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!

40 Grove Avenue Vineyard Haven MA

Vineyard Haven, MA40 Grove Avenue

Price$2,500,000

Est. Mortgage: $/month

MLS Number 35851

  • Residential
  • Square Feet 5000
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

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

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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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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209 Cove Road Vineyard Haven MA

Vineyard Haven, MA209 Cove Road

Price$1,195,000

Est. Mortgage: $/month

MLS Number 35680

  • Residential
  • Square Feet 2283
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

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: 3.69% last updated on Nov 7, 2019
* 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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122 Cove Road Vineyard Haven MA

Vineyard Haven, MA122 Cove Road

Price$649,000

Est. Mortgage: $/month

MLS Number 35158

  • Condominium
  • Village West Chop
  • Square Feet 1800
  • Bedrooms 2
  • Bathroom 2

Elegant, sun-drenched center unit. Just over a mile from town nestled in a private area on the way to West Chop is Tashmoo Woods, a community with a mix of townhouse condos and single family homes. The light and bright living room has soaring cathedral ceilings with a wood burning fireplace, hardwood floors and doors that open to a private back deck. The dining area has a window seat flanked by built-ins. There is a spacious master bedroom with 4 piece en suite bath. Kitchen features marble counters and white cabinets. There is a second bedroom with an en suite that completes the second floor. One+ car garage also has ample storage space. An outdoor shower too! Tashmoo Wood 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. Easy access to town, ferries, Mink Meadows and more. The first floor of this unit was renovated in 2010 with cherry floors and a new kitchen. Additional photos will be added this week.

Listed by Island Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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
  • Village Tashmoo
  • Square Feet 5732
  • Bedrooms 6
  • Bathroom 6

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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$899,000

Est. Mortgage: $/month

MLS Number 35164

  • Residential
  • Village Downtown
  • Square Feet 1579
  • Bedrooms 3
  • Bathroom 2

Tucked away by The Lagoon in Vineyard Haven, this Cape with pool makes an ideal, and convenient, Island vacation home. The first floor features two living space divided by a center set of stairs. There is a formal Living Room with vaulted ceiling and beams, stone fireplace, and second floor open balcony. The other living space, is an open Lounge/TV Room and eat-in Kitchen. The lounge area has sofa and TV. The Kitchen has a large dining bar. A sliding door opens to the pool area for outdoor entertaining. Just off the lounge area is a separate Den/Office with vaulted ceiling, that also opens to the back deck and pool area. The first floor Master Bedroom also has a sliding door to the deck and pool area. Also on the first floor is a full bath with laundry area. The other two Bedrooms are upstairs and share a full bath. Outdoor living centers around the gunite pool with its surround, large deck, and nicely manicured gardens and grounds. There are lounging and dining areas. Downtown Vineyard Haven is a short bike or car ride away. Pool is not heated. Property has an established rental history. 2019 is rented 6 weeks - $30,000. Rental rates range from $2700 a week to $5700 a week.

Listed by Point B Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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 2 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.

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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

Vineyard Haven, MA103 Main Street

Price$13,500,000

Est. Mortgage: $/month

MLS Number 33742

  • Residential
  • Village West Chop
  • Square Feet 7046
  • Bedrooms 5
  • Bathroom 4

VINEYARD HAVEN HARBOR WATERFRONT WITH A POOL - A premier location on Vineyard Haven Harbor with expansive views of all the activity. Set back on 1.7A, with 146' of private beach, this property offers a spectacular pool, surrounding landscaping, and a 5 bedroom, 7,046 sf home, 2 car garage impeccably designed by premier architect, Patrick Ahearn. 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, where you will enjoy the smell of the ocean, breezes, and feeling of what summer is all about on the Vineyard. The outstanding dining room overlooks the entire harbor and is centrally located beyond the foyer. The south wing of the first floor includes the formal living room with fireplace, all season porch, and study. The second floor is devoted to the master suite and guest quarters with broad views which deliver varying angles of the Harbor. A long balcony hallway leads to the master suite on the right with an over sized 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. The north wing of the house is devoted to three guest bedrooms. A fifth bedroom studio is above the 2 car garage, with sleeping quarters, bath, living space, and kitchenette. It has a private access from the garage or accessed from the guest suite on the second floor. A stunning property with stunning views with proximity to town and the ferry.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 2019
* 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 A VisitAsk A QuestionMore Details

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