Vineyard Haven Homes

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  /36

  $2,325,000

  $270K PRICE DROP Pending

  • 4 Beds
  • 4 Baths
  • 2,288 Sq Ft

  54 Amelia's Crossing, Tisbury, MA 02568

  COASTAL CHIC RETREAT IN VINEYARD HAVEN. Located less than five blocks from Main Street in Vineyard Haven, this classically styled home is perfectly positioned for easy access to restaurants, shops, the harbor, and the ferry, offering the ideal blend of in-town convenience, relaxed island living, and timeless Vineyard appeal. The open-designed living area flows seamlessly to the outdoor living

  

  Wendy Harman

  Compass

  54 Amelia's Crossing, Tisbury, MA 02568
• Explore Vineyard Haven

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  /8

  $6,000 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • House for Rent

  33 Kennebago Ave Vh414, Tisbury, MA 02568

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This beautiful home has lots of open space for cooking, yard activities or just plain relaxing. Private association beach overlooking the Elizabethan Islands. Plan a sunset picnic on the beach or plan in the morning to see the rays of sun break on the water.

  Karen Overtoom Karen M. Overtoom R.E.

  33 Kennebago Ave Vh414, Tisbury, MA 02568
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  /42

  $1,300,000

  Sold Feb 13, 2026

  169 Clover Hill Dr, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,809 Sq Ft
  • Built 1977

  Last Sold Summary

  • 4% Below List Price
  • $719/SF
  • 9 Days On Market

  Current Estimated Value $1,418,628

  Last Listing Agent Stephanie Roache Donnelly + Co

  169 Clover Hill Dr, Vineyard Haven, MA 02568
• 

  

  /2

  Est $1,032,845

  Not Listed For Sale

  299 Franklin St, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,286 Sq Ft
  • Built 1950

  299 Franklin St, Vineyard Haven, MA 02568
• 

  

  

  /35

  $2,325,000

  $270K PRICE DROP Under Contract

  • 4 Beds
  • 4 Baths
  • 2,288 Sq Ft

  54 Amelias Crossing, Vineyard Haven, MA 02568

  COASTAL CHIC RETREAT IN VINEYARD HAVEN. Located less than five blocks from Main Street in Vineyard Haven, this classically styled home is perfectly positioned for easy access to restaurants, shops, the harbor, and the ferry, offering the ideal blend of in-town convenience, relaxed island living, and timeless Vineyard appeal. The open-designed living area flows seamlessly to the outdoor living

  

  Wendy Harman

  Compass | Point B

  54 Amelias Crossing, Vineyard Haven, MA 02568
• 

  

  /27

  $18,840 Per Month

  • 3 Beds
  • 2.5 Baths
  • House for Rent

  21 William St Vh430, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,710. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely elegant home with wonderful art and furnishings. Once you step in the front door you will fall in love with this lovely home. Each room is a delight. Large nicely appointed kitchen with easy access to a beautiful dining room. A formal living room is next to a less

  Karen Overtoom Karen M. Overtoom R.E.

  21 William St Vh430, Tisbury, MA 02568
• 

  /2

  $525,000

  Sold May 29, 2026

  0 Lyle Ln Unit 2A, Vineyard Haven, MA 02568

  • Land
  • 31,180 Sq Ft
  • $733,445 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK

  0 Lyle Ln Unit 2A, Vineyard Haven, MA 02568
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  /2

  Est $1,389,002

  Not Listed For Sale

  45 Pine Tree Ln, Vineyard Haven, MA 02568

  • 3 Beds
  • 3 Baths
  • 1,400 Sq Ft
  • Built 1961

  45 Pine Tree Ln, Vineyard Haven, MA 02568
• 

  

  /9

  $1,395,000

  Open Sat 12PM - 3PM $100K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,304 Sq Ft

  33 Alyssa Ln, Vineyard Haven, MA 02568

  Country Living so close to Town! Lovely 4 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space . Open kitchen, dining & entertainment area. Sliders open to Large side deck. High Ceilings Wood floors Living Room with additional nook. Half bath. Interior stairs to lower level with office/bedroom, half bath, private exterior entrance and garage. 2nd floor has large primary

  

  Stephanie Burke

  Portfolio Properties

  33 Alyssa Ln, Vineyard Haven, MA 02568
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  /34

  $25,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • 2,334 Sq Ft
  • House for Rent

  100 Connie's Way Vh401, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,250. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

  Karen Overtoom Karen M. Overtoom R.E.

  100 Connie's Way Vh401, Tisbury, MA 02568
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  /26

  $1,935,000

  Sold May 06, 2026

  34 Davis St, Tisbury, MA 02568

  • 3 Beds
  • 3.5 Baths
  • 2,453 Sq Ft
  • Built 2025

  Last Sold Summary

  • 19% Below List Price
  • $789/SF
  • 160 Days On Market

  Last Listing Agent Andrew McElhinney Compass LLC

  34 Davis St, Tisbury, MA 02568
• 

  

  /5

  Est $2,552,473

  Not Listed For Sale

  21 Old Oklahoma Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 1,657 Sq Ft
  • Built 1948

  21 Old Oklahoma Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK
• 

  

  /12

  $750,000

  Under Contract

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft

  52 Summer St, Vineyard Haven, MA 02568

  "Sandcastle" has been lovingly enjoyed by the current owner for the past 20 years. This charming one-bedroom, one-bath cottage (NOT in the Nitrogen Management Overlay District) features, an open living room, kitchen area and a cozy office nook—ideal for working remotely. A deck just off the kitchen provides the perfect spot for outdoor dining, morning coffee, or relaxing in the fresh Vineyard

  Susie Wallo Compass LLC

  52 Summer St, Vineyard Haven, MA 02568
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  /12

  $7,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,435 Sq Ft
  • House for Rent

  43 Edgartown Rd, Vineyard Haven, MA 02568

  Located off of Edgartown-Vineyard Haven Road, close to down-town and bike path, this 3 bedroom, 2 bath property is being offered year round to the right tenants. The home has been completely renovated, is being offered fully furnished and features an open floor plan with wood floors on the first level, wall to wall carpet in the upstairs bedrooms and an in-ground pool in the backyard. Available

  Karen Overtoom Karen M. Overtoom R.E.

  43 Edgartown Rd, Vineyard Haven, MA 02568
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  /27

  $1,560,000

  Sold Jan 15, 2026

  36 Ferro Way, Tisbury, MA 02568

  • 5 Beds
  • 3.5 Baths
  • 4,032 Sq Ft
  • Built 2020

  Last Sold Summary

  • 4% Below List Price
  • $387/SF
  • 37 Days On Market

  Current Estimated Value $1,690,530

  Last Listing Agent Hope O'Brien Compass LLC

  36 Ferro Way, Tisbury, MA 02568
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  /35

  Est $1,243,750

  Not Listed For Sale

  29 Dunham Ave, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,368 Sq Ft
  • Built 1965

  29 Dunham Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK
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  /21

  $1,895,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,864 Sq Ft

  Unlisted Address

  Rarely does such a unique, waterfront location become available. With amazing, 180+ degree views of the lagoon from one side of the property, and the Vineyard Haven Harbor on the north side of the property. Wake up to glorious sunrises. Be entertained by a variety of waterfowl throughout the seasons. Have your vessel at the ready right off the shore. The moment you walk onto the property, the

  Michele Moore Island Real Estate

  Unlisted Address
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  /8

  $17,500 Per Month

  • 8 Beds
  • 4.5 Baths
  • 3,876 Sq Ft
  • House for Rent

  550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!!!!!! Classic vineyard cottage with large open indoor and outdoor spaces to choose from while you and your family create memories to last a lifetime. Enjoy creating appetizers or three course meals in the newly renovated kitchen, bask in the light filled sun room or one of several covered porches while you take in the smell of fresh ocean air and relaxing

  Karen Overtoom Karen M. Overtoom R.E.

  550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568
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  /26

  $800,000

  Sold Jun 04, 2026

  17 Mariner Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1983

  Last Sold Summary

  • 11% Below List Price
  • $694/SF
  • 32 Days On Market

  Current Estimated Value $867,058

  Last Listing Agent Karl Olsen Carlson & Company, LLC

  17 Mariner Rd, Vineyard Haven, MA 02568
• 

  

  /13

  Est $803,570

  Not Listed For Sale

  32 Clark Ave, Vineyard Haven, MA 02568

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1968

  32 Clark Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Diana Gilmore Island Real Estate
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  /39

  $3,295,000

  • 5 Beds
  • 4 Baths
  • 2,330 Sq Ft

  29 and 33 Lagoon Pond Rd, Tisbury, MA 02568

  Rare Downtown Vineyard Haven Compound Offering! An exceptional opportunity to own two separate properties being offered together in the heart of Vineyard Haven. Just moments from the ferry terminal, restaurants, shops, and the harbor, this unique package offers the ideal blend of luxury living, investment potential, and an amenity that is nearly impossible to find in town with expansive parking.

  Madelyn Silvia Wallace & Co. Sotheby's International Realty

  29 and 33 Lagoon Pond Rd, Tisbury, MA 02568
• 

  

  /18

  $10,000 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft
  • House for Rent

  100 Franklin Terrace Vh411, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming 3 bedroom home offers open living, dining and kitchen space that open to a screened-in porch and patio. You are located in a peaceful setting yet with-in walking distance to Lake Tashmoo, town beaches, and the Vineyard Haven Village for dining, shopping and

  Karen Overtoom Karen M. Overtoom R.E.

  100 Franklin Terrace Vh411, Tisbury, MA 02568
• 

  

  /26

  $1,800,000

  Sold Oct 15, 2025

  82 Skiff Ave, Tisbury, MA 02568

  • 3 Beds
  • 3.5 Baths
  • 1,913 Sq Ft
  • Built 2020

  Last Sold Summary

  • 10% Below List Price
  • $941/SF
  • 128 Days On Market

  Current Estimated Value $1,758,122

  Last Listing Agent Lenny Altieri Premier Properties

  82 Skiff Ave, Tisbury, MA 02568
• 

  

  /18

  Est $683,950

  Not Listed For Sale

  5 Village Ct Unit 3, Vineyard Haven, MA 02568

  • 2 Beds
  • 1 Bath
  • 658 Sq Ft
  • Built 1972

  5 Village Ct Unit 3, Vineyard Haven, MA 02568

  Last Sold Summary

  • 87 Days On Market

  Last Listing Agent Martha Smith C McManus Realty Group
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  /38

  $1,325,000

  $25K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,714 Sq Ft

  116 Franklin Terrace, Vineyard Haven, MA 02568

  Nestled on a quiet street just moments from the heart of Vineyard Haven, this well-maintained 4 BR, 3 BA home offers a winning blend of comfort, privacy, and classic island appeal. The sun-filled main level features an open-concept living area flowing seamlessly into a bright, updated kitchen with center island, ideal for everyday living and casual entertaining. Two 1st floor bedrooms and a full

  Pricila Ray Keller Wiliams Realty Cape Cod & Colonial Partners

  116 Franklin Terrace, Vineyard Haven, MA 02568
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  /25

  $10,800 Per Month

  • 2 Beds
  • 4 Baths
  • 1,800 Sq Ft
  • House for Rent

  256 Sandpiper Lane Vh417, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This well appointed condo will make you feel comfortable and at home the moment you walk in. Swimming, kayaking, tennis, walking trails, and shopping are all at your finger tips. Mink Meadows Golf Course is just a stroll down the street as well. Enjoy all the Island has

  Karen Overtoom Karen M. Overtoom R.E.

  256 Sandpiper Lane Vh417, Tisbury, MA 02568
• 

  

  /16

  $530,000

  Sold Aug 07, 2026

  124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568

  • 2 Beds
  • 1 Bath
  • 704 Sq Ft
  • Built 1953

  Last Sold Summary

  • 19% Below List Price
  • $753/SF
  • 270 Days On Market

  Current Estimated Value $612,029

  Last Listing Agent Rene Jackson Island Real Estate

  124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
• 

  /2

  Est $6,838,254

  Not Listed For Sale

  103 Main St, Vineyard Haven, MA 02568

  • 5 Beds
  • 6 Baths
  • 6,546 Sq Ft
  • Built 2008

  103 Main St, Vineyard Haven, MA 02568
• 

  

  /37

  $3,999,999

  $500K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,715 Sq Ft

  94 Weaver Ln, Vineyard Haven, MA 02568

  Perched high above Lagoon Pond, this exceptional Martha's Vineyard estate offers a rare convergence of natural beauty, refined comfort, and Island living at its finest. Set on 2.25 secluded acres, panoramic views stretch across the shimmering waters, a private haven for kayaking, sailing, and peaceful exploration. Inside, four bedrooms and three full bathrooms are complemented by generous windows

  Emma Kennedy Sandpiper Realty, Inc.

  94 Weaver Ln, Vineyard Haven, MA 02568
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  /15

  $7,500 Per Month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  83 Ashtons Way, Vineyard Haven, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $1,875. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This two bedroom cottage is set in a private setting in the woods, just a short distance to downtown Vineyard Haven. Sleeps four comfortably, open living space, deck and outside shower. If rented with the main house, access to private association beach and golf would be

  Karen Overtoom Karen M. Overtoom R.E.

  83 Ashtons Way, Vineyard Haven, MA 02568
• 

  /2

  $505,000

  Sold Sep 26, 2025

  02 John Hoft Rd Unit 2, Tisbury, MA 02568

  • Land
  • 1.3 Acres
  • $388,462 per Acre

  Last Sold Summary

  • 5% Below List Price
  • 120 Days On Market

  Last Listing Agent Tony Tobia Tobia Real Estate, LTD

  02 John Hoft Rd Unit 2, Tisbury, MA 02568
• 

  

  /19

  Not Listed For Sale

  43 Look St, Vineyard Haven, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 1,714 Sq Ft
  • Built 1900

  43 Look St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Andrew McElhinney Compass LLC
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  /19

  $7,950,000

  $3M PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 2,794 Sq Ft

  33 Goethals Way, Vineyard Haven, MA 02568

  A rare opportunity -- a Vineyard harbor front property with a Victorian gambrel cottage restored to its original grandeur of a century ago, an expansive front yard, 180 degree commanding views of the active harbor, private sandy beach, and unmatched serenity. You have the opportunity to own one of the finest estates gracing the Vineyard Haven harbor front -- so admired by all visitors to the

  Buder Team Sandpiper Realty, Inc.

  33 Goethals Way, Vineyard Haven, MA 02568
• 

  

  /17

  $12,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • House for Rent

  223 Sandpiper Lane Vh405, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three bedroom two bath condo is just a short walk to association tennis, pool and the beach. Comfortable easy summer living with outdoor shower, spacious deck, and central AC for those really hot August days!Amenities include Direct TV DVD set up. There is an open

  Karen Overtoom Karen M. Overtoom R.E.

  223 Sandpiper Lane Vh405, Tisbury, MA 02568
• 

  

  /38

  $1,500,000

  Sold Jan 23, 2026

  128 W Spring St, Vineyard Haven, MA 02568

  • 5 Beds
  • 3.5 Baths
  • 2,436 Sq Ft
  • Built 2013

  Last Sold Summary

  • 14% Below List Price
  • $616/SF
  • 145 Days On Market

  Current Estimated Value $1,180,390

  Last Listing Agent David Dickinson Compass

  128 W Spring St, Vineyard Haven, MA 02568
• 

  

  /10

  Est $991,817

  Not Listed For Sale

  345 Franklin St, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,012 Sq Ft
  • Built 1986

  345 Franklin St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Nora Jardin Island Real Estate
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  /39

  $4,050,000

  $645K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 2,606 Sq Ft

  95 Hines Point Rd, Vineyard Haven, MA 02568

  A rare opportunity, this Hines Point waterfront compound offers expansive views of the Lagoon and 100 feet of private beach. The home was built and has been enjoyed by the same family for gathering and summer recreation over generations. The main house offers an open first floor layout with high ceilings and large windows facing the water where you can watch sunrise over the water. A first floor

  Elissa Lash Tea Lane Associates

  95 Hines Point Rd, Vineyard Haven, MA 02568
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  /35

  $112,000 Per Month

  • 6 Beds
  • 9 Baths
  • 5,732 Sq Ft
  • House for Rent

  31 Lamberts Cove Road Vh434, Tisbury, MA 02568

  Karen Overtoom Karen M. Overtoom R.E.

  31 Lamberts Cove Road Vh434, Tisbury, MA 02568
• 

  

  /6

  $160,000

  Sold Aug 03, 2026

  60 Beach Rd Unit 240 - Building 2 -, Vineyard Haven, MA 02568

  • 1 Bed
  • 1 Bath
  • 381 Sq Ft
  • Built 1958

  Last Sold Summary

  • 11% Below List Price
  • $420/SF
  • 0 Days On Market

  Last Listing Agent Rene Jackson Island Real Estate

  60 Beach Rd Unit 240 - Building 2 -, Vineyard Haven, MA 02568
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  /38

  Est $2,017,870

  Not Listed For Sale

  83 Dolan Ave, Vineyard Haven, MA 02568

  • 5 Beds
  • 4.5 Baths
  • 3,841 Sq Ft
  • Built 1994

  83 Dolan Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Courtney Marek Sandpiper Realty

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