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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8 Tuthill Lane and 27 Braleys Way Edgartown MA 02539

MLS Number 36831

  • Residential
  • Mls Status Active
  • Village Downtown
  • Bedrooms 9
  • Bathroom 10

This incredibly private waterfront compound, uniquely located just minutes from historic Downtown Edgartown, is being offered for the first time in more than 30 years. This classic Martha’s Vineyard retreat offers it all: a private sandy beach, boat access, more than 10,000-sq. ft. of living space in two homes, pool, barn, and endless sunsets. This unique combination would typically only be found in remote locations up island, yet here you can feel completely out of town while being a short stroll or bike ride into Edgartown and all it has to offer. Sited on three meticulously landscaped acres overlooking Eel Pond and Edgartown Harbor, nearly every room from the five-bedroom main house and four-bedroom guest house enjoys unobstructed water views. A sophisticated yet comfortable setting, this Island compound offers unmatched privacy. The main residence features multiple living areas and a restful primary bedroom suite with sun deck, spacious bathroom and a private office with fireplace. Other features include a gourmet kitchen with sitting area, home office, study, pool room, four guest bedroom suites, and an oversized screened porch, perfect for summer entertaining. The guest house is equally inviting and offers welcoming living and dining area, a screened porch, family room, playful bunkroom, two additional guest bedrooms, oversized primary bedroom suite with private deck, and a three-car garage. The gunite pool and spa provide panoramic water views are surrounded by a bluestone patio, classic stonewalls, and lush plantings of colorful roses and hydrangeas. The expansive lawn leads to the water's edge on Eel pond where you can enjoy easy access to Edgartown Harbor and beyond from your private beach where the owners can keep a boat. This desirable private waterfrontage allows you to spend summers clamming, kayaking, paddle boarding, swimming and boating. A truly remarkable Island escape in Edgartown that epitomizes the best of Martha’s Vineyard in one of its most coveted locations.

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 02568

Vineyard Haven, MA103 Main Street

Price$13,500,000

Est. Mortgage: $/month

MLS Number 37110

  • Residential
  • Mls Status Active
  • Village West Chop
  • Bedrooms 5
  • Bathroom 5

A luxurious in-town, waterfront estate overlooking Vineyard Haven Harbor - The Vineyard has always been the place to go for rest and relaxation; it is an oasis of beauty and tranquility in a vintage seaside setting. 103 Main Street offers an exquisitely designed home nestled on 1.7 acres with expansive views of the boats coming and going and yet it is right in the Village just steps from boutiques and coffee shops, restaurants and theaters. This shingle style coastal New England home, designed by respected architect Patrick Ahearn, has 6,500 sf of living space and is warm and friendly with space to accommodate everyone. The terraced pool and abundance of casual outdoor living space is private but takes full advantage of the spectacular setting. A must see!

Listed by Sandpiper Realty

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 02575

West Tisbury, MA44 Forest Road

Price$12,800,000

Est. Mortgage: $/month

MLS Number 34815

  • Residential
  • Mls Status Active
  • Village Lambert's Cove
  • Bedrooms 6
  • Bathroom 4

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: 3.04% last updated on Apr 15, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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9 Briggs Road Edgartown MA 02539

Edgartown, MA9 Briggs Road

Price$12,500,000

Est. Mortgage: $/month

MLS Number 37475

  • Residential
  • Mls Status Active
  • Village South Shore
  • Bedrooms 6
  • Bathroom 6.5

This amazing, newly built home lies on nearly 5-acres of beautifully landscaped grounds with 385 ft of private pond frontage. The attention to detail and elegant style of the house is abundant. The main residence features a spacious and open floor plan with entry hall, large living room with fireplace, gourmet kitchen and eat-in area, all of which have tall ceilings and oversized doors and windows facing the pool, gardens and waterviews. There is a large 1st floor master bedroom suite and 4 second floor bedrooms with private baths. The 2-car carriage house compliments the main house architecture and offers a large 2nd floor space that could be utilized for any number of uses including additional bedrooms. The in-ground pool, patios, retaining walls and gardens are meticulously designed and 2 different paths offer access to the ponds edge for boating and beach access. Too many features to mention in a peaceful and private setting yet located less than 10 minutes to downtown Edgartown.

Listed by Landvest MV

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 West Tisbury MA 02575

West Tisbury, MA37

Price$10,500,000

Est. Mortgage: $/month

MLS Number 34587

  • Residential
  • Mls Status Active
  • Village Central
  • Bedrooms 9
  • Bathroom 8

"Stillpoint", this stunning compound is reintroduced with a fresh perspective and price. Stillpoint is the feeling when you enter this tranquil estate in West Tisbury on beautiful Martha's Vineyard. Classical New England elegance is combined with European influences that immediately transport one to Tuscany or the Cotswold's whilst encompassing quintessential American style. This 50 acre country estate is comprised of three dwellings; the elegant main Federal style home dates from 1795 and was brought to the Vineyard in 1987 from it's original site in the Berkshires. Complete with swimming pool and pool house, gorgeous landscaping and views over Priester Pond. Classical proportions provide 4 comfortable en suite bedrooms, ample living and entertaining rooms, and a fabulous gourmet kitchen with double doors to an amazing brick floor conservatory/sun room with bar area and another set of French doors to the pool terrace and gardens. The home is surrounded by beautiful landscaping including an Italian inspired terrace complete with fountain and meadow views. At the opposite end of the pool is a studio/ pool house currently used as an art studio. Across the driveway is a contemporary barn, built by South Mountain Company in 2012. The 2700 square foot barn is currently used as an event space, workshop and art space, but the building could easily convert to additional living space. A bank of solar roof panels provide power for this structure plus the main house. There's a outdoor fire pit and established vegetable garden. Across the lawn from the main home is an equally immaculate second home, which has been restored with the most impeccable attention to detail and taste. The Luce Athearn House, dates to 1714 and has 5 bedrooms and 4 bathrooms. see full description under "2nd dwelling". The whole property has so many unique and interesting places to explore and just be at one with nature and the surrounding . 50 acres of meadow, woodland and frontage on two ponds.....and if that isn't enough, the property abuts Polly Hill arboretum and Land bank conservation land. A Stillpoint one feels like one could be anywhere in the world yet its just a 5 minute drive to West Tisbury center. A 10 minute drive to the airport or to the Vineyard Haven ferry. When it's time to finally leave one is left with a feeling of gratitude at being able to experience this jewel of a property. The peace and tranquility will draw you back.

Listed by Tea Lane Associates

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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54 Morse Street Edgartown MA 02539

Edgartown, MA54 Morse Street

Price$8,950,000

Est. Mortgage: $/month

MLS Number 37851

  • Residential
  • Mls Status Active
  • Village Downtown
  • Bedrooms 7
  • Bathroom 6.5

As you enter through the breezeway get ready to be captivated by this Edgartown Village Oasis! “Less is more“. This property packs a punch from within! As you proceed through the gorgeous mudroom into the living room/parlor. Step down into his/her private office or proceed ahead into the formal living/dining room. Notice the faux marble walls and the exquisite random width floor planks of reclaimed hardwood from yesteryear! Follow them to a guest suite and bath and full laundry! Walking past the elegant powder room step into a timeless gourmet kitchen with all the tools one needs including a cozy bay window seat which is perfect for starting the day sipping coffee and reading the paper. Proceed to the open family room with gorgeous built-ins and a stunning stone fireplace. A perfect hang out for the whole family! Everything overlooks this estate setting with a private pool, cabana,outdoor kitchen, and fire pit. Perfect for summer soirees! Mature landscaping and a beautiful reclaimed brick wall create privacy the likes you have never seen! Off to the corner of the lot is a private two bedroom cathedral bungalow with everything you would expect! The main house second-floor master is right out of a magazine and there are also two other large bedrooms en-suite. There is an additional family room/gym in the lower level and one of the most eclectic wine cellars you will ever see! This completes the main house. There is also an oversized two car garage with an fabulous loft style apartment Which is perfect for older kids or your au pair/nanny! Bring your clothes ,furniture and family for This is a very special home!

Listed by Jane Brown Assoc.

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 02575

West Tisbury, MA52 Middle Road

Price$8,750,000

Est. Mortgage: $/month

MLS Number 35777

  • Residential
  • Mls Status Active
  • Village Central
  • Bedrooms 7
  • Bathroom 7

The Kenney compound consists of the authentic updated 1719 Tilton House, wonderful estate cottage and stunning pool and a remarkable cathedral like barn and outdoor stone encircled paddock. The 1719 Tilton House is the perfect blend of authentic early American design and decor with 21st Century comfort and convenience. The Tilton House was lovingly restored and renovated in 2000 to its original splendor and doubled in size adding a modern kitchen, spacious sun room, two bedrooms, two full baths, a 4th fireplace and many other features. The 2006 superbly designed and decorated large cottage and exquisite pool area with incomparable Lew French stone sculptures compliments the 18th Century Tilton House. In addition, there is a large cathedral like barn often called the most stunning barn in the northeast. This combination of two homes, pool and barn on 25 private pastoral acres make this paradise one of the finest Vineyard estates. Words do not do justice to this property which has been a desirable venue for important charitable and cultural events over the last decade. QUANSOO BEACH LOT available separately !

Listed by Tea Lane Associates

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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56 North Neck Road Edgartown MA 02539

Edgartown, MA56 North Neck Road

Price$8,400,000

Est. Mortgage: $/month

MLS Number 37136

  • Residential
  • Mls Status Active
  • Village Chappy
  • Bedrooms 7
  • Bathroom 6.5

PRIVACY & LUXURY ON MARTHA'S VINEYARD - this is a rare chance to own a sprawling 18.4-acre estate on Chappaquiddick as it has been in the same family for over 40 years. Surrounded by acres of conservation land, and next to the Royal & Ancient Chappaquiddick Links, this multi-generational estate offers an exquisite Main house (8335sqft), a second residence (1319sqft), Gunite pool with outdoor shower, tennis court, and 4 bay garage with finished space (708sqft) over the garage. The main house, remodeled in 2005, offers striking panoramic views of Cape Pogue Sound, gourmet kitchen with upgraded top-of-the-line stainless steel appliances including a wine fridge, 2 full Viking ovens, 2 Sub Zero fridges and granite countertops; multiple decks for outdoor living, a wet bar in the lower level adjacent to the pool & patio and an office perfect for working from home. The second residence has 3 bedrooms, a full kitchen, 2 full bathroom, an outdoor shower, multi-level deck and a screened-in porch. The Bunk House has 1 bedroom, kitchenette, living area & a full bathroom. This estate offers multiple land plots allowing for potential expansion opportunities. This property comes with deeded Beach Access

Listed by Martha's Vineyard Seacoast Properties

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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11 Motick Trail Edgartown MA 02539

Edgartown, MA11 Motick Trail

Price$8,295,000

Est. Mortgage: $/month

MLS Number 37962

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 8
  • Acreage 1.5

Visionary owners joined forces with acclaimed interior designer John Stefanon to build this one-of-a-kind Martha’s Vineyard estate. Situated on a private 1.5 acres, this era-defining estate exudes quality from every angle, and is less than two miles to South Beach and moments to downtown Edgartown. Every facet is perfectly crafted and is a culmination of the rarest, most unique materials with top-of-the-line appliances and amenities. Highlights include three laundry rooms, three outdoor showers, gym, yoga studio, outdoor kitchen + fire pit, 18 X 50 gunite pool, in-ground spa, an oversized garage with room for three cars, seven full custom bathrooms + 2 half bathrooms, a detached pool house, and multiple work-from-home office spaces. Imbued with style & sophistication, you will be able to enjoy indoor/outdoor living, amazing sunsets, and state-of-the-art technology. Live the island life you've always dreamed of in the most sought-after Katama location. Additional 1.53 Acre buildable lot is available separately.

Listed by Keller Williams Realty

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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47 and 31 Hatch Road Vineyard Haven MA 02568

Vineyard Haven, MA47 and 31 Hatch Road

Price$7,950,000

Est. Mortgage: $/month

MLS Number 37396

  • Residential
  • Mls Status Active
  • Village West Chop
  • Bedrooms 7
  • Bathroom 6

Elegant and refined, this exceptional estate property is sited on 1.3 acres. Located in the coveted Hatch Road neighborhood, this 2 home property boasts incredible architectural detail with all the modern amenities. As you enter the property via a winding gravel drive past an expansive lawn, you come to a setting not found so close to downtown Vineyard Haven. The main house dates back to 1900 and has been meticulously renovated and features a gourmet kitchen open to a dining room with french doors looking out to a rose garden, a spacious first floor master bedroom suite, dramatic great room with 20 foot ceilings with wood detail, and an inviting screened-in porch leading out to a private brick patio. The home features 4 additional guest bedrooms on the second floor. The guest house was designed in 2008 and built by a prominent Martha’s Vineyard builder. The wood detail includes aged lumber and the walls are warmly lined with recycled barnwood. Stunning museum quality terrazzo flooring inlaid with wood beams and terrazzo countertops are featured in the spacious great room, gourmet kitchen and dining room. Other guest house amenities include two bedrooms with en suite baths each with stunning wide plank flooring, and a spacious loft perfect for a home office. A home gym/pool house, outdoor kitchen, 2 car-garage and pool complete this rare offering.

Listed by Wallace & Co. Sotheby's

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$
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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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25 Pierce Lane Edgartown MA 02539

Edgartown, MA25 Pierce Lane

Price$7,950,000

Est. Mortgage: $/month

MLS Number 38037

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 6
  • Acreage 0.23

THE BEST OF BOTH WORLDS - Edgartown village with privacy. This compound is located on Pierce Lane, a quiet side street just steps from the hustle and bustle of the village. The quarter acre property has been perfectly laid out, with the house and garage enveloping the outdoor living area and pool, providing a secluded sanctuary. The property was subdivided from the original Dr. Pierce estate and the house was built in 2015, designed by architect Stephen Pogue. Views from the property are of Sheriff's Meadow Pond with Eel Pond and Nantucket Sound in the distance. A gate from the backyard leads to a trail that meanders around the pond and features many unique species of plants and animals. From the dining room, step out to the screened porch, which opens to the bluestone patio where you'll find outdoor living at its best. There is a large fireplace and seating area, as well as a dining table. The pool features a hot tub and ample bluestone surround for those days that call for lounging.

Listed by Wallace & Co. Sotheby's

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$
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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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0 Slough Cove Road Edgartown MA 02539

Edgartown, MA0 Slough Cove Road

Price$7,495,000

Est. Mortgage: $/month

MLS Number 38041

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 6
  • Acreage 5.2

PRE-CONSTRUCTION: ULTRA LUXE 5-ACRE ESTATE IN KATAMA. Plans are underway for the construction of this luxurious, architect-designed estate, near South Beach in Katama. Located on 5.2 private acres and sited amid a natural landscape of meadows, eastern cedar, scrub and post oaks the south-facing property enjoys beautiful afternoons and brilliant sunsets with the sounds of the ocean nearby. Exposed beams and soaring high ceilings in the main living spaces offer the grandness of an extraordinary luxury home while providing an air of casual barefoot elegance. This stunning home will feature top-notch architectural details and craftsmanship throughout (specifications available upon request). The floor plan was perfectly designed to maximize indoor-outdoor living and entertaining around the resort-like backyard with large screened porch, pergolas, wood-burning fireplace, bluestone terrace and charcoal gunite pool surrounded by lounge decks. This unique property offers the opportunity to create your own signature island retreat -- perfectly blending farm, field and seaside living and creating an idyllic home to gather family and friends for many years to come. The expansive multi-acre parcel will allow for a tennis court, extensive gardens, a horse barn or other possibilities. Get in early and enjoy the opportunity to customize colors and finishes. This property is slated for completion by Summer, 2022!

Listed by Point B Realty LLC

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$
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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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"Based on information submitted to MA_LINKMV as of April 19, 2021 . All data is obtained from various sources and has not been, and will not be, verified by broker or MA_LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing."