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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!

103 Main Street Vineyard Haven MA

Vineyard Haven, MA103 Main Street

Price$13,500,000

Est. Mortgage: $/month

MLS Number 37110

  • Residential
  • Square Feet 7046
  • Bedrooms 5
  • Bathroom 4
  • Half Bath 2

THE ULTIMATE WATERFRONT RETREAT - The Vineyard has always been the place to go for R&R, and if you needed it in the past, you certainly need it now. It is the oasis of beauty and tranquility in a vintage community. This property offers the best of the Island. Located on Vineyard Haven Harbor, the home sits on a large 1.7A parcel of land, which provides privacy, spectacular views of harbor activity, yet steps away from the Village for your morning coffee, afternoon shopping, and dinner and theater in the evening. A unique feature is proximity to the ferry to come to and leave the Island easily. Think of it - the kids who will probably be with you a lot more, Mom and Dad, who will visit, and the family workforce can easily use the Vineyard home as "operation center," adjusting to the new lifestyle perfectly. Designed by premier architect Patrick Ahearn, with 7,045 sf, the home is warm and friendly with space to accommodate everyone's needs. The large kitchen with sitting room and fireplace opens to a screened porch. A dramatic stone fireplace is the focal point of the sitting area on the porch with generous room for dining for twelve with views of Harbor activity. This space is the hub of the house. There is a large, quiet office on the first floor for serious work along with a smaller office space off the kitchen. A grand formal dining room with a fireplace and living room is designed for special occasions. Another all-season sun porch on the first floor provides additional space for a variety of activities. The informal and formal areas connect with an outdoor patio. The master bedroom suite with a sitting area occupies the south wing of the second floor and is cleverly separated from the activity of the household. Three more bedrooms are in the north wing of the house. Another expansive deck connects both wings. The views from the first floor are spectacular, and they become panoramic and magnificent on the second floor. There is a guest suite over the two car garage which can be accessed from the outside or the adjoining deck on the second floor. The piece de resistance is the widow's walk offering the most brilliant views. The terraced pool and built-in outside grill overlooking the Harbor complete this perfect Vineyard home.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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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37 Pasture Gate Road Vineyard Haven MA

Vineyard Haven, MA37 Pasture Gate Road

Price$5,250,000

Est. Mortgage: $/month

MLS Number 37071

  • Residential
  • Square Feet 7604
  • Bedrooms 5
  • Bathroom 4
  • Half Bath 2

THE PERFECT VINEYARD RETREAT THAT HAS IT ALL! This property offers all the room you need for today's "stay-at-home" environment. There are wings, lofts, and a private guest suite above the garage, providing a myriad of independent locations and common areas to gather at the beginning and end of the day. The grand entrance sets the tone of this Vineyard estate located on 3.15 acres of land. The home overlooks pastoral fields with surrounding woodlands to create a peaceful setting to retreat amid the dynamics of today's world. The pool area and custom-designed pool house provide an expansive outdoor living space full of sun and fresh air. The owners chose the location in the Tashmoo Association because of the proximity to Vineyard Haven Village and the amenities of the community, which provides tennis, and a dock. An up-Island property in a down-Island location. A grand foyer invites you to the living room on the right with fireplace and French doors to the back patio. The dining room connects the living room to the kitchen, which is more than generous with a breakfast area overlooking the gardens and pool. Open from the kitchen is a custom family/sunroom with views over the fields and horse farm beyond. Behind the kitchen and powder room is a classic study that can convert from a workspace to a den for a social gathering or to watch the game. There are four bedrooms in the main house on the second floor and a third-floor loft. A guest suite is located above the two-car garage with private access. One of the dramatic additions is another living room with fireplace, vaulted, lighted ceiling, bar and powder room with French doors to the pool. 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 7,604 sf is not quite enough for your new "stay-at-home" lifestyle, the renovated 2 bedroom cottage at 19 Chappaquonsett is also available as is the horse farm at 67 Lamberts Cove Road.

Listed by Sandpiper Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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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344 Greenwood Avenue Vineyard Haven MA

Vineyard Haven, MA344 Greenwood Avenue

Price$1,100,000

Est. Mortgage: $/month

MLS Number 36465

  • Residential
  • Square Feet 1566
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.3

Impeccable Four bedroom home (one bedroom on ground level) with two full baths. There are many upgrades to this home from a row of full view doors that face the rear pool area, quartz counter tops, beautiful wood floors on the main living area and maple flooring upstairs. Plenty of closet space and beautiful Art niches complete this "forever" home. Cozy up to the fireplace to read a book or swim in the refreshing heated pool. Home comes mostly furnished so move right in and begin to enjoy this end of street location. Close to town which allows easy access to shopping, bus, steamship and ocean swimming.

Listed by Anchor Realty of Martha's Vineyard

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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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78 Mitchell Road Vineyard Haven MA

Vineyard Haven, MA78 Mitchell Road

Price$1,575,000

Est. Mortgage: $/month

MLS Number 37017

  • Multi-Family
  • Village West Chop
  • Bedrooms 5
  • Bathroom 3

WEST CHOP WITH PRIVATE ASSOCIATION BEACH AND POOL - The Mink Meadows Association is one of the gems of Vineyard Haven. Quiet and private with a rural sensibility while still being close to Tisbury town center, the association offers property owners access to a beautiful private beach, and proximity to the lovely Mink Meadows golf club. It's an easy 1.5 mile bike ride or walk to the Vineyard Haven shops and restaurants. This sunny two story home and guest house with private pool is located on over 2 acres within the Mink Meadows Association in the West Chop neighborhood. The home has friendly farmhouse style with open concept living, lots of light, vaulted ceilings, a wood burning fireplace, three bedrooms, two bathrooms, a screened in porch, and two bonus spaces currently used as a playroom and family room. There is also a sweet two bedroom apartment above the barn with plenty of storage space. The house and guest house are separated by the private in ground pool for lots of summer family fun. There are numerous rental options at this property. The main house has a new six bedroom septic, the guest house is tied into a separate two bedroom system. The dwellings both have heat pumps for heat and AC. The 2.15 acre property offers plenty of grassy yard space and is situated off of a well maintained dirt road. Mink Meadows is across from West Chop Woods - perfect for fall and spring walks. The beach is a 10 minute walk from the house. It is a wonderful place to call home year round and an excellent investment opportunity!

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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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79 David Avenue Vineyard Haven MA

Vineyard Haven, MA79 David Avenue

Price$1,850,000

Est. Mortgage: $/month

MLS Number 37019

  • Residential
  • Village Lambert's Cove
  • Square Feet 4156
  • Bedrooms 5
  • Bathroom 3

EXCEPTIONALLY CRAFTED, EUROPEAN STYLE SANCTUARY - LAMBERT'S COVE - Rarely does one find a home that is at once approachable and exquisitely styled. Do not let the modest entrance fool you! This property offers an abundance of space to entertain and relax with friends and loved ones. Unique details abound. Margot Datz has painted delightful details throughout the house. With a rambling and unusual floor plan, each unique room leads to yet another inspired space. If you live in the kitchen, you will covet this inspired room adorned with a Turbo Chef oven and every thoughtful detail to assist the artful Chef. In addition to the bedrooms in the main part of the home, there is a private guest wing on the lower level. A fieldstone lined path leads to a lower meadow area that is ready for a pool or tennis court and Guesthouse. A brand new Bocce court was just completed. Engineered plans for a six bedroom septic are complete and a permit pending to transform this property for maximum use and enjoyment. Bordered on one side by Vineyard Open Land Foundation property and by the Wakeman Center on another, privacy abounds.

Listed by Point B Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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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15 Chapde Lane Vineyard Haven MA

Vineyard Haven, MA15 Chapde Lane

Price$1,300,000

Est. Mortgage: $/month

MLS Number 36809

  • Residential
  • Village Lagoon
  • Square Feet 2344
  • Bedrooms 4
  • Bathroom 3

NEW CONSTRUCTION, almost finished! A delightful home nestled in a quiet "cul de sac" within strolling distance to both the Lagoon and downtown. Featuring a gourmet kitchen that will include top-shelf appliances and an island that can seat up to eight people. This one of a kind house that is perfect for entertaining! There are two "owner suites", including one on the first floor that features a delightful soaking tub. Need a Home office? The bright and "airy" lower level could be another "owner's suite", or a media room, or a large home office. There is even space for a small swimming pool The septic system can accommodate six bedrooms. When you include the third floor and the lower level, this house has almost 4000 sq ft of usable space. Broker has an equity interest.

Listed by Arrowhead Homes

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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
  • Village Lambert's Cove
  • Square Feet 7050
  • Bedrooms 5
  • Bathroom 5

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: 2.87% last updated on Sep 17, 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
  • Village Lagoon
  • 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: 2.87% last updated on Sep 17, 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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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: 2.87% last updated on Sep 17, 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$9,999,500

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: 2.87% last updated on Sep 17, 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$9,999,500

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: 2.87% last updated on Sep 17, 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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