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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12 Guernsey Lane Edgartown MA

Edgartown, MA12 Guernsey Lane

Price$16,500,000

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: 3.65% last updated on Jan 16, 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: 3.65% last updated on Jan 16, 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$11,750,000

Est. Mortgage: $/month

MLS Number 35777

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

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: 3.65% last updated on Jan 16, 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: 3.65% last updated on Jan 16, 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.

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$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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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22 Peases Point Way South Edgartown MA

Edgartown, MA22 Peases Point Way South

Price$7,500,000

Est. Mortgage: $/month

MLS Number 35675

  • Residential
  • Square Feet 9058
  • Bedrooms 5
  • Bathroom 6
  • Half Bath 3

Custom built by and for high end Island builder so endless details abound! The 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!

Listed by Landvest MV

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$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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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19 Pierce Lane Edgartown MA

Edgartown, MA19 Pierce Lane

Price$5,925,000

Est. Mortgage: $/month

MLS Number 35295

  • Residential
  • Square Feet 7516
  • Bedrooms 5
  • Bathroom 6
  • Half Bath 1

Located on charming and quiet Pierce Lane yet only blocks from the activities of downtown Edgartown, lies this grand and distinctively styled 5-bedroom residence. The 8,500 square feet of well appointed living space features a 2-story entrance foyer with grand staircase, large living room with fireplace, a gourmet kitchen with eat-in area, dining room and TV room/den with fireplace. The above-mentioned room all have French doors leading to covered porches, one with fireplace and one with built-in exterior grill. There is a ground floor bedroom and four 2nd floor bedrooms, all with private baths. The luxurious master suite has a fireplace as well as a private deck with exterior fireplace. The lower level offers a boat themed billiard/game room with bar, theatre room and large exercise room with sauna, steam shower and full bath. This level also offers interior entrance to a finished 2-car garage. The residence is in excellent condition and lies behind mature tall privets on the street side, while offering a large rear private yard with swimming pool, Jacuzzi and water view of Vineyard Sound. One must see this property to appreciate all that it offers.

Listed by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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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7 Clay Pit Lane Aquinnah MA

Aquinnah, MA7 Clay Pit Lane

Price$5,800,000

Est. Mortgage: $/month

MLS Number 35397

  • Residential
  • Square Feet 5000
  • Bedrooms 5
  • Bathroom 4
  • Half Bath 1

Stunning waterfront home with panoramic waterviews. The home was designed by Hutker Associates, built by Andrew Flake, and landscaped by Michael Van Valkenburgh - three of the most renowned names in Martha's Vineyard home creation. Little wonder it was featured on the cover of Beautiful Home magazine and has been included in several other home design magazines and books. The 5000 sq ft house with 5 bedrooms and swimming pool is a finished product and is being sold turnkey minus artwork and some personal pieces of furniture. The living spaces are supremely elegant and take full advantage of the spectacular water views from almost every room - in front of you Menemsha Pond and Red Beach, and to the north, Vineyard Sound. The landscape and gardens are a masterpiece. A walkway and boardwalk leads down to a private beach on Menemsha Pond where a mooring is being conveyed along with a classic 12 1/2' Herreshoff sailboat.

Listed by Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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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515 State Road Aquinnah MA

Aquinnah, MA515 State Road

Price$5,000,000

Est. Mortgage: $/month

MLS Number 35089

  • Residential
  • Square Feet 4000
  • Bedrooms 4
  • Bathroom 4
  • Half Bath 1

A top-to-bottom 2018 renovation by one of New York's hottest design teams and a top local builder resulted in this "beach chic" waterview home in Aquinnah with a stunning pool area. It is being sold turnkey with gorgeous furniture and fixtures. The list of details is too numerous to enumerate, and the house has to be experienced to be truly appreciated. The images provide an inkling of the quality of the renovation and design choices (see "photo gallery"). A complete list of design specifications is available from the listing broker. Enjoy water views of Quitsa Pond, Menemsha Pond, and the Atlantic Ocean from the main level of the house, and even more breathtaking views from the roof deck. In addition to the completely renovated interior and one of the most divine pool areas on Martha's Vineyard, there is extravagant landscaping and stonework to be enjoyed. Note: Assessment does not reflect multimillion dollar renovation 2017-2018.

Listed by Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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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7 Scrub Oak Drive Edgartown MA

Edgartown, MA7 Scrub Oak Drive

Price$4,990,000

Est. Mortgage: $/month

MLS Number 35554

  • Residential
  • Square Feet 5068
  • Bedrooms 5
  • Bathroom 5
  • Half Bath 2

Welcome to Scrub Oak: a stunning water view compound in Katama with a luxurious pool and hot-tub. The home sits less than 1,500 feet away from South Beach. Completely renovated and expanded by a top designer, the home comfortably sleeps 16 individuals. Large wraparound mahogany decks bring the indoors out, and allows one to appreciate the incredible views. Highlights include 3 master suites, a wine cellar room, a volley ball court, rolling lawns, two outdoor showers, an exterior stone fireplace, custom masonry, and a 1,040 square foot pool. A large detached garage and guesthouse allows friends, family, and renters to enjoy a relaxed vacation with utter privacy. Enjoy the home or take advantage of the amazing rental history. Rental history on request. Capable of $275k+ for the 2020 season. Furnishings are negotiable. Come enjoy this resort like compound.

Listed by Keller Williams Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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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16 Witchwood Lane Edgartown MA

Edgartown, MA16 Witchwood Lane

Price$4,425,000

Est. Mortgage: $/month

MLS Number 36125

  • Residential
  • Square Feet 4724
  • Bedrooms 5
  • Bathroom 4
  • Half Bath 2

Katama with deepwater dock slip - Five bedroom Katama house with swimming pool and a slip on a deepwater dock. This property in the distinguished Witchwood neighborhood is nestled on 3.5 acres and is set back from the road for ultimate privacy. The large stately home awaits your updates or can be lived in its current well-maintained condition. There are multiple living spaces both formal and casual. On the first level there is a large master bedroom en suite; a large living room with double-sided wood-burning fieldstone fireplace; a formal dining room; and a casual dining area with open kitchen. The second level has 2 bedroom en suites along with 2 more bedrooms that share a full bath. To complete this offering there is an attached 3-car garage, gunite pool, and a large deck for outdoor dining and relaxation amidst the mature plantings. A guest house is permitted. Enjoy the amenities of the Witchwood Association which include the use of 2 tennis courts and an assigned slip on the deep-water pier that accommodates boats up to 35'.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 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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