19,907

Dukes County, MA Homes

Section Image
  • /29

    $3,990,000

    $510K PRICE DROP Pending
    • 5 Beds
    • 6 Baths
    • 5,598 Sq Ft

    71 Stoney Hill Rd, Vineyard Haven, MA 02568

    A combination of luxury, comfort, and natural beauty, this expansive custom, 6,000+ square foot, five bedroom, post and beam home is sited on more than seven acres of land, surrounded by more than 200 acres of Land Bank property. From the moment you step inside, you'll be captivated by the attention to detail and the high-end finishes throughout. The open concept layout allows for seamless flow

    Sheila Morse Island Real Estate

    71 Stoney Hill Rd, Vineyard Haven, MA 02568
  • /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 $1,549,765

    Last Listing Agent Kathleen Kendrick Kendrick Real Estate

    190 Longview Rd, Vineyard Haven, MA 02568
    • /26

      Est $1,080,588

      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

  • /2

    $625,000

    Pending
    • Land
    • 12,196 Sq Ft
    • $2,232,143 per Acre

    77 Sixth Street N St, Edgartown, MA 02568

    *All information should be confirmed with the town boards. From BOH - Lot can support a 2 bedroom system with a standard Title 5 or 3 bedrooms with an enhanced system. From Water Department - Town water runs down Sixth Street N. Buyer will need to hook up from the road. From Building/Zoning Department - Lot can support a house and an ADU, by right, with proper permitting. From Wastewater Dept. -

    Sheila Morse Island Real Estate

    77 Sixth Street N St, Edgartown, MA 02568
  • /2

    $1,125,000

    Sold Jan 23, 2026

    96 Manchester Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 3,192 Sq Ft
    • Built 1999

    Last Sold Summary

    • 2% Below List Price
    • $352/SF
    • 7 Days On Market

    Current Estimated Value $1,158,235

    Last Listing Agent Michele Moore Island Real Estate

    96 Manchester Ave, Oak Bluffs, MA 02557
    • /28

      Est $1,304,469

      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

  • /37

    $3,195,000

    • 5 Beds
    • 4.5 Baths
    • 3,881 Sq Ft

    10 N Bog Rd, Edgartown, MA 02539

    Set on 2.2 private acres in Edgartown, this exceptional five-bedroom home with a heated saltwater pool offers the ideal blend of privacy, comfort, and convenience. Perfectly located just moments from Morning Glory Farm, South Beach, the bike path, and downtown Edgartown Village, the property provides easy access to some of the island’s most sought-after destinations while maintaining a peaceful,

    Michele Casavant Vineyard Village Realty

    10 N Bog 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 $1,742,371

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

    209 Cove Rd, Vineyard Haven, MA 02568
    • /37

      Est $1,220,941

      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

  • /7

    $2,795,000

    • Land
    • 3.05 Acres
    • $916,393 per Acre

    Lot 4A Browns Farm Ln Unit Portion of 10, Edgartown, MA 02539

    Located off Meetinghouse Way, this 3-acre parcel offers something truly special: room to breathe. Open pasture rolls across the heart of the property, while bordering woodland creates a setting that feels private yet open and airy. The location is less than 2.5 miles from Main Street and South Beach, offering convenient access to both town amenities and the sand and surf of the south shore.

    Courtney Marek Sandpiper Realty

    Lot 4A Browns Farm Ln Unit Portion of 10, 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 $1,614,062

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

    453 Lighthouse Rd, Aquinnah, MA 02535
    • /49

      Est $1,848,207

      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

  • /45

    $7,950,000

    • 4 Beds
    • 4.5 Baths
    • 7,766 Sq Ft

    2 Lexington Ave, Edgartown, MA 02539

    NEW CONSTRUCTION: Experience modern Katama luxury in this thoughtfully designed new construction by Morgan Studio, a husband-and-wife–led boutique design firm. A turn-key offering for elevated indoor-outdoor living, the residence features soaring ceilings, a fluid floor plan with multiple gathering spaces, abundant natural light through oversized windows, and exceptional materials and finishes

    Peyton Wallace Studio Realty

    2 Lexington Ave, Edgartown, MA 02539
  • /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
    • /15

      Est $1,170,056

      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

  • /22

    $5,500,000

    • 2 Beds
    • 1 Bath
    • 808 Sq Ft

    17 Chockers Ln, Chilmark, MA 02535

    Perfectly situated on Nashaquitsa Pond, this charming two-bedroom cottage offers sweeping views of Quitsa and Menemsha Pond from a rare vantage point few properties can match. The cottage includes private beach rights to Short Beach and dock access for a mooring. Inside, hand-painted floors and a warm, unpretentious interior reflect the authentic character of Old Vineyard — a property that has

    Julianna Flanders Flanders Real Estate

    17 Chockers Ln, Chilmark, MA 02535
  • /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
    • /22

      Est $1,178,218

      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

  • /37

    $15,000,000

    • 7 Beds
    • 9 Baths
    • 6,462 Sq Ft

    14 Cow Bay Rd, Edgartown, MA 02539

    Set within the prestigious Cow Bay Association, one of the island’s most exclusive and sought-after enclaves, this extraordinary 1.5-acre estate embodies the pinnacle of refined coastal living. Accessed via private road through protected land, the property includes access to over 2,000 feet of private shoreline, beach cabanas, Trapps Pond and potential mooring. Despite its remarkable seclusion,

    Gerrett Conover Landvest MV

    14 Cow Bay Rd, Edgartown, MA 02539
  • /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 $7,346,949

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

    51 Squibnocket Farm Rd, Chilmark, MA 02535
    • /26

      Est $1,554,087

      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

  • /3

    $639,000

    • Land
    • 13,068 Sq Ft
    • $2,130,000 per Acre

    52 Heath Hen Ln, Vineyard Haven, MA 02568

    GOOD TO GO! This sunny 13,000-square-foot sunny 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

    Tina Miller Donnelly + Co.

    52 Heath Hen Ln, Vineyard Haven, MA 02568
  • /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
    • /30

      Est $2,498,724

      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

  • /13

    $2,500,000

    • 1 Bed
    • 1 Bath
    • 726 Sq Ft

    18 Allen Farm Rd, Chilmark, MA 02535

    Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1+ bedroom cottage with screened porch. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, especially for solar designs. The cottage is offered full furnished with exception of some art and a few

    Patty Kendall Kendall & Kendall

    18 Allen Farm Rd, Chilmark, MA 02535
  • /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 $2,732,346

    Last Listing Agent Bill Rossi Studio Realty

    31 N Slope Ln, Chilmark, MA 02535
    • /45

      Est $1,162,831

      Not Listed For Sale

      5 Rock Pond Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,618 Sq Ft
      • Built 1999
      5 Rock Pond Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 145 Days On Market

  • /4

    $1,449,000

    $251K PRICE DROP Pending
    • Land
    • 3.9 Acres
    • $371,538 per Acre

    34 Ebens Ln, Chilmark, MA 02535

    Settled high on a peaceful ridge this 3.9-acre property is being offered with a long-term lease for 2.5 acres of prime restricted agricultural farmland abutting the property and the Tiasquam River. With the river running along the edge of the property this area is ideal for growing flowers, vegetables, and/or arbors. The land may also be used for grazing and housing livestock along with any

    Thomas Wallace Wallace & Co. Sotheby's

    34 Ebens Ln, Chilmark, MA 02535
  • /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 $1,157,876

    Last Listing Agent Fran Agnoli The Agency

    14 21st St N, Edgartown, MA 02539
    • /30

      Est $1,579,897

      Not Listed For Sale

      12 Lily Farm Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,560 Sq Ft
      • Built 1991
      12 Lily Farm Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 198 Days On Market

  • /9

    $2,700,000

    • 4 Beds
    • 4.5 Baths
    • 2,750 Sq Ft

    6 Laura's Way, Edgartown, MA 02568

    Welcome to the opportunity to own a brand-new, GORGEOUS, custom-built home in Edgartown, set on a one-acre plot with a detached 900 sq ft accessory dwelling. The main residence opens to an inviting two-story foyer, leading to an expansive, living room featuring a wall of glass sliders. The gourmet kitchen is a chef’s dream, boasting Bosch appliances, a large quartz-topped island with seating for

    Michele Casavant Vineyard Village Realty

    6 Laura's Way, Edgartown, 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 $1,033,665

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

    6 Sachem Way, Oak Bluffs, MA 02557
    • /22

      Est $1,187,303

      Not Listed For Sale

      41 Old County Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1.5 Baths
      • 1,264 Sq Ft
      • Built 1983
      41 Old County Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 216 Days On Market

  • /2

    $799,000

    • Land
    • 39,996 Sq Ft
    • $870,181 per Acre

    22 Bramble Path Unit 214, West Tisbury, MA 02568

    Flat building lot centrally located in West Tisbury. A perc test has been completed which supports a four bedroom Title Five septic system. It is the Buyers responsibility to install utilities, well and septic.

    Michele Casavant Vineyard Village Realty

    22 Bramble Path Unit 214, West Tisbury, 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 $3,065,759

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

    78 Winemack St, Oak Bluffs, MA 02557
    • /17

      Est $1,221,185

      Not Listed For Sale

      22 Briarwood Ln, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,241 Sq Ft
      • Built 2018
      22 Briarwood Ln, Vineyard Haven, MA 02568

      Last Sold Summary

      • 4 Days On Market

  • /33

    $869,000

    • 1 Bed
    • 1 Bath
    • 797 Sq Ft

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

    In the heart of Downtown Oak Bluffs walk to everything from this Circuit Avenue location Unit #5 comes with an amazing roof top deck that is only shared with one other condo (#4). This well appointed sleeps 4 with custom wood features and a staircase to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area,, large bedroom with alcove, a sleep nook, a tiled

    Lisa Lucier Anchor Realty of MV

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
  • /23

    $949,000

    Sold Jun 23, 2025

    345 Franklin St, Vineyard Haven, MA 02568

    • 3 Beds
    • 1.5 Baths
    • 1,012 Sq Ft
    • Built 1986

    Last Sold Summary

    • $938/SF
    • 3 Days On Market

    Current Estimated Value $944,009

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

    345 Franklin St, Vineyard Haven, MA 02568
    • /25

      Est $5,625,567

      Not Listed For Sale

      135 Capawock Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3.5 Baths
      • 2,921 Sq Ft
      • Built 2001
      135 Capawock Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 7 Days On Market

  • /42

    $5,875,000

    Pending
    • 4 Beds
    • 4.5 Baths
    • 3,800 Sq Ft

    62 N Summer St, Edgartown, MA 02539

    Village dreams come true... STUNNINGLY CRAFTED, **this four-bedroom five bath property in Edgartown Village with Garage is truly a rare find! Situated on a corner lot just two blocks north of Main Street and two blocks from the Harbor, it features walking convenience and luxury in one package. Main and second floors combine over 3,800 square feet of spacious, elegant living. The partially

    Lisa Gilberto C McManus Realty Group

    62 N Summer St, Edgartown, MA 02539

Showing Results 481 - 520, Page 13 of 18

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