Vineyard Haven Homes with a Pool

Scroll down to find current homes with pools for sale in Martha's Vineyard, MA's town of Vineyard Haven. Look through a variety of listings including luxury homes, cottages, condos and many more. Register with our site to save your favorite properties, and you can get email updates when new listings match your search criteria. For more information, questions, or to schedule a showing, please contact us today!

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

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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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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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62 Weaver Court, Vineyard Haven, MA

Price$1,495,000

Est. Mortgage: $/month

MLS Number 33549

  • Residential
  • Square Feet 4557
  • Bedrooms 3
  • Bathroom 4
  • Half Bath 1

IDYLLIC ISLAND RETREAT. Privately set on 1.2-acres of beautiful landscaped grounds and gardens, this classically styled New England colonial is an idyllic retreat for gathering family and friends and creating many years of treasured Vineyard memories! Built as a dream home by an accomplished builder/owner, this meticulous home offers over 4500 square feet of living space perfectly designed for easy living and entertaining. The home has plenty of extra space to comfortably accommodate guests -- including an expansive third-floor living space with views of Vineyard Haven Harbor PLUS another private living space above the attached garage. The warm and inviting first floor living areas open out onto an expansive mahogany deck, perfect for alfresco dining and entertaining during the summer months and there is also room to install an in-ground pool (Conservation Commission approvals in-hand). Vineyard Haven Village is just a mile away -- offering convenient access to ferries, restaurants, shopping, movie theaters and more! Enjoy a brisk walk into town for your morning coffee or breakfast at Art Cliff Diner or The Black Dog. Savor quiet afternoon walks at the nearby Land Bank Ramble Trail Preserve. Stroll to the nearby public beach and boat launch on The Lagoon and launch your kayak, canoe or paddle board for an enjoyable afternoon out on the water. This beautifully crafted home embodies all the best of island living and is ideal for seasonal or year round living, a multi-generational retreat or a great vacation rental property. An exceptional home -- at an exceptional value!!

Listed by Point B Realty LLC

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$
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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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27 Hatch Road, Vineyard Haven, MA

Price$3,199,000

Est. Mortgage: $/month

MLS Number 33426

  • Residential
  • Square Feet 3797
  • Bedrooms 6
  • Bathroom 4
  • Half Bath 1

Rare opportunity to own 3 floors of spectacular water-views! Come view this 6 bedroom, 4 1/2 bath brand new construction on Hatch Road. Custom-built, energy-efficient retreat sited on a wooded and landscaped 3/4 acre lot includes a five-bedroom, three-level home and a detached one-bedroom carriage house. Beautifully styled and fully furnished, the main house features an open floor plan, three floors, and stunning views of Vineyard Haven harbor and East Chop. The main floor boasts 9-foot ceilings and crown molding, a great room with 50-inch HDTV and media room set-up, gas fireplace, a stunning chef's style kitchen with center island, granite and quartz countertops, six-burner Thermador gas range, Thermador microwave and dishwasher, a master suite with large walk-in closet, jetted spa tub, tiled shower, and twin French door access to rear bluestone patio, laundry room with frontload washer and dryer, walk-in pantry and 1/2 bathroom. The dining room exits through French doors to large screened-in porch with a cathedral ceiling, fan, and outdoor speakers. Second floor boasts second master suite with twin walk-in closets, tiled shower, and twin French door access to covered side porch with stunning views of the harbor. Second floor also features bedrooms 3 and 4 with third full bath. Third floor features a Nantucket dormer with spectacular views of East Chop and a sliding glass door that open onto a sun deck with sweeping views of East Chop and Vineyard Haven harbor. Rough-in plumbing on third floor can accommodate another bathroom or wet bar. Third floor can serve as fifth bedroom, office, art studio, or entertainment suite. Rich hardwood floors installed throughout entire house. Ceiling fans in great room, all bedrooms, and covered side porch. Relax in rocking chairs on the Nantucket styled front porch. Three-zone FHA heat and A/C, and expanded outdoor shower. Custom landscaped yard features mature trees including one of the few California Sequoia trees in the northeast. There is plenty of room on the property to add a pool with town approval. Gorgeous private brand new Carriage House over a spacious 2-car garage. Custom designed kitchen, stainless appliances with granite countertops, 1 full bath, 1 queen bedroom, hardwood floors throughout, front load washer and dryer, large living room, cable, wireless, 50-inch HDTV with surround sound, private mahogany deck, and outdoor shower.

Listed by Premier Properties

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$
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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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161 Sandpiper Lane, Vineyard Haven, MA

MLS Number 33338

  • Condominium
  • Village West Chop
  • Square Feet 1780
  • Bedrooms 2
  • Bathroom 3

A wonderful opportunity to purchase a property in Tashmoo Woods, a private community of single family homes and condominiums on more than 100 acres in Vineyard Haven. This well appointed townhouse is bright, open and spacious with large windows, a fireplace, and a cathedral ceilings. The sun-filled living room opens onto a raised deck with a peaceful view of the surrounding woods. The condominium also features a charming eat-in kitchen, separate dining area, full bathroom, and cozy bonus room (currently being used as a home office) on the main level. A master suite and guest bedroom, both with ensuite bathrooms and ample closet space make up the second floor. Adding to the living space is a finished walkout basement, currently being used as a family room and space for overflow guests. This home was built as part of Phase One of Tashmoo Woods, which means it offers additional features like charming built-in shelving and a full walk out basement. Central air, a garage, and outdoor shower are other features of the unit. The home has been well cared for and has a strong rental history. The association boasts a community pool, tennis courts, a private boat landing and dock onto Lake Tashmoo, walking trails and access to both town and association beaches. Nearby is Mink Meadows Golf Club and the port of Vineyard Haven for dining and shopping. The Property Owners Association takes care of the condo exterior, the roads, and community spaces (pool, tennis courts, beach access) so you can enjoy all the Island has to offer with less of the stress of property ownership.

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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64 West Pasture Lane, Vineyard Haven, MA

Price$1,449,000

Est. Mortgage: $/month

MLS Number 33190

  • Residential
  • Village Lambert's Cove
  • Square Feet 2905
  • Bedrooms 4
  • Bathroom 2

Pilot Hill Farm with Private Association Beach less than 1 mile from the house. Perched on a hill in the desirable neighborhood of Pilot Hill Farm is an enchanted and tranquil home that has gone through a masterful transformation since 2014. The front porch wraps its arms around you as it ushers you into the tiled foyer. At first glance, you can tell that this is no ordinary home. Take a right and enter into the open eat-in kitchen, family and dining rooms. The newly renovated gourmet kitchen with a 6-burner Thermador range will make every chef and would-be chef smile. Marble countertops, farm sink, panelized appliances, pantry/office space are just a few of the other special features in this space. Open to a casual dining area, family room and formal dining area, meals can be prepared while enjoying the company of friends and family. The abundance of windows and skylights in this home have been thoughtfully placed throughout to take full advantage of the day's light. Enjoy your morning coffee in the screened-in porch overlooking the private backyard or venture out onto the sprawling deck. Spacious living room has a wood burning fireplace and French doors that open to the deck. This home is uniquely designed with 2 second floor wings: Tucked up a private staircase is the master suite with newly updated bath with a double vanity, Jacuzzi tub and separate shower. Up the second staircase are three more bedrooms with a newly updated bath and laundry room. Spend warm days at the Pilot Hill association beach and cool evenings in the hot tub. The grounds have been brought to life with the many gardens and stone walls. You must see to appreciate that this property is truly a special "peace" of Martha's Vineyard. Please see the attached list of the many improvements this home has received since 2014 which includes a new septic. There is plenty of room to add a pool!

Listed by Island Real Estate

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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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484 Main Street, Vineyard Haven, MA

Price$1,495,000

Est. Mortgage: $/month

MLS Number 33137

  • Residential
  • Village West Chop
  • Square Feet 2755
  • Bedrooms 5
  • Bathroom 3

It is RARE to find a charming, traditional home with nearly 2 ACRES of land - AND be walking distance to all that down town Vineyard Haven has to offer - the movie theater, restaurants, shops, and the Playhouse! Located on a lovely, coveted stretch of Main St. equal distance between the village and West Chop, the discerning buyer will see that opportunity abounds at this exceptional find. Outside features park-like grounds offering tranquility and privacy. A bonus vintage structure encompassing a single garage and 405 square foot wood shop/studio is in the rear. Inside the appealing front door is a welcoming foyer and stairs to the second floor. On the right is a den (or bedroom) with shelving. On the left are double pocket doors leading into the expansive living room with wood-burning fireplace. Off the living room is a first floor bedroom and bathroom. Also off the living room is a large light-filled dining room with a lovely bank of windows overlooking the park-like grounds. The mudroom, kitchen and pantry are at the back. Upstairs has a master bedroom and bath plus two more bedrooms that share a hall bathroom. Other bonus spaces include two unfinished attics. The boiler, electrical service, insulation, sheet rock, and oak floors were updated in recent years. You could live in this house now with all its period charm, or renovate to your personal tastes. Septic is designed for five bedrooms and passed Title 5 inspection. There is enough land for a guest house and/or pool. It is a quick walk to Grove Ave. beach, just perfect for a morning dip. Also, it is near the Yacht Club where the kids can have lunch with their buddies after the morning sailing lesson. Don't miss out on this singular beauty just waiting for the buyer with vision.

Listed by Viewpoints

$
$
%
$/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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161 Sandpiper Lane, Vineyard Haven, MA

MLS Number 32420

  • Condominium
  • Village West Chop
  • Square Feet 1750
  • Bedrooms 2
  • Bathroom 3

Spacious Tashmoo Woods Condo with Full Basement! - Just over a mile from town nestled in a private area on the way to West Chop is the exclusive Tashmoo Woods, a community with a mix of townhouse style condos and single family homes. This private, end unit townhouse is simply a step above the rest with many features not found in other units. This unit it one of the premiere units on the property. The light and bright living room has soaring cathedral ceilings with a fireplace, hardwood floors and French doors that open to a large deck. Eat-in kitchen has stainless appliances and an abundance of cabinets and a pantry. A den and full bath finish the first floor. The second level features two spacious bedrooms with en suites. The master has a tiled bath with Jacuzzi tub, double vanity and shower. One of the unique features of this unit is the full, partially finished basement with large windows. There is an additional storage area and the detached garage just outside the front door. An outdoor shower too! This lovely condo is conveniently located to all of the Tashmoo Woods Association amenities include swimming pool with pool house, wifi and lounging chairs, tennis courts, playground, basketball court, private beach on the Vineyard Sound plus 15 acres of land with frontage and a small dock on Lake Tashmoo. Central air conditioning plus a full dehumidification system. Easy access to town, ferries, Mink Meadows and more. Empty and ready for immediate occupancy.

Listed by Island Real Estate

$
$
%
$/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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48 Sandpiper Lane, Vineyard Haven, MA

Price$1,299,000

Est. Mortgage: $/month

MLS Number 32353

  • Residential
  • Village Tashmoo
  • Square Feet 2260
  • Bedrooms 4
  • Bathroom 3

WEST CHOP - NEW CONSTRUCTION: Elegant and uniquely styled home in desirable Tashmoo Woods, on the last remaining lot within view of Mink Meadows Golf Course. This home has tremendous curb appeal. Front entrance via a vestibule, creating a nice transition into the home. Main living level has an Open Floor Plan, 9 foot high ceilings, striking 'two over two' oversized windows, Custom Trim Detail, Wood Burning fireplace and Wide Oak flooring throughout. Living room flows seamlessly to the dining area and kitchen. Large Custom Kitchen with Cream Cabinets (including oversized upper cabinets and numerous roll out shelves) beautiful mink colored Quartz counter tops, complementary Sea Glass backsplash and Stainless Steel appliances with a Cook's gas stove. Kitchen looks out over back yard and woodlands towards Mink Meadows and is adjacent to the garage for ease of access with groceries! Ground Floor Master Suite with Custom Trim and Wainscoting throughout, Walk in Closet, Double Vanity, Large Custom Tiled shower with Seamless Glass door. Upstairs to the Second Master Bedroom Suite, also with a Double Vanity, Quartz counters, Custom Closets, Custom Tiled floors and Shower with Seamless Glass Enclosure, Separate Water Closet and Custom Trim Detail! Two additional guest bedrooms share a bathroom with Tiled Tub and Wainscoting. Access to large storage area over garage. Second floor also has Wide Oak Flooring throughout, not a carpet in sight!! Multi zone Central Air-conditioning and forced hot air Heat. Full Basement. Front porch with Mahogany deck and Blue Stone Patio in rear yard off dining area. Mahogany clad Outdoor shower. Tashmoo Woods has numerous amenities including Association Tennis, Swimming Pool, Clubhouse, Dock and Private Beach Access. Minutes to Lake Tashmoo, Mink Meadows Golf, West Chop Club, Vineyard Haven Yacht Club, Restaurants, Shopping and Ferry. Move in ready. Empty and easy to show! Tax figure is for land only. Building is too new and has not yet been assessed.

Listed by Alisan Lohan-Conway Properties

$
$
%
$/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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