Vineyard Haven Homes

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  $1,495,000 Open Fri 12PM - 3PM

  • 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

  (508) 687-6441

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

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  /16

  $5,000 per month

  • 1 Bath
  • 400 Sq Ft
  • House for Rent

  90 Edgartown Rd, Vineyard Haven, MA 02568

  *Summer Weekly Rate** Inquire For Long-term Off-Season Rates. Renovated Studio Cottage on Martha's Vineyard w/private feel. Within walking distance to shops, dining, and the ferry. Lots of trees for year-round enjoyment. Open floor plan with Murphy bed for additional space and a large comfortable sofa, galley kitchen with granite countertops, stainless steel appliances, amazing tiled bathroom

  Kim Seawright Generations Realty Group

  90 Edgartown Rd, 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

  Current Estimated Value $1,337,071

  Last Listing Agent Stephanie Roache Donnelly + Co

  169 Clover Hill Dr, Vineyard Haven, MA 02568
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  Est $1,380,281 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

  Last Sold Summary

  • 12% Below List Price
  • $884/SF

  • Last Sold Price $1,237,500

  Last Listing Agent Sheila Morse Island Real Estate
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  /26

  $1,999,000 Pending

  • 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 LLC

  34 Davis St, Tisbury, 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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  /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 $1,678,573

  Last Listing Agent Lenny Altieri Premier Properties

  82 Skiff Ave, Tisbury, MA 02568
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  /5

  Est $2,374,536 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

  • 1% Below List Price
  • $1,447/SF
  • 0 Days On Market

  • Last Sold Price $2,398,500
  • Dec 19, 2024

  Last Listing Agent LINK Email Cache LINK
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  /41

  $1,975,000

  • 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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  /21

  $9,500 per month

  • 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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  $1,325,000 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 $1,296,533

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

  191 Spring Hill Rd, Vineyard Haven, MA 02568
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  Est $1,812,977 Not Listed For Sale

  179 Main St, Vineyard Haven, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 1 Sq Ft
  • Built 1840

  179 Main St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 18% Above List Price
  • $1,535,625/SF
  • 14 Days On Market

  • Last Sold Price $1,535,625
  • Jul 14, 2023

  Last Listing Agent Judy Federowicz Landmarks at TODAY Real Estate
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  /24

  $2,925,000

  • 5 Beds
  • 4 Baths
  • 3,704 Sq Ft

  21 Davis St, Vineyard Haven, MA 02568

  Ideally located just minutes from the heart of Vineyard Haven, 21 Davis Street offers exceptional island living in this beautifully crafted five-bedroom, four-bathroom home with 3,704 square feet of thoughtfully designed living space. Rich hardwood flooring, custom cabinetry, elegant Restoration Hardware vanities, and custom tilework throughout the bathrooms reflect the care and craftsmanship the

  Paul Pertile The Agency

  21 Davis St, Vineyard Haven, MA 02568
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  $13,500 per month

  • 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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  /25

  $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 $965,478

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

  345 Franklin St, Vineyard Haven, MA 02568
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  Est $1,228,845 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

  • 1% Above List Price
  • $892/SF
  • 0 Days On Market

  • Last Sold Price $1,220,000
  • Jul 26, 2024

  Last Listing Agent LINK Email Cache LINK
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  $3,990,000

  • 5 Beds
  • 5 Baths
  • 5,598 Sq Ft

  71 Stoney Hill Rd, Vineyard Haven, MA 02568

  A combination of luxury, comfort, and natural beauty, this expansive custom, five bedroom, post and beam home is sited on more than eight acres of land, surrounded by acres of Land Bank property. From the moment you step inside, you'll be captivated by the attention to detail and the high-end finishes throughout. The open concept layout allows for seamless flow from one room to the next, perfect

  Sheila Morse Island Real Estate

  71 Stoney Hill Rd, Vineyard Haven, MA 02568
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  $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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  $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 $1,180,142

  Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

  160 Bernard Cir, Vineyard Haven, MA 02568
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  /13

  Est $839,038 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

  • 8% Above List Price
  • $1,011/SF
  • 17 Days On Market

  • Last Sold Price $776,500
  • Mar 05, 2025

  Last Listing Agent Diana Gilmore Island Real Estate
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  /4

  $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. Featuring 4 spacious bedrooms, 4 full and one half bath. This thoughtfully designed home offers generous space. Step outside into your private oasis, complete with an in-ground pool (36' x18') — perfect for sun-soaked afternoons and evening gatherings. Situated in a

  Lisa Gilberto C McManus Realty Group

  9 Hagerty Dr, Tisbury, MA 02568
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  $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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  $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 $1,086,499

  Last Listing Agent Katherine Donahue Sandpiper Realty Inc

  112 W Spring St, Vineyard Haven, MA 02568
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  Est $659,510 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

  • 7% Above List Price
  • $935/SF
  • 87 Days On Market

  • Last Sold Price $615,000
  • Dec 17, 2024

  Last Listing Agent Martha Smith C McManus Realty Group
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  $2,495,000

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft

  268 Tashmoo Ave, Vineyard Haven, MA 02568

  Welcome to this meticulously maintained home which features an attractive open kitchen with an island that seats four. The kitchen has a wall of built in appliances and a walk-in pantry for ease of cooking. The kitchen flows into the open dining area and lounge area with a wall of sliding glass doors that lead to the large outdoor entertaining area which features a lounge area and two eating

  Michele Casavant Vineyard Village Realty

  268 Tashmoo Ave, Vineyard Haven, MA 02568
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  $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
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  $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 $1,178,574

  Last Listing Agent Sheila Morse Island Real Estate

  31 Davis St, Vineyard Haven, MA 02568
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  Est $4,624,402 Not Listed For Sale

  225 Bigelow Rd, Vineyard Haven, MA 02568

  • 5 Beds
  • 8 Baths
  • 5,305 Sq Ft
  • Built 1976

  225 Bigelow Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 13% Above List Price
  • $773/SF
  • 56 Days On Market

  • Last Sold Price $4,100,000
  • Jul 31, 2023

  Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's International Realty
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  $1,950,000

  • 2 Beds
  • 2.5 Baths
  • 1,460 Sq Ft

  378 State Rd, Vineyard Haven, MA 02568

  MIXED USE PROPERTY WITH PROFESSIONAL OFFICES AND TWO-BEDROOM APARTMENT - Extensively renovated mixed-use property offering commercial + residential use in a high-visibility location on State Road in Tisbury. This versatile property presents a true live-work opportunity with strong income-producing potential.The first floor offers four offices including a reception area, 1.5 baths, and a

  Lesley Heidt Sandpiper Realty Inc

  378 State Rd, Vineyard Haven, MA 02568
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  /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
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  $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 $6,249,791 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

  Last Sold Summary

  • 48% Below List Price
  • $1,833/SF
  • 202 Days On Market

  • Last Sold Price $12,000,000
  • Apr 17, 2024

  Last Listing Agent Tom Wallace Wallace & Co. Sotheby's International Realty
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  $2,250,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,867 Sq Ft

  237 Lagoon Pond Rd, Vineyard Haven, MA 02568

  Ideally located at the beginning of Hines Point, this light-filled, well-maintained home offers a central setting with easy access to the Lagoon, the MV Museum, and town. Public water access is just a short walk away, making it easy to enjoy all the benefits of this special area.Set on a gentle rise overlooking the Lagoon, the home is filled with natural light and offers beautiful water

  Alison Rich Carroll & Vincent R.E.

  237 Lagoon Pond Rd, 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
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  $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 $1,253,266

  Last Listing Agent David Dickinson Compass

  128 W Spring St, Vineyard Haven, MA 02568
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  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

  • $592/SF
  • 19 Days On Market

  • Last Sold Price $1,015,000
  • Apr 16, 2024

  Last Listing Agent Andrew McElhinney Compass LLC
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  /46

  $1,975,000

  • 3 Beds
  • 2.5 Baths
  • 1,902 Sq Ft

  81 Leland Ave, Vineyard Haven, MA 02568

  Close to town with exceptional indoor / outdoor flow & privacy.Consider this beautifully designed home just minutes from town. The first floor features a bright, open kitchen + dining area flowing into a welcoming living room with a fireplace. From there, step onto a spacious deck—ideal for al fresco dining and lounging—complete with direct access to a hot tub and nearby outdoor

  Jill Napior Tea Lane Associates

  81 Leland Ave, 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
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  /30

  $1,525,000 Sold Jun 18, 2025

  54 Lake St, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 2,016 Sq Ft
  • Built 1967

  Last Sold Summary

  • 12% Below List Price
  • $756/SF
  • 110 Days On Market

  Current Estimated Value $1,570,313

  Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty

  54 Lake St, Vineyard Haven, MA 02568
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  Est $1,474,820 Not Listed For Sale

  101 Dunham Ave, Vineyard Haven, MA 02568

  • 5 Beds
  • 3 Baths
  • 2,287 Sq Ft
  • Built 1982

  101 Dunham Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 23% Above List Price
  • $525/SF
  • 0 Days On Market

  • Last Sold Price $1,200,000
  • Jul 07, 2023

  Last Listing Agent LINK Email Cache LINK

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