20,059

Dukes County, MA Homes

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  • /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
  • /19

    $17,600 total monthly price

    • 4 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • House for Rent

    50 Carls Way, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Looking for that perfect setting with a water view? This is the one!!This cute cape is privately set with a water view and direct water access to Town Pond. You can dock your canoes and kyacks here and access Tisbury Great Pond and then right out to the beach. There are

    Karen Overtoom Karen M. Overtoom R.E.

    50 Carls Way, West Tisbury, MA 02575
  • /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

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    4 Quail Run Unit 2, Oak Bluffs, MA 02557
    • /27

      Est $980,330 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,116 Sq Ft

      84 Pine Tree Rd, Vineyard Haven, MA 02568

      84 Pine Tree Rd, Vineyard Haven, MA 02568
  • /9

    $4,995,000 Pending

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

    64 Crowell Ln, Tisbury, MA 02568

    Welcome to your Vineyard Dream in the heart of West Chop! Built by Novo Builds, a renowned construction company that is recognized for their innovative designs and high-quality craftsmanship. Novo Builds is set to enhance the landscape of this iconic island with their latest development.This stunning new build offers the perfect blend of modern luxury and coastal charm, making it an ideal

    Joe & Nicole Holland Vineyard Dream Realty LLC

    64 Crowell Ln, Tisbury, MA 02568
  • /17

    $17,600 total monthly price

    • 4 Beds
    • 4 Baths
    • 2,676 Sq Ft
    • House for Rent

    40 Summer Cir, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and living room surrounded by windows and decks with an outdoor table and extra seating. An "upside down" house with the living

    Karen Overtoom Karen M. Overtoom R.E.

    40 Summer Cir, West Tisbury, MA 02575
  • /48

    $5,250,000 Sold Jul 02, 2025

    14 Katama Farm Rd N, Edgartown, MA 02539

    • 3 Beds
    • 4.5 Baths
    • 2,869 Sq Ft
    • Built 1988

    Last Sold Summary

    • 5% Below List Price
    • $1,830/SF
    • 54 Days On Market

    Last Listing Agent Courtney Marek Sandpiper Realty Inc

    14 Katama Farm Rd N, Edgartown, MA 02539
    • /17

      Est $1,708,341 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,260 Sq Ft

      55 Pinehurst Rd, Edgartown, MA 02539

      55 Pinehurst Rd, Edgartown, MA 02539
  • /53

    $3,750,000

    • 5 Beds
    • 6.5 Baths
    • 4,372 Sq Ft

    139 Main St, Vineyard Haven, MA 02568

    Nestled just two blocks from Vineyard Haven's working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses--now gracefully combined into a single half-acre parcel--this home offers rare space, privacy, and timeless character in one of the island's most approachable villages. From the moment you step through the welcoming

    Leslie Floyd Portfolio Properties

    139 Main St, Vineyard Haven, MA 02568
  • /21

    $8,000 total monthly price

    • 1 Bed
    • 1 Bath
    • 936 Sq Ft
    • House for Rent

    10 James Pond Way, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a

    Karen Overtoom Karen M. Overtoom R.E.

    10 James Pond Way, 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 $1,713,354

    Last Listing Agent Michele Moore Island Real Estate

    12 Martha's Park Rd, Oak Bluffs, MA 02557
    • /47

      Est $2,540,322 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 3,627 Sq Ft

      24 Peacegate Way, Vineyard Haven, MA 02568

      24 Peacegate Way, Vineyard Haven, MA 02568
  • /69

    $4,175,000

    • 6 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
  • /20

    $12,000 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,068 Sq Ft
    • House for Rent

    76 Ben Chase Rd Wt136, West Tisbury, MA 02575

    Experience a wonderful glimpse of country living in the peaceful, quiet setting of Serene Pond Cottage! This charming Martha's Vineyard retreat features a cozy interior with ample natural light, a private deck where you can take your breakfast and coffee, and a tree-lined backyard to enjoy on lazy summer days. Comfortable three bedroom single story home with one brand new renovated full bath with

    Karen Overtoom Karen M. Overtoom R.E.

    76 Ben Chase Rd Wt136, West Tisbury, MA 02575
  • /32

    $1,675,000 Sold Dec 08, 2025

    78 Whalers Walk, Edgartown, MA 02539

    • 3 Beds
    • 2.5 Baths
    • 1,914 Sq Ft
    • Built 1999

    Last Sold Summary

    • 7% Below List Price
    • $875/SF
    • 100 Days On Market

    Last Listing Agent Dawn Bellante Sandpiper Realty Inc

    78 Whalers Walk, Edgartown, MA 02539
    • /16

      Est $1,260,734 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,150 Sq Ft

      31 Music St, Vineyard Haven, MA 02568

      31 Music St, Vineyard Haven, MA 02568
  • /5

    $1,300,000 Pending

    • Land
    • 0.5 Acre
    • $2,600,000 per Acre

    58 Marthas Rd Unit 70, Edgartown, MA 02539

    Island Grove Building Lot - A highly desirable Edgartown location near Morning Glory Farm, the Village, and South Beach. The 1/2 acre parcel is conforming in nature, allowing for maximum development. With approval for 6 bedrooms with sewer tie-in, the opportunities are endless! A great opportunity to get into this terrific community. *SELLER FINANCING AVAILABLE*

    Katie Donahue Sandpiper Realty

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

    $30,000 total monthly price

    • 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
  • /39

    $4,762,500 Sold May 14, 2025

    69 Division Rd, Edgartown, MA 02539

    • 6 Beds
    • 5.5 Baths
    • 5,103 Sq Ft
    • Built 2024

    Last Sold Summary

    • 18% Below List Price
    • $933/SF
    • 411 Days On Market

    Current Estimated Value $4,935,414

    Last Listing Agent Jennifer DaSilva Compass | Point B

    69 Division Rd, Edgartown, MA 02539
    • /29

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,800 Sq Ft

      30 Mill Hill Rd, Edgartown, MA 02539

      30 Mill Hill Rd, Edgartown, MA 02539
  • /69

    $1,299,000 Pending

    • 4 Beds
    • 3 Baths
    • 2,961 Sq Ft

    208 Irenes Way, Tisbury, MA 02568

    ***NOW OFFERED TURN KEY*** At just $439/sqft this is a great opportunity to own your vey own slice of Martha's Vineyard! New Carpet just installed & Fresh Paint upstairs! Ready for you to move right in! Welcome to this 4 bedroom 3 bathroom 2,961 square foot home! With high ceilings throughout and a open, first floor layout. First floor bedroom, full bath and laundry. New kitchen and appliances

    Emma Kiley Bryant Landmarks at TODAY Real Estate

    208 Irenes Way, Tisbury, MA 02568
  • /29

    $10,900 total monthly price

    • 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
  • /45

    $990,000 Sold Feb 19, 2025

    5 Rock Pond Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,618 Sq Ft
    • Built 1999

    Last Sold Summary

    • 14% Below List Price
    • $612/SF
    • 145 Days On Market

    Current Estimated Value $1,051,364

    Last Listing Agent Kerry Quinlan-Potter Breakwater MV

    5 Rock Pond Rd, Vineyard Haven, MA 02568
    • /17

      Est $1,337,495 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,503 Sq Ft

      165 Weaver Ln, Vineyard Haven, MA 02568

      165 Weaver Ln, Vineyard Haven, MA 02568
  • /8

    $475,000

    • Land
    • 0.52 Acre
    • $913,462 per Acre

    36 Boylston Dr Unit 1.329, Edgartown, MA 02539

    Buildable lot in an established Edgartown neighborhood. Approvals are in hand for the construction of a single-family residential structure not to exceed 3 bedrooms and not to exceed 1,850 square feet of heated living area (screened porches, patios, etc are not included in this square footage). Note that this property cannot be used as a seasonal home or short-term rental. Septic plan has been

    Mark Jenkins Wallace & Co. Sotheby's

    36 Boylston Dr Unit 1.329, Edgartown, MA 02539
  • /13

    $15,000 total monthly price

    • 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

    $1,600,000 Sold Feb 04, 2025

    493 South Rd, Chilmark, MA 02535

    • Land
    • 3.6 Acres
    • $444,444 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Julianna Flanders Flanders Real Estate

    493 South Rd, Chilmark, MA 02535
    • /21

      Est $1,553,727 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,066 Sq Ft

      23 Anthiers Way, Edgartown, MA 02539

      23 Anthiers Way, Edgartown, MA 02539
  • /36

    $3,350,000

    • 3 Beds
    • 2.5 Baths
    • 2,686 Sq Ft

    4 Nomans Watch Rd, Aquinnah, MA 02535

    Perched on 2.7 acres in one of Aquinnah’s most breathtaking settings, this beautifully sited coastal retreat offers sweeping views over the Atlantic and Noman’s Land from its elevated position. Designed to embrace the light and scenery, the main level features an open living/dining/kitchen area wrapped in walls of windows—an airy, sun-soaked space where ocean views take center stage. The

    Jen O'Hanlon Compass | The O'Hanlon Group

    4 Nomans Watch Rd, Aquinnah, MA 02535
  • /22

    $20,000 total monthly price

    • 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
  • /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

    Last Listing Agent Natalie Conroy Conroy & Company R.E., Inc.

    126 Border Rd, Vineyard Haven, MA 02568
    • /17

      Est $1,060,717 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 934 Sq Ft

      10 Briarwood Ln, Vineyard Haven, MA 02568

      10 Briarwood Ln, Vineyard Haven, MA 02568
  • /17

    $725,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,068 Sq Ft

    181 Circuit Ave, Oak Bluffs, MA 02557

    Location, location, location!! This chic, turnkey cottage has been completely renovated! Park your car, drop your bags and walk to everything - beaches, shops, restaurants, parks and the ferry! Enjoy the front deck, backyard patio or saunter across to Veira Park. Perfect family getaway or a great investment property with strong rental income history! Enjoy this adorable home all year around!

    Jennifer B. DaSilva Compass

    181 Circuit Ave, Oak Bluffs, MA 02557
  • /9

    $19,000 total monthly price

    • 6 Beds
    • 2.5 Baths
    • 2,155 Sq Ft
    • House for Rent

    17 Umbagog Ave Wt109, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three story home is located in a very desirable area off of Lambert's Cove Road, Makonikey, with access to a private association beach and walking trails. There are four plus bedrooms and bright and open living spaces that lead out to a deck and a screened-in porch.

    Karen Overtoom Karen M. Overtoom R.E.

    17 Umbagog Ave Wt109, 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

    Last Listing Agent Susie Wallo Compass

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

      Est $2,646,248 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,276 Sq Ft

      232 Lagoon Pond Rd, Vineyard Haven, MA 02568

      232 Lagoon Pond Rd, Vineyard Haven, MA 02568
  • /7

    $400,000

    • Land
    • 0.2 Acre
    • $2,000,000 per Acre

    99 Cygnet Way Unit 103, Chilmark, MA 02535

    Escape the crowds at Lucy Vincent and Squibnocket and take advantage of this very rare opportunity to own a private, 17 member, Atlantic Ocean beach lot at Thumb Cove (abuts Hancock Beach). Included in the sale of this property is a deeded .2 acres of sandy beach, a deeded parking spot at Chilmark Pond and the right to launch boats from a dock in the pond. Sail, kayak, row, swim(!) or motor

    Russell Maloney Russell Maloney Real Estate

    99 Cygnet Way Unit 103, Chilmark, MA 02535
  • /2

    $10,000 total monthly price

    • 6 Beds
    • 3.5 Baths
    • 2,100 Sq Ft
    • House for Rent

    15 Crowell Lane Wt119, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!Seven Gates Farm. This property has three ponds, overlooks rolling meadows and is very charming. Located in Seven Gates Farm association, the property affords access to association tennis and two miles of private beach as well as miles of walking trails. Bookings for tennis are available at the office for a slight fee.There is a $25 trash charge per

    Karen Overtoom Karen M. Overtoom R.E.

    15 Crowell Lane Wt119, 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 $823,421

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

    25 Oak Ave, Oak Bluffs, MA 02557
    • /23

      Not Listed For Sale

      • 6 Beds
      • 3.5 Baths
      • 2,229 Sq Ft

      51 Blueberry Ridge Ln, Chilmark, MA 02535

      51 Blueberry Ridge Ln, Chilmark, MA 02535

Showing Results 281 - 320, Page 8 of 18

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