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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65 Butlers Cove Road Edgartown MA

Edgartown, MA65 Butlers Cove Road

Price$19,500,000

Est. Mortgage: $/month

MLS Number 34264

  • Residential
  • Square Feet 10000
  • Bedrooms 6
  • Bathroom 6
  • Half Bath 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: 2.99% last updated on Jul 30, 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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8 Tuthill Lane and 27 Braleys Way Edgartown MA

MLS Number 36831

  • Residential
  • Square Feet 10398
  • Bedrooms 9
  • Bathroom 9
  • Half Bath 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: 2.99% last updated on Jul 30, 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: 2.99% last updated on Jul 30, 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 36595

  • Residential
  • Square Feet 5500
  • Bedrooms 6
  • Bathroom 6
  • Half Bath 1

Newly built extraordinary six bedroom, six and a half bath 5500 square foot architect designed home on 4.8 acres of rolling woodlands, open meadow and 385 feet of direct waterfront at Nashamois Point on Edgartown Great Pond. Home features an elegant first floor Master Suite, an exquisite gourmet kitchen with two center islands, quartz counters, 6 burner Wolf gas stove, SubZero refrigerator, two dishwashers, two wine coolers, and custom cabinetry. There is a spacious living room with gas fireplace and triple arched doors leading out to a covered porch, in ground pool, and blue stone patio in the fenced back yard all with spectacular water views. On the second floor there are four ensuite bedrooms, three of which have private balconies with fantastic water views and for those times when the whole family gathers there is a sixth bedroom and bath in the lower level and room to build two additional bedrooms over the garage if desired. For those memorable boating and beach outings there is a boat and motor in the garage for trips to the sand, surf, and sun of an Atlantic Ocean beach minutes away and 6 kayaks for enjoying the blue Herons, Swans, and Osprey while exploring the five fingers of the Great Pond.

Listed by American Real Estate LLC

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$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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 Bath 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: 2.99% last updated on Jul 30, 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 Bath 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 pool, cabana and patio creates 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: 2.99% last updated on Jul 30, 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 Bath 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: 2.99% last updated on Jul 30, 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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%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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 Bath 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: 2.99% last updated on Jul 30, 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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93 South Water Street Edgartown MA

Edgartown, MA93 South Water Street

Price$7,500,000

Est. Mortgage: $/month

MLS Number 33715

  • Residential
  • Square Feet 5207
  • Bedrooms 5
  • Bathroom 5
  • Half Bath 1

Located within Edgartown's charming Historic District and offering magical views across a tidal pond to Edgartown Harbor, lies this unique 5 bedroom residence. The home underwent a complete renovation in 2010 preserving every historic detail while introducing a fresh and stylish flair. The first floor offers a gourmet kitchen, family room, dining room and large living room with fireplace and French doors leading to the harbor facing deck. The 2nd floor offers 4 bedrooms and 3 baths. There is an entire wing offering an dramatic master bedroom suite with a 20 foot high, cathedral ceiling, an office, sitting room and luxurious bathroom. The lower level offers a second living space, bathroom and walkout to the covered grill area, exterior shower and pool / terrace area. Complimenting the property is a 2-car garage and perfectly landscaped lot which stretches from South Water Street to the waters edge, all located less than three blocks from Main Street.

Listed by Landvest MV

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$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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31 Lamberts Cove Road Vineyard Haven MA

MLS Number 35174

  • Residential
  • Square Feet 5732
  • Bedrooms 6
  • Bathroom 6
  • Half Bath 3

Tashmoo Farm, originally built before the Revolutionary War, has been meticulously and tastefully restored to preserve the historic character and grandeur. This gracious home is in pristine condition and now features 6 bedrooms, 5 full baths, 3 half baths, several sitting rooms, a more formal living room, dining room and family room. All new heating and A/C. The newly renovated kitchen includes 2 Sub Zero refrigerators, a Bosche dishwasher, Thermador double ovens and a five burner stove top. Many complimenting features include original moldings, 7 fireplaces, wide pine and fir floors and all new windows. A har-tru tennis court, gunite pool and a delightful pool house were added in the late 1990's. The pool house is accessible to both tennis and pool through oversized doors that lead to private patios covered by a pergola. It's is well equipped for entertaining with grill area and wet bar, a changing room and full bath. Beautifully landscaped grounds with expansive lawns overlooking rolling meadows, extensive perennial gardens surrounded by stone walls offers exceptional privacy. Access to Lake Tashmoo and the association dock.

Listed by Karen M. Overtoom R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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17B East Pasture Road Aquinnah MA

Aquinnah, MA17B East Pasture Road

Price$6,350,000

Est. Mortgage: $/month

MLS Number 33320

  • Residential
  • Square Feet 5000
  • Bedrooms 5
  • Bathroom 6
  • Half Bath 2

Perched above Menemsha Pond, this exquisite new five-bedroom home combines state-of-the-art construction with all the elements for the ideal Vineyard experience including some of the best water views on the island, Menemsha Pond access via walking path, heated Gunite pool, and the privacy and protection of abutting conservation land with no building allowed between this house and Menemsha Pond. This substantial and tasteful home with contemporary style has been thoughtfully designed into the surroundings. Only the finest craftsmanship and materials were used including Lutron lighting, Will Parry custom doors, local custom cabinetry, walnut floors, and two solar flowers which track the sun as a 5kw system. With an open floor plan for everyday living and plenty of room to expand when entertaining guests, this smart layout includes all bedroom/bathroom suites and a dedicated gym or yoga room with full bathroom. Flowing from the indoors out, through the screened porch and expansive deck, to the rolling landscape beyond, stone walls and pathways lead you from the main house to the detached guest suite and on to the pool and pool house where sliding cedar barn doors reveal an outdoor kitchen area and indoor changing room and bathroom. From there, the walking path to the pond awaits. Deeded view easement and deeded pond access with beach usage included. This section of Menemsha Pond is lovely and shallow, where little ones could spend hours playing safely and being entertained by the wildlife. Seller currently has two moorings on the pond and will transfer. Additionally, Aquinnah home ownership gives you Philbin Beach on the south shore and dog-friendly Lobsterville beach on the north shore. This is a rare opportunity for new high-end construction and an unparalleled combination of elements creating an experience that is truly the best of up-island living!

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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