19,346

Dukes County, MA Homes

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  • /42

    $9,000,000

    $499K PRICE DROP
    • 4 Beds
    • 7 Baths
    • 5,902 Sq Ft

    43 Peases Point Way S, Edgartown, MA 02539

    Behind its classic Village façade lies a home that reimagines Edgartown living, where timeless architecture meets bright, light-filled interiors and an effortless sense of modern luxury. Just moments from Main Street and the harbor, it offers the rare opportunity to enjoy the best of the Village from a residence designed for the way people live and entertain today. Exceptional craftsmanship and

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    43 Peases Point Way S, Edgartown, MA 02539
  • /12

    $6,180 Per Month

    • 3 Beds
    • 3.5 Baths
    • 1,872 Sq Ft
    • House for Rent

    44 Music St Wt153, West Tisbury, MA 02575

    PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

    Karen Overtoom Karen M. Overtoom R.E.

    44 Music St Wt153, 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 $907,676

    Last Listing Agent Susie Wallo Compass

    69 Summit Ave, Vineyard Haven, MA 02568
    • /32

      Est $2,368,903

      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

      Last Listing Agent Kerry Bourne Grade A Realty

  • /17

    $1,500,000

    $200K PRICE DROP Pending
    • Land
    • 37,026 Sq Ft
    • $1,764,706 per Acre

    4 Wilson's Landing Unit 49.2, Edgartown, MA 02539

    Build your dream home in Katama just 2 miles to the parking area at South Beach, and the same distance to the heart of vibrant Edgartown village. This wooded parcel of vacant land is almost an acre in size and will support SEVEN bedrooms once tied into town sewer. Swimming pool and Accessory Dwelling Unit are allowed "by right" (certain restrictions apply to ADUs; an unrestricted 900 sq ft

    Mark Jenkins Wallace & Co. Sotheby's

    4 Wilson's Landing Unit 49.2, Edgartown, MA 02539
  • /29

    $10,900 Per Month

    • 3 Beds
    • 1 Bath
    • 936 Sq Ft
    • House for Rent

    58 Forest Rd Wt140, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,725.. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming rustic home is set within Seven Gates Farm in West Tisbury. Walk down your own path to a beautiful private association beach. There are shared tennis courts and miles of walking trails.

    Karen Overtoom Karen M. Overtoom R.E.

    58 Forest Rd Wt140, West Tisbury, MA 02575
  • /40

    $650,000

    Sold Sep 10, 2025

    25 Oak Ave, Oak Bluffs, MA 02557

    • 2 Beds
    • 0.5 Baths
    • 759 Sq Ft
    • Built 1900

    Last Sold Summary

    • 4% Below List Price
    • $856/SF
    • 251 Days On Market

    Current Estimated Value $787,720

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

    25 Oak Ave, Oak Bluffs, MA 02557
    • /22

      Est $2,053,183

      Not Listed For Sale

      10 N Abels Hill Rd, Chilmark, MA 02535

      • 4 Beds
      • 3 Baths
      • 2,850 Sq Ft
      • Built 1978
      10 N Abels Hill Rd, Chilmark, MA 02535

      Last Sold Summary

      • 354 Days On Market

      Last Listing Agent Elissa Lash Tea Lane Associates

  • /39

    $4,050,000

    $645K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 2,606 Sq Ft

    95 Hines Point Rd, Vineyard Haven, MA 02568

    A rare opportunity, this Hines Point waterfront compound offers expansive views of the Lagoon and 100 feet of private beach. The home was built and has been enjoyed by the same family for gathering and summer recreation over generations. The main house offers an open first floor layout with high ceilings and large windows facing the water where you can watch sunrise over the water. A first floor

    Elissa Lash Tea Lane Associates

    95 Hines Point Rd, Vineyard Haven, MA 02568
  • /13

    $15,000 Per Month

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • House for Rent

    19 Lighthouse Road Aq605, Aquinnah, MA 02535

    This family-friendly, three-bedroom retreat on Lighthouse Road in Aquinnah offers all the comforts of home with stunning water views of the Vineyard Sound and the Elizabeth Islands. It is beautifully decorated and nicely furnished. The home features stylish post-and-beam architecture. The main level features cathedral ceilings, wrap-around picture windows and skylights. The main level opens out

    Karen Overtoom Karen M. Overtoom R.E.

    19 Lighthouse Road Aq605, Aquinnah, MA 02535
  • /2

    $612,500

    Sold Jul 29, 2026

    77 Sixth Street N St, Edgartown, MA 02568

    • Land
    • 12,196 Sq Ft
    • $2,187,500 per Acre

    Last Sold Summary

    • 2% Below List Price
    • 13 Days On Market

    Last Listing Agent Sheila Morse Island Real Estate

    77 Sixth Street N St, Edgartown, MA 02568
    • /23

      Not Listed For Sale

      51 Blueberry Ridge Ln, Chilmark, MA 02535

      • 6 Beds
      • 3.5 Baths
      • 2,229 Sq Ft
      • Built 1989
      51 Blueberry Ridge Ln, Chilmark, MA 02535

      Last Sold Summary

      • 11 Days On Market

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

  • /20

    $2,425,000

    • 2 Beds
    • 2 Baths
    • 895 Sq Ft

    131 N Water St Unit 62, Edgartown, MA 02539

    LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 62 at 131 N. Water Street is a beautifully appointed 865± 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 62, Edgartown, MA 02539
  • /31

    $50,000 Per Month

    • 5 Beds
    • 5 Baths
    • 2,975 Sq Ft
    • House for Rent

    17 Edgartown Bay Rd Ed328, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Private Beach, Waterfront, Mooring and Dock!! Spend your days looking at beautiful Katama Bay. Dock your boat or relax at your private beach. This large Classic Vineyard Home sleeps 10, has two living rooms, protected porch area and a really great front yard leading to

    Karen Overtoom Karen M. Overtoom R.E.

    17 Edgartown Bay Rd Ed328, Edgartown, MA 02539
  • /31

    $1,000,000

    Sold Jun 01, 2026

    73 & 0 Old Country Ln, Vineyard Haven, MA 02568

    • 2 Beds
    • 1 Bath
    • 1,040 Sq Ft
    • Built 1978

    Last Sold Summary

    • 13% Below List Price
    • $962/SF
    • 217 Days On Market

    Last Listing Agent Julianna Flanders Flanders Real Estate

    73 & 0 Old Country Ln, Vineyard Haven, MA 02568
    • /2

      Est $1,807,932

      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

  • /15

    $1,925,000

    • 5 Beds
    • 1 Bath
    • 2,232 Sq Ft

    8 Pequot Ave, Oak Bluffs, MA 02557

    Directly Across from Inkwell Beach, this Victorian Queen has stood the test of time. Partially insulated to extend the season, the new kitchen and bath are cozy in winter and open and bright in summer. 5 bedrooms, 1.5 baths with an outdoor shower, there's plenty of room for family and friends. The front porch has been a gathering place for 50+ years, and the views have not been expanded. So much

    Kerry Quinlan-Potter Breakwater MV

    8 Pequot Ave, Oak Bluffs, MA 02557
  • /25

    $80,000 Per Month

    • 4 Beds
    • 4.5 Baths
    • 3,800 Sq Ft
    • House for Rent

    7 Mill Hill Farms Rd Ed315, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $20,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Gorgeous new 4 bedroom 4 bath home. Top of the line finishes and appliances. Gourmet kitchen, screened in porch with fireplace and TV. Pool with swim up bar, hot tub and grilling area. This is a cream of the crop Katama house is a short distance to downtown Edgartown and

    Karen Overtoom Karen M. Overtoom R.E.

    7 Mill Hill Farms Rd Ed315, Edgartown, MA 02539
  • /2

    $965,000

    Sold Sep 04, 2025

    62 Jernegan Ave, Edgartown, MA 02539

    • 3 Beds
    • 1 Bath
    • 1,886 Sq Ft
    • Built 1998

    Last Sold Summary

    • $512/SF
    • 0 Days On Market

    Current Estimated Value $1,105,895

    Last Listing Agent LINK Email Cache LINK

    62 Jernegan Ave, Edgartown, MA 02539
    • /44

      Est $1,790,815

      Not Listed For Sale

      30 Hillside Path, Vineyard Haven, MA 02568

      • 3 Beds
      • 4 Baths
      • 3,114 Sq Ft
      • Built 1999
      30 Hillside Path, Vineyard Haven, MA 02568

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Stephanie Roache Donnelly + Co

  • /46

    $6,250,000

    • 5 Beds
    • 2.5 Baths
    • 2,269 Sq Ft

    34 Edys Island Way, Chilmark, MA 02535

    Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by an Island legacy family, this property is unique among Island estates for its combination of privacy yet convenience, seclusion yet expansive views. The property is only a

    Jill Napior Tea Lane Associates

    34 Edys Island Way, Chilmark, MA 02535
  • /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
  • /28

    $2,401,000

    Sold Jan 06, 2026

    46 Bold Meadow Rd, Edgartown, MA 02539

    • 4 Beds
    • 3.5 Baths
    • 2,372 Sq Ft
    • Built 1992

    Last Sold Summary

    • $1,012/SF
    • 14 Days On Market

    Current Estimated Value $2,500,516

    Last Listing Agent Julianna Flanders Flanders Real Estate

    46 Bold Meadow Rd, Edgartown, MA 02539
    • /31

      Est $2,523,816

      Not Listed For Sale

      106 Panhandle Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3.5 Baths
      • 3,310 Sq Ft
      • Built 1991
      106 Panhandle Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 80 Days On Market

      Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.

  • /42

    $2,250,000

    • 4 Beds
    • 3 Baths
    • 1,918 Sq Ft

    21 & 25 Fulling Mill Rd, Chilmark, MA 02535

    Jessie Holtham Wallace & Co. Sotheby's International Realty

    21 & 25 Fulling Mill Rd, Chilmark, MA 02535
  • /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
  • /10

    $4,895,000

    Sold Feb 13, 2026

    64 Crowell Ln, Tisbury, MA 02568

    • 5 Beds
    • 6.5 Baths
    • 4,216 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Below List Price
    • $1,161/SF
    • 307 Days On Market

    Current Estimated Value $3,285,841

    Last Listing Agent Joe & Nicole Holland Vineyard Dream Realty LLC

    64 Crowell Ln, Tisbury, MA 02568
    • /37

      Est $2,150,497

      Not Listed For Sale

      24 Pulpit Ln, Edgartown, MA 02539

      • 3 Beds
      • 2 Baths
      • 2,097 Sq Ft
      • Built 2001
      24 Pulpit Ln, Edgartown, MA 02539

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Susie Wallo Compass

  • /41

    $1,975,000

    $175K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,680 Sq Ft

    33 Lagoon Pond Rd, Vineyard Haven, MA 02568

    Brand new construction in the heart of downtown Vineyard Haven! This pristine and thoughtfully designed 3-bedroom, 3-bathroom home offers modern downtown living just steps away from the ferry terminal, restaurants, shops and all that Vineyard Haven has to offer. Where luxury meets sophisticated coastal charm complete with an open floor plan, luxury kitchen featuring quartz countertops, custom

    Madelyn Silvia Wallace & Co. Sotheby's International Realty

    33 Lagoon Pond 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
  • /27

    $1,775,000

    Sold Sep 10, 2025

    13 Hotchkiss Ln, Edgartown, MA 02539

    • 3 Beds
    • 2.5 Baths
    • 2,328 Sq Ft
    • Built 2001

    Last Sold Summary

    • 9% Below List Price
    • $762/SF
    • 61 Days On Market

    Current Estimated Value $2,022,103

    Last Listing Agent Joan Dunayer Martha's Vineyard R.E.

    13 Hotchkiss Ln, Edgartown, MA 02539
    • /2

      Est $1,914,015

      Not Listed For Sale

      54 Bold Meadow Rd, Edgartown, MA 02539

      • 3 Beds
      • 3 Baths
      • 2,026 Sq Ft
      • Built 1993
      54 Bold Meadow Rd, Edgartown, MA 02539

  • /48

    $839,000

    $60K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 804 Sq Ft

    26 Winthrop Ave, Oak Bluffs, MA 02557

    This little gem is waiting to be polished. Hidden behind a wall of vegetation on Winthrop Avenue, an 'oasis', with tons of potential. Existing one bedroom, two story house situated on a 1/3 Acre of land, a 14,810 sq.ft. level lot. Land is large enough for a house and guest house when meeting ZBA requirements, or build a new house and leave existing structure as an Accessory Dwelling Unit when in

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    26 Winthrop Ave, Oak Bluffs, MA 02557
  • /36

    $56,800 Per Month

    • 5 Beds
    • 4 Baths
    • 3,000 Sq Ft
    • House for Rent

    2 Nonamessett Rd, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING.Newly renovated architect designed home with every amenity. Cook's gourmet kitchen, open plan living/dining room, second living room, lots of outdoor patio and deck space, Set in a private 7 acre property with wildflower meadow. Relax around the beautiful in ground pool

    Karen Overtoom Karen M. Overtoom R.E.

    2 Nonamessett Rd, Edgartown, MA 02539
  • /5

    $1,200,000

    Sold Jan 22, 2026

    58 Marthas Rd Unit 70, Edgartown, MA 02539

    • Land
    • 21,780 Sq Ft
    • $2,400,000 per Acre

    Last Sold Summary

    • 8% Below List Price
    • 179 Days On Market

    Last Listing Agent Katherine Donahue Sandpiper Realty

    58 Marthas Rd Unit 70, Edgartown, MA 02539
    • /19

      Est $1,170,101

      Not Listed For Sale

      31 9th St N, Edgartown, MA 02539

      • 2 Beds
      • 1.5 Baths
      • 1,275 Sq Ft
      • Built 1972
      31 9th St N, Edgartown, MA 02539

      Last Sold Summary

      • 45 Days On Market

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

  • /36

    $2,260,000

    $335K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,810 Sq Ft

    4 High Meadow Ln, Oak Bluffs, MA 02557

    Set within the coveted Meadow View Farms community, this exceptional post-and-beam residence offers timeless craftsmanship, generous living spaces, and nearly an acre of private beautifully landscaped grounds with significant potential for expansion.A full-length farmer’s porch creates a gracious arrival and provides the perfect setting to relax. Inside, the sun-drenched main level is defined

    Kate Burnside Portfolio Properties

    4 High Meadow Ln, Oak Bluffs, MA 02557
  • /22

    $20,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,400 Sq Ft
    • House for Rent

    709 Old County Rd Wt134, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY. The weekly price in August is $5,000. per week. See website for additional weekly pricing. Mill Pond House is a completely restored 1890s farmhouse on the old Mill Pond in historic West Tisbury. Remodeled by the present owner, an interior designer, it is beautifully appointed with antiques and charming accessories. An old pine floor and columns add to the

    Karen Overtoom Karen M. Overtoom R.E.

    709 Old County Rd Wt134, West Tisbury, MA 02575
  • /2

    $1,000,000

    Sold Oct 21, 2025

    32 Pine St, Edgartown, MA 02539

    • 3 Beds
    • 1 Bath
    • 979 Sq Ft
    • Built 1940

    Last Sold Summary

    • $1,021/SF
    • 0 Days On Market

    Current Estimated Value $1,089,187

    Last Listing Agent LINK Email Cache LINK

    32 Pine St, Edgartown, MA 02539
    • /33

      Est $4,958,547

      Not Listed For Sale

      62 S Water St, Edgartown, MA 02539

      • 4 Beds
      • 3.5 Baths
      • 2,807 Sq Ft
      • Built 1825
      62 S Water St, Edgartown, MA 02539

      Last Sold Summary

      • 187 Days On Market

      Last Listing Agent Gerrett Conover Landvest MV

Showing Results 281 - 320, Page 8 of 18

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