19,346

Dukes County, MA Homes

Section Image
  • /15

    $1,000,000

    Sold May 13, 2026

    140 Midland Ave, Tisbury, MA 02568

    • 4 Beds
    • 4 Baths
    • 1,999 Sq Ft
    • Built 1974

    Last Sold Summary

    • 33% Below List Price
    • $500/SF
    • 2 Days On Market

    Last Listing Agent Tina Miller Donnelly + Co

    140 Midland Ave, Tisbury, MA 02568
    • /15

      Est $1,041,430

      Not Listed For Sale

      20 Leonard Cir, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,152 Sq Ft
      • Built 1984
      20 Leonard Cir, Vineyard Haven, MA 02568

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Roy Cutrer LAER Realty Partners

  • /17

    $2,595,000

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    131 N Water St Unit 22, Edgartown, MA 02539

    LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 22 at 131 N. Water Street is a beautifully appointed 960± sq. ft., second-floor condominium featuring 2 bedrooms and 2 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 22, Edgartown, MA 02539
  • /28

    $1,400,000

    Sold Nov 26, 2025

    5 Scottys Ln, Vineyard Haven, MA 02568

    • 4 Beds
    • 1.5 Baths
    • 1,592 Sq Ft
    • Built 1968

    Last Sold Summary

    • 22% Below List Price
    • $879/SF
    • 126 Days On Market

    Current Estimated Value $1,666,291

    Last Listing Agent Idalyn Macchia Gilstad Wallace & Co. Sotheby's

    5 Scottys Ln, Vineyard Haven, MA 02568
    • /43

      Est $2,041,405

      Not Listed For Sale

      21 Brushy Ln, Edgartown, MA 02539

      • 4 Beds
      • 2.5 Baths
      • 1,668 Sq Ft
      • Built 1984
      21 Brushy Ln, Edgartown, MA 02539

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Jayne Isford Ocean Park Realty Inc

  • /30

    $3,995,000

    • 6 Beds
    • 3.5 Baths
    • 3,070 Sq Ft

    30 & 40 Elias Ln, West Tisbury, MA 02575

    A beautiful pastoral, private family compound in West Tisbury, on 7.5 glorious acres of meadow comprised of two parcels, offers a rare opportunity. Elias Lane is a quiet country road tucked behind Misty Meadows and just minutes from West Tisbury village. The property features a lovingly maintained 4 BDR main house with a well appointed kitchen, recent sun porch addition an elegant Lew French

    Elissa Lash Tea Lane Associates

    30 & 40 Elias Ln, West Tisbury, MA 02575
  • /34

    $3,746,925

    Sold Nov 14, 2025

    39 Sengekontacket Rd, Edgartown, MA 02539

    • 4 Beds
    • 3.5 Baths
    • 2,861 Sq Ft
    • Built 1974

    Last Sold Summary

    • 8% Below List Price
    • $1,310/SF
    • 114 Days On Market

    Current Estimated Value $3,668,740

    Last Listing Agent Jayne Isford Ocean Park Realty Inc

    39 Sengekontacket Rd, Edgartown, MA 02539
    • /2

      Est $2,344,640

      Not Listed For Sale

      5 Marsh Hawk Cir, Edgartown, MA 02539

      • 3 Beds
      • 3 Baths
      • 2,139 Sq Ft
      • Built 1983
      5 Marsh Hawk Cir, Edgartown, MA 02539

  • /40

    $5,250,000

    Pending
    • 4 Beds
    • 3 Baths
    • 1,714 Sq Ft

    21 Eliot Ave, Chilmark, MA 02535

    An iconic retreat in Chilmark, this totally renovated beach house captures sweeping views of the Atlantic Ocean, Stonewall Beach, and Stonewall Pond. The design honors the timeless simplicity of its coastal setting with elegant, understated finishes that allow the extraordinary vistas to take center stage. Designed for effortless indoor-outdoor living, the home's light-filled spaces open to

    Mark Jenkins Wallace & Co. Sotheby's

    21 Eliot Ave, Chilmark, MA 02535
  • /2

    $24,000,000

    Sold Jan 28, 2026

    177 Katama Rd, Edgartown, MA 02539

    • 5 Beds
    • 4 Baths
    • 3,728 Sq Ft
    • Built 1900

    Last Sold Summary

    • $6,438/SF
    • 0 Days On Market

    Current Estimated Value $12,778,312

    Last Listing Agent Thomas Leclair Landvest MV

    177 Katama Rd, Edgartown, MA 02539
    • /34

      Not Listed For Sale

      391 Middle Rd, Chilmark, MA 02535

      • 6 Beds
      • 4.5 Baths
      • 3,859 Sq Ft
      • Built 1941
      391 Middle Rd, Chilmark, MA 02535

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Jill Napior Tea Lane Associates

  • /32

    $1,595,000

    • 3 Beds
    • 3.5 Baths
    • 2,739 Sq Ft

    40 Hidden Cove Rd Unit 2, Oak Bluffs, MA 02557

    Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a

    Rose Ryley Wallace & Co. Sotheby's International Realty

    40 Hidden Cove Rd Unit 2, Oak Bluffs, MA 02557
  • /37

    $1,705,000

    Sold Mar 24, 2026

    2 Farm Path, Oak Bluffs, MA 02557

    • 4 Beds
    • 3 Baths
    • 3,058 Sq Ft
    • Built 1992

    Last Sold Summary

    • 15% Below List Price
    • $558/SF
    • 347 Days On Market

    Current Estimated Value $1,733,576

    Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate

    2 Farm Path, Oak Bluffs, MA 02557
    • /41

      Est $2,276,385

      Not Listed For Sale

      70 Marthas Rd, Edgartown, MA 02539

      • 3 Beds
      • 2.5 Baths
      • 1,875 Sq Ft
      • Built 2000
      70 Marthas Rd, Edgartown, MA 02539

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Melanie Prescott Compass

  • /30

    $6,995,000

    • 4 Beds
    • 3 Baths
    • 2,624 Sq Ft

    103 Edgartown Bay Rd, Edgartown, MA 02539

    Perfectly positioned along the serene shores of Katama Bay, this property offers a front-row seat to nature’s grandeur. Residents will revel in sweeping, 180-degree vistas where the tranquil waters of the bay meet the dramatic horizon of South Beach and the Atlantic Ocean. As you enter the property from Edgartown Bay Road, the home’s timeless architecture and expansive front lawn make an

    Bonnie Pierce Wallace & Co. Sotheby's

    103 Edgartown Bay Rd, Edgartown, MA 02539
  • /23

    $1,500,000

    Sold Sep 25, 2025

    190 Longview Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1995

    Last Sold Summary

    • 15% Below List Price
    • $1,071/SF
    • 43 Days On Market

    Current Estimated Value $1,692,286

    Last Listing Agent Kathleen Kendrick Kendrick Real Estate

    190 Longview Rd, Vineyard Haven, MA 02568
    • /24

      Est $1,685,003

      Not Listed For Sale

      92 Winyah Cir, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 2,625 Sq Ft
      • Built 1983
      92 Winyah Cir, Vineyard Haven, MA 02568

      Last Sold Summary

      • 78 Days On Market

      Last Listing Agent Doug Burke Signal House Group at Compass

  • /30

    $3,100,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,525 Sq Ft

    6 Kent Harbor Rd, Edgartown, MA 02539

    DOWN HARBOR OPPORTUNITY! Introducing 6 Kent Harbor, a full acre of land in an ideal location for your next build or renovation project. Equidistant between South Beach and Edgartown Village, Down Harbor offers residents a walking path to a private sandy shoreline on Katama Bay. The existing 1972 ranch-style home has 1,525 sq ft with 3 bedrooms, 2 baths, living room and galley kitchen. Sliding

    Cheri Mason Landvest MV

    6 Kent Harbor Rd, Edgartown, MA 02539
  • /24

    $1,600,000

    Sold Jul 23, 2026

    109 Litchfield Rd, Edgartown, MA 02539

    • 3 Beds
    • 2.5 Baths
    • 1,962 Sq Ft
    • Built 1987

    Last Sold Summary

    • 2% Below List Price
    • $815/SF
    • 7 Days On Market

    Current Estimated Value $1,740,764

    Last Listing Agent Katherine Donahue Sandpiper Realty

    109 Litchfield Rd, Edgartown, MA 02539
    • /34

      Est $1,248,239

      Not Listed For Sale

      160 Bernard Cir, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,606 Sq Ft
      • Built 1977
      160 Bernard Cir, Vineyard Haven, MA 02568

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

  • /32

    $1,140,000

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

    4 Rock Pond, West Tisbury, MA 02575

    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

    Trish Lyman Compass | Point B

    4 Rock Pond, West Tisbury, MA 02575
  • /20

    $1,050,000

    Sold Jun 29, 2026

    12 Wheelhouse Way, Oak Bluffs, MA 02557

    • 3 Beds
    • 1.5 Baths
    • 1,487 Sq Ft
    • Built 1999

    Last Sold Summary

    • 4% Below List Price
    • $706/SF
    • 125 Days On Market

    Current Estimated Value $1,068,435

    Last Listing Agent Dawn Bellante Sandpiper Realty, Inc.

    12 Wheelhouse Way, Oak Bluffs, MA 02557
    • /2

      Est $1,318,146

      Not Listed For Sale

      201 Spring St, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 2,080 Sq Ft
      • Built 1976
      201 Spring St, Vineyard Haven, MA 02568

  • /52

    $2,195,000

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

    7 Pip'N Rd, Edgartown, MA 02539

    A true Chappaquiddick escape — where the outdoors is as much a part of the home as anything inside. Tucked within three acres of park-like grounds, meadows and woodland, this rustic yet comfortable compound of two log houses is built for friends and family who love the land, the water, and everything in between.Gather around the custom firepit under a canopy of stars, soak in the sauna and

    Dawn Bellante-Holand Sandpiper Realty

    7 Pip'N Rd, Edgartown, MA 02539
  • /81

    $1,650,000

    Sold Jan 09, 2026

    209 Cove Rd, Vineyard Haven, MA 02568

    • 4 Beds
    • 3.5 Baths
    • 2,194 Sq Ft
    • Built 1997

    Last Sold Summary

    • 15% Below List Price
    • $752/SF
    • 182 Days On Market

    Current Estimated Value $1,778,296

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

    209 Cove Rd, Vineyard Haven, MA 02568
    • /39

      Est $3,508,076

      Not Listed For Sale

      25 Oxcart Rd, Aquinnah, MA 02535

      • 3 Beds
      • 1.5 Baths
      • 1,008 Sq Ft
      • Built 1953
      25 Oxcart Rd, Aquinnah, MA 02535

      Last Sold Summary

      • 0 Days On Market

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

  • /13

    $6,750,000

    • Land
    • 2.11 Acres
    • $3,199,052 per Acre

    5 Atlantic Dr Unit 5.2, Edgartown, MA 02539

    Located in one of Katama’s most coveted neighborhoods, this 2.11-acre parcel offers stunning ocean views and a direct path to South Beach. Surrounded by high-end homes and just minutes from Edgartown Village, it’s an ideal setting for a custom-built retreat with room for a four bedroom residence with pool and views over the dunes. A rare opportunity to own in this prestigious coastal enclave.

    Deb Levin Studio Realty

    5 Atlantic Dr Unit 5.2, Edgartown, MA 02539
  • /39

    $1,575,000

    Sold Jan 09, 2026

    453 Lighthouse Rd, Aquinnah, MA 02535

    • 3 Beds
    • 4 Baths
    • 2,308 Sq Ft
    • Built 1970

    Last Sold Summary

    • 12% Below List Price
    • $682/SF
    • 169 Days On Market

    Current Estimated Value $1,668,338

    Last Listing Agent We Close Deals Team Lamacchia Realty, Inc.

    453 Lighthouse Rd, Aquinnah, MA 02535
    • /16

      Est $1,908,899

      Not Listed For Sale

      8 Marsh Hawk Cir, Edgartown, MA 02539

      • 5 Beds
      • 2 Baths
      • 1,632 Sq Ft
      • Built 1980
      8 Marsh Hawk Cir, Edgartown, MA 02539

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Emma Kennedy Sandpiper Realty

  • /21

    $1,300,000

    $145K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,738 Sq Ft

    22 Oklahoma Ave, Vineyard Haven, MA 02568

    3 BEDROOM HOUSE + 1 BEDROOM APARTMENT! A rare opportunity in a convenient Vineyard Haven neighborhood. This move-in ready property features a 3 BR, 1.5 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset your mortgage. The main house features a stunning sun-room, a cheerful efficient kitchen, and a

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

    22 Oklahoma Ave, Vineyard Haven, MA 02568
  • /44

    $8,178,500

    Sold Oct 27, 2025

    94 Menemsha Inn Rd, Chilmark, MA 02535

    • 6 Beds
    • 4.5 Baths
    • 4,104 Sq Ft
    • Built 2001

    Last Sold Summary

    • 3% Below List Price
    • $1,993/SF
    • 38 Days On Market

    Last Listing Agent Julianna Flanders Flanders Real Estate

    94 Menemsha Inn Rd, Chilmark, MA 02535
    • /42

      Est $1,942,284

      Not Listed For Sale

      44 Music St, Vineyard Haven, MA 02568

      • 4 Beds
      • 5 Baths
      • 2,172 Sq Ft
      • Built 1984
      44 Music St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 66 Days On Market

      Last Listing Agent Jill Napior Tea Lane Associates

  • /69

    $3,950,000

    Open Sun 12PM - 2PM $225K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,397 Sq Ft

    19 Kitts Field Cir, Edgartown, MA 02539

    Old World Vineyard Charm Meets Modern Katama Living. Welcome to this beautifully crafted Katama family compound, a private, thoughtfully designed estate offering timeless elegance and exceptional amenities. Nestled near Edgartown Village, this stunning property includes a four-bedroom main residence with three levels of living space, a charming two-bedroom guest house, pool house, pool, spa,

    Michele Casavant Vineyard Village Realty

    19 Kitts Field Cir, Edgartown, MA 02539
  • /13

    $1,187,500

    Sold Jun 12, 2026

    54 Columbian Ave, Oak Bluffs, MA 02557

    • 4 Beds
    • 2 Baths
    • 1,764 Sq Ft
    • Built 1989

    Last Sold Summary

    • 8% Below List Price
    • $673/SF
    • 93 Days On Market

    Current Estimated Value $1,217,640

    Last Listing Agent Katrina Lima Donnelly + Co

    54 Columbian Ave, Oak Bluffs, MA 02557
    • /23

      Est $2,047,455

      Not Listed For Sale

      50 Campbell Rd, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,370 Sq Ft
      • Built 1994
      50 Campbell Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Julianna Flanders Flanders Real Estate

  • /5

    $639,000

    • Land
    • 12,998 Sq Ft
    • $2,141,421 per Acre

    52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568

    GOOD TO GO! This sunny 13,000-square-foot lot is ready for your Vineyard home. The property comes with a complete six-bedroom septic design prepared by Vineyard Land Surveying, allowing for both a main house and guest house. With key planning work already completed, this is an outstanding opportunity to move forward with confidence and begin the building process. Conveniently located just off

    Tina Miller Donnelly + Co

    52 Heath Hen Ln Unit 5, Vineyard Haven, MA 02568
  • /33

    $915,000

    Sold Apr 17, 2026

    400 Edgartown-Vineyard Haven Rd, Edgartown, MA 02539

    • 2 Beds
    • 2 Baths
    • 1,352 Sq Ft
    • Built 2001

    Last Sold Summary

    • 16% Below List Price
    • $677/SF
    • 286 Days On Market

    Last Listing Agent Kelly Mercier The Agency

    400 Edgartown-Vineyard Haven Rd, Edgartown, MA 02539
    • /6

      Est $2,839,914

      Not Listed For Sale

      71 Runner Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,935 Sq Ft
      • Built 1982
      71 Runner Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

  • /2

    $794,000

    • 2 Beds
    • 1 Bath
    • 624 Sq Ft

    60R Carol Ln, Oak Bluffs, MA 02557

    Tucked away down a quiet lane just moments from downtown Oak Bluffs, sits this charming home. Nestled on just over an 8,400 sq. ft. lot, the property offers compact single-story living, ideal for those seeking simplicity while being close to everything the island. The bright, open concept features a living area and kitchen with breakfast bar. Ample storage and a stackable washer/dryer complete

    Michele Moore Island Real Estate

    60R Carol Ln, Oak Bluffs, MA 02557
  • /10

    $10,500,000

    Sold Mar 12, 2026

    51 Squibnocket Farm Rd, Chilmark, MA 02535

    • 4 Beds
    • 2.5 Baths
    • 3,200 Sq Ft
    • Built 1981

    Last Sold Summary

    • 9% Below List Price
    • $3,281/SF

    Current Estimated Value $8,227,387

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

    51 Squibnocket Farm Rd, Chilmark, MA 02535

Showing Results 441 - 480, Page 12 of 18

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