Dukes County, MA Homes

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  $4,500,000

  • 15 Beds
  • 12.5 Baths
  • 7,250 Sq Ft

  11 Macs Ln, Tisbury, MA 02568

  A unique opportunity to own a one of a kind property complete with fourteen bedrooms, flanked with large picture windows and water views from all three living levels. Currently being run as a state licensed, private pay, assisted living facility. In addition to the fourteen bedrooms and twelve full baths and one half bath, in the main building, there is a private owners apartment on the first

  Madelyn Silvia Wallace & Co. Sotheby's

  11 Macs Ln, Tisbury, MA 02568
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  $50,000 total monthly price

  • 4 Beds
  • 3 Baths
  • 3,237 Sq Ft
  • House for Rent

  29 Naushon Rd Wt142, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfortable single level 4 BR 3 bath home has central air and heat. Enjoy summer star-studded skies from your patio or through skylights in each bedroom.

  Karen Overtoom Karen M. Overtoom R.E.

  29 Naushon Rd Wt142, West Tisbury, MA 02575
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  $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 $1,757,793

  Last Listing Agent Michele Moore Island Real Estate

  12 Martha's Park Rd, Oak Bluffs, MA 02557
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  /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
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  $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
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  $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
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  $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
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  /17

  Est $1,348,387 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
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  $4,695,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 4,003 Sq Ft

  97 Longview Rd, Vineyard Haven, MA 02568

  This beautifully designed post-and-beam home features stunning views of the Vineyard Sound, Elizabeth Islands, and unforgettable sunsets. Surrounded by beautiful stone walls and perfectly sited on 2.2 acres, this serene property offers a combination of luxury and comfort, exuding tranquility and timeless charm. The main home spans three spacious levels, all opening onto generous decks ideal for

  Stephanie Roache Donnelly + Co

  97 Longview Rd, Vineyard Haven, MA 02568
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  /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
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  $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 $4,955,657

  Last Listing Agent Jennifer DaSilva Compass | Point B

  69 Division Rd, Edgartown, MA 02539
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  /21

  Est $1,498,188 Not Listed For Sale

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

  23 Anthiers Way, Edgartown, MA 02539

  23 Anthiers Way, Edgartown, MA 02539
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  $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
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  $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
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  $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 $1,045,307

  Last Listing Agent Kerry Quinlan-Potter Breakwater MV

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

  Est $1,100,157 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
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  $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
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  /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
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  $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

  Current Estimated Value $1,678,092

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

  126 Border Rd, Vineyard Haven, MA 02568
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  Est $2,564,442 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
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  /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
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  /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
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  $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
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  /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
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  $400,000 Pending

  • 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
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  $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
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  $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 $808,207

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

  25 Oak Ave, Oak Bluffs, MA 02557
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  Est $1,567,885 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,144 Sq Ft

  323 Lamberts Cove Rd, Vineyard Haven, MA 02568

  323 Lamberts Cove Rd, Vineyard Haven, MA 02568
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  $857,000

  • Land
  • 0.39 Acre
  • $2,209,902 per Acre

  24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568

  OAK BLUFFS - A Rare Opportunity to purchase an 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.

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568
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  $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
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  $1,600,000 Sold Jan 06, 2026

  44 Tiffany Dr, Oak Bluffs, MA 02557

  • 4 Beds
  • 4 Baths
  • 3,927 Sq Ft
  • Built 1987

  Last Sold Summary

  • 24% Below List Price
  • $407/SF
  • 115 Days On Market

  Last Listing Agent Sheila Morse Island Real Estate

  44 Tiffany Dr, Oak Bluffs, MA 02557
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  Est $1,664,838 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,114 Sq Ft

  30 Hillside Path, Vineyard Haven, MA 02568

  30 Hillside Path, Vineyard Haven, MA 02568
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  $2,950,000

  • 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
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  $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
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  $1,000,000 Sold Dec 12, 2025

  1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557

  • 2 Beds
  • 2.5 Baths
  • 1 Sq Ft
  • Built 2001

  Last Sold Summary

  • 9% Below List Price
  • $1,000,000/SF
  • 13 Days On Market

  Last Listing Agent Lisa Lucier Anchor Realty of MV

  1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557
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  /31

  Est $2,617,392 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,310 Sq Ft

  106 Panhandle Rd, Vineyard Haven, MA 02568

  106 Panhandle Rd, Vineyard Haven, MA 02568
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  $2,950,000

  • 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
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  $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
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  /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 $1,034,012

  Last Listing Agent LINK Email Cache LINK

  62 Jernegan Ave, Edgartown, MA 02539
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  Est $2,045,834 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  119 Herring Creek Rd, Edgartown, MA 02539

  119 Herring Creek Rd, Edgartown, MA 02539

Showing Results 281 - 320, Page 8 of 18