19,346

Dukes County, MA Homes

Section Image
    • /18

      Est $1,378,339

      Not Listed For Sale

      108 Charles Neck Way, Vineyard Haven, MA 02568

      • 3 Beds
      • 1.5 Baths
      • 1,512 Sq Ft
      • Built 1986
      108 Charles Neck Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 99 Days On Market

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

  • /17

    $2,875,000

    • 3 Beds
    • 3 Baths
    • 1,061 Sq Ft

    131 N Water St Unit 96, Edgartown, MA 02539

    LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 96 at 131 N. Water Street is a beautifully appointed 1061± sq. ft., second and third-floor condominium featuring 3 beds and 3 baths in the heart of Edgartown.This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel’s renowned amenities and services.

    Mitzi Lawlor Corcoran Property Advisors

    131 N Water St Unit 96, Edgartown, MA 02539
  • /24

    $3,050,000

    Sold Apr 15, 2026

    35 New York Ave, Oak Bluffs, MA 02568

    • 7 Beds
    • 5 Baths
    • 3,880 Sq Ft
    • Built 1884

    Last Sold Summary

    • 13% Below List Price
    • $786/SF
    • 23 Days On Market

    Last Listing Agent Emma Kennedy Sandpiper Realty, Inc.

    35 New York Ave, Oak Bluffs, MA 02568
    • /26

      Not Listed For Sale

      137 Charles Neck Way, Vineyard Haven, MA 02568

      • 5 Beds
      • 4 Baths
      • 2,610 Sq Ft
      • Built 1986
      137 Charles Neck Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Rebecca V Conroy Conroy & Company R.E., Inc.

  • /39

    $3,495,000

    • 4 Beds
    • 4 Baths
    • 3,200 Sq Ft

    64 Christiantown Rd, Vineyard Haven, MA 02568

    This stunning 3,200 sq. ft. architectural home features a bright, open layout defined by vaulted ceilings and rich hardwood floors. The gourmet kitchen, appointed with high-end finishes including silestone countertops, flows seamlessly into both a cozy family room and an elegant living room, anchored by a gorgeous dual-sided brick fireplace. With 4 bedrooms, 4 full bathrooms, and 2 dedicated home

    Karen Overtoom Karen M. Overtoom R.E.

    64 Christiantown Rd, Vineyard Haven, MA 02568
  • /34

    $2,475,000

    Sold Sep 05, 2025

    31 N Slope Ln, Chilmark, MA 02535

    • 4 Beds
    • 3.5 Baths
    • 2,300 Sq Ft
    • Built 1983

    Last Sold Summary

    • 15% Below List Price
    • $1,076/SF
    • 117 Days On Market

    Current Estimated Value $2,936,209

    Last Listing Agent Bill Rossi Studio Realty

    31 N Slope Ln, Chilmark, MA 02535
    • /35

      Est $1,845,655

      Not Listed For Sale

      55 Charles Neck Way, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,654 Sq Ft
      • Built 1984
      55 Charles Neck Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 182 Days On Market

      Last Listing Agent Wendy Harman Compass | Point B

  • /18

    $250,000

    • 1 Bed
    • 1 Bath
    • 331 Sq Ft

    27 Island Inn Rd Unit D17, Oak Bluffs, MA 02568

    Island Inn ....tucked behind the ever-popular Noman's Restaurant. Located off the Beach Road in Oak Bluffs. Fully furnished and updated 2nd floor studio. New: floors, appliances, television, mini-split AC and two double mattresses, Fully furnished galley kitchen. Use the convenient bike path to State Beach and then further on into Edgartown ...OR a short distance north to Oak Bluffs center, ferry

    Patti Dean Wiggy's Pond Real Estate

    27 Island Inn Rd Unit D17, Oak Bluffs, MA 02568
  • /22

    $1,100,000

    Sold Apr 30, 2026

    14 21st St N, Edgartown, MA 02539

    • 3 Beds
    • 1.5 Baths
    • 1,304 Sq Ft
    • Built 1978

    Last Sold Summary

    • 8% Below List Price
    • $844/SF
    • 141 Days On Market

    Current Estimated Value $1,120,984

    Last Listing Agent Fran Agnoli The Agency

    14 21st St N, Edgartown, MA 02539
    • /2

      Est $1,397,297

      Not Listed For Sale

      16 Elias Ln, Vineyard Haven, MA 02568

      • 1 Bed
      • 2 Baths
      • 856 Sq Ft
      • Built 1993
      16 Elias Ln, Vineyard Haven, MA 02568

  • /2

    $789,000

    $68K PRICE DROP
    • Land
    • 16,892 Sq Ft
    • $2,034,554 per Acre

    24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568

    OAK BLUFFS - EIGHT (8) BEDROOM LOT. This already cleared, oversized lot, 16,895sq.ft., (more than 1/3 acre) comes with an Approved Eight (8) Bedroom Septic Design, ready to build. Exceptional potential for a spacious custom home, family compound, or a rental property. Utilities are available by the lot, which significantly reduces development costs and time. Convenient access from both Towanticut

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568
  • /16

    $970,000

    Sold Dec 08, 2025

    6 Sachem Way, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 1,546 Sq Ft
    • Built 1973

    Last Sold Summary

    • 8% Above List Price
    • $627/SF
    • 4 Days On Market

    Current Estimated Value $1,062,214

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

    6 Sachem Way, Oak Bluffs, MA 02557
    • /26

      Est $1,093,848

      Not Listed For Sale

      4 Elias Ln, Vineyard Haven, MA 02568

      • 1 Bed
      • 1 Bath
      • 1,182 Sq Ft
      • Built 1977
      4 Elias Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Stephanie Roache Donnelly + Co

  • /31

    $1,140,000

    $35K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,059 Sq Ft

    4 Rock Pond Rd, Vineyard Haven, MA 02568

    4 Rock Pond Road offers a rare opportunity to enjoy the best of community-centered living in one of Martha’s Vineyard’s most unique and thoughtfully designed neighborhoods. Located within the Island Cohousing community in West Tisbury, this 4-bedroom, 2-bath home combines warmth, functionality, sustainability, and connection in a peaceful natural setting.Built by South Mountain Company, the home

    Patricia Lyman Compass

    4 Rock Pond Rd, Vineyard Haven, MA 02568
  • /22

    $2,899,000

    Sold Oct 01, 2025

    78 Winemack St, Oak Bluffs, MA 02557

    • 4 Beds
    • 2 Baths
    • 1,889 Sq Ft
    • Built 1956

    Last Sold Summary

    • $1,535/SF
    • 0 Days On Market

    Current Estimated Value $3,206,924

    Last Listing Agent Susan Austin Austin R.E. Properties of MV

    78 Winemack St, Oak Bluffs, MA 02557
    • /28

      Est $1,318,233

      Not Listed For Sale

      175 Oak Ln, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1986
      175 Oak Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Joanna Fairchild eXp Realty

  • /25

    $2,950,000

    $250K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,268 Sq Ft

    23 Thaxter Ln, Edgartown, MA 02539

    OPEN AND AIRY COASTAL RETREAT WITH EASY ACCESS TO SOUTH BEACH and EDGARTOWN VILLAGE. Welcome to this tri-level contemporary home in the heart of KATAMA. This home offers the perfect blend of spacious indoor-outdoor living with three levels of outdoor decking nestled amongst mature vegetation and a quick stroll to South Beach. The home features vaulted ceilings, two first floor bedroom en-suites,

    Michele Casavant Vineyard Village Realty

    23 Thaxter Ln, Edgartown, MA 02539
  • /138

    $4,800,000

    Sold Sep 24, 2025

    264 Katama Rd, Edgartown, MA 02539

    • 4 Beds
    • 4.5 Baths
    • 4,167 Sq Ft
    • Built 2020

    Last Sold Summary

    • 3% Below List Price
    • $1,152/SF
    • 50 Days On Market

    Current Estimated Value $4,959,876

    Last Listing Agent Alisan Lohan-Conway Alisan Lohan-Conway Properties

    264 Katama Rd, Edgartown, MA 02539
    • /24

      Est $1,282,032

      Not Listed For Sale

      110 Otis Bassett Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft
      • Built 1972
      110 Otis Bassett Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Jennifer O'hanlon Compass LLC

  • /12

    $2,495,000

    $755K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 936 Sq Ft

    9 N Neck Rd, Edgartown, MA 02539

    COMMANDING WATER VIEWS ON CHAPPAQUIDDICK - This beloved fishing cottage rests high above one of the premier fishing areas on the island of Chappaquiddick. Set apart from the hustle and bustle of downtown, but within easy reach of all Edgartown offers, the pristine views over the wilds of Cape Pogue and the outer harbor bring peace and serenity for all who visit. Fishing, clamming, swimming,

    Leslie C. Floyd Portfolio Properties

    9 N Neck Rd, Edgartown, MA 02539
  • /20

    $1,295,000

    Sold Sep 05, 2025

    2 Upper Douglas Ln, Oak Bluffs, MA 02557

    • 4 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • Built 1988

    Last Sold Summary

    • 3% Below List Price
    • $818/SF
    • 5 Days On Market

    Current Estimated Value $1,354,671

    Last Listing Agent Lynn Buder Sandpiper Realty

    2 Upper Douglas Ln, Oak Bluffs, MA 02557
    • /37

      Est $1,261,884

      Not Listed For Sale

      43 Skiffs Ln, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,316 Sq Ft
      • Built 1991
      43 Skiffs Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Chelsea Brennan Lamacchia Realty, Inc.

  • /22

    $8,900,000

    • 4 Beds
    • 8 Baths
    • 7,767 Sq Ft

    4 Jacobs Neck Rd, Edgartown, MA 02539

    Great Potential with Pond & Beach Access ~Set on ten private wooded acres in the Boldwater community, this unique property combines privacy, flexibility, and exceptional potential. It includes a beautifully appointed guest house ready to enjoy, plus an approximately 5,400 sq. ft. structure offering the opportunity to create a custom main residence with a swimming pool. Owners enjoy deeded

    Deb Hancock Hancock Real Estate

    4 Jacobs Neck Rd, Edgartown, MA 02539
  • /14

    $1,800,000

    Sold Dec 23, 2025

    19 Katama Dr, Edgartown, MA 02539

    • 3 Beds
    • 1.5 Baths
    • 1,188 Sq Ft
    • Built 1984

    Last Sold Summary

    • 28% Below List Price
    • $1,515/SF
    • 70 Days On Market

    Last Listing Agent Emma Kennedy Sandpiper Realty

    19 Katama Dr, Edgartown, MA 02539
    • /49

      Est $1,884,103

      Not Listed For Sale

      75 Skiffs Ln, Vineyard Haven, MA 02568

      • 4 Beds
      • 2.5 Baths
      • 2,548 Sq Ft
      • Built 1984
      75 Skiffs Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 186 Days On Market

      Last Listing Agent Kelly Mercier The Agency

  • /6

    $2,795,000

    • Land
    • 0 Sq Ft

    Lot 4B Browns Farm Ln, Edgartown, MA 02539

    Tucked off Meetinghouse Way, this 3-acre parcel offers an opportunity to create something lasting on the Vineyard. Open pasture sweeps across the property's core, framed by bordering woodland that lends a sense of privacy without sacrificing the light and openness that makes the setting so appealing. Just under 2.5 miles from the Village and South Beach, the location balances seclusion with easy

    Courtney Marek Sandpiper Realty, Inc.

    Lot 4B Browns Farm Ln, Edgartown, MA 02539
  • /42

    $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
    • 106 Days On Market

    Current Estimated Value $1,845,380

    Last Listing Agent Katherine Donahue Sandpiper Realty

    35 Tower Ridge Rd, Oak Bluffs, MA 02557
    • /15

      Est $1,216,663

      Not Listed For Sale

      14 Galway Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 1.5 Baths
      • 1,338 Sq Ft
      • Built 1966
      14 Galway Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Michele Casavant Vineyard Village Realty

  • /30

    $3,200,000

    • 4 Beds
    • 6 Baths
    • 3,428 Sq Ft

    19 Llewellyn Way, Edgartown, MA 02539

    Perfectly situated just moments from the bike path, Edgartown Village, and South Beach, this exceptional Edgartown compound offers the best of Vineyard living. The main house is filled with warmth and character, featuring soaring ceilings, exposed beams, and an inviting open living area centered around a custom stone fireplace. Thoughtfully designed and perfectly sited for privacy, the Casita

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    19 Llewellyn Way, Edgartown, MA 02539
  • /30

    $815,000

    Sold Nov 14, 2025

    17 Siloam Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 907 Sq Ft
    • Built 1870

    Last Sold Summary

    • 2% Below List Price
    • $899/SF
    • 100 Days On Market

    Current Estimated Value $870,780

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    17 Siloam Ave, Oak Bluffs, MA 02557
    • /3

      Est $1,466,692

      Not Listed For Sale

      362 State Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • Built 1953
      362 State Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 62 Days On Market

      Last Listing Agent Nora Jardin Island Real Estate

  • /43

    $2,475,000

    • 4 Beds
    • 4 Baths
    • 3,039 Sq Ft

    99 The Blvd, Edgartown, MA 02539

    Welcome to a beautifully renovated custom contemporary colonial located just 1/3 mile from the Sengekontacket Pond boat landing. Perfect for kayaking, paddleboarding, and coastal living, this builder-owned home seamlessly blends classic Vineyard charm with modern luxury. The bright, open-concept main floor features a wood-burning fireplace, custom kitchen, and direct access to a private backyard

    Jennifer DaSilva Compass | Point B

    99 The Blvd, Edgartown, MA 02539
  • /2

    $6,825,000

    Sold Jan 05, 2026

    662 Chappaquonsett Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 3 Baths
    • 1,914 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Below List Price
    • $3,566/SF
    • 0 Days On Market

    Current Estimated Value $5,303,543

    Last Listing Agent Jill Napior Tea Lane Associates

    662 Chappaquonsett Rd, Vineyard Haven, MA 02568
    • /22

      Est $1,244,290

      Not Listed For Sale

      496 Lamberts Cove Rd, Vineyard Haven, MA 02568

      • 2 Beds
      • 1 Bath
      • 1,286 Sq Ft
      • Built 1955
      496 Lamberts Cove Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 212 Days On Market

      Last Listing Agent Stephanie Roache Donnelly + Co

  • /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
  • /36

    $3,700,000

    Sold May 28, 2026

    122 Old Farm Rd, Chilmark, MA 02535

    • 5 Beds
    • 4 Baths
    • 3,413 Sq Ft
    • Built 1790

    Last Sold Summary

    • 38% Below List Price
    • $1,084/SF
    • 261 Days On Market

    Current Estimated Value $1,631,500

    Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

    122 Old Farm Rd, Chilmark, MA 02535
    • /26

      Est $1,506,198

      Not Listed For Sale

      33 Hidden Village Rd, Vineyard Haven, MA 02568

      • 5 Beds
      • 2.5 Baths
      • 1,968 Sq Ft
      • Built 1980
      33 Hidden Village Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 73 Days On Market

      Last Listing Agent Elissa Lash Tea Lane Associates

  • /24

    $375,000

    • 1 Bed
    • 192 Sq Ft

    1 Old Field Rd, Aquinnah, MA 02535

    A bucolic 3.36 +/- acre wooded parcel in Aquinnah, offering privacy and natural beauty with a brook running through the property. A seasonal one-room camp, built in the 1970s, sits on the land — a simple retreat for a lucky Buyer.The lot falls within the Special Ways District and is impacted by wetlands, which limits the buildable envelope and requires a 150-ft setback. However, the parcel

    Julianna Flanders Flanders Real Estate

    1 Old Field Rd, Aquinnah, MA 02535
  • /25

    $1,300,000

    Sold Dec 18, 2025

    23 Laurel Ave, Oak Bluffs, MA 02557

    • 4 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 1900

    Last Sold Summary

    • 13% Below List Price
    • $1,042/SF
    • 64 Days On Market

    Current Estimated Value $1,376,058

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

    23 Laurel Ave, Oak Bluffs, MA 02557
    • /30

      Est $2,535,298

      Not Listed For Sale

      41 Hidden Village Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 3 Baths
      • 2,540 Sq Ft
      • Built 1981
      41 Hidden Village Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 335 Days On Market

      Last Listing Agent Rebecca V Conroy Conroy & Company R.E., Inc.

Showing Results 481 - 520, Page 13 of 18

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