Bedrooms 9
  • Bathroom 7
  • Half Baths 2

"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: 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 Beach Pebble Road West Tisbury MA

West Tisbury, MA30 Beach Pebble Road

Price$9,985,000

Est. Mortgage: $/month

MLS Number 35654

  • Residential
  • Square Feet 6228
  • Bedrooms 4
  • Bathroom 3
  • Half Baths 2

This stylish waterfront home tucked into the North Shore was designed and built by Tom Tate. The current owners purchased the property in 2017 and continued to work with Tate Builders to enhance and finish the home to incorporate a completely finished lower level, an infinity swimming pool, pool cabana, two car garage and extensive landscaping with stylized stone work by Vineyard artisan, Eben Armor. The four bedroom home includes a private master wing with huge custom lift-and-slide glass doors that open to the north shore water views. There are three further guest bedrooms, also with luxurious bathrooms, and one that has the same large glass doors that open to the pool side decks and cabana. The bathrooms all have frame-less glass showers and teak finished details. The open contemporary kitchen with solid teak kitchen island that spans the length of the kitchen incorporates the dining area with another set of custom glass sliding doors that open on to the sun deck seamlessly connecting the house with the beautifully landscaped exterior . The living room has a Isokern European fireplace and a set of glass doors to the outside living space and pool. The finished lower level has large living room/entertainment room with a kitchen/bar. A climate-controlled wine tasting room, private office, gym with “natural light wall”, laundry room second TV/Den and storage. State of the art systems have been installed and designed with every consideration to comfort and easy beach front living. One can choose to swim in the ocean from your private beach or take a dip in the heated pool. This elegant home sits high on the bluff overlooking the Vineyard Sound and the Elizabeth Islands. The 25 x 15 foot pool is 7 and a half feet at the deep end and blends nicely into the landscape with the ocean view cabana and deck area to create an additional secluded oasis for guests and family to enjoy. No expense has been spared on this beautiful waterfront property which truly has to be seen to understand. This is an incredible opportunity to buy a finished modern home like no other on Martha's Vineyard.

Listed by Tea Lane Associates

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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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56 North Neck Road Edgartown MA

Edgartown, MA56 North Neck Road

Price$9,850,000

Est. Mortgage: $/month

MLS Number 37136

  • Residential
  • Square Feet 9686
  • Bedrooms 7
  • Bathroom 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

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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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139 Little Homers Pond Road Lot 5A West Tisbury MA

MLS Number 36480

  • Residential
  • Square Feet 3542
  • Bedrooms 4
  • Bathroom 3
  • Half Baths 2

This is a Martha's Vineyard ocean front estate like no other available. A private oasis on over 13 acres with a Har-Tru tennis court, 12,000 bottle wine cellar, salt water swimming pool, hot tub, gym, sauna and steam room. The views are expansive over the open meadows and Atlantic Ocean beach which is exclusive to this property. One of the strongest features of this estate is that a new owner can have two main dwellings onsite creating a compound in the privacy of what this association offers. In addition to owning and potentially developing 46 acres with a few members, this property also shares the ownership of 141 acres of conservation land that protects the value of this private enclave. The home was designed by Gary Graham of Graham Meus, Inc. - the design embraces the easy beach lifestyle which this property represents. All of the rooms offer sunlight and ocean views. The home is designed with three different wings which are connected by decks on the first and second floor. This is a playful approach to island living allowing for great communal spaces and privacy if desired. It is quite special to have a property with so many amenities already existing onsite. This is a tremendous and unusual opportunity to own ocean front acreage so closely located to Edgartown and the airport yet still feeling so secluded. The estate has 1200 feet of exclusive private south shore sandy beach.

Listed by Tea Lane Associates

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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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52 Middle Road West Tisbury MA

West Tisbury, MA52 Middle Road

Price$8,750,000

Est. Mortgage: $/month

MLS Number 35777

  • Residential
  • Square Feet 8700
  • Bedrooms 7
  • Bathroom 7
  • Acreage 25.2

The Kenney compound consists of the authentic updated 1719 Tilton House, wonderful estate cottage and stunning pool and a remarkable cathedral like barn and outdoor stone encircled paddock. The 1719 Tilton House is the perfect blend of authentic early American design and decor with 21st Century comfort and convenience. The Tilton House was lovingly restored and renovated in 2000 to its original splendor and doubled in size adding a modern kitchen, spacious sun room, two bedrooms, two full baths, a 4th fireplace and many other features. The 2006 superbly designed and decorated large cottage and exquisite pool area with incomparable Lew French stone sculptures compliments the 18th Century Tilton House. In addition, there is a large cathedral like barn often called the most stunning barn in the northeast. This combination of two homes, pool and barn on 25 private pastoral acres make this paradise one of the finest Vineyard estates. Words do not do justice to this property which has been a desirable venue for important charitable and cultural events over the last decade.

Listed by Tea Lane Associates

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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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12 Boldwater Road Edgartown MA

Edgartown, MA12 Boldwater Road

Price$8,750,000

Est. Mortgage: $/month

MLS Number 36993

  • Residential
  • Square Feet 12800
  • Bedrooms 7
  • Bathroom 9
  • Half Baths 3

This unique and remarkable Martha's Vineyard retreat is one of the Island's finest private compounds, on 10 acres of beautifully landscaped and natural grounds. The home, designed by noted architecture firm Robert AM Stern, includes over 11,000 sq. ft. of exquisite and recently renovated living areas, sweeping decks, and porches. The expansive great room has 10 ft. windows and a fireplace up to the 20 ft. cathedral ceiling. Every interior space is appointed with the highest level of detail and craftsmanship. A curved staircase leads up to the private master suite, with a beautifully appointed cathedral ceiling bedroom, covered deck, and 2 full bathrooms with walk-in closets. There are an additional 6 bedrooms, with 5 full bathrooms and 3 half-baths in the main house. The large gourmet kitchen is exquisitely outfitted. The octagonal dining room has a fireplace, and provides a 270-degree view of the expansive rear gardens and pool. There is a library with fireplace, a private office with fireplace, large decks off the great room and dining room for outdoor entertaining and dining, and a grill area. The finished lower level includes a children's playroom, wine cellar, recreation area, laundry room, and storage closets. The heated garage accommodates 2 cars and storage. There is ample additional parking for guests. The lawn area features flower gardens, and further back, an organic vegetable garden, adjoining blueberry patch, and flower-cutting garden. The 20 ft. by 60 ft. pool and Jacuzzi are nestled between the main house and the pool house, which has an enclosed heated porch, gym, massage room, sauna, and full bathroom. The compound offers extraordinary privacy, bounded in back by a large forest preservation area, while located within a ten-minute drive to downtown Edgartown, the airport, and golf club. The Boldwater Association provides tennis courts, convenient private access to Edgartown Great Pond for small boating, and a private south shore beach.

Listed by Landvest MV

$
$
%
$/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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