Dukes County, MA Homes

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  /138

  $4,800,000

  Sold Sep 24, 2025

  264 Katama Rd, Edgartown, MA 02539

  • 4 Beds
  • 4.5 Baths
  • 4,167 Sq Ft
  • Built 2020

  Last Sold Summary

  • 3% Below List Price
  • $1,152/SF
  • 50 Days On Market

  Current Estimated Value $4,807,374

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

  264 Katama Rd, Edgartown, MA 02539
• 

  

  /2

  Est $2,385,623

  Not Listed For Sale

  84 Cuttyhunk Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 4 Baths
  • 2,396 Sq Ft
  • Built 2001

  84 Cuttyhunk Ave, Vineyard Haven, MA 02568
• 

  

  

  /4

  $2,995,000

  • 4 Beds
  • 4.5 Baths
  • 3,024 Sq Ft

  9 Hagerty Dr, Tisbury, MA 02568

  West Chop Dream Home in the Making! Experience the charm of this brand-new Shingle Style Colonial, currently under construction. Featuring 4 spacious bedrooms, 4 full and one half bath. This thoughtfully designed home offers generous space. Venture outside into your private oasis, complete with an in-ground pool (36' x18') — perfect for sun-soaked afternoons and evening gatherings. Situated in a

  Lisa Gilberto C McManus Realty Group

  9 Hagerty Dr, Tisbury, MA 02568
• 

  

  

  /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 $1,361,639

  Last Listing Agent Lynn Buder Sandpiper Realty

  2 Upper Douglas Ln, Oak Bluffs, MA 02557
• 

  

  

  /24

  Est $950,688

  Not Listed For Sale

  19 Speed Andrews Way, Vineyard Haven, MA 02568

  • 3 Beds
  • 1 Bath
  • 1,016 Sq Ft
  • Built 1972

  19 Speed Andrews Way, Vineyard Haven, MA 02568

  Last Sold Summary

  • 20 Days On Market
• 

  

  /4

  $1,325,000

  • Land
  • 4.28 Acres
  • $309,579 per Acre

  0 N Road 15 Belhaven Way Unit 4-2, Chilmark, MA 02535

  Set just off North Road, this exceptional parcel offers a rare opportunity to build in a setting rich with natural beauty. Recently subdivided, this land combines privacy, character and thoughtful positioning. The lot is perfectly sited capturing serene woodland views and the natural contours of Middle Line Ridge. A 600ft stonewall lines the western property line, creating a timeless sense of

  Stacy Ickes Donnelly + Co

  0 N Road 15 Belhaven Way Unit 4-2, Chilmark, MA 02535
• 

  

  /14

  $1,800,000

  Sold Dec 23, 2025

  19 Katama Dr, Edgartown, MA 02539

  • 3 Beds
  • 1.5 Baths
  • 1,188 Sq Ft
  • Built 1984

  Last Sold Summary

  • 28% Below List Price
  • $1,515/SF
  • 70 Days On Market

  Last Listing Agent Emma Kennedy Sandpiper Realty

  19 Katama Dr, Edgartown, MA 02539
• 

  

  /54

  Est $5,181,712

  Not Listed For Sale

  14 E Sound Ln, Vineyard Haven, MA 02568

  • 4 Beds
  • 4 Baths
  • 2,470 Sq Ft
  • Built 1978

  14 E Sound Ln, Vineyard Haven, MA 02568

  Last Sold Summary

  • 635 Days On Market
• 

  

  /40

  $1,695,000

  • 4 Beds
  • 2 Baths
  • 1,342 Sq Ft

  58 Road To the Plains, Edgartown, MA 02539

  Turnkey Katama Home—Beautifully furnished and move-in ready, this updated coastal retreat offers relaxed Island living with a strong rental history and effortless ownership. Outdoor highlights include a 19-foot heated swim spa and Jacuzzi set on an expansive wood deck, an outdoor shower, bluestone fire pit patio, multiple lounging spaces, decks, and wooded privacy for serene entertaining. Inside,

  Stephanie Roache Donnelly + Co.

  58 Road To the Plains, Edgartown, MA 02539
• 

  

  /42

  $1,700,000

  Sold Nov 03, 2025

  35 Tower Ridge Rd, Oak Bluffs, MA 02557

  • 3 Beds
  • 4 Baths
  • 2,558 Sq Ft
  • Built 1986

  Last Sold Summary

  • 20% Below List Price
  • $665/SF
  • 106 Days On Market

  Current Estimated Value $1,746,228

  Last Listing Agent Katherine Donahue Sandpiper Realty

  35 Tower Ridge Rd, Oak Bluffs, MA 02557
• 

  

  /35

  Est $1,846,443

  Not Listed For Sale

  83 William Norton Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 3.5 Baths
  • 1,907 Sq Ft
  • Built 1999

  83 William Norton Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 62 Days On Market
• 

  

  /78

  $35,000,000

  • 8 Beds
  • 8 Baths
  • 6,841 Sq Ft

  146 Quenames Rd, Chilmark, MA 02535

  Set on 60 acres along one of the most private and unspoiled stretches of Atlantic coastline in Chilmark, this exceptional estate offers a rare combination of scale, privacy, and enduring coastal beauty. With over 800 feet of direct ocean frontage, the property commands expansive views while maintaining a true sense of seclusion, an increasingly scarce offering on Martha’s Vineyard. A gated drive

  Grace Hagerty Grace Hagerty Real Estate Inc

  146 Quenames Rd, Chilmark, MA 02535
• 

  

  /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

  Current Estimated Value $783,440

  Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  17 Siloam Ave, Oak Bluffs, MA 02557
• 

  

  /31

  Est $1,694,393

  Not Listed For Sale

  97 Snake Hollow, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,822 Sq Ft
  • Built 1981

  97 Snake Hollow, Vineyard Haven, MA 02568

  Last Sold Summary

  • 6 Days On Market
• 

  

  /13

  $1,295,000

  Pending

  • 4 Beds
  • 2 Baths
  • 1,764 Sq Ft

  54 Columbian Ave, Oak Bluffs, MA 02557

  Nestled in a quiet Oak Bluffs neighborhood, this charming, sun-filled four-bedroom, two-bath home sits on a spacious corner lot and offers an ideal opportunity for both seasonal and year-round living. The home features a functional layout with a cozy wood burning stove and abundant natural light throughout. The main level offers a spacious living area open to a kitchen, both with wide plank

  Katrina Lima Donnelly + Co

  54 Columbian Ave, Oak Bluffs, MA 02557
• 

  /2

  $6,825,000

  Sold Jan 05, 2026

  662 Chappaquonsett Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 3 Baths
  • 1,914 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Below List Price
  • $3,566/SF
  • 0 Days On Market

  Current Estimated Value $4,543,714

  Last Listing Agent Jill Napior Tea Lane Associates

  662 Chappaquonsett Rd, Vineyard Haven, MA 02568
• 

  

  /41

  Est $1,853,708

  Not Listed For Sale

  93 Hvoslef Way, Vineyard Haven, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 2,044 Sq Ft
  • Built 2007

  93 Hvoslef Way, Vineyard Haven, MA 02568

  Last Sold Summary

  • 51 Days On Market
• 

  /2

  $595,000

  $55K PRICE DROP Pending

  • Land
  • 11,630 Sq Ft
  • $2,228,464 per Acre

  5 Temahigan Ave Unit 4-139-0, Oak Bluffs, MA 02568

  Serious Seller.......Price will be discounted for cash sale................A perfect Vineyard location that is convenient to beaches, a bike path and both downtown Oak Bluffs and Vineyard Haven. This is a unique location in an area of very substantial homes. Per an island engineer, your future house can possibly have up to seven bedrooms and have up to three floors. Include on the property

  Ed Charter Arrowhead Homes

  5 Temahigan Ave Unit 4-139-0, Oak Bluffs, MA 02568
• 

  

  /36

  $3,700,000

  Sold May 28, 2026

  122 Old Farm Rd, Chilmark, MA 02535

  • 5 Beds
  • 4 Baths
  • 3,413 Sq Ft
  • Built 1790

  Last Sold Summary

  • 38% Below List Price
  • $1,084/SF
  • 261 Days On Market

  Current Estimated Value $1,664,000

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

  122 Old Farm Rd, Chilmark, MA 02535
• 

  

  /16

  Est $1,780,358

  Not Listed For Sale

  585 Herring Creek Rd, Vineyard Haven, MA 02568

  • 2 Beds
  • 1 Bath
  • 704 Sq Ft
  • Built 1950

  585 Herring Creek Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 10 Days On Market
• 

  

  /5

  $439,500

  • Land
  • 24,393 Sq Ft
  • $784,821 per Acre

  5 Candle Maker Cir, Edgartown, MA 02539

  Located on a quiet cul-de-sac in a private Edgartown neighborhood, this half-acre parcel offers the perfect setting for your Martha's Vineyard home. Centrally located, the property provides easy access to the bike path and State Forest walking trails. With the recent Massachusetts Affordable Homes Act, this lot is now buildable and will include an approved 3-bedroom septic plan. The site allows

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  5 Candle Maker Cir, Edgartown, MA 02539
• 

  

  /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

  Current Estimated Value $1,326,953

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

  23 Laurel Ave, Oak Bluffs, MA 02557
• 

  

  /44

  Est $7,912,362

  Not Listed For Sale

  1115 Main St, Vineyard Haven, MA 02568

  • 11 Beds
  • 10 Baths
  • 7,026 Sq Ft
  • Built 1893

  1115 Main St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 280 Days On Market
• 

  

  /12

  $1,495,000

  $80K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  47 Quenames Rd, Chilmark, MA 02535

  On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural

  Dawn Bellante-Holand Sandpiper Realty

  47 Quenames Rd, Chilmark, MA 02535
• 

  

  /44

  $1,525,000

  Sold Feb 03, 2026

  105 Stoney Hill Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 1,815 Sq Ft
  • Built 1986

  Last Sold Summary

  • 8% Below List Price
  • $840/SF
  • 60 Days On Market

  Current Estimated Value $1,641,964

  Last Listing Agent Lisa Da Silva Signal House Group at Compass

  105 Stoney Hill Rd, Vineyard Haven, MA 02568
• 

  

  /47

  Est $2,324,029

  Not Listed For Sale

  42 Hagerty Dr, Vineyard Haven, MA 02568

  • 4 Beds
  • 4.5 Baths
  • 2,569 Sq Ft
  • Built 1970

  42 Hagerty Dr, Vineyard Haven, MA 02568

  Last Sold Summary

  • 58 Days On Market
• 

  

  /3

  $1,650,000

  • Land
  • 1.57 Acres
  • $1,050,955 per Acre

  63 Division Rd Unit 46, Edgartown, MA 02539

  LOT #4 - The last lot available in this 5-lot Edgartown subdivision! Division Road is located between Meshacket and Meetinghouse Way, less than 1 mile from the center of town. This concept was thoughtfully and creatively developed in an effort to create a new and upcoming neighborhood. The new residences will be able to accommodate up to 7 bedrooms, and offer the opportunity to create your own

  Cheri Mason Landvest MV

  63 Division Rd Unit 46, Edgartown, MA 02539
• 

  

  /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

  Current Estimated Value $1,317,619

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

  32 MacHipscat Trail, Vineyard Haven, MA 02568
• 

  

  /16

  Est $1,360,285

  Not Listed For Sale

  222 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

  • 2 Beds
  • 3 Baths
  • 1,750 Sq Ft
  • Built 1988

  222 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

  Last Sold Summary

  • 8 Days On Market
• 

  

  /12

  $1,200,000

  • Land
  • 10,890 Sq Ft
  • $4,800,000 per Acre

  0 Temahigan Ave Unit 160, Oak Bluffs, MA 02568

  Welcome to # 0 Temahigan Ave & Dover Street, Oak Bluffs.Build Your Martha’s Vineyard Dream Home.Rare opportunity to own a level, cleared corner lot in desirable Oak Bluffs, with paved roads bordering two sides, ready for construction of your Martha’s Vineyard dream home. Approved for up to 6 bedrooms, this exceptional property includes an approved 6-bedroom septic design, with room for a

  Rene Ben David Ocean Park Realty Inc

  0 Temahigan Ave Unit 160, Oak Bluffs, MA 02568
• 

  

  /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

  Current Estimated Value $2,469,307

  Last Listing Agent Kristin Buck Donnelly + Co

  8 Old Dunhams Corner Way, Edgartown, MA 02539
• 

  

  /28

  Est $1,229,456

  Not Listed For Sale

  208 Sandpiper Ln Unit 11, Vineyard Haven, MA 02568

  • 2 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Built 1988

  208 Sandpiper Ln Unit 11, Vineyard Haven, MA 02568

  Last Sold Summary

  • 15 Days On Market
• 

  

  /31

  $2,395,000

  $55K PRICE DROP

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

  25 Fulling Mill Rd, Chilmark, MA 02535

  Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to

  Thomas Wallace Wallace & Co. Sotheby's

  25 Fulling Mill Rd, Chilmark, MA 02535
• 

  

  /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
• 

  

  /86

  Est $1,581,571

  Not Listed For Sale

  176 Sandpiper Ln Unit 11, Vineyard Haven, MA 02568

  • 3 Beds
  • 3.5 Baths
  • 2,455 Sq Ft
  • Built 1988

  176 Sandpiper Ln Unit 11, Vineyard Haven, MA 02568

  Last Sold Summary

  • 187 Days On Market
• 

  

  /16

  $710,000

  Open Thu 10AM - 12PM

  • 1 Bed
  • 1 Bath
  • 542 Sq Ft

  66 Canonicus Ave, Oak Bluffs, MA 02557

  The Pinkletink Could be Yours!!! This unspoiled 1950's cottage is named for the Island's tiny frogs who "sing" the announcement of spring. The location is sublime, just 5 blocks from Inkwell Beach and only a few more to the top of Circuit Avenue, while feeling miles away in this quiet location near Farm Pond. Cherished by its owners for decades, the cottage has been lovingly maintained while

  Candy DaRosa Feiner Real Estate

  66 Canonicus Ave, Oak Bluffs, MA 02557
• 

  

  /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
• 

  

  /19

  Est $1,320,995

  Not Listed For Sale

  193 Franklin Terrace, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft
  • Built 1972

  193 Franklin Terrace, Vineyard Haven, MA 02568

  Last Sold Summary

  • 487 Days On Market
• 

  

  /64

  $2,579,000

  • 4 Beds
  • 2 Baths
  • 1,399 Sq Ft

  34 Windemere Rd, Oak Bluffs, MA 02557

  Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  34 Windemere Rd, Oak Bluffs, MA 02557
• 

  

  /24

  $2,125,000

  Sold Oct 30, 2025

  30 Sengekontacket Rd, Oak Bluffs, MA 02557

  • 4 Beds
  • 3 Baths
  • 2,262 Sq Ft
  • Built 1978

  Last Sold Summary

  • 11% Below List Price
  • $939/SF
  • 265 Days On Market

  Current Estimated Value $2,218,495

  Last Listing Agent Cassie Courtney Wallace & Co. Sotheby's

  30 Sengekontacket Rd, Oak Bluffs, MA 02557

Showing Results 521 - 560, Page 14 of 18