Dukes, MA Homes

• 

  

  

  /39

  $3,299,000

  • 3 Beds
  • 3.5 Baths
  • 3,082 Sq Ft

  53 Stoney Hill Rd, Vineyard Haven, MA 02568

  Nestled in one of the island’s most sought-after locations, this exceptional property offers refined coastal living with access to the famed Lambert’s Cove Beach yet a short drive to VH.Thoughtfully designed, it features 3 spacious bedrooms each with an en suite bath, providing comfort and privacy for all. Primary suite is a true retreat with a brand new luxurious bathroom. At the heart of the

  Jennifer B. DaSilva Compass

  53 Stoney Hill Rd, Vineyard Haven, MA 02568
• 

  Explore West Tisbury

• 

  

  

  /14

  $8,400 per month

  • 4 Beds
  • 3 Baths
  • 2,148 Sq Ft
  • House for Rent

  39 Old Coach Rd, West Tisbury, MA 02568

  Summer weekly rental only! June weekly rate is $8,400 and July weekly rate is $10,000/week - Sunday to Saturday. Recently renovated 4 bedroom, 3 bathroom home that sits on a private 2 acre lot in West Tisbury MA! This large cape house has just been update with new stainless steel appliances, new kitchen cabinets and countertops. Other updates include, new bathroom vanities and hardware,

  Joseph D'Amico Dee Development Company

  39 Old Coach Rd, West Tisbury, MA 02568
• 

  

  

  /42

  $2,900,000 Sold Jul 03, 2025

  • 4,476 Sq Ft
  • $648/SF
  • 347 Days On Market

  • 7 Beds
  • 5.5 Baths
  • Built 1997

  67 Hidden Village Rd, Vineyard Haven, MA 02568

  Picturesquely sited on a spacious 4.6-acre parcel this remarkable property is the perfect Vineyard retreat offering a luxurious home, guest house, fenced pastures, and a large barn. Just minutes from Lamberts Cove Beach and all the conveniences of West Tisbury Center, the location is ideal. Designed with three distinctive living levels providing spacious yet private surroundings. The main living

  Stephanie Roache Donnelly + Co.

  67 Hidden Village Rd, Vineyard Haven, MA 02568
• 

  

  

  /40

  Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 4,500 Sq Ft

  1005 State Rd, West Tisbury, MA 02575

  1005 State Rd, West Tisbury, MA 02575
• 

  

  

  /30

  $3,900,000

  • 4 Beds
  • 2 Baths
  • 2,813 Sq Ft

  179 Tisbury Ln E, West Tisbury, MA 02575

  Seven Gates Farm: This warm and convivial home in one of the island’s most desirable communities is less than 1/10th of a mile to the private association beach. The house was designed to accentuate indoor-outdoor living; there is generous decking for morning or afternoon sun, and a screened porch which is the perfect place to enjoy shade and breeze after a day spent at one of the nearby beaches.

  Mark Jenkins Wallace & Co. Sotheby's

  179 Tisbury Ln E, West Tisbury, MA 02575
• 

  

  /10

  $8,500 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

  Karen Overtoom Karen M. Overtoom R.E.

  29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
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  /36

  $1,950,000 Sold Jul 02, 2025

  • 2,691 Sq Ft
  • $725/SF
  • 30 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1976

  51 Black Brook Crossing Rd, West Tisbury, MA 02568

  This charming 4 bed/2.5 bath Cape style home is set in a perfect setting, carefully sited on 1 acre bordered by a beautiful stone wall with mature plantings. Newly renovated kitchen with plenty of cabinets and storage, quartz counters and dining room with sliders to a screened-in porch. There is a den and living room with access to a spacious deck. The Great Room features cathedral ceilings,

  Brenda Galligan Karen M. Overtoom R.E.

  51 Black Brook Crossing Rd, West Tisbury, MA 02568
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  /30

  Est $2,500,413 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,555 Sq Ft

  10 Crow Hollow Rd, Vineyard Haven, MA 02568

  10 Crow Hollow Rd, Vineyard Haven, MA 02568
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  /59

  $2,550,000

  • 4 Beds
  • 3 Baths
  • 2,983 Sq Ft

  157 Ben Chase Rd, West Tisbury, MA 02575

  You will find this outstanding property at the end of a quiet country lane in West Tisbury nestled alongside hundreds of acres of conservation land and walking trails that extend all the way to Lamberts Cove Road. The setting is magical - 4 acres of rolling lawns with specimen trees and ponds. There are multiple structures to allow you to customize this compound to your personal needs. The main

  Madelyn Silvia Wallace & Co. Sotheby's

  157 Ben Chase Rd, West Tisbury, MA 02575
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  /8

  $11,800 per month

  • 4 Beds
  • 4 Baths
  • 2,612 Sq Ft
  • House for Rent

  46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

  Karen Overtoom Karen M. Overtoom R.E.

  46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
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  /2

  $1,595,000 Sold Jul 01, 2025

  • 1,176 Sq Ft
  • $1356/SF

  • 2 Beds
  • 2 Baths
  • Built 1998

  10 Red Pony Rd, West Tisbury, MA 02568

  Pastoral and perfect. Room to grow or just move in.

  Lisa Da silva Compass | Point B

  10 Red Pony Rd, West Tisbury, MA 02568
• 

  

  /4

  Est $2,968,039 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,789 Sq Ft

  188 Pond Rd, Vineyard Haven, MA 02568

  188 Pond Rd, Vineyard Haven, MA 02568
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  /65

  $2,690,000

  • 6 Beds
  • 4 Baths
  • 2,618 Sq Ft

  55 Old House Way, West Tisbury, MA 02575

  Lambert’s Cove/West Tisbury- custom-built contemporary farmhouse style . 4 bedrooms & 3 bathrooms in main house & 2 bedrooms & 1 bath guest cottage on 3 acres in a private neighborhood. Enter Main house from the covered porch -matching custom arch doors lead you to either the mudroom/laundry room-kitchen entry, or the living room. The kitchen has Mexican tiled floor & granite counters with

  Leslie Graham Anchor Realty of Martha's Vineyard

  55 Old House Way, West Tisbury, MA 02575
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  /12

  $6,180 per month

  • 3 Beds
  • 3.5 Baths
  • 1,872 Sq Ft
  • House for Rent

  44 Music St Wt153, West Tisbury, MA 02575

  PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

  Karen Overtoom Karen M. Overtoom R.E.

  44 Music St Wt153, West Tisbury, MA 02575
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  /32

  $3,925,000 Sold Jul 01, 2025

  • 5,603 Sq Ft
  • $701/SF
  • 238 Days On Market

  • 6 Beds
  • 7 Baths
  • Built 1995

  140 Merry Farm Rd, Vineyard Haven, MA 02568

  Site of the original Rainbow Farm, this 8.05-acre parcel is one of the most beautiful pieces of land in West Tisbury. The warm and convivial 5,000 sq ft home with its 4 bedrooms looks out onto a setting that is as if from a bygone era, the vast fields stretching into the distance. The spring-fed pond is a centerpiece of the pastoral view. The home itself has many surprising and charming design

  Mark Jenkins Wallace & Co. Sotheby's

  140 Merry Farm Rd, Vineyard Haven, MA 02568
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  /34

  Est $2,551,353 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 1 Sq Ft

  248 Pond Rd, Vineyard Haven, MA 02568

  248 Pond Rd, Vineyard Haven, MA 02568
• 

  

  /46

  $3,476,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,669 Sq Ft

  140 Pond Rd, Vineyard Haven, MA 02568

  Welcome to this beautifully updated and privately situated home in one of West Tisbury’s most desirable associations. Residents enjoy exclusive access to tennis courts, walking trails, horse pastures and Tisbury Great Pond. Designed for both comfort and luxury, this spacious 4+ bedroom, 3 bathroom property is ideal as a year-round residence or upscale vacation retreat.The first floor

  Jon Hartzband Martha's Vineyard Island-Wide Realty

  140 Pond Rd, Vineyard Haven, MA 02568
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  /12

  $15,000 per month

  • 5 Beds
  • 6.5 Baths
  • 4,137 Sq Ft
  • House for Rent

  41 Naushon Rd Wt116, Aquinnah, MA 02575

  Stunning water views from this expansive beachfront estate in Makonikey off Lambert's Cove Rd. Enjoy the large living area with comfortable couches, floor to ceiling windows and french doors for seamless indoor to outdoor living and dining. There is a fully equipped kitchen. Some folks will enjoy the treadmill and elliptical while watching boats pass by or even play squash in the indoor squash

  Karen Overtoom Karen M. Overtoom R.E.

  41 Naushon Rd Wt116, Aquinnah, MA 02575
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  /20

  $821,000 Sold Jun 17, 2025

  • Land
  • 1.40 Acres
  • $586,429 per Acre

  • 0 Days On Market

  168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568

  Large 1.4 Acre Corner lot in Vineyard Meadow Farms South side of West Tisbury Road. Private, flat, level parcel, paved dead end road with no unnecessary through traffic. Six bedrooms, a 3,000SF Main House, a 2,000SF detached/attached Secondary Building allowed per the Town. Pool allowed with standard Special permit. Centrally located to all Island Towns. Great neighborhood. Great location with

  Janna O'Loughlin Portfolio Real Estate, Inc.

  168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568
• 

  

  /25

  Est $2,093,611 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,636 Sq Ft

  131 Shubael Weeks Path, Vineyard Haven, MA 02568

  131 Shubael Weeks Path, Vineyard Haven, MA 02568
• 

  

  /34

  $2,495,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,879 Sq Ft

  24 Alex Way, Vineyard Haven, MA 02568

  24 Alex Way is an opportunity to embrace the extraordinary Elias and Langmuir legacy which dramatically changed a 140 acre rural West Tisbury landscape in 1972 into the Nat's Farm community of 26 home sites. The home overlooks the 56 acres that Nat's Farm donated to Sheriff's Meadow Foundation and the incomparable Misty Meadows Equine Learning Center and homes along Elias Lane. Jane Langmuir,

  Elissa Lash Tea Lane Associates

  24 Alex Way, Vineyard Haven, MA 02568
• 

  

  /8

  $8,250 per month

  • 7 Beds
  • 5 Baths
  • 3,528 Sq Ft
  • House for Rent

  227 S Gate Rd Wt120, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through

  Karen Overtoom Karen M. Overtoom R.E.

  227 S Gate Rd Wt120, West Tisbury, MA 02575
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  /18

  $1,219,000 Sold Jun 16, 2025

  • 1,512 Sq Ft
  • $806/SF
  • 99 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1986

  108 Charles Neck Way, Vineyard Haven, MA 02568

  This charming reverse-style home is ideally located near Long Point Beach and offers a perfect blend of comfort and functionality for year-round living or seasonal getaways. The first floor features three spacious bedrooms, a full bath, and a convenient laundry room. On the second floor, you'll find soaring cathedral ceilings and an open-concept living area, complete with a cozy living room,

  Alyssa Halisky Wallace & Co. Sotheby's

  108 Charles Neck Way, Vineyard Haven, MA 02568
• 

  

  /36

  Est $2,321,551 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,436 Sq Ft

  377 State Rd, Vineyard Haven, MA 02568

  377 State Rd, Vineyard Haven, MA 02568
• 

  

  /30

  $2,495,000 Pending

  • 5 Beds
  • 4 Baths
  • 2,685 Sq Ft

  35 Woody Bottom Rd, West Tisbury, MA 02575

  This Cape style 5 bed/ 3.5 bath home is located in a nice area privately sited on 3 acres. This home features a comfortable floor plan that includes a fully equipped kitchen with center island, custom cabinetry and granite counters. Just off the kitchen is a sunny breakfast room, a separate dining room, a spacious living room with fireplace and 2 sets of sliders to a backyard deck. There is a

  Brenda Galligan Karen M. Overtoom R.E.

  35 Woody Bottom Rd, West Tisbury, MA 02575
• 

  

  /8

  $18,500 per month

  • 4 Beds
  • 3.5 Baths
  • 1,714 Sq Ft
  • House for Rent

  4 Windy Way Wt143, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! The 3.3 acre private setting is most picturesque with its positioning in private Upper Makonikey , the long circular driveway , its grassy lawn, and rolling landscape fields . Only a short distance away is over 3,000 feet of PRIVATE sandy association Beaches , directly below , with two nearby parking lot access-ways . Nestled onto this promontory is a

  Karen Overtoom Karen M. Overtoom R.E.

  4 Windy Way Wt143, West Tisbury, MA 02575
• 

  

  /20

  $1,150,000 Sold Jun 13, 2025

  • 1,374 Sq Ft
  • $837/SF
  • 43 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  46 Old Coach Rd, Vineyard Haven, MA 02568

  Charming and Spacious 3-Bedroom Cape with large Loft and Deck Welcome to your dream West Tisbury home! This comfortable and spacious 3-bedroom, 2-bath Cape boasts a thoughtfully designed floor plan perfect for comfortable living. The first-floor features two bedrooms and a full bath, ideal for use as sleeping quarters or a home office. Moving to the second floor, discover privacy with a third

  Lisa Gilberto C McManus Realty Group

  46 Old Coach Rd, Vineyard Haven, MA 02568
• 

  

  /14

  Est $2,704,037 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,926 Sq Ft

  30 Pond Ln, Vineyard Haven, MA 02568

  30 Pond Ln, Vineyard Haven, MA 02568
• 

  

  /8

  $3,200,000

  • Land
  • 19 Acres
  • $165,803 per Acre

  32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575

  A Rare Offering in West Tisbury — Over 19 Acres of OpportunityAn exceptional opportunity to own just over 19 acres in the heart of rural West Tisbury. This expansive parcel offers tremendous flexibility, with potential for multiple dwellings or subdivision into a thoughtfully designed niche development. Ideally situated near all island towns, the property is also just minutes from the

  Jill Napior Tea Lane Associates

  32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
• 

  /2

  $10,000 per month

  • 6 Beds
  • 3.5 Baths
  • 2,100 Sq Ft
  • House for Rent

  15 Crowell Lane Wt119, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!Seven Gates Farm. This property has three ponds, overlooks rolling meadows and is very charming. Located in Seven Gates Farm association, the property affords access to association tennis and two miles of private beach as well as miles of walking trails. Bookings for tennis are available at the office for a slight fee.There is a $25 trash charge per

  Karen Overtoom Karen M. Overtoom R.E.

  15 Crowell Lane Wt119, West Tisbury, MA 02575
• 

  

  /3

  $1,695,000 Sold May 30, 2025

  • 1,296 Sq Ft
  • $1308/SF

  • 2 Beds
  • 2 Baths
  • Built 1960

  5 Vincent Rd, Vineyard Haven, MA 02568

  NOT LISTED IN LINK

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  5 Vincent Rd, Vineyard Haven, MA 02568
• 

  

  /36

  Est $1,288,385 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft

  16 Rock Pond Rd, Vineyard Haven, MA 02568

  16 Rock Pond Rd, Vineyard Haven, MA 02568
• 

  

  /21

  $1,675,000

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft

  111 Charles Neck Way, Vineyard Haven, MA 02568

  Tucked away on 1.6 wooded acres in West Tisbury, this classic Cape-style home offers both privacy and convenience, with easy access to the charm of Up-Island and the amenities of Down-Island. Located on a paved road near Long Point Beach, it also includes coveted access to Lambert's Cove Beach. The bright, open interior features a living and dining area with a wood-burning fireplace, a kitchen

  Emma Kennedy Sandpiper Realty Inc

  111 Charles Neck Way, Vineyard Haven, MA 02568
• 

  

  /8

  $4,800 per month

  • 3 Beds
  • 3 Baths
  • 3,279 Sq Ft
  • House for Rent

  165 Christiantown Rd, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

  Karen Overtoom Karen M. Overtoom R.E.

  165 Christiantown Rd, West Tisbury, MA 02575
• 

  

  /15

  $1,150,000 Sold May 30, 2025

  • 1,338 Sq Ft
  • $859/SF
  • 48 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1966

  14 Galway Rd, Vineyard Haven, MA 02568

  Welcome to 14 Galway Road, West Tisbury. The home and property have been lovingly maintained and used by the same family since the home was built. It offers an open eat-in kitchen/living room design with a masonry fireplace. On the first floor are two bedrooms, one full bathroom, a linen closet, and hidden washer and dryer along the hallway. The stairway brings you to a second floor which

  Michele Casavant Vineyard Village Realty

  14 Galway Rd, Vineyard Haven, MA 02568
• 

  

  /49

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,092 Sq Ft

  670 State Rd, Vineyard Haven, MA 02568

  670 State Rd, Vineyard Haven, MA 02568
• 

  

  /25

  $1,295,000

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft

  140 Longview Rd, Vineyard Haven, MA 02568

  Nestled in the hills of Longview, less than 1 mile from beautiful Lambert's Cove Beach, this 3-bedroom retreat is a cozy year-round home or an airy summer getaway - whatever your needs might be. The vaulted ceilings throughout the home allow it to live much larger than its square footage - and the expansive front deck stretches the living space all through the spring, summer and even fall

  Candy DaRosa Feiner Real Estate

  140 Longview Rd, Vineyard Haven, MA 02568
• 

  

  /42

  $19,000 per month

  • 6 Beds
  • 6.5 Baths
  • 6,950 Sq Ft
  • House for Rent

  40 Sweet William Way, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the

  Karen Overtoom Karen M. Overtoom R.E.

  40 Sweet William Way, West Tisbury, MA 02575
• 

  

  /26

  $1,850,000 Sold May 14, 2025

  • 2,610 Sq Ft
  • $709/SF
  • 8 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1986

  137 Charles Neck Way, Vineyard Haven, MA 02568

  Fantastic opportunity to buy a two house compound in West Tisbury close to Long Point Beach access. A perfect investment, rental income generator or to host extended family and guests.Two well built houses on 1.6 acres, that have been impeccably maintained by the original owner. Offering a total of 5 bedrooms, 4 bathrooms, 2 outdoor showers and 2 garages. There is a charming garden shed and low

  Rebecca V Conroy Conroy & Company R.E., Inc.

  137 Charles Neck Way, Vineyard Haven, MA 02568
• 

  

  /16

  Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,275 Sq Ft

  26 Chappaquiddick Ave, Vineyard Haven, MA 02568

  26 Chappaquiddick Ave, Vineyard Haven, MA 02568

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