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

Price$21,000,000

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: 3.82% last updated on Jun 13, 2019
* 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 Guernsey Lane Edgartown MA

Price$17,500,000

Est. Mortgage: $/month

MLS Number 34675

  • Residential
  • Square Feet 6346
  • Bedrooms 6
  • Bathroom 6
  • Half Bath 3

This spectacular Edgartown harbor front compound was newly built in 2009 and offers 3 buildings with over 7,000 sq. ft. of classically designed living space offering great flexibility in use. The main residence offers a cathedral ceiling living room with fireplace and antique beams. The home has a very livable floor plan with great flow. The 1st floor also includes a large kitchen, dining room, office, den and screened porch. The second floor has 4 bedrooms with 4 baths, two of which have access to a water facing deck. All of the above offers tremendous views over Edgartown Harbor to Chappaquiddick and across Katama Bay to South Beach. There is also a lower level with media room, large living room, powder room and private entrance from the exterior. There is a 3-car carriage house with an additional 2 bedrooms, living room and kitchenette. The rear yard is beautifully landscaped with a large pool, Jacuzzi, grill area and spacious pool deck. Lastly, there's a pool house with bunk beds and separate laundry and a garden storage shed. The 2.1-acres of property offers expansive manicured lawns sloping down to over 120 ft. of harbor frontage, deep-water pier and mooring. This property is located down a quiet drive, 1 mile from town and represents one of the great Edgartown Harbor properties.

Listed by Landvest MV

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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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", where time stands still. This is the feeling when you enter this tranquil historic 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: 3.82% last updated on Jun 13, 2019
* 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

Price$14,000,000

Est. Mortgage: $/month

MLS Number 34815

  • Residential
  • Square Feet 4436
  • Bedrooms 5
  • 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: 3.82% last updated on Jun 13, 2019
* 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

Price$13,500,000

Est. Mortgage: $/month

MLS Number 33742

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

VINEYARD HAVEN HARBOR WATERFRONT WITH A POOL - A premier location on Vineyard Haven Harbor with expansive views of all the activity. Set back on 1.7A, with 146' of private beach, this property offers a spectacular pool, surrounding landscaping, and a 5 bedroom, 7,046 sf home, 2 car garage impeccably designed by premier architect, Patrick Ahearn. A dramatic foyer separates the casual side of the house from the more formal rooms. The spacious kitchen to the left, with a view of the Harbor, incorporates a casual sitting area with fireplace and a separate bar area. Wide French doors open to a large porch with stone fireplace, where you will enjoy the smell of the ocean, breezes, and feeling of what summer is all about on the Vineyard. The outstanding dining room overlooks the entire harbor and is centrally located beyond the foyer. The south wing of the first floor includes the formal living room with fireplace, all season porch, and study. The second floor is devoted to the master suite and guest quarters with broad views which deliver varying angles of the Harbor. A long balcony hallway leads to the master suite on the right with an over sized walk in closet, bath and French doors overlooking the lawn and pool to the Harbor beyond. Next to the master suite is a stairway to the widows' walk and the Harbor and stars. The north wing of the house is devoted to three guest bedrooms. A fifth bedroom studio is above the 2 car garage, with sleeping quarters, bath, living space, and kitchenette. It has a private access from the garage or accessed from the guest suite on the second floor. A stunning property with stunning views with proximity to town and the ferry.

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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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34 Cow Bay Road Edgartown MA

Price$12,750,000

Est. Mortgage: $/month

MLS Number 34810

  • Residential
  • Square Feet 8310
  • Bedrooms 8
  • Bathroom 7
  • Half Bath 3

This spectacular compound is located in the very special Cow Bay section of Edgartown - featuring gorgeous private association Nantucket Sound beach and easy access to town. Built in 2004 to the highest standards, this designer curated home blends the best of New England tradition and contemporary family life features in 7500 sq ft of living space. Traditionally defined rooms integrate seamlessly with one other - allowing for modern family living as well as privacy. All primary living spaces and bedrooms face the water with unobstructed views across Trapps Pond, the barrier beach, Nantucket sound and on a clear day, the Cape. Covered and screened porches provide mesmerizing water views, and both sunrises and sunsets in all conditions. The three-car mahogany paneled garage complements the no-detail spared, but understated and easy to maintain design features of the entire property. Recreation alternatives abound - at the wide private beach which includes shared cabana use and storage - and at home with ping-pong and billiards rooms, a gorgeous 60 ft swimming pool, two outdoor showers, and a barn outbuilding which houses a regulation squash court, wet-bar, lounging space and more. The 2.3 acres of pond-front property are beautifully landscaped with cutting and herb gardens and expansive lawns and fields of wildflowers that combine with stunning views across Trapps Pond and the barrier beach. There is rarely a reason to leave this home. Cow Bay shares over 20 acres of common land just a stone's throw away from downtown Edgartown.

Listed by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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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Lot 5 at Homers Pond West Tisbury MA

Price$12,500,000

Est. Mortgage: $/month

MLS Number 34297

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 2
  • Acreage 22.2

This 22.2-acre South Shore ocean front property offers a four-bedroom residence with salt-water swimming pool, hot tub, Har-Tru tennis court and an impressive underground 12,000 bottle-capacity wine cellar. The home was designed by Gary Graham of Graham Meus, Inc. to highlight the home's proximity to the beach. Each bedroom and living space has wonderful views of the ocean. The residence features a media room, exercise room, office, two sitting rooms, three full bathrooms, two half bathrooms, two outdoor showers and five fireplaces. The home is divided into three wings, which are connected by decks on both the first and second floors. As one of the lots in Homers Pond Association, you commonly own 141 acres of conservation restricted land which provides a majestic entrance to the properties. In addition you are one of 3 lots that commonly own over 46 acres of association land which can be improved to offer any number of usages and represents great value. One can also walk directly from the property through the dunes to access over 1,200 sf of private beach. With engineering and utilities in place, tremendous build ability and the ultimate secluded location, this is an amazing opportunity.

Listed by Landvest MV

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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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10 & 12 Boldwater Road Edgartown MA

Price$12,000,000

Est. Mortgage: $/month

MLS Number 35256

  • Residential
  • Square Feet 11900
  • Bedrooms 7
  • Bathroom 8
  • Half Bath 3

AUCTION: Bid June 25-28. Previously $12M. Without Reserve. Open Thurs-Sun 1-4PM & by Appt. At the end of two curving, tree-lined drives, the estate includes 22 magnificent acres of trees, pastures, and ponds. Offering privacy and spectacular indoor-outdoor living, this unique and remarkable compound features a stately seven-bedroom home. Designed by world-famous Robert A.M. Stern Architects, every room is appointed with the highest level of craftsmanship. French doors open up to an expansive wraparound deck allowing parties to flow outdoors. Spend summers by the resort-style pool and grilling al fresco dinners. The second level is reserved for the master bedroom suite, with private balconies and his and hers closets and bathrooms. Bordered by a forest preserve, the expansive property offers future possibilities while retaining its secluded and natural vibe. Agent Remarks: Call Concierge Auctions at 858.750.5362 or visit ConciergeAuctions.com for details.

Listed by Landvest MV

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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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22 Peases Point Way South & 11 Tilton Way Edgartown MA

MLS Number 32348

  • Residential
  • Square Feet 11190
  • Bedrooms 10
  • Bathroom 9
  • Half Bath 3

Custom built by and for high end Island builder so endless details abound! This LEED CERTIFIED house measures over 9,000 square feet with 5 ample bedrooms, 6 full baths and 3 powder rooms. It is wide open with rambling qualities to accommodate generational family gatherings. Easy going and aristocratic simultaneously blending old with new using sustainable materials including 200 year old flooring and beams. Perfect for summer entertaining with large covered porch complete with dining for 12, 2 fireplaces and wonderful living area overlooking the pool, yard and gardens. Every amenity possible including steam shower, sauna, 2 outside showers, hot tub, gym, theater, game room, mahogany inside/outside bar, office and breathtaking Lew French living room fireplace set in an inverted hull mahogany ceiling with 3 balconies overlooking this Great Room. Absolutely spectacular and a must see! Plus separate 5 bedroom, 3 bath carriage house.

Listed by Hob Knob Realty, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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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1 Azalea Lane Chilmark MA

Price$8,250,000

Est. Mortgage: $/month

MLS Number 34126

  • Residential
  • Square Feet 2511
  • Bedrooms 5
  • Bathroom 3
  • Half Bath 1

Rarest of the rare - Ocean-view Chilmark home with swimming pool, 440 feet of private ocean beach, and big, beauteous ocean views. The house is being completely renovated and price shown is for the completed product. Note that the images shown are of the house BEFORE renovation. Detached garage.

Listed by Wallace & Co. Sotheby's

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$
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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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: 3.82% last updated on Jun 13, 2019
* 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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86 Turkeyland Cove Road Edgartown MA

Price$6,500,000

Est. Mortgage: $/month

MLS Number 34101

  • Residential
  • Square Feet 2723
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

Located front and center on Turkeyland Cove, a wide finger of Edgartown Great Pond, this 3.5 acre property is sublime. With water views from nearly every room, the elegantly crafted home was designed for easy living but with an eye for beauty everywhere you look. The pool area, set away from the house in its own garden, is simply magical; the bedrooms each have handsome en suite baths; the study is a cozy retreat while the family room is made expansive with its walls of windows; and, oh, that kitchen! Add to all of this your deeded access to an ocean beach and you have an unmatched retreat ready for making memories for years to come.

Listed by Karen M. Overtoom R.E.

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 2019
* 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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