19,907

Dukes County, MA Homes

Section Image
  • /13

    $1,645,000

    • Land
    • 3.32 Acres
    • $495,482 per Acre

    26 Flint Hill Rd, West Tisbury, MA 02575

    Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides— a setting no

    Dawn Bellante Sandpiper Realty, Inc.

    26 Flint Hill Rd, West Tisbury, MA 02575
  • /20

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • House for Rent

    11 Hammett Ln, Chilmark, MA 02535

    ** WEEKLY SUMMER RATE** Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    11 Hammett Ln, Chilmark, MA 02535
  • /2

    $1,100,000

    Sold Oct 29, 2025

    11 Quammox Rd, Edgartown, MA 02539

    • 2 Beds
    • 1 Bath
    • 685 Sq Ft
    • Built 1940

    Last Sold Summary

    • $1,606/SF
    • 0 Days On Market

    Current Estimated Value $1,221,184

    Last Listing Agent LINK Email Cache LINK

    11 Quammox Rd, Edgartown, MA 02539
    • /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

  • /33

    $1,599,000

    • 3 Beds
    • 2.5 Baths
    • 1,645 Sq Ft

    7 Ploughshare Ln, Oak Bluffs, MA 02557

    Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an

    Emma Kennedy Sandpiper Realty, Inc.

    7 Ploughshare Ln, Oak Bluffs, MA 02557
  • /8

    $19,000 Per Month

    • 5 Beds
    • 5 Baths
    • 3,137 Sq Ft
    • House for Rent

    19 Morse St, Edgartown, MA 02539

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated historical home in the heart of Edgartown Village, close to Fuller Street & Lighthouse Beaches. Beautifully designed interior with open gourmet kitchen and pickled hardwood floors, marble countertops, top of the line appliances and a large center island. Cozy family room with fireplace, formal living room, office/den and a full bath all

    Karen Overtoom Karen M. Overtoom R.E.

    19 Morse St, Edgartown, MA 02539
  • /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
    • /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

  • /27

    $8,950,000

    $1M PRICE DROP
    • 5 Beds
    • 7 Baths
    • 4,078 Sq Ft

    1 Field Club Dr, Edgartown, MA 02539

    Nestled in the prestigious Field Club, this extraordinary five-bedroom compound epitomizes luxurious island living. This residence exudes timeless elegance and modern sophistication. Upon entering, the foyer sets the tone with a warm and inviting glow. The main level boasts an open-concept layout, featuring a gourmet chef's kitchen adorned with top-of-the-line appliances, granite countertops, and

    Thomas Wallace Wallace & Co. Sotheby's

    1 Field Club Dr, Edgartown, MA 02539
  • /23

    $24,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,637 Sq Ft
    • House for Rent

    56 Chilmark Rd, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Relax and enjoy this majestic estate you will call home during your stay. This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation

    Karen Overtoom Karen M. Overtoom R.E.

    56 Chilmark Rd, Chilmark, MA 02535
  • /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
    • /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

  • /48

    $5,850,000

    • 6 Beds
    • 6.5 Baths
    • 3,608 Sq Ft

    9 Ridge Hill Rd, Chilmark, MA 02535

    Set on three beautifully landscaped acres, this exceptional six-bedroom property offers a seamless blend of modern farmhouse design and timeless Vineyard appeal. The estate features a five-bedroom, five and a half bathroom main residence, along with a one-bedroom guest suite above a two-car barn. Thoughtfully designed in collaboration with the owner and Yankee Barn Homes, and featured in Country

    Alexis Holden Tea Lane Associates

    9 Ridge Hill Rd, Chilmark, MA 02535
  • /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
  • /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
    • /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

  • /27

    $14,250,000

    $4M PRICE DROP
    • 6 Beds
    • 9 Baths
    • 4,820 Sq Ft

    68 N Water St, Edgartown, MA 02539

    This expansive historic compound in the heart of Edgartown village offers the perfect blend of old-world charm and modern luxury. Just steps away from Edgartown’s finest restaurants and shops, this stunning property has been completely renovated by Stern McCafferty Architecture + Interiors, showcasing a harmonious balance of contemporary design and traditional architectural details. Upon

    Thomas Wallace Wallace & Co. Sotheby's

    68 N Water St, Edgartown, MA 02539
  • /18

    $10,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,439 Sq Ft
    • House for Rent

    24 Nat's Farm Lane Wt113, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Charming three bedroom home located in a private neighborhood close to bike path, walking trails and public tennis courts. Just a short drive to Lambert's Cove Beach, West Tisbury Village and down island restaurants and shops.Amenities include High definition TV, wifi

    Karen Overtoom Karen M. Overtoom R.E.

    24 Nat's Farm Lane Wt113, 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
    • /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

  • /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
  • /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
  • /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 $1,661,098

      Not Listed For Sale

      55 Pinehurst Rd, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 1,260 Sq Ft
      • Built 1996
      55 Pinehurst Rd, Edgartown, MA 02539

  • /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
  • /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
  • /27

    $1,800,000

    Sold Dec 02, 2025

    16 Schoolhouse Rd, Edgartown, MA 02539

    • 4 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • Built 1999

    Last Sold Summary

    • 8% Below List Price
    • $1,029/SF
    • 123 Days On Market

    Current Estimated Value $1,911,179

    Last Listing Agent Lesley Heidt Sandpiper Realty

    16 Schoolhouse Rd, Edgartown, MA 02539
    • /16

      Est $1,232,999

      Not Listed For Sale

      31 Music St, Vineyard Haven, MA 02568

      • 3 Beds
      • 1.5 Baths
      • 1,150 Sq Ft
      • Built 1817
      31 Music St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /41

    $2,195,000

    • 5 Beds
    • 3.5 Baths
    • 2,628 Sq Ft

    7 Pipn Cir, Edgartown, MA 02539

    Life on Chappaquiddick has a rhythm all its own — and this exceptional compound is designed to savor every moment of it.Set on three park-like acres of meadows and woodland, two freshly painted log cabin-style homes offer a private world apart. The three-bedroom main house is open and generous, with living spaces that flow seamlessly from inside to out. The two-bedroom guest house is its own

    Dawn Bellante Sandpiper Realty, Inc.

    7 Pipn Cir, Edgartown, MA 02539
  • /10

    $11,000 Per Month

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

    15 Price's Way Ed322, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is an inviting and affordable home with air-conditioning. As you see from the pictures the sun is welcomed through many sliders and windows. Inside the furnishings are simple but well chosen. There is a splitter in the living area that cools the downstairs. The

    Karen Overtoom Karen M. Overtoom R.E.

    15 Price's Way Ed322, Edgartown, MA 02539
  • /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
    • /29

      Not Listed For Sale

      30 Mill Hill Rd, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 2,800 Sq Ft
      • Built 1850
      30 Mill Hill Rd, Edgartown, MA 02539

      Last Sold Summary

      • 4 Days On Market

  • /36

    $1,845,000

    • 5 Beds
    • 3 Baths
    • 2,552 Sq Ft

    10 Danls Way, West Tisbury, MA 02575

    Historic West Tisbury Farmhouse with Guest Cottage Set on 1.27 acres in the heart of West Tisbury, this historic four-bedroom farmhouse and separate one-bedroom guest cottage offer a rare opportunity to create a quintessential Martha’s Vineyard family compound. Ideally located near Alley’s General Store, 7a Foods, and North Tisbury Village, the property also provides convenient access to beaches

    Emma Bryant Studio Realty

    10 Danls Way, West Tisbury, MA 02575
  • /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
  • /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
    • /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

  • /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
  • /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
  • /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
    • /43

      Not Listed For Sale

      7 N Bog Rd, Edgartown, MA 02539

      • 3 Beds
      • 3 Baths
      • 2,094 Sq Ft
      • Built 1994
      7 N Bog Rd, Edgartown, MA 02539

      Last Sold Summary

      • 276 Days On Market

Showing Results 241 - 280, Page 7 of 18

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