Vineyard Haven Homes

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  $1,495,000

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

  33 Alyssa Ln, Vineyard Haven, MA 02568

  Country Living so close to Town! Lovely 3/4 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space. with half bath. Open kitchen, dining & entertainment area. Large side deck. 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 bedroom with cathedral

  

  Stephanie Burke

  Portfolio Properties

  (508) 687-6441

  33 Alyssa Ln, Vineyard Haven, MA 02568
• Explore Vineyard Haven

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  /21

  $9,500 total monthly price

  • 4 Beds
  • 2 Baths
  • 1,579 Sq Ft
  • House for Rent

  155 Skiff Ave, Vineyard Haven, MA 02568

  **SUMMER RENTAL ONLY** RATE IS WEEKLY** Enjoy the serenity of a four bedroom, two full bathroom peaceful oasis complete with private in-ground pool. Close to lively dining and boutiques of downtown Vineyard Haven. Unwind at neighborhood beaches; Eastville, Owen Park, Tashmoo beaches all just a few minutes drive from your vacation retreat.This lovely home spread over 1600ft of living area provides

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  155 Skiff Ave, Vineyard Haven, MA 02568
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  $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

  Last Listing Agent Stephanie Roache Donnelly + Co

  169 Clover Hill Dr, Vineyard Haven, MA 02568
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  /2

  Est $1,388,663 Not Listed For Sale

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

  45 Pine Tree Ln, Vineyard Haven, MA 02568

  45 Pine Tree Ln, Vineyard Haven, MA 02568
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  $1,999,000

  • 4 Beds
  • 3 Baths
  • 2,730 Sq Ft

  5 Pine Tree Ln, Vineyard Haven, MA 02568

  Blending 1920s charm with modern luxury, this beautifully renovated home is tucked away in the sought-after West Chop area of Vineyard Haven. Just steps from the neighborhood beach on the pristine shores of Vineyard Sound, this elegant seaside retreat offers the perfect mix of historic character and contemporary comfort. Inside, a thoughtfully designed floor plan welcomes you with generous living

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  5 Pine Tree Ln, Vineyard Haven, MA 02568
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  $13,500 total monthly price

  • 5 Beds
  • 5.5 Baths
  • 3,000 Sq Ft
  • House for Rent

  14 Bernard Cir, Vineyard Haven, MA 02568

  ** SUMMER WEEKLY RATE ** Private and luxurious BRAND NEW contemporary chic 5 BED 5.5 BATH home perfectly situated close to downtown Vineyard Haven yet set amongst a rural and peaceful WEST CHOP adjacent neighborhood. Indulge and unwind in the PRIVATE HEATED SALTWATER IN-GROUND POOL surrounded by opulent outdoor living and dining area highlighted by covered al-fresco kitchen, BBQ grill and bar -

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  14 Bernard Cir, Vineyard Haven, MA 02568
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  $2,860,000 Sold Mar 10, 2025

  49 William St, Vineyard Haven, MA 02568

  • 5 Beds
  • 4.5 Baths
  • 3,752 Sq Ft
  • Built 1836

  Last Sold Summary

  • 12% Below List Price
  • $762/SF
  • 290 Days On Market

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's International Realty

  49 William St, Vineyard Haven, MA 02568
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  /5

  Est $2,512,811 Not Listed For Sale

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

  21 Old Oklahoma Rd, Vineyard Haven, MA 02568

  21 Old Oklahoma Rd, Vineyard Haven, MA 02568
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  $2,250,000

  • 5 Beds
  • 3.5 Baths
  • 3,250 Sq Ft

  28 Pine Tree Ln, Vineyard Haven, MA 02568

  Enjoy beach-close living—just 0.2 miles to the shore—in sought-after West Chop. This welcoming 5BR/3.5BA colonial blends classic Vineyard character with modern comforts, including central air, an updated kitchen, and three fireplaces. Approximately 3,152± sq ft (expanded from 2,632± with a 520± sq ft finished space over the garage) offers flexible, easy flow to a large fenced backyard with a

  Lisa Da Silva Compass | Point B

  28 Pine Tree Ln, Vineyard Haven, MA 02568
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  $17,500 total monthly price

  • 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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  $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 $1,646,192

  Last Listing Agent Lenny Altieri Premier Properties

  82 Skiff Ave, Tisbury, MA 02568
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  Est $1,849,834 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1 Sq Ft

  179 Main St, Vineyard Haven, MA 02568

  179 Main St, Vineyard Haven, MA 02568
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  $2,295,000

  • 4 Beds
  • 3.5 Baths
  • 2,690 Sq Ft

  151 Tashmoo Ave, Vineyard Haven, MA 02568

  The Colonial Style home with wrap around porch is beautifully maintained and nicely sited on almost a half acre. The first floor is thoughtfully designed and offers an open floor plan that includes an ample mudroom with half bath and is just off the side porch that takes you into the well equipped kitchen with a center island, stainless appliances, custom cabinetry and dining room with sliders to

  Brenda Galligan Karen M. Overtoom R.E.

  151 Tashmoo Ave, Vineyard Haven, MA 02568
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  $6,000 total monthly price

  • 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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  $1,325,000 Sold Jun 30, 2025

  191 Spring Hill Rd, Vineyard Haven, MA 02568

  • 5 Beds
  • 4 Baths
  • 2,292 Sq Ft
  • Built 1992

  Last Sold Summary

  • 5% Below List Price
  • $578/SF
  • 10 Days On Market

  Current Estimated Value $1,258,388

  Last Listing Agent Madelyn Silvia Wallace & Co. Sotheby's

  191 Spring Hill Rd, Vineyard Haven, MA 02568
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  Est $1,210,459 Not Listed For Sale

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

  29 Dunham Ave, Vineyard Haven, MA 02568

  29 Dunham Ave, Vineyard Haven, MA 02568
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  $2,995,000

  • 4 Beds
  • 4.5 Baths
  • 3,024 Sq Ft

  9 Hagerty Dr, Tisbury, MA 02568

  West Chop Dream Home in the Making!Experience the charm of this brand-new Shingle Style Colonial, currently under construction—where modern luxury meets timeless elegance. Featuring 4 spacious bedrooms, 4 full baths, and a half bath, this inviting home offers ample space for relaxing, entertaining, and everything in between. You will be wired for sound with speakers inside and poolside so

  Lisa Gilberto C McManus Realty Group

  9 Hagerty Dr, Tisbury, MA 02568
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  $18,840 total monthly price

  • 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
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  $949,000 Sold Jun 23, 2025

  345 Franklin St, Vineyard Haven, MA 02568

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

  Last Sold Summary

  • $938/SF
  • 49 Days On Market

  Current Estimated Value $938,316

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's International Realty

  345 Franklin St, Vineyard Haven, MA 02568
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  /18

  Est $644,549 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 658 Sq Ft

  5 Village Ct Unit 3, Vineyard Haven, MA 02568

  5 Village Ct Unit 3, Vineyard Haven, MA 02568
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  $1,999,000

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

  34 Davis St, Tisbury, MA 02568

  NEW CONSTRUCTION - Designed by Outlands Design and built by McElhinney Construction, this home exemplifies modern coastal design. 34 Davis Street delivers the perfect balance of sophistication and relaxed island living. Positioned to offer both privacy and proximity to the Island's harbors, shops, and beaches. Spread across two thoughtfully designed levels, the interiors are bathed in natural

  Andrew McElhinney Compass Massachusetts, LLC

  34 Davis St, Tisbury, MA 02568
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  /18

  $10,000 total monthly price

  • 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
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  $1,050,000 Sold Jun 30, 2025

  160 Bernard Cir, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,606 Sq Ft
  • Built 1977

  Last Sold Summary

  • 12% Below List Price
  • $654/SF
  • 45 Days On Market

  Current Estimated Value $1,091,009

  Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

  160 Bernard Cir, Vineyard Haven, MA 02568
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  Est $4,514,456 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 5,305 Sq Ft

  225 Bigelow Rd, Vineyard Haven, MA 02568

  225 Bigelow Rd, Vineyard Haven, MA 02568
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  $2,495,000

  • 3 Beds
  • 3.5 Baths
  • 3,530 Sq Ft

  61 Causeway Rd, Vineyard Haven, MA 02568

  Welcome to this fabulous property nestled just a short stroll from all the best of Vineyard Haven. Easily accessible and within close proximity to the ferry, downtown shops, restaurants, galleries, Owen Park Beach, and the MV Playhouse, the location is ideal. This beautifully designed home has been lovingly maintained and offers a wonderful balance of Vineyard charm and modern convenience.

  Stephanie Roache Donnelly + Co

  61 Causeway Rd, Vineyard Haven, MA 02568
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  $10,800 total monthly price

  • 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
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  $776,500 Sold Mar 05, 2025

  32 Clark Ave, Vineyard Haven, MA 02568

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

  Last Sold Summary

  • 7% Below List Price
  • $1,011/SF
  • 17 Days On Market

  Current Estimated Value $789,751

  Last Listing Agent Diana Gilmore Island Real Estate

  32 Clark Ave, Vineyard Haven, MA 02568
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  Est $7,322,137 Not Listed For Sale

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

  103 Main St, Vineyard Haven, MA 02568

  103 Main St, Vineyard Haven, MA 02568
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  /42

  $2,150,000

  • 3 Beds
  • 3 Baths
  • 1,680 Sq Ft

  33 Lagoon Pond Rd, Vineyard Haven, MA 02568

  Brand new construction in the heart of downtown Vineyard Haven! This pristine and thoughtfully designed 3-bedroom, 3-bathroom home offers modern downtown living just steps away from the ferry terminal, restaurants, shops and all that Vineyard Haven has to offer. Where luxury meets sophisticated coastal charm complete with an open floor plan, luxury kitchen featuring quartz countertops, custom

  Madelyn Silvia Wallace & Co. Sotheby's International Realty

  33 Lagoon Pond Rd, Vineyard Haven, MA 02568
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  /15

  $7,500 total monthly price

  • 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
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  /2

  $1,067,000 Sold Sep 26, 2025

  112 W Spring St, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 1,503 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $710/SF
  • 95 Days On Market

  Current Estimated Value $1,101,318

  Last Listing Agent Katherine Donahue Sandpiper Realty Inc

  112 W Spring St, Vineyard Haven, MA 02568
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  /19

  Not Listed For Sale

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

  43 Look St, Vineyard Haven, MA 02568

  43 Look St, Vineyard Haven, MA 02568
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  /19

  $10,500,000

  • 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
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  $25,000 total monthly price

  • 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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  /19

  $1,095,000 Sold May 02, 2025

  31 Davis St, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,945 Sq Ft
  • Built 1966

  Last Sold Summary

  • 2% Above List Price
  • $563/SF
  • 5 Days On Market

  Current Estimated Value $1,165,193

  Last Listing Agent Sheila Morse Island Real Estate

  31 Davis St, Vineyard Haven, MA 02568
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  /25

  Est $1,562,510 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,287 Sq Ft

  101 Dunham Ave, Vineyard Haven, MA 02568

  101 Dunham Ave, Vineyard Haven, MA 02568
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  /30

  $1,595,000

  • 5 Beds
  • 3 Baths
  • 1,810 Sq Ft

  22 Old Lighthouse Rd, Vineyard Haven, MA 02568

  Located in a quiet enclave off Main Street, Vineyard Haven and just a half-mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for entertaining. The design is casual but practical,

  Jessie Holtham Wallace & Co. Sotheby's International Realty

  22 Old Lighthouse Rd, Vineyard Haven, MA 02568
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  $12,000 total monthly price

  • 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
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  /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
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  Est $2,779,375 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 2,728 Sq Ft

  89 Main St, Vineyard Haven, MA 02568

  89 Main St, Vineyard Haven, MA 02568

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