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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245, 223 & 221 John Cottle Road, West Tisbury, MA

MLS Number 33945

  • Residential
  • Square Feet 10915
  • Bedrooms 9
  • Bathroom 9
  • Half Bath 1

Breathtaking waterfront estate set on nearly 15 acres offering unrivaled privacy, dramatic views, sandy beach and multiple dwellings. The main residence is a 10,000sf masterpiece with eight bedrooms on three levels. Abundant windows found in nearly every room overlook the sumptuous grounds and the awe inspiring water views. Detached from the main residence is a charming yet fully equipped two story- guest cottage. Picturesque gardens and handsome stonework lead to the sanctuary like pool and spa. Set to the east is a vintage cottage with a sprawling lawn leading to the ocean and sitting high above the trees is a contemporary five bedroom residence with captivating views. One complete and very rare waterfront package on one of the most treasured shorelines. This offering includes 223 & 221 John Cottle Road, LINK ID 33024. Square footage and bedrooms/baths for those residences are not included in the noted ELA and bedroom/bath count above.

Listed by Sandpiper Realty

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Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

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%
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Federal 30-year interest rate: 4.52% last updated on Jul 19, 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

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

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Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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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The Residence Lot at South Shore Estates, West Tisbury, MA

MLS Number 33982

  • Residential
  • Square Feet 3500
  • Bedrooms 4
  • Bathroom 4
  • Half Bath 1

THE RESIDENCE LOT: This 25.8-acre (+/-) oceanfront property contains 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 house is within walking distance from the 1200' of private beach. The residence features a media room, exercise room, office, two sitting rooms, three full bathrooms, two half bathrooms (one with adjacent steam bath and a separate cedar sauna), 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. This thoughtful layout provides the owner and his or her guests with ample privacy and the opportunity for solitude, if desired. The owner of this lot may build a guest home in addition to the existing four-bedroom home. The owner shares use of the 141 acres of conservation land for hiking and trail running with the other owners of South Shore Estates. SOUTH SHORE ESTATES: Only from above can one appreciate the superlative qualities of South Shore Estates. This pristine 308-acre South Shore enclave features ten buildable lots, one with an existing four-bedroom home and another with a one-bedroom beach house, almost ½ mile of sandy shoreline, 141 acres of conservation land, and a 35-acre pond. The amount of privacy this sprawling property offers is rarely found on the island, and yet South Shore Estates is close to the airport and less than ten miles from Edgartown. Each lot can accommodate a main house and a guest house. South Shore Estates spans nearly one half-mile of shoreline on the Atlantic Ocean. Only residents and guests of South Shore Estates are permitted to use this enormous stretch of beach, therefore it remains exceptionally private. 1200' of this shoreline is shared among the owners for their personal use, and the remaining 1200' expanse is Protected Habitat Beach. Only select owners of South Shore Estates are permitted to walk across this pristine beach to access the 1200' private beach. For those seeking serenity, expansive views down the South Shore, and sublime privacy, there is no better venue than this beach. See website: https://www.thesouthshoreestates.com.

Listed by South Light Property LLC

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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$12,650,000

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

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

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Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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$7,800,000

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

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

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Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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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37 Pasture Gate Road, Vineyard Haven, MA

Price$7,000,000

Est. Mortgage: $/month

MLS Number 33630

  • Residential
  • Square Feet 7604
  • Bedrooms 5
  • Bathroom 4
  • Half Bath 2

A prestigious home designed by a meticulous owner. Built by the current residents in l988, the property has evolved over the years in updates and numerous expansion projects. When you love where you live, a property such as this is the result. The owners chose the location in the Tashmoo Association because of the tranquil pastoral setting overlooking the grazing fields, the amenities of the community which provide tennis, dock and beach and the close proximity to Vineyard Haven Village; a combined feeling of up and down Island. With 3.15 acres of land there was more than adequate room to create a spacious estate setting. As you approach the house the feeling of relaxed elegance is apparent. It is evident that the expansive home with 7,604 sf of living space will offer room for all. The surrounding landscape and natural, wooded open space creates an exceptional setting. The unusual details in the house are everywhere from the formal living room and dining room, the large well-designed kitchen, the newer addition year round sun porch, the wonderful den to retreat to, and the newest addition, a contemporary incredible living room/dining room with fireplace and custom designed ceiling, to name a few highlights. An exceptionally large pool area has room for many lounge chairs and tables for dining along with a pool house with full kitchen. Beyond the pool area and above the oversized two car garage is a fifth bedroom suite. The second floor is dedicated to the en suite master bedroom, three guest rooms and an unusual common room with high ceilings and many windows to be used as a second floor family room or elegant office. A finished third floor is there for your interpretation. The sale also includes a beach lot (32C/4 and 32D/4) just before the opening to Lake Tashmoo with beach access on the Lake and the Sound. Boating from the association dock to your private location, anchoring your boat for a picnic or digging clams for dinner puts the frosting on the cake or the Vine in Vineyard. In the event you need more space for your family compound the totally renovated, fully furnished cottage on 1.06 A at 19 Chappaquonsett (54C/ 2) is also available at $1.5M. See photos attached to this listing. This property provides all the components to establish a family estate for generations to come on this magical Island of Martha's Vineyard.

Listed by Sandpiper Realty

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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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17B East Pasture Road, Aquinnah, MA

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. Construction almost complete! 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 and produce 12kw. 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

{$office->Name}

Hancock Real Estate
PO Box 460
Chilmark MA, 02535
Office: 508-645-2544

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 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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