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: 4.65% last updated on Sep 20, 2018
* 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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79 Turkeyland Cove Road, Edgartown, MA

Price$16,250,000

Est. Mortgage: $/month

MLS Number 33803

  • Residential
  • Square Feet 6892
  • Bedrooms 7
  • Bathroom 8
  • Half Bath 1

This stunning custom home sits on 29 +/- private acres directly on the Edgartown Great Pond. Custom-designed by Bradenburger Taylor Lombardo Architects from San Francisco, and built by reputable Island builder, John Early, this unique & lavish home is in a league by itself. The long and winding driveway, sprawling lawn and incredible water views make for the perfect family compound setting for generations to come. The nearly 7,000 sq ft main residence is finished with the finest details and is designed with 7 bedrooms, and 8.5 baths, multiple seating and entertaining spaces, a modern Chef's kitchen, and a formal circular dining room surrounded by a wall of windows overlooking the grounds. The spacious and dramatic living room space boasts vaulted ceilings with exposed steel beams and a focal point stone fireplace. There are two guest wings and an impressive master suite with fireplace, private sun deck and spectacular water views. Your summer days can be spent poolside in a garden-like setting with the sounds of the waves lapping in the distance, or exploring the expansive Great Pond and outer barrier beach for a full day on the water. A property of this stature needs to be seen to be experienced.

Listed by Landvest MV

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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$14,500,000

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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

A matchless property on a matchless Island. A premier location on Vineyard Haven Harbor with expansive views of all the activity, a large 1.7A parcel of land which provides unique privacy, a dramatically designed pool and surrounding landscaping, and a 5 bedroom, 7,046 sf home, 2 car garage impeccably designed by premier architect, Patrick Ahearn. The spaces are designed for casual living or an elegant cocktail party. 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. The many windows gets you closer to the smell of the ocean, breezes and feeling of what summer is all about; beaching, boating, watching the ferry in action, good food and good company. Leaving the casual side of the home and meandering beyond the dining room, the south wing of the first floor includes the formal living room with fireplace, all season porch and study. The different textures in each room, from the paneled study, to the softly toned living room and porch adds an element of contrast. The second floor is devoted to the master suite and guest quarters with broad views which deliver varying angles of the Harbor. A long balconied hallway, a gallery for intriguing art, leads to the master suite on the right with an oversized 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. A highly technical powered hatch opens that space for the “Mary Poppins” view. The north wing of the house is devoted to three guest bedrooms. A fifth bedroom studio is privately located above the 2 car garage. It includes sleeping quarters, bath, living space and kitchenette. It has private access from the garage or can be accessed from the guest suite on the second floor. Located on Main Street, the size of the parcel of land allowed the house to be located behind a well- planted front yard which screens all the activity and still provides a tremendous amount of room on the water side for a patio with built in grill, pool with gracious surround and a broad lawn that rolls directly to the water. The written word and videos are powerful tools however in this instance; this is a property that must be visited.

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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 34075

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

This unique MV retreat is one of the Island's finest private compounds, on 22 acres of landscaped grounds, with an extraordinary home designed by Robert A.M. Stern Architects. Every room is appointed with the highest level of craftsmanship. There are 2 curving driveways, one that passes between 2 private ponds, and leads to the residence of over 11,000 sq. ft., with exquisite living areas, sweeping decks and porches. There are 7 bedrooms 7.5 baths. Visitors arrive in the 2-story entrance foyer with a sweeping curved staircase to the 2nd floor. Ahead are a library with fireplace, a private office with fireplace, and entrances to the great room. The expansive great room invites the outdoors with a 20-ft cathedral ceiling, a fireplace up to the ceiling, and 10-foot French doors that lead to a wraparound deck. The octagonal dining room with fireplace has walls of windows overlooking the manicured back lawn. The large gourmet kitchen is exquisitely outfitted. Off to one side is a cozy breakfast nook with built-in seating. A pantry, mudroom, office, half-bathroom, and 2-car heated garage are beyond. The graciously staircase from the foyer leads to a 2nd floor reserved for the master suite, which includes the master bedroom and French doors leading to 2 decks, as well as his-and-her walk-in closets/baths. There are 3 more bedrooms, each with full en-suite bathrooms, in the East wing, and 3 more at the West end of the house. The finished lower lever includes a sitting room, half bath, a children's playroom, a wine cellar, ample storage space, and laundry room. Off the back terrace is a 20X60 ft pool and separate Jacuzzi. The pool house features a screened porch and a gas fireplace. Inside are a full gym, sauna, massage room, and full bath. The lawn area features flower gardens, and further back, an organic vegetable garden, adjoining blueberry patch, and flower-cutting garden. The compound offers extraordinary privacy, bounded in back by 150 acres of conservation land. Yet the property is within a 10-minute drive to downtown Edgartown, the airport, and a noted golf club. The Boldwater Association provides tennis courts, private access to Edgartown Great Pond for small boating, and a private South Shore beach.

Listed by Landvest MV

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$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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96 Beach Road, Edgartown, MA

Price$11,950,000

Est. Mortgage: $/month

MLS Number 33506

  • Residential
  • Square Feet 10804
  • Bedrooms 6
  • Bathroom 6
  • Half Bath 2

This dramatic compound is set amidst 150 acres of conservation land. Completed in 2010, and offering over 10,000 square feet of living space, this five-bedroom / seven-bath custom home affords every amenity with exceptional finishes. Some highlights of this remarkable home include a large chef's kitchen and family room with stone fireplace, a formal dining room and a cathedral ceiling great room with French doors opening onto an expansive bluestone patio. A finished lower level offers a gym with sauna, a billiards room and bar with fireplace, a media room and additional living space. Stunning views from every room in the home overlook Sengekontacket Pond and beyond to Nantucket Sound. The property also offers a three-car garage with one-bedroom carriage house above, an outdoor kitchen, screened porch with fireplace and a luxurious infinity edge pool, spa and pool house - all situated on more than 150 feet water frontage with mooring.

Listed by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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81 Squibnocket Farm Road, Chilmark, MA

Price$11,600,000

Est. Mortgage: $/month

MLS Number 32757

  • Residential
  • Square Feet 4852
  • Bedrooms 4
  • Bathroom 4
  • Acreage 5.9

Home, water and community are the highlights of this extraordinary property. Award winning architect Bernard Wharton & Allan Shope designed a breathtaking 4 bedroom 4 bath home. Each room enjoys marvelous ocean and meadow views and is complimented by exquisite floor to ceiling design details which make it the most interesting home on the Vineyard. The multi year collaboration of architect, interior designer, builder and owners ceated a home beyond stunning -- this collective genius created a home which is exciting, charming and livable. Like a great artistic masterpiece, it gets better over time. The owners have felt this way every day for 20 years. This exquisite home on 6 private acres embraces the natural wonder of the endless Chilmark, West Tisbury and Edgarown shoreline with the Edgartown Water Tower in clear view 14 miles away. The home and coastline splendor is further enhanced by the private 450+ acre Squibnocket community with 1.5 miles of pond front, 2 miles of ocean front, 300+ acres of conservation and shared with only 12 other homes. 123 of these conservation acres abut this property on one side and 17 conservation acres abut on another side. This paradise is considered the finest waterfront community on the east coast. (see Virtual Tour)

Listed by Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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: 4.65% last updated on Sep 20, 2018
* 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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32 Boldwater Road, Edgartown, MA

Price$8,450,000

Est. Mortgage: $/month

MLS Number 33674

  • Residential
  • Square Feet 4519
  • Bedrooms 5
  • Bathroom 4
  • Half Bath 1

This amazing property is one of the premier ocean facing properties in the exclusive Boldwater area of Edgartown. The well-designed and meticulously constructed residence offers open living areas, countless unique features and an abundance of windows and doors facing the water and the beautiful landscaped grounds. The main residence offers 4-bedrooms and 3.5-baths as well as detached guest quarters with private bath above the 2-car garage. In addition, the property has a large swimming pool, pool house, expansive yard and open views to the barrier beach and Atlantic Ocean. The 20.8-acre lot offers expansive fields with stonewalls, a private pond and several trails that lead to the sandy shore offering private boating access. There is an additional adjoining 14.4-acre building lot available separately if desired. Included in the Boldwater Association are the usage of tennis courts and a private beach.

Listed by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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

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: 4.65% last updated on Sep 20, 2018
* 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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19 Pierce Lane, Edgartown, MA

Price$7,500,000

Est. Mortgage: $/month

MLS Number 32920

  • Residential
  • Square Feet 5900
  • Bedrooms 4
  • Bathroom 6
  • Half Bath 1

Elegant and stately custom built home in the heart of Edgartown Village. The home exudes an Old World charm along with all of the amenities required by today's discerning buyers. Extensive detail work throughout, including a whimsical "boat bar" in the basement entertainment area. The main level has ample room for entertaining, with French doors leading from the living room to a covered deck with electric screens for summer comfort. The chef's kitchen features double Sub Zero refrigerators, two Miele dishwashers and an eight burner Viking Stove with griddle and double ovens. The home boasts 4 indoor fireplaces, 4 bedrooms with ensuites, multiple sitting areas, and balconies looking out to the large backyard and pool area, past Sheriff's Meadow to the Vineyard sound.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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