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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.

Vineyard Haven Homes for Sale with a Pool

For more information, questions, or to schedule a showing, please contact Sandpiper Realty today!

43 Edgartown Road Vineyard Haven MA

Vineyard Haven, MA43 Edgartown Road

Price$799,000

Est. Mortgage: $/month

MLS Number 36498

  • Residential
  • Square Feet 1583
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.1599

Prime location in Vineyard Haven, this restored and updated three bedroom home is ½ mile from the harbor and features a pool! New kitchen with granite countertops, hardwoods on first floor, and bonus detached studio. This fun summer getaway is close to downtown restaurants, shopping and the beach and is privately tucked away off the street. Enjoy this little oasis yourself, or rent it out for income! Can be shown 8/9, 8/16, 8/23. Tenants in place.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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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155 Skiff Avenue Vineyard Haven MA

Vineyard Haven, MA155 Skiff Avenue

Price$949,500

Est. Mortgage: $/month

MLS Number 36646

  • Residential
  • Square Feet 1579
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.33

Charming home with pool within walking distance to downtown Vineyard Haven and Lagoon. This charming cape with pool is ideal Vineyard home. The first floor features two living spaces divided by a center set of stairs. There is a formal living room with vaulted ceilings, beams and a charming stone fireplace. The other living space is an open concept lounge/TV room off the kitchen. The atrium room can be converted into a dining area. Sliding doors open to the deck and gorgeous yard with in gunite pool. The first floor master bedrooms also has sliding doors out to the patio. There is a full bathroom and laundry. Two bedrooms upstairs share a full bath. Property has had an established rental history with rates ranging from $2700 to $5700 a week. Please watch virtual tour and see attached floor plan.

Listed by Point B Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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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645 Lamberts Cove Road Vineyard Haven MA

MLS Number 36604

  • Residential
  • Square Feet 7050
  • Bedrooms 5
  • Bathroom 5
  • Half Bath 1

This commanding, 11+ acre estate offers so much to be appreciated. The spacious hilltop home has gracious and serene interiors, with outstanding water views from nearly every room of its 4 levels. With 3 living rooms and 5 bedrooms, there is room here for everyone to join in the fun, while the 7,000 square feet of living space was designed to allow for plenty of options for quiet moments - to work in the extraordinary 2nd floor office, workout in the 4th level gym, or simply while away a lazy day watching the ferries come and go or imagining yourself out there with the fishermen on Middle Ground and cheering them on to bring in a big one. The rest of the gang can swim and play in the pool, create a grand feast in either the indoor or the outdoor kitchen, head down the hill to the association beach or have a game of hide and seek in the acres of woodland and meadow. Oh, and don't forget those sunsets - or the 4th of July fireworks that can be seen fired off from Woods Hole to Hyannis! On the practical side, the property is comprised of 3 conforming lots on which other homes can be built or which can be sold separately. The undulating landscape invites the creation of outdoor "rooms", while affording absolute privacy from neighbors and traffic from Lambert's Cove Road. You are only a 10-minute drive to all of Main Street's conveniences while feeling light years away from bustling crowds. Offered fully furnished and equipped, much of the artwork, both inside and in the sculpture park, will be made available to the buyer by separate purchase.

Listed by Karen M. Overtoom R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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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124 Skiff Avenue Vineyard Haven MA

Vineyard Haven, MA124 Skiff Avenue

Price$430,000

Est. Mortgage: $/month

MLS Number 36564

  • Condominium
  • Square Feet 716
  • Bedrooms 2
  • Bathroom 1

Spacious in-town 2 bedroom condo units adjoins association swimming pool and is in great condition with numerous recent updates (roof, windows, paint). Scenic view of Vineyard Haven Harbor from the yard area. Shared storage area and community laundry. Easy access to town, ferry and beach. Great value!

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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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14 Pine Street Vineyard Haven MA

Vineyard Haven, MA14 Pine Street

Price$2,590,000

Est. Mortgage: $/month

MLS Number 36490

  • Residential
  • Village Downtown
  • Square Feet 3858
  • Bedrooms 5
  • Bathroom 3

Proudly sited on a hill in Tisbury village, this beautiful and stately home was painstakingly restored to preserve historic features while creating a fresh, modern living environment. Original heart pine floors and grand staircase, original interior shutters and antique lighting fixtures add charm while all new electrical, plumbing, wiring, HVAC, in-floor heat, Sonos sound, and Ecobee smart thermostats make it relevant for living today. At the heart of the home you will find the gorgeous eat-in kitchen which is open to a cozy sitting room with fireplace. The formal dining room and living room are located off the foyer. There is a first-floor bedroom suite, privately situated past the back entry and mud room area. The upstairs master suite features a luxurious bathroom and an adjacent office or reading space. Four bedrooms plus media room (or fifth bedroom). The third floor is wide open and ready for whatever your family needs. From there you can access the widow's walk with views of the harbor. The outdoor space is expansive and features a large stone patio with privacy pergola and three outbuildings. Six-bedroom septic system. Guest house and pool are possible. Walk to Main Street and the ferry. This property is move-in ready for the buyer who appreciates old world beauty along with the ease and comfort of modern construction.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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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40 Grove Avenue Vineyard Haven MA

Vineyard Haven, MA40 Grove Avenue

Price$2,250,000

Est. Mortgage: $/month

MLS Number 35851

  • Residential
  • Village West Chop
  • Square Feet 5000
  • Bedrooms 4
  • Bathroom 3

This wonderful combination of old and new sits in a historic spot formerly known as Holmes Hole, home to many sea captains. This is a gardener's eden with an oversized lot filled with perennials, a spectacular pool surrounded by cutting flowers, small cabana, and a charming fish pond. Enjoy water views from your large deck or take a short walk to the sandy beach at the end of the lane. Totaling 5000 sq. ft., boasting 4 bedrooms and several bathrooms, this partially renovated house with an addition was done with a discerning eye and master workmanship. The newer section includes a fabulous master suite with peeks of the water. The downstairs focuses on a magnificent yard and pool, with formal and informal areas to enjoy all seasons. The older bungalow section of the house also enjoys peeks of the water and charm of years gone by. This is a truly unique and whimsical spot in a great neighborhood near the Vineyard Haven Yacht Club, downtown Vineyard Haven, and the West Chop woods. Do not miss this rare opportunity to enjoy the best of both worlds.

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

209 Cove Road Vineyard Haven MA

Vineyard Haven, MA209 Cove Road

Price$999,000

Est. Mortgage: $/month

MLS Number 35680

  • Residential
  • Village West Chop
  • Square Feet 2283
  • Bedrooms 4
  • Bathroom 3

Tashmoo Wood Home - Bright and airy Expanded Cape is the best of all worlds. Home is light-filled and features four bedrooms and 3.5 baths which include 2 master bedroom suites and 2 first floor bedrooms. The open living and dining areas have cathedral ceilings. Well-appointed kitchen has a bay window with eating nook, granite counters and ample cabinets. Enjoy indoor/outdoor living on the spacious screened-in porch with skylights and a ceiling fan and provides a glimpse of Mink Meadows golf course. The lower level is a finished family/rec room. Additional features include central air conditioning, irrigation system, alarm system and a 1+ car garage. Laundry room. Two miles to town and close to Mink Meadows Golf Course. Tashmoo Wood Association has a beautiful pool, tennis courts, basketball court, playground and big and small boat access to a Lake Tashmoo with plenty of parking. A perfect home for your life on the Vineyard. Solid rental history.

Listed by Island Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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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1153 Main Street Vineyard Haven MA

Vineyard Haven, MA1153 Main Street

Price$10,499,000

Est. Mortgage: $/month

MLS Number 33954

  • Residential
  • Village West Chop
  • Square Feet 5345
  • Bedrooms 8
  • Bathroom 6

Located on a winding private road, this original 1896 West Chop waterfront home was completely renovated to exacting standards in 1992. With 8 bedrooms and 6 and a half bathrooms, and a classical layout with formal and informal areas in which to relax and pass the time, this home encompasses all that this desirable location provides for family gatherings and summer memories at West Chop. A stately front entrance leads to the formal living room with adjoining separate sitting room, with fireplace, that opens to the expansive water facing porch providing active views of the Vineyard Sound and additional entertaining space to while away a lazy summer afternoon. The home offers an exceptional combination of elegant charm and modern amenities including the large gourmet kitchen breakfast room, with Wolf and Sub Zero appliances, bespoke cabinetry and a butler's pantry that leads through to the formal dining room. The staircase leads to a large master suite with a full bath, office and balcony overlooking the water. Three further bedrooms and 2 additional bathrooms occupy the remainder of the second floor with 4 further bedrooms and 3 baths on the third floor. The huge walk out basement was created during the renovation, and could be finished to create living space for a wine cellar, family room or gym. The home was fully air conditioned in 2019 and there is potential to add a pool. Directly in front of the property is a beautiful private conservation trust protected beach ideal for sunning, swimming, tide rides to the dock, kayaking, fishing and of course breathtaking water views and dreamy sunsets. This is a rare opportunity to buy in the heart of West Chop. Privately located, yet close to Mink Meadows Golf, the Vineyard Haven Yacht Club and conveniently close to ferry service, hospital and town center restaurants and shops. West Chop is a unique Vineyard community where families have enjoyed the fellowship of friends and neighbors for generations. See further description under "Comments/Directions" for the benefits of being part of the West Chop community in this special North Shore setting.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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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1153 Main Street Vineyard Haven MA

Vineyard Haven, MA1153 Main Street

Price$10,499,000

Est. Mortgage: $/month

MLS Number 33535

  • Residential
  • Village West Chop
  • Square Feet 5345
  • Bedrooms 8
  • Bathroom 6

This three-story shingle-style air conditioned home on Vineyard Sound, an easy walk to the West Chop Club, epitomizes the relaxed elegance of late 19th-century seaside living. Beautifully restored and decorated, the 5,345-sf house ideally located on a peaceful private road, includes eight bedrooms, multiple formal and informal gathering areas, and wide porches with spectacular water views. A superb example of traditional coastal New England architecture with its cedar shingles and abundance of windows, gables, and gambrels, this meticulously maintained house was built in 1897 and renovated in the early 1990s, paying tribute to its historical detail while adding many amenities. A spacious gourmet kitchen, outfitted with high-end appliances, adjoins a casual dining/lounging area and connects through a butler's pantry to the formal dining room. Two living rooms, one with a large fireplace, comfortably accommodate a large gathering. The expansive master suite includes a balcony with water views, brick fireplace, spacious master bath, and adjoining sitting room and office. The .59-acre property makes the most of its dramatic setting with graceful perennial gardens, open lawns, and most importantly multiple possible sites for a pool. A private path leads to the West Chop Trust's north shore beach for lazy days in the sun, tide rides, and fishing. Just two miles from the center of Vineyard Haven, a West Chop classic similar to this home rarely comes on the market, and provides the perfect setting to create memories of your own for generations to come. This private community affords easy access to beaches, independence and activities for all members, and an appealing lifestyle away from the hustle and bustle of other parts of the island. We are happy to provide all the wonderful amenities available in the West Chop area.

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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