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

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: 3.73% last updated on Sep 19, 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

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: 3.73% last updated on Sep 19, 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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147 Fairfield Avenue Vineyard Haven MA

MLS Number 35599

  • Residential
  • Square Feet 1092
  • Bedrooms 3
  • Bathroom 1
  • Acreage 0.2193

This in town Vineyard Haven home is cute as a button. It's been well loved over the years and is shown by the new Harvey windows and the newer Weil Mclain Oil burner. This is a beautiful ranch style home with 3 bedrooms and 1 bath, and a bright spacious floor plan. The Oak hardwood floors add charm that you will not find in newer homes, and you'll love the delightfully updated kitchen. Use your imagination on the breezeway, a blank canvas just off the kitchen and leading to the oversized (23X16) garage. Large dry full basement with owners storage and large fenced yard ready for summer games. Walk to town, shopping and the beach. EZ to Show! Septic is two cesspools tied in secession has passed title V inspection as of 7/19, one of the two cesspools in located on neighboring lot via a easement.

Listed by Laer Realty Partners

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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33 Woodlawn Avenue Vineyard Haven MA

Price$1,195,000

Est. Mortgage: $/month

MLS Number 34434

  • Residential
  • Square Feet 2241
  • Bedrooms 5
  • Bathroom 3
  • Acreage 0.64

This CASUALLY ELEGANT CLASSIC HOME sits on a beautifully established lot, close to town yet incredibly private. Sitting on the generous 2/3 acre is the thoughtfully renovated home, a large shed, a pool and pool house! The interior features antique pine floors, renovated bathrooms, a spacious living room for television, a second living room with a wood-burning fireplace for conversation, a formal dining room, and a huge, cheerful, eat-in kitchen with updated cabinets, butcher block counters, and Bosch and Jenn-Air stainless steel appliances. There is ample space for everyone to spread out - 5 bedrooms and 3 bathrooms total, including a first floor master with private bathroom and deck, and a second bedroom on the first floor which is just by the second full bathroom with laundry. Upstairs are 3 more bedrooms with a large full bathroom to share. The grounds are lush with established rhododendrons, beech trees, Japanse maple, a flower garden, and a charming arbor draped in a privet. After the beach, take a dip in the 32' x 18' HEATED SWIMMING POOL, complete with a new pump, new heater, new liner, and new red cedar fence! A new roof, a large deck just perfect for outdoor meals, completes the package. A great price for this rare find in down town Vineyard Haven! Solid rental history. Some furnishings available for sale.

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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

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: 3.73% last updated on Sep 19, 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: 3.73% last updated on Sep 19, 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

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: 3.73% last updated on Sep 19, 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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222 Sandpiper Lane Vineyard Haven MA

MLS Number 34801

  • Condominium
  • Village Tashmoo
  • Square Feet 1737
  • Bedrooms 2
  • Bathroom 3

Top-of-the-line Tashmoo Woods townhouse with access to all the association amenities. This updated year-round condo is in meticulous condition. The vaulted cathedral ceilings in the Great Room allow for natural light to pour in through the oversized picture windows. The eat-in kitchen was renovated with all stainless steel appliances, soapstone countertops, and travertine tile floor. There is plenty of outdoor deck space for entertaining and because this is an end unit, privacy is assured as there are no neighbors in sight. Tashmoo Woods offers year-round living at its best. Tashmoo Woods sits on 100 acres and is surrounded by several miles of walking trails, 4 tennis courts, association swimming pool, 15 acres of association beach on the Vineyard Sound, and a small boat landing located on Lake Tashmoo. Tranquil and private, this community is nevertheless just a short distance to the vibrant village of Vineyard Haven with its restaurants, movie theater, and shopping. Please contact broker for direction to summer exterior images.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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

Price$11,750,000

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: 3.73% last updated on Sep 19, 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

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: 3.73% last updated on Sep 19, 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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48 Sandpiper Lane Vineyard Haven MA

Price$1,259,000

Est. Mortgage: $/month

MLS Number 32353

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

WEST CHOP - 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!

Listed by Alisan Lohan-Conway Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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