11,368

Vineyard Haven, MA Homes

Section Image
  • /31

    $5,995,000

    • 3 Beds
    • 3 Baths
    • 2,234 Sq Ft

    43 Sengekontacket Rd, Oak Bluffs, MA 02557

    Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside

    Peyton Wallace Studio Realty

    43 Sengekontacket Rd, Oak Bluffs, MA 02557
  • /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
  • /3

    $665,000

    Sold Mar 06, 2026

    2 Hope's Way Unit 31, Oak Bluffs, MA 02557

    • Land
    • 11,133 Sq Ft
    • $2,601,721 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 37 Days On Market

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    2 Hope's Way Unit 31, Oak Bluffs, MA 02557
    • /10

      Est $944,009

      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

  • /6

    $599,000

    • Land
    • 3,049 Sq Ft
    • $8,557,143 per Acre

    112 Dukes County Ave, Oak Bluffs, MA 02557

    Downtown Oak Bluffs B1-zoned parcel offering a rare mixed-use development opportunity in one of Martha's Vineyard's most iconic and active locations. Conveniently located near Inkwell Beach, Oak Bluffs Harbor, the Steamship Authority, day-trip ferry services, Circuit Avenue, and Ocean Park.This level lot includes an existing poured concrete foundation and MVC-approved plans by Sullivan &

    Rose Ryley Wallace & Co. Sotheby's International Realty

    112 Dukes County Ave, Oak Bluffs, MA 02557
  • /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
  • /2

    $880,000

    Sold Oct 17, 2025

    5 Johns Way, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 1,365 Sq Ft
    • Built 1987

    Last Sold Summary

    • $645/SF
    • 0 Days On Market

    Current Estimated Value $1,003,652

    Last Listing Agent LINK Email Cache LINK

    5 Johns Way, Oak Bluffs, MA 02557
    • /38

      Est $2,020,751

      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

  • /9

    $1,395,000

    $600K PRICE DROP
    • 0.5 Baths
    • 1,283 Sq Ft

    4 Lagoon Pond Rd, Vineyard Haven, MA 02568

    Located at the five corners, this rare commercial property presents an opportunity to set your future business venture up for success. This prime location captures the attention of every single vehicle disembarking the Vineyard Haven Ferry! There are 2.5 parking spots included. Please note that the bike shop business is not for sale. This offering is solely for the real estate. The sellers

    Jarrett Hurwitz Keller Williams Realty

    4 Lagoon Pond Rd, Vineyard Haven, MA 02568
  • /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
  • /2

    $1,390,000

    Sold Jul 22, 2025

    57 Colonial Dr, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,299 Sq Ft
    • Built 1984

    Last Sold Summary

    • $1,070/SF
    • 0 Days On Market

    Current Estimated Value $1,145,136

    Last Listing Agent LINK Email Cache LINK

    57 Colonial Dr, Vineyard Haven, MA 02568
    • /2

      Est $2,759,984

      Not Listed For Sale

      89 Main St, Vineyard Haven, MA 02568

      • 4 Beds
      • 5 Baths
      • 2,728 Sq Ft
      • Built 1830
      89 Main St, Vineyard Haven, MA 02568

  • /47

    $5,450,000

    • 4 Beds
    • 5.5 Baths
    • 3,300 Sq Ft

    8 Paddock Rd, Oak Bluffs, MA 02557

    Refined Vineyard Living in The Preserve - Set atop a knoll overlooking sweeping grassland and the pond, this exceptional residence embodies the perfect balance of classic coastal architecture and modern sophistication. Located within the prestigious enclave of The Preserve, the home offers a combination of privacy, elegance, and seamless indoor-outdoor living. At its core, an expansive great room

    Lesley Heidt Sandpiper Realty

    8 Paddock Rd, Oak Bluffs, MA 02557
  • /41

    $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
  • /30

    $1,050,000

    Sold Oct 06, 2025

    4 Quail Run Unit 2, Oak Bluffs, MA 02557

    • 2 Beds
    • 1.5 Baths
    • 1,323 Sq Ft
    • Built 1972

    Last Sold Summary

    • 11% Below List Price
    • $794/SF
    • 62 Days On Market

    Current Estimated Value $1,052,291

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    4 Quail Run Unit 2, Oak Bluffs, MA 02557
    • /31

      Est $1,445,421

      Not Listed For Sale

      48 Puritan Dr, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,999 Sq Ft
      • Built 1985
      48 Puritan Dr, Vineyard Haven, MA 02568

      Last Sold Summary

      • 25 Days On Market

  • /58

    $2,895,000

    • 5 Beds
    • 4 Baths
    • 2,300 Sq Ft

    27 Spring St, Vineyard Haven, MA 02568

    Located in the William Street Historic District, this elegant Greek Revival home, built in 1842, has stood the test of time and has been thoughtfully expanded and renovated in recent years. This five-bedroom, four-bath residence combines historic character with modern comforts. The home features a gracious living room, dining room, office, and an inviting kitchen/breakfast room. There are five

    Alexis Holden Tea Lane Associates

    27 Spring St, Vineyard Haven, MA 02568
  • /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
  • /36

    $2,900,000

    Sold Mar 30, 2026

    63 Bayes Hill Rd, Oak Bluffs, MA 02557

    • 4 Beds
    • 5 Baths
    • 5,165 Sq Ft
    • Built 1988

    Last Sold Summary

    • $561/SF
    • 35 Days On Market

    Current Estimated Value $2,879,613

    Last Listing Agent Casandra Hyland Sandpiper Realty, Inc.

    63 Bayes Hill Rd, Oak Bluffs, MA 02557
    • /14

      Est $1,529,527

      Not Listed For Sale

      13 Saddle Club Rd, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 2,717 Sq Ft
      • Built 1988
      13 Saddle Club Rd, Edgartown, MA 02539

      Last Sold Summary

      • 43 Days On Market

  • /20

    $899,000

    • 2 Beds
    • 1 Bath
    • 990 Sq Ft

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

    In the heart of Downtown Oak Bluffs this Restless Winds Penthouse condominium Unit #4 on 2nd floor comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a nautical feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest

    Lisa Lucier Anchor Realty of MV

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
  • /19

    $30,000 Per Month

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

    37 Sachem Cir, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself

    Karen Overtoom Karen M. Overtoom R.E.

    37 Sachem Cir, West Tisbury, MA 02575
  • /23

    $1,800,000

    Sold Aug 26, 2025

    12 Martha's Park Rd, Oak Bluffs, MA 02557

    • 4 Beds
    • 1.5 Baths
    • 1,351 Sq Ft
    • Built 1910

    Last Sold Summary

    • 1% Below List Price
    • $1,332/SF
    • 0 Days On Market

    Current Estimated Value $1,802,199

    Last Listing Agent Michele Moore Island Real Estate

    12 Martha's Park Rd, Oak Bluffs, MA 02557
    • /32

      Est $1,789,852

      Not Listed For Sale

      11 Pine Tree Ln, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,240 Sq Ft
      • Built 1960
      11 Pine Tree Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 179 Days On Market

  • /10

    $3,995,000

    • Land
    • 1.92 Acres
    • $2,083,985 per Acre

    98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568

    Farm Neck Golf Club – Undeveloped Water View Parcel with Membership A truly rare opportunity to acquire a 1.92-acre undeveloped parcel within the prestigious Farm Neck Golf Club community, one of the last remaining opportunities of its kind. This exceptional offering features sweeping water views over Sengekontacket Pond to the Vineyard Sound, creating a stunning backdrop for your future Martha’s

    Andrew McElhinney Compass LLC

    98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568
  • /34

    $12,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft
    • House for Rent

    267 Great Plains Road Wt117, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Large spacious home with open concept living and dining area. This house has gorgeous hardwood floors throughout, separate media room, and loads of natural sunlight. It also features an exceptionally large master bedroom with en-suite bath, and private deck. There is

    Karen Overtoom Karen M. Overtoom R.E.

    267 Great Plains Road Wt117, West Tisbury, MA 02575
  • /12

    $860,000

    Sold Feb 09, 2026

    8 Hitchings Cir, Oak Bluffs, MA 02557

    • 2 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1985

    Last Sold Summary

    • 6% Below List Price
    • $698/SF
    • 22 Days On Market

    Last Listing Agent Peyton Wallace Studio Realty

    8 Hitchings Cir, Oak Bluffs, MA 02557
    • /2

      Est $957,142

      Not Listed For Sale

      84 Pine Tree Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,116 Sq Ft
      • Built 1980
      84 Pine Tree Rd, Vineyard Haven, MA 02568

  • /4

    $809,000

    • Land
    • 16,988 Sq Ft
    • $2,074,359 per Acre

    7 Highland Ave, Vineyard Haven, MA 02568

    Rare opportunity in East Chop. Beautiful lot in a serene, wooded area, walking distance to town, beach, and ferries. Secluded yet accessible. This is a pre-existing nonconforming lot, with a legal opinion letter attached stating buildability. Buyer to perform all due diligence regarding town building requirements. Opportunity for buyer to design to their own specifications.

    Shera Toledo eXp Realty, LLC

    7 Highland Ave, Vineyard Haven, MA 02568
  • /14

    $14,200 Per Month

    • 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
  • /31

    $1,685,000

    Sold Oct 09, 2025

    126 Border Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 3 Baths
    • 2,251 Sq Ft
    • Built 1979

    Last Sold Summary

    • 16% Below List Price
    • $749/SF
    • 337 Days On Market

    Current Estimated Value $1,847,030

    Last Listing Agent Natalie Conroy Conroy & Company R.E., Inc.

    126 Border Rd, Vineyard Haven, MA 02568
    • /2

      Est $1,466,708

      Not Listed For Sale

      23 Anthiers Way, Edgartown, MA 02539

      • 4 Beds
      • 3 Baths
      • 2,066 Sq Ft
      • Built 1950
      23 Anthiers Way, Edgartown, MA 02539

  • /33

    $1,725,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,588 Sq Ft

    225 Lamberts Cove Rd, Vineyard Haven, MA 02568

    This year-round home, situated less than half a mile from Lambert’s Cove Beach, boasts fine craftsmanship and character in a peaceful, wooded environment. Inside, the open living room features wide plank floors, cathedral ceilings with beams, and a central brick fireplace that connects seamlessly to the updated kitchen.

    Brenda Galligan Karen M. Overtoom R.E.

    225 Lamberts Cove Rd, Vineyard Haven, MA 02568
  • /28

    $38,000 Per Month

    • 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
  • /19

    $980,000

    Sold Aug 11, 2025

    249 County Rd, Oak Bluffs, MA 02557

    • 1 Bed
    • 2 Baths
    • 1,401 Sq Ft
    • Built 2005

    Last Sold Summary

    • 7% Below List Price
    • $700/SF
    • 83 Days On Market

    Current Estimated Value $1,039,384

    Last Listing Agent Katherine Donahue Sandpiper Realty

    249 County Rd, Oak Bluffs, MA 02557
    • /32

      Est $2,416,214

      Not Listed For Sale

      232 Lagoon Pond Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 4 Baths
      • 2,276 Sq Ft
      • Built 1970
      232 Lagoon Pond Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 220 Days On Market

  • /20

    $640,000

    • 1 Bed
    • 1 Bath
    • 354 Sq Ft

    2 Lincoln Ave, Oak Bluffs, MA 02568

    Nestled in the heart of the historic Martha’s Vineyard Camp Meeting Association, this beautifully updated suite cottage offers the rare opportunity for year-round living in Oak Bluffs’ campground community. Fully renovated in 2023, including kitchen, bath, floors and winterization, the home seamlessly blends classic Vineyard charm with modern comfort — featuring upgraded systems and finishes that

    Stacy Ickes Donnelly + Co.

    2 Lincoln Ave, Oak Bluffs, MA 02568
  • /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
  • /2

    $825,000

    Sold Dec 03, 2025

    69 Summit Ave, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 1998

    Last Sold Summary

    • $661/SF
    • 1 Day On Market

    Current Estimated Value $852,061

    Last Listing Agent Susie Wallo Compass

    69 Summit Ave, Vineyard Haven, MA 02568
    • /2

      Est $1,717,360

      Not Listed For Sale

      323 Lamberts Cove Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,144 Sq Ft
      • Built 1900
      323 Lamberts Cove Rd, Vineyard Haven, MA 02568

Showing Results 121 - 160, Page 4 of 18

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