Vineyard Haven, MA Homes

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  $5,325,000

  • 6 Beds
  • 4 Baths
  • 2,890 Sq Ft

  4 Canonicus Ave, Oak Bluffs, MA 02557

  Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  4 Canonicus Ave, Oak Bluffs, MA 02557
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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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  $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 $1,251,341

  Last Listing Agent David Dickinson Compass

  128 W Spring St, Vineyard Haven, MA 02568
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  Est $1,761,016 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

  • 15% Above List Price
  • $1,535,625/SF
  • 14 Days On Market

  Last Sold Price $1,535,625

  Last Listing Agent Judy Federowicz Landmarks at TODAY Real Estate
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  $625,000

  • Land
  • 0.34 Acre
  • $1,815,277 per Acre

  0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

  Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

  Andrew McElhinney Compass LLC

  0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
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  $32,500 total monthly price

  • 6 Beds
  • 4.5 Baths
  • 3,222 Sq Ft
  • House for Rent

  100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. 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 &83 Ashtonw Vh408, Tisbury, MA 02568
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  $1,700,000 Sold Nov 03, 2025

  35 Tower Ridge Rd, Oak Bluffs, MA 02557

  • 3 Beds
  • 4 Baths
  • 2,558 Sq Ft
  • Built 1986

  Last Sold Summary

  • 20% Below List Price
  • $665/SF
  • 118 Days On Market

  Current Estimated Value $1,741,804

  Last Listing Agent Katherine Donahue Sandpiper Realty Inc

  35 Tower Ridge Rd, Oak Bluffs, MA 02557
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  Est $1,164,790 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

  • 5% Below List Price
  • $892/SF
  • 0 Days On Market

  Last Sold Price $1,220,000

  Last Listing Agent LINK Email Cache LINK
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  $4,500,000

  • 15 Beds
  • 12.5 Baths
  • 7,250 Sq Ft

  11 Macs Ln, Tisbury, MA 02568

  A unique opportunity to own a one of a kind property complete with fourteen bedrooms, flanked with large picture windows and water views from all three living levels. Currently being run as a state licensed, private pay, assisted living facility. In addition to the fourteen bedrooms and twelve full baths and one half bath, in the main building, there is a private owners apartment on the first

  Madelyn Silvia Wallace & Co. Sotheby's International Realty

  11 Macs Ln, Tisbury, MA 02568
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  $64,000 total monthly price

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

  385 Barnes Rd Ob534, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in

  Karen Overtoom Karen M. Overtoom R.E.

  385 Barnes Rd Ob534, Oak Bluffs, MA 02557
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  $1,995,000 Sold Aug 29, 2025

  26 Box Turtle Ln, Oak Bluffs, MA 02557

  • 4 Beds
  • 3.5 Baths
  • 2,891 Sq Ft
  • Built 1980

  Last Sold Summary

  • $690/SF
  • 5 Days On Market

  Current Estimated Value $2,267,004

  Last Listing Agent Jayne Isford Ocean Park Realty Inc

  26 Box Turtle Ln, Oak Bluffs, MA 02557
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  Est $765,972 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

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

  Last Sold Price $776,500

  Last Listing Agent Diana Gilmore Island Real Estate
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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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  $20,000 total monthly price

  • 3 Beds
  • 3 Baths
  • House for Rent

  40 Hidden Cove Rd, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living room with views and bedrooms

  Karen Overtoom Karen M. Overtoom R.E.

  40 Hidden Cove Rd, Oak Bluffs, MA 02557
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  $995,000 Sold Nov 06, 2025

  2 Flamingo Dr, Edgartown, MA 02539

  • 3 Beds
  • 1 Bath
  • 990 Sq Ft
  • Built 1983

  Last Sold Summary

  • 5% Below List Price
  • $1,005/SF
  • 5 Days On Market

  Current Estimated Value $1,069,326

  Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate

  2 Flamingo Dr, Edgartown, MA 02539
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  Est $657,746 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

  Last Listing Agent Martha Smith C McManus Realty Group
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  $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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  $24,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,257 Sq Ft
  • House for Rent

  5 Laurel Ave, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage décor and beautiful bamboo floors. Entertainment options include

  Karen Overtoom Karen M. Overtoom R.E.

  5 Laurel Ave, Oak Bluffs, MA 02557
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  $1,890,000 Sold Aug 29, 2025

  1 Thames Ct, Edgartown, MA 02539

  • 4 Beds
  • 3 Baths
  • 3,270 Sq Ft
  • Built 1981

  Last Sold Summary

  • $578/SF
  • 38 Days On Market

  Current Estimated Value $2,178,740

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

  1 Thames Ct, Edgartown, MA 02539
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  Est $2,489,601 Not Listed For Sale

  23 Oak Ln, Vineyard Haven, MA 02568

  • 6 Beds
  • 4.5 Baths
  • 3,035 Sq Ft
  • Built 2007

  23 Oak Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 4% Above List Price
  • $791/SF
  • 213 Days On Market

  Last Sold Price $2,400,000

  Last Listing Agent Lynn Buder Sandpiper Realty Inc
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  $835,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  51 Lantern Ln, Vineyard Haven, MA 02568

  Find your sweet spot in this charming starter home, ideally located on a quiet street yet within an effortless walk of everything. Forget the car and get your steps in! You're a short jaunt to essentials like Cronig's Market and Shirley's Hardware, AND local favorites including The Maker, Black Dog Cafe, Island Fresh Pizza, Pie Chicks, and Island Adventures Mini Golf. Also within walking distance

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

  51 Lantern Ln, Vineyard Haven, MA 02568
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  $20,000 total monthly price

  • 4 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • House for Rent

  291 Barnes Rd Ob516, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.

  Karen Overtoom Karen M. Overtoom R.E.

  291 Barnes Rd Ob516, Oak Bluffs, MA 02557
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  $899,000 Sold Jul 11, 2025

  8 Rock Ave, Oak Bluffs, MA 02557

  • 3 Beds
  • 1.5 Baths
  • 955 Sq Ft
  • Built 1871

  Last Sold Summary

  • $941/SF
  • 6 Days On Market

  Current Estimated Value $924,470

  Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  8 Rock Ave, Oak Bluffs, MA 02557
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  Est $2,724,233 Not Listed For Sale

  5 Bold Meadow Cir, Edgartown, MA 02539

  • 4 Beds
  • 3.5 Baths
  • 3,252 Sq Ft
  • Built 1995

  5 Bold Meadow Cir, Edgartown, MA 02539

  Last Sold Summary

  • 12% Above List Price
  • $750/SF
  • 45 Days On Market

  Last Sold Price $2,438,500

  Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate
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  $610,000

  • 2 Beds
  • 1 Bath
  • 704 Sq Ft

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

  MOVE RIGHT IN! This sunny end unit is being offered furnished! Spacious living area opens to an eat-in kitchen with a new Bosch dishwasher. Bedroom number one has a queen bed. Bedroom two has two single beds. Conveniently located within close proximity to Main Street shops, the ferry and bus terminal, and the scenic bike path that extends across the island. At the bottom of the hill you will find

  Rene Jackson Island Real Estate

  124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
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  $14,200 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  59 Prospect Ave Ob502, Oak Bluffs, MA 02557

  THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. This immaculate home is located in a quiet neighborhood that is just a bike ride's distance from several lovely beaches as well as the center of Oak Bluffs. The home offers open living spaces, generously proportioned sunny bedrooms and is well equipped.

  Karen Overtoom Karen M. Overtoom R.E.

  59 Prospect Ave Ob502, Oak Bluffs, MA 02557
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  $980,000 Sold Mar 26, 2025

  11 Fairway Dr, Oak Bluffs, MA 02557

  • 2 Beds
  • 1 Bath
  • 1,608 Sq Ft
  • Built 1969

  Last Sold Summary

  • 18% Below List Price
  • $609/SF
  • 191 Days On Market

  Current Estimated Value $1,077,844

  Last Listing Agent Sandra Grymes Martha's Vineyard Island-Wide Realty

  11 Fairway Dr, Oak Bluffs, MA 02557
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  Est $4,551,446 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

  • 11% Above List Price
  • $773/SF
  • 56 Days On Market

  Last Sold Price $4,100,000

  Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's International Realty
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  $1,250,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft

  112 3rd St N, Edgartown, MA 02568

  Nestled on a lush and private parcel close to The Boulevard, this contemporary three-bedroom, two-bath residence offers the perfect blend of style and comfortable living. Highlights include a gas fireplace, wood floors, an expansive deck to relax on, and established gardens. There’s even a shed to store all your summer gear. Enjoy this oasis as is or use as a foundation for future

  Kristin Buck Donnelly + Co.

  112 3rd St N, Edgartown, MA 02568
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  $18,000 total monthly price

  • 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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  $865,000 Sold Apr 17, 2025

  4 Quail Run Rd Unit 17, Edgartown, MA 02539

  • 2 Beds
  • 2 Baths
  • 1,208 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Below List Price
  • $716/SF
  • 2 Days On Market

  Last Listing Agent Wendy Harman Compass

  4 Quail Run Rd Unit 17, Edgartown, MA 02539
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  Est $1,727,162 Not Listed For Sale

  21 Bold Meadow Ln, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,971 Sq Ft
  • Built 1991

  21 Bold Meadow Ln, Edgartown, MA 02539

  Last Sold Summary

  • 26% Above List Price
  • $698/SF
  • 34 Days On Market

  Last Sold Price $1,375,000

  Last Listing Agent Martha Smith C McManus Realty Group
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  $849,000

  • 1 Bed
  • 1 Bath
  • 803 Sq Ft

  26 Winthrop Ave, Oak Bluffs, MA 02557

  Hidden behind a wall of vegetation on Winthrop Avenue this is a little 'oasis' of a piece of land. One bedroom house situated on a 1/3 Acre, 14,810 sq.ft. level lot. One side of the property is lush with vegetation and the opposite side is clear. It is one lot in total and may not be subdivided. The existing house has been lived in year round. Only .6 of a mile to Oak Bluffs Harbor and .5 mile

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  26 Winthrop Ave, Oak Bluffs, MA 02557
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  $38,000 total monthly price

  • 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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  $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 $1,617,960

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

  54 Lake St, Vineyard Haven, MA 02568
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  Est $1,350,742 Not Listed For Sale

  46 Windsor Dr, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,520 Sq Ft
  • Built 1987

  46 Windsor Dr, Edgartown, MA 02539

  Last Sold Summary

  • 13% Above List Price
  • $786/SF
  • 22 Days On Market

  Last Sold Price $1,195,000

  Last Listing Agent Francine Agnoli The Agency Martha's Vineyard
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  $475,000

  • Land
  • 0.52 Acre
  • $913,462 per Acre

  36 Boylston Dr, Edgartown, MA 02539

  Buildable lot in an established Edgartown neighborhood. Approvals are in hand for the construction of a single-family residential structure not to exceed 3 bedrooms and not to exceed 1,850 square feet of heated living area (screened porches, patios, etc are not included in this square footage). Note that this property cannot be used as a seasonal home or short-term rental. Septic plan has been

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  36 Boylston Dr, Edgartown, MA 02539
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  $50,000 total monthly price

  • 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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  $4,150,000 Sold Feb 19, 2026

  97 Longview Rd, Vineyard Haven, MA 02568

  • 5 Beds
  • 5.5 Baths
  • 4,003 Sq Ft
  • Built 2008

  Last Sold Summary

  • 12% Below List Price
  • $1,037/SF
  • 74 Days On Market

  Last Listing Agent Stephanie Roache Donnelly + Co.

  97 Longview Rd, Vineyard Haven, MA 02568
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  Est $6,872,105 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

  • 43% Below List Price
  • $1,833/SF
  • 202 Days On Market

  Last Sold Price $12,000,000

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

Showing Results 81 - 120, Page 3 of 18