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!

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 IN-TOWN CLASSIC has been brought to life (and up to date) by the current owners. The interior features antique pine floors, renovated bathrooms, a spacious living room for television, a second living room with a wood-burning fireplace for reading and conversation, a formal dining room, and a roomy, 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, a flower garden, and a charming arbor draped in a privet. Plenty of room for all to relax around the incredible 32' x 18' HEATED SWIMMING POOL, complete with a new pump, new heater, new liner, and new red cedar fence! A pool house, storage shed, new roof, and 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

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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

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$
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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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: 3.75% last updated on Jul 11, 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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161 Sandpiper Lane Vineyard Haven MA

MLS Number 35215

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

Bright and Airy Tashmoo Woods Condo! End unit with a basement! 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. This private, end unit townhouse is simply a step above the rest with many features not found in many of the other units. The light and bright living room has soaring cathedral ceilings with a wood burning fireplace, hardwood floors and French doors that open to a large deck. Large eat-in kitchen has 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, walk-out basement. One+ car garage also has ample storage space. 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. New carpet and fresh paint make this unit ready for immediate occupancy.

Listed by Island Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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$959,000

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 heatedProperty has an established rental history. 2019 is rented 5 weeks $28,500. Rental rates range from $2700 a week to $5700 a week.

Listed by Point B Realty LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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: 3.75% last updated on Jul 11, 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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188 Sandpiper Lane Vineyard Haven MA

MLS Number 34523

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

The best kept secret on the island, Tashmoo Woods offers year-round living in a community of 100 acres and is surrounded by miles of walking trails, 15 acres of association beach on the Vineyard Sound, 4 tennis courts and association swimming pool. This tastefully appointed townhouse has had numerous upgrades over the years. A new gas fireplace is the center piece of the comfortable living area with cathedral ceilings and wonderful light coming from all new Andersen windows. The dining area has newly built in display cabinets. The remodeled eat-in kitchen is finished with granite counter tops and stainless-steel appliances. All three bathrooms have been redone, with the master bath featuring a double sink marble counter top and decorative tile. A new heating system has been installed, with an automatic system for heat control and monitoring while away. There is a partially finished walk out basement that would make a wonderful media room or exercise space. Furnishings are available for purchase separately.

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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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37 Pasture Gate Road Vineyard Haven MA

Price$5,250,000

Est. Mortgage: $/month

MLS Number 33630

  • Residential
  • Village Tashmoo
  • Square Feet 7604
  • Bedrooms 5
  • Bathroom 4

A prestigious home designed by a meticulous owner. 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 provides tennis, a dock, beach and the proximity to Vineyard Haven Village. 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 space create an exceptional setting. The details in the house abound from the formal living room and dining room, the large well-designed kitchen, the newer addition year round sun porch, the beautiful 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 extensive pool area has room for many lounge chairs and tables for dining along with a pool house. A fifth bedroom suite is above the oversized 2 car garage. The second floor is dedicated to the en suite master bedroom, three guest rooms, and a superior bonus room with high ceilings and large windows. 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. If you need more space for your family compound, the 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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: 3.75% last updated on Jul 11, 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$1,299,000

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: 3.75% last updated on Jul 11, 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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