Dukes, MA Homes

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  /26

  $1,597,500

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  190 Longview Rd, Vineyard Haven, MA 02568

  Ask listing office. This property is in West Tisbury, 02575 NOT Tisbury 02568

  Kathleen Kendrick Kathleen Kendrick

  190 Longview Rd, Vineyard Haven, MA 02568
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  /28

  $38,000 per month

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft
  • House for Rent

  17 Otis Bassett Rd, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT MONTHLY. AUGUST WEEKLY IS $9,500. SEE OUR WEB SITE FOR WEEKLY PRICING!!!!!Are you looking for the perfect back yard Oasis? Well here it is!! Surrounding a large pool you will be able to relax on the expansive deck areas that include plenty of space for gathering. Inside is an amazing kitchen with every amenity you could want. Coffee lovers will appreciate a regular

  Karen Overtoom Karen M. Overtoom R.E.

  17 Otis Bassett Rd, West Tisbury, MA 02575
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  /13

  $2,050,000 Sold May 01, 2025

  • 1,007 Sq Ft
  • $2036/SF
  • 0 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 2016

  16 Red Coat Hill Rd, Vineyard Haven, MA 02568

  Exquisite West Tisbury Property: A Unique Opportunity.Discover the allure of a truly exceptional property nestled on 4.85 stunning acres in the serene locale of West Tisbury. This opportunity is not one to be missed, as it combines elegance, foresight, and sustainability in perfect harmony.The home is adorned with beautiful beams throughout, with nickelboard and shiplap covering the walls and

  Joe & Nicole Holland Vineyard Dream Realty LLC

  16 Red Coat Hill Rd, Vineyard Haven, MA 02568
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  /36

  Est $2,520,452 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,791 Sq Ft

  225 Great Plains Rd, Vineyard Haven, MA 02568

  225 Great Plains Rd, Vineyard Haven, MA 02568
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  /36

  $1,495,000

  • 4 Beds
  • 2 Baths
  • 1,332 Sq Ft

  40 Scotchmans Ln, Vineyard Haven, MA 02568

  A home with history, built in the early 1800s this dwelling was originally built on a local farm and moved to its present location in the 1920's. The structure sits nestled amongst mature plantings and out buildings facing the Mill Brook. The studio and covered patio offer opportunities to entertain, relax and reflect. This 3.76 parcel was created from a larger parcel by the owner (see attached

  Jim Osmundsen Donnelly + Co.

  40 Scotchmans Ln, Vineyard Haven, MA 02568
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  /8

  $18,000 per month

  • 3 Beds
  • 2.5 Baths
  • House for Rent

  71 Bartmus Luce Road Wt154, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard Views available. It is a short

  Karen Overtoom Karen M. Overtoom R.E.

  71 Bartmus Luce Road Wt154, West Tisbury, MA 02575
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  /50

  $3,000,000 Sold Apr 29, 2025

  • 3,311 Sq Ft
  • $906/SF

  • 3 Beds
  • 3 Baths
  • Built 2000

  34 S Pond Rd, Vineyard Haven, MA 02568

  Stunning Deep Bottom Pond property with an oversized 3.77-acre lot surrounded by Mother Nature’s beauty, with exclusive association access to Tisbury Great Pond and private tennis courts. This beautiful home is lovingly maintained and ready for immediate occupancy. Through the welcoming grand foyer, a cathedral-ceiling living room with a fabulous wood-burning fireplace, and slider doors leading

  Stephanie Roache Donnelly + Co

  34 S Pond Rd, Vineyard Haven, MA 02568
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  /34

  Est $1,628,990 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft

  84 Christiantown Rd, Vineyard Haven, MA 02568

  84 Christiantown Rd, Vineyard Haven, MA 02568
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  /12

  $1,325,000

  • Land
  • 4.12 Acres
  • $321,602 per Acre

  25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568

  This beautiful wooded 4.12 acre parcel of land is peaceful, serene and ready to build. The well is installed, boundaries staked, perc test approved for a five-bedroom home and a septic plan designed. This is an opportunity to realize your vision and build a home that reflects your lifestyle. The large, flat building envelope offers many siting possibilities and, should you choose, the property

  Abby Rabinovitz Tea Lane Associates

  25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568
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  /19

  $17,600 per month

  • 4 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • House for Rent

  50 Carls Way, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Looking for that perfect setting with a water view? This is the one!!This cute cape is privately set with a water view and direct water access to Town Pond. You can dock your canoes and kyacks here and access Tisbury Great Pond and then right out to the beach. There are

  Karen Overtoom Karen M. Overtoom R.E.

  50 Carls Way, West Tisbury, MA 02575
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  /35

  $1,837,500 Sold Apr 18, 2025

  • 1,654 Sq Ft
  • $1111/SF
  • 182 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1984

  55 Charles Neck Way, Vineyard Haven, MA 02568

  LONG POINT BEACH RETREAT. Privately set on 1.6 acres in the highly-coveted Long Point area of West Tisbury, this reverse style beach house is an idyllic island retreat. The open-designed Great Room features vaulted ceilings and a wall of sliding glass doors that open out to an expansive deck, perfect for indoor-outdoor summer living and entertaining. There are also screened porches on both

  Wendy Harman Compass | Point B

  55 Charles Neck Way, Vineyard Haven, MA 02568
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  /36

  Est $2,245,934 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 2,705 Sq Ft

  9 Heather Trail, Vineyard Haven, MA 02568

  9 Heather Trail, Vineyard Haven, MA 02568
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  /76

  $3,995,000

  • 5 Beds
  • 3 Baths
  • 2,791 Sq Ft

  20 James Pond Way, Vineyard Haven, MA 02568

  Nestled on a serene 4.5-acre parcel of land off Lambert's Cove Road, this exquisite property offers unparalleled privacy, views and direct access to James Pond and beyond to the Land Bank's Lambert's Cove Beach property. In addition to the custom heated Gunite pool, the expansive yard provides space for many outdoor activities while relishing the tranquility of the location. The residence

  Sheila Morse Island Real Estate

  20 James Pond Way, Vineyard Haven, MA 02568
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  /21

  $8,000 per month

  • 1 Bed
  • 1 Bath
  • 936 Sq Ft
  • House for Rent

  10 James Pond Way, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a

  Karen Overtoom Karen M. Overtoom R.E.

  10 James Pond Way, West Tisbury, MA 02575
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  /22

  $1,150,000 Sold Apr 11, 2025

  • 1,264 Sq Ft
  • $910/SF
  • 216 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1983

  41 Old County Rd, Vineyard Haven, MA 02568

  Let your imagination run wild with this peaceful, pastoral property centrally located between down and up-island. This home is perfectly sited on just over 2 acres and is ready for your vision. The cape-style main house features a spacious wrap around deck and an open floor plan on the first level. The entire home is outfitted with hardwood floors. According to the West Tisbury Board of Health,

  Jared Bicknell Compass | The O'Hanlon Group

  41 Old County Rd, Vineyard Haven, MA 02568
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  /18

  Est $1,863,909 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,461 Sq Ft

  29 Brook Hollow Rd, Vineyard Haven, MA 02568

  29 Brook Hollow Rd, Vineyard Haven, MA 02568
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  /28

  $1,695,000

  • 4 Beds
  • 1.5 Baths
  • 1,592 Sq Ft

  5 Scottys Ln, Vineyard Haven, MA 02568

  Attention Developers and Island Lovers! Take note of this rare opportunity in a prime West Tisbury Location with a new price! This mid-century home with excellent bones fronts on Seth's Pond, a beloved locale perfect for swimming, paddle-boarding, and kayaking. 5 Scotty's Lane has an existing 4-bedroom main house with the first floor and lower walk-out level equaling 2,704 of finished space. This

  Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

  5 Scottys Ln, Vineyard Haven, MA 02568
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  /26

  $50,000 per month

  • 4 Beds
  • 3 Baths
  • 3,237 Sq Ft
  • House for Rent

  29 Naushon Rd Wt142, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfortable single level 4 BR 3 bath home has central air and heat. Enjoy summer star-studded skies from your patio or through skylights in each bedroom.

  Karen Overtoom Karen M. Overtoom R.E.

  29 Naushon Rd Wt142, West Tisbury, MA 02575
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  /30

  $1,175,000 Sold Mar 20, 2025

  • 1,389 Sq Ft
  • $846/SF
  • 173 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  12 W Farm Rd, West Tisbury, MA 02575

  Welcome to 12 West Farm Road, a delightful classic cape nestled among beautiful mature evergreens in the Coffins Field neighborhood of West Tisbury. This well-kept home features 3 bedrooms and 2 bathrooms, offering 1,389 square feet of cozy and inviting living space. Skylighted ceilings and an open first-floor living/cooking/dining area combination provide a spacious feeling for everyday

  Carson Crissman Compass | Point B

  12 W Farm Rd, West Tisbury, MA 02575
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  /16

  Est $1,345,870 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft

  31 Music St, Vineyard Haven, MA 02568

  31 Music St, Vineyard Haven, MA 02568
• 

  

  /108

  $4,800,000

  • 6 Beds
  • 5 Baths
  • 2,960 Sq Ft

  104 Pond View Farm Rd, Vineyard Haven, MA 02568

  An exceptional Waterfront Compound on Tisbury Great Pond. Located across the Tisbury Great Pond from the exclusive Blue Heron Farm, this remarkable waterfront property offers a rare opportunity to own a serene compound with two homes and a private permitted dock—ideal for boating to the Atlantic barrier beach, fishing, kayaking, and enjoying the peaceful beauty of the pond.Both the main house and

  Alexis Holden Tea Lane Associates

  104 Pond View Farm Rd, Vineyard Haven, MA 02568
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  /29

  $10,900 per month

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft
  • House for Rent

  58 Forest Rd Wt140, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,725.. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming rustic home is set within Seven Gates Farm in West Tisbury. Walk down your own path to a beautiful private association beach. There are shared tennis courts and miles of walking trails.

  Karen Overtoom Karen M. Overtoom R.E.

  58 Forest Rd Wt140, West Tisbury, MA 02575
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  /22

  $1,115,000 Sold Mar 14, 2025

  • 1,286 Sq Ft
  • $867/SF
  • 212 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1955

  496 Lamberts Cove Rd, Vineyard Haven, MA 02568

  Two peaceful acres on coveted Lamberts Cove Road with access to Lamberts Cove Beach and proximity to West Tisbury Center and Conservation Land. This property boasts mature plantings, various trees, and much Mother Nature offers, including a small pond. The home has been completely renovated and enjoys hardwood floors, skylights, a wood stove, and other special features such as antique

  Stephanie Roache Donnelly + Co

  496 Lamberts Cove Rd, Vineyard Haven, MA 02568
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  /17

  Est $1,082,396 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 934 Sq Ft

  10 Briarwood Ln, Vineyard Haven, MA 02568

  10 Briarwood Ln, Vineyard Haven, MA 02568
• 

  

  /45

  $19,500,000

  • 7 Beds
  • 6 Baths
  • 3,344 Sq Ft

  104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535

  This beautiful 2-parcel compound totals 9.5-acre of land and 600 feet of private Vineyard Sound beach. There is a renovated 4-bedroom beach cottage on one of the parcels which includes all modern amenities and offers spectacular views from almost every room. The second parcel has an older 3-bedroom home located high on a ridge. Both parcels offer wonderful walking paths to the sandy beach below.

  Thomas Leclair Landvest MV

  104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535
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  /20

  $12,000 per month

  • 3 Beds
  • 1 Bath
  • 1,068 Sq Ft
  • House for Rent

  76 Ben Chase Rd Wt136, West Tisbury, MA 02575

  Experience a wonderful glimpse of country living in the peaceful, quiet setting of Serene Pond Cottage! This charming Martha's Vineyard retreat features a cozy interior with ample natural light, a private deck where you can take your breakfast and coffee, and a tree-lined backyard to enjoy on lazy summer days. Comfortable three bedroom single story home with one brand new renovated full bath with

  Karen Overtoom Karen M. Overtoom R.E.

  76 Ben Chase Rd Wt136, West Tisbury, MA 02575
• 

  

  /17

  $1,300,000 Sold Mar 03, 2025

  • 1,241 Sq Ft
  • $1048/SF
  • 4 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2018

  22 Briarwood Ln, Vineyard Haven, MA 02568

  This Recently Constructed Carriage House in Vineyard Haven is the epitome of thoughtful planning with custom details and exceptional finishes throughout. The sunny second level has an open floor living and kitchen area with vaulted ceilings. Highlights include a farmer’s sink, quartz countertops, pull out kitchen cabinets and self-closing drawers. There are two bedrooms, one is ensuite and the

  Carol Shore Donnelly + Co

  22 Briarwood Ln, Vineyard Haven, MA 02568
• 

  

  /36

  Est $1,636,556 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,144 Sq Ft

  323 Lamberts Cove Rd, Vineyard Haven, MA 02568

  323 Lamberts Cove Rd, Vineyard Haven, MA 02568
• 

  

  /22

  $1,449,000

  • 3 Beds
  • 1.5 Baths
  • 1,404 Sq Ft

  32 MacHipscat Trail, Vineyard Haven, MA 02568

  This Cape Style home privately sited on 1.89 acres at the end of a cul-de-sac abutting conservation land with many walking trails. Nice features include spacious living spaces that include a well equipped kitchen with custom cherry cabinets, dining room, living room with fireplace, wood stove and french doors that lead you out to a private patio and backyard. Second floor offers two guest

  Brenda Galligan Karen M. Overtoom R.E.

  32 MacHipscat Trail, Vineyard Haven, MA 02568
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  /22

  $20,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • House for Rent

  709 Old County Rd Wt134, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY. The weekly price in August is $5,000. per week. See website for additional weekly pricing. Mill Pond House is a completely restored 1890s farmhouse on the old Mill Pond in historic West Tisbury. Remodeled by the present owner, an interior designer, it is beautifully appointed with antiques and charming accessories. An old pine floor and columns add to the

  Karen Overtoom Karen M. Overtoom R.E.

  709 Old County Rd Wt134, West Tisbury, MA 02575
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  /45

  $990,000 Sold Feb 19, 2025

  • 1,618 Sq Ft
  • $612/SF
  • 145 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1999

  5 Rock Pond Rd, Vineyard Haven, MA 02568

  Fantastic opportunity to own a South Mountain designed and built home in the coveted Island Co-Housing community. House #5 sits back from the community road with a great side yard, patio and outdoor shower.3 Large Bedrooms include a downstairs master w/ensuite bath off the living room area with a mid-way access leading to a private patio. The entryway opens on the kitchen, with thick shaker style

  Kerry Quinlan-Potter Breakwater MV

  5 Rock Pond Rd, Vineyard Haven, MA 02568
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  /17

  Est $1,422,592 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft

  2 Pond View Farm Rd, Vineyard Haven, MA 02568

  2 Pond View Farm Rd, Vineyard Haven, MA 02568
• 

  

  /30

  $1,695,000

  • 3 Beds
  • 2 Baths
  • 1,986 Sq Ft

  251 State Rd, Vineyard Haven, MA 02568

  This private and pastoral year-round home with fine craftsmanship and loads of character is a classic up-island refuge, yet in a location that is central on the island and convenient to town. Abutting Land Bank property, the charming home features an open living and dining room with wide plank floors and beams flowing into the kitchen, all surrounding a central brick fireplace. An expansive

  Meg Bodnar Tea Lane Associates

  251 State Rd, Vineyard Haven, MA 02568
• 

  

  /19

  $30,000 per month

  • 5 Beds
  • 4 Baths
  • 3,600 Sq Ft
  • House for Rent

  37 Sachem Cir, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself

  Karen Overtoom Karen M. Overtoom R.E.

  37 Sachem Cir, West Tisbury, MA 02575
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  /49

  $1,750,000 Sold Jan 31, 2025

  • 2,548 Sq Ft
  • $687/SF
  • 186 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1984

  75 Skiffs Ln, Vineyard Haven, MA 02568

  Located on a beautiful, private 2.6 acre lot, this well-maintained home is move-in ready and awaiting your personal touch! Pool, manicured yard, plentiful parking, attached garage, large basement, outdoor shower and many more features make this spacious family home versatile and accommodating to your needs. You're able to enjoy the patio and pool with a built in fire pit during the summer months

  Kelly Mercier Match Point Properties

  75 Skiffs Ln, Vineyard Haven, MA 02568
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  /30

  Est $1,535,358 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft

  88 Hopps Farm Rd, Vineyard Haven, MA 02568

  88 Hopps Farm Rd, Vineyard Haven, MA 02568
• 

  

  /37

  $1,349,000

  • 4 Beds
  • 2 Baths
  • 2,059 Sq Ft

  4 Rock Pond Rd, Vineyard Haven, MA 02568

  4 Bedroom ++ home, has room for your family and your in-home business. This is the home that has it all. An abundance of light, space and potential. A large Atrium off the living room invites in the light and warmth of outside, creating an oasis of possibilities-The expansive open living-kitchen-dining area has space for all to gather, the wood stove and kitchen bringing warmth and sunlight into

  Kerry Quinlan-Potter Breakwater MV

  4 Rock Pond Rd, Vineyard Haven, MA 02568
• 

  

  /17

  $17,600 per month

  • 4 Beds
  • 4 Baths
  • 2,676 Sq Ft
  • House for Rent

  40 Summer Cir, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and living room surrounded by windows and decks with an outdoor table and extra seating. An "upside down" house with the living

  Karen Overtoom Karen M. Overtoom R.E.

  40 Summer Cir, West Tisbury, MA 02575
• 

  

  /31

  $2,525,000 Sold Jan 17, 2025

  • 3,310 Sq Ft
  • $763/SF
  • 80 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1991

  106 Panhandle Rd, Vineyard Haven, MA 02568

  With easy access to the West Tisbury Village, this lovely 4 bedroom, 3.5 bath home is privately sited on 1.4 acres overlooking a protected pasture. Many nice features include open living spaces, a well equipped kitchen with stainless steel appliances, a center island and granite. The sun-filled great room with oversized windows offer peaceful views of the meadow, a cathedral ceiling and sliders

  Brenda Galligan Karen M. Overtoom R.E.

  106 Panhandle Rd, Vineyard Haven, MA 02568
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  /33

  Est $1,896,538 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,508 Sq Ft

  163 Charles Neck Way, Vineyard Haven, MA 02568

  163 Charles Neck Way, Vineyard Haven, MA 02568

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