Dukes County, MA Homes

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  /20

  $1,295,000 Sold Sep 05, 2025

  2 Upper Douglas Ln, Oak Bluffs, MA 02557

  • 4 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1988

  Last Sold Summary

  • 3% Below List Price
  • $818/SF
  • 5 Days On Market

  Current Estimated Value $1,257,177

  Last Listing Agent Lynn Buder Sandpiper Realty

  2 Upper Douglas Ln, Oak Bluffs, MA 02557
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  /16

  Est $1,886,916 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 704 Sq Ft

  585 Herring Creek Rd, Vineyard Haven, MA 02568

  585 Herring Creek Rd, Vineyard Haven, MA 02568
• 

  

  

  /37

  $3,850,000 Pending

  • 5 Beds
  • 4 Baths
  • 3,840 Sq Ft

  8 High St, Edgartown, MA 02539

  A Coveted Village OpportunitySet on one of Edgartown’s most cherished streets, this in-town property offers an exceptional blend of charm, location, and potential. Just moments from Main Street, the harbor, and the Island’s finest dining and shops, 8 High Street features both a main residence and a guest cottage quietly nestled on a well-positioned lot. Inside, the home is filled with warmth

  Valene Pires The Agency

  8 High St, Edgartown, MA 02539
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  /35

  $1,786,000 Sold Dec 27, 2024

  15 Bold Meadow Ln, Edgartown, MA 02539

  • 3 Beds
  • 3.5 Baths
  • 1,715 Sq Ft
  • Built 1991

  Last Sold Summary

  • 2% Below List Price
  • $1,041/SF
  • 8 Days On Market

  Current Estimated Value $1,816,387

  Last Listing Agent Wendy Harman Compass

  15 Bold Meadow Ln, Edgartown, MA 02539
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  /44

  Est $7,776,027 Not Listed For Sale

  • 11 Beds
  • 10 Baths
  • 7,026 Sq Ft

  1115 Main St, Vineyard Haven, MA 02568

  1115 Main St, Vineyard Haven, MA 02568
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  /25

  $1,895,000

  • 4 Beds
  • 2.5 Baths
  • 2,064 Sq Ft

  99 Old Purchase Rd, Edgartown, MA 02539

  Welcome to this charming post and beam-style home, privately located at the end of a cul-de-sac on .71 acres with proximity to over 50 acres of Land Bank and Sheriff's Meadow land with multiple trails and paths. Conveniently located to the bike path, Morning Glory Farm, the heart of Edgartown, and Meetinghouse Way, with direct access to South Beach, the location is ideal. The floor plan was

  Stephanie Roache Donnelly + Co

  99 Old Purchase Rd, Edgartown, MA 02539
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  /2

  $3,900,000 Sold Mar 06, 2025

  57 S Summer St, Edgartown, MA 02539

  • 4 Beds
  • 3 Baths
  • 2,181 Sq Ft
  • Built 1880

  Last Sold Summary

  • $1,788/SF
  • 0 Days On Market

  Current Estimated Value $4,001,090

  Last Listing Agent Bonnie Pierce Wallace & Co. Sotheby's

  57 S Summer St, Edgartown, MA 02539
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  /47

  Est $2,271,133 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 2,569 Sq Ft

  42 Hagerty Dr, Vineyard Haven, MA 02568

  42 Hagerty Dr, Vineyard Haven, MA 02568
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  /51

  $9,795,000

  • 6 Beds
  • 7 Baths
  • 6,135 Sq Ft

  52 S Summer St, Edgartown, MA 02539

  The historic Captain Ellsworth West House is a landmark property in the very heart of downtown Edgartown, offering an extraordinary combination of history, charm, and modern luxury. Just steps from Edgartown’s celebrated restaurants, galleries, shops, and harbor, this rare estate provides both the convenience of in-town living and the privacy of a graciously designed compound. The main residence

  Alyssa Halisky Wallace & Co. Sotheby's

  52 S Summer St, Edgartown, MA 02539
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  /27

  $2,695,000 Sold Dec 27, 2024

  484 Main St, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 3,310 Sq Ft
  • Built 1888

  Last Sold Summary

  • 4% Below List Price
  • $814/SF
  • 14 Days On Market

  Current Estimated Value $2,570,352

  Last Listing Agent Lenny Altieri Premier Properties

  484 Main St, Vineyard Haven, MA 02568
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  /16

  Est $1,420,672 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,750 Sq Ft

  222 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

  222 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568
• 

  

  /20

  $1,300,000

  • 4 Beds
  • 2 Baths
  • 1,566 Sq Ft

  344 Greenwood Ave, Vineyard Haven, MA 02568

  This move-in ready four-bedroom, being offered fully furnished, delivers effortless living, simply bring your swimsuit and settle in. Featuring an open and inviting layout, the living space seamlessly extends to the large deck and heated pool, perfect for relaxing or entertaining. Conveniently located just one mile from the shops and restaurants of downtown Vineyard Haven and less than two miles

  Katie Donahue Sandpiper Realty

  344 Greenwood Ave, Vineyard Haven, MA 02568
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  /30

  $815,000 Sold Nov 14, 2025

  17 Siloam Ave, Oak Bluffs, MA 02557

  • 3 Beds
  • 1 Bath
  • 907 Sq Ft
  • Built 1870

  Last Sold Summary

  • 2% Below List Price
  • $899/SF
  • 100 Days On Market

  Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  17 Siloam Ave, Oak Bluffs, MA 02557
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  /28

  Est $1,346,818 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  208 Sandpiper Ln Unit 11, Vineyard Haven, MA 02568

  208 Sandpiper Ln Unit 11, Vineyard Haven, MA 02568
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  /41

  $8,900,000 Pre-Foreclosure

  • 8 Beds
  • 9 Baths
  • 8,560 Sq Ft

  150 E Chop Dr, Oak Bluffs, MA 02557

  Big Bluff. The crown jewel of East Chop. Timeless elegance and unmatched craftsmanship on the shores of Martha’s Vineyard. Renowned architect M. Hutker and preeminent builder J.G.Early teamed up to create this magnificent waterfront estate. 8,500 Sq. ft. of pure luxury. Open-concept living with large picture windows, a chef’s kitchen with island, high-end appliances, wet bar, and sunlit breakfast

  Moira Lown Coldwell Banker Realty - Wellesley

  150 E Chop Dr, Oak Bluffs, MA 02557
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  /2

  $250,500 Sold Mar 04, 2025

  38 N Water St Unit R-2, Edgartown, MA 02539

  • 2 Beds
  • 2 Baths
  • 797 Sq Ft
  • Built 1890

  Last Sold Summary

  • 9% Below List Price
  • $314/SF
  • 73 Days On Market

  Last Listing Agent Dawn Bellante Sandpiper Realty Inc

  38 N Water St Unit R-2, Edgartown, MA 02539
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  /18

  Est $1,409,026 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  76 Boxberry Ave, Vineyard Haven, MA 02568

  76 Boxberry Ave, Vineyard Haven, MA 02568
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  /26

  $1,595,000

  • 5 Beds
  • 3 Baths
  • 1,810 Sq Ft

  22 Old Lighthouse Rd, Vineyard Haven, MA 02568

  This spacious 5-bedroom, 3-bathroom home is located in a quiet enclave off Main Street, Vineyard Haven. Just half a mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for

  Jessie Holtham Wallace & Co. Sotheby's

  22 Old Lighthouse Rd, Vineyard Haven, MA 02568
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  /52

  $2,470,000 Sold Feb 28, 2025

  2 Green Ave, Edgartown, MA 02539

  • 4 Beds
  • 3.5 Baths
  • 2,351 Sq Ft
  • Built 1760

  Last Sold Summary

  • 23% Below List Price
  • $1,051/SF
  • 180 Days On Market

  Current Estimated Value $2,613,424

  Last Listing Agent Wendy Harman Compass | Point B

  2 Green Ave, Edgartown, MA 02539
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  /46

  Est $1,487,816 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,096 Sq Ft

  140 Tashmoo Ave, Vineyard Haven, MA 02568

  140 Tashmoo Ave, Vineyard Haven, MA 02568
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  /30

  $985,000

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  22 Clark Ave, Vineyard Haven, MA 02568

  A Sweet Spot to call Home. West Chop charms are many in this delightful setting. Acres upon acres of nearby conservation trails make walks, hikes and bike rides an easy daily appeal. Equal distance to Owen Little Way town beach and Vineyard Haven Main Street shops and amenities as well as harbor and ferry port. This move-in ready Clark Avenue abode offers the magic formula of single level living

  Helena Kirschenbaum Studio Realty

  22 Clark Ave, Vineyard Haven, MA 02568
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  /25

  $1,300,000 Sold Dec 18, 2025

  23 Laurel Ave, Oak Bluffs, MA 02557

  • 4 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1900

  Last Sold Summary

  • 13% Below List Price
  • $1,042/SF
  • 64 Days On Market

  Last Listing Agent Sandra Grymes Martha's Vineyard Island-Wide Realty

  23 Laurel Ave, Oak Bluffs, MA 02557
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  /21

  Est $1,243,870 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,416 Sq Ft

  284 Daggett Ave, Vineyard Haven, MA 02568

  284 Daggett Ave, Vineyard Haven, MA 02568
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  /47

  $2,375,000

  • 6 Beds
  • 4.5 Baths
  • 2,970 Sq Ft

  128 & 136 Spring St, Vineyard Haven, MA 02568

  A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street—two adjacent properties being sold together to create a unique, flexible compound just moments from the Tisbury School and downtown Vineyard Haven. With a spacious main residence and a separate guest house, this rare combination presents a compelling opportunity for multigenerational living, seasonal enjoyment,

  David Dickinson Compass | Point B

  128 & 136 Spring St, Vineyard Haven, MA 02568
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  /19

  $1,330,000 Sold Oct 17, 2025

  32 MacHipscat Trail, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,404 Sq Ft
  • Built 1983

  Last Sold Summary

  • 11% Below List Price
  • $947/SF
  • 112 Days On Market

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

  32 MacHipscat Trail, Vineyard Haven, MA 02568
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  /23

  Est $877,830 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 836 Sq Ft

  95 Summer St, Vineyard Haven, MA 02568

  95 Summer St, Vineyard Haven, MA 02568
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  /46

  $1,345,000

  • 3 Beds
  • 2 Baths
  • 1,862 Sq Ft

  249 State Rd, Vineyard Haven, MA 02568

  PRICE REDUCED $150,000!! LARGE LOT ALLOWS ADDITIONAL STRUCTURE perfect for art gallery, business office, studio, etc. Possibilities are endless! WALK TO TOWN, FERRY AND BEAUTIFULLY FURNISHED! This beautifully restored 3-bedroom, 2-bath home has touches from the old Vineyard—a sun porch for napping or reading, a large yard with magnificant magnolia tree, and a detached garage for your Island car.

  Barbara Twiss Laer Realty Partners

  249 State Rd, Vineyard Haven, MA 02568
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  /37

  $2,340,000 Sold Dec 19, 2025

  8 Old Dunhams Corner Way, Edgartown, MA 02539

  • 4 Beds
  • 4.5 Baths
  • 2,912 Sq Ft
  • Built 1998

  Last Sold Summary

  • 10% Below List Price
  • $804/SF
  • 47 Days On Market

  Last Listing Agent Kristin Buck Donnelly + Co

  8 Old Dunhams Corner Way, Edgartown, MA 02539
• 

  

  /21

  Est $957,413 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,186 Sq Ft

  26 Midland Ave, Vineyard Haven, MA 02568

  26 Midland Ave, Vineyard Haven, MA 02568
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  /16

  $1,295,000

  • Land
  • 4.4 Acres
  • $294,318 per Acre

  37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535

  This quiet and lovely four-and-a-half-acre lot in Chilmark is set on a gentle rise, bounded on one side by an old stone wall. The land features graceful trees and a distant water view is possible from a second floor. The lot has been staked, including a proposed home site at the highest elevation. There are so many outstanding possibilities for a future Buyer to build their dream home on this

  Elissa Lash Tea Lane Associates

  37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535
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  /17

  $1,200,000 Sold Oct 28, 2025

  211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1987

  Last Sold Summary

  • 25% Below List Price
  • $714/SF
  • 209 Days On Market

  Last Listing Agent Jim Feiner Feiner Real Estate

  211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568
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  /19

  Est $1,104,896 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,235 Sq Ft

  160 Spring Hill Rd, Vineyard Haven, MA 02568

  160 Spring Hill Rd, Vineyard Haven, MA 02568
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  /52

  $4,900,000

  • 5 Beds
  • 5.5 Baths
  • 5,394 Sq Ft

  23 Pinehurst Rd, Edgartown, MA 02539

  New Construction with POOL, GUEST HOUSE and PRIMARY HOME, all within close proximity to Main Street, Edgartown. This gorgeous four bedroom gambrel home offers comfort and ease of coastal luxurious living. The primary home welcomes you with a two story foyer which opens to a large great room with a gourmet kitchen, with a bar area and a central island offering seating for at least four. The

  Michele Casavant Vineyard Village Realty

  23 Pinehurst Rd, Edgartown, MA 02539
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  /12

  $1,250,000 Sold Oct 23, 2025

  25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568

  • Land
  • 4.12 Acres
  • $303,398 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 127 Days On Market

  Last Listing Agent Abby Rabinovitz Tea Lane Associates

  25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568
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  /53

  Est $1,231,658 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,861 Sq Ft

  18 Goah Way, Vineyard Haven, MA 02568

  18 Goah Way, Vineyard Haven, MA 02568
• 

  

  /46

  $1,299,000

  • 3 Beds
  • 3 Baths
  • 1,750 Sq Ft

  185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

  Experience sun-drenched living in one of Tashmoo Woods’ most desirable floor plans. This beautifully maintained 3-bedroom, 3-bath home offers full access to the coveted Tashmoo Woods amenities, including a pristine pool and pool house, multiple tennis courts, a children’s play area, a private launch on Lake Tashmoo, and a beautiful Association beach on the Sound. Inside, soaring ceilings and

  Candy DaRosa Feiner Real Estate

  185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
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  /2

  $5,000,000 Sold Jun 30, 2025

  93 Oyster Pond Rd Unit 10, Edgartown, MA 02539

  • Land
  • 4.1 Acres
  • $1,219,512 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK

  93 Oyster Pond Rd Unit 10, Edgartown, MA 02539
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  /35

  Est $1,482,724 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft

  26 Heath Hen Ln, Vineyard Haven, MA 02568

  26 Heath Hen Ln, Vineyard Haven, MA 02568
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  /15

  $2,490,000

  • Land
  • 7.08 Acres
  • $351,695 per Acre

  2 Jacob's Neck Rd Unit 2, Edgartown, MA 02539

  Build your dream home or homes on the special 7.1 acre private wooded property surrounding a beautiful 4.5 acre meadow in the grand Boldwater Association (BWA) on the glorious Edgartown Great Pond with approx. 3,000 ft of private barrier beach. BWA is 40 homesites on 450 acres with 150 acres of conservation abutting another 1,500 acres of conservation and a few large estates - all convenient to

  Robert Kenney Tea Lane Associates

  2 Jacob's Neck Rd Unit 2, Edgartown, MA 02539
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  /2

  $2,450,000 Sold Apr 01, 2025

  80 N Summer St, Edgartown, MA 02539

  • 4 Beds
  • 3 Baths
  • 2,012 Sq Ft
  • Built 1925

  Last Sold Summary

  • $1,218/SF
  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK

  80 N Summer St, Edgartown, MA 02539

Showing Results 561 - 600, Page 15 of 18