19,346

Dukes County, MA Homes

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  • /41

    $2,195,000

    • 5 Beds
    • 3.5 Baths
    • 2,628 Sq Ft

    7 Pipn Cir, Edgartown, MA 02539

    Life on Chappaquiddick has a rhythm all its own — and this exceptional compound is designed to savor every moment of it.Set on three park-like acres of meadows and woodland, two freshly painted log cabin-style homes offer a private world apart. The three-bedroom main house is open and generous, with living spaces that flow seamlessly from inside to out. The two-bedroom guest house is its own

    Dawn Bellante Sandpiper Realty, Inc.

    7 Pipn Cir, Edgartown, MA 02539
  • /5

    $2,995,000

    Sold Sep 04, 2025

    9 Turkeyland Cove Rd, Edgartown, MA 02539

    • Land
    • 3.01 Acres
    • $995,017 per Acre

    Last Sold Summary

    • 2 Days On Market

    Current Estimated Value $3,293,392

    Last Listing Agent Wendy Harman Compass

    9 Turkeyland Cove Rd, Edgartown, MA 02539
    • /47

      Est $2,108,648

      Not Listed For Sale

      16 Fishermans Knot Rd, Edgartown, MA 02539

      • 3 Beds
      • 3.5 Baths
      • 2,417 Sq Ft
      • Built 2002
      16 Fishermans Knot Rd, Edgartown, MA 02539

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Jennifer DaSilva Compass | Point B

  • /38

    $4,500,000

    • 4 Beds
    • 3.5 Baths
    • 2,836 Sq Ft

    38 Pinehurst Rd, Edgartown, MA 02539

    NEWLY BUILT 4-BEDROOM HOME WITH POOL – 10-Minute WALK TO TOWN,Enjoy modern living in this beautifully furnished, recently built 4-bedroom home featuring a heated saltwater pool and a stylish 20' x 30' entertainment barn—all just a short walk to downtown Edgartown.The home offers two floors of bright, elegant living space with 3.5 beautifully designed bathrooms, an open kitchen and family

    Michele Casavant Vineyard Village Realty

    38 Pinehurst Rd, Edgartown, MA 02539
  • /38

    $3,930,000

    Sold Jun 29, 2026

    71 Stoney Hill Rd, Vineyard Haven, MA 02568

    • 5 Beds
    • 5 Baths
    • 5,598 Sq Ft
    • Built 2007

    Last Sold Summary

    • 13% Below List Price
    • $702/SF
    • 372 Days On Market

    Current Estimated Value $3,898,952

    Last Listing Agent Sheila Morse Island Real Estate

    71 Stoney Hill Rd, Vineyard Haven, MA 02568
    • /30

      Est $1,617,835

      Not Listed For Sale

      54 Lake St, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 2,016 Sq Ft
      • Built 1967
      54 Lake St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 110 Days On Market

      Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty

  • /18

    $239,000

    • 1 Bed
    • 1 Bath
    • 316 Sq Ft

    33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568

    Want to own a slice of Martha's Vineyard? As an owner of this studio style "Condo-tel", you will enjoy the convenience of worry free ownership. This unit has newer flooring, an updated bathroom, updated kitchenette and a cathedral ceiling. This is casual resort style living that includes association pool, 3 tennis courts, playground, and shared grilling area. This wonderful location borders Farm

    Rene Jackson Island Real Estate

    33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568
  • /20

    $1,000,000

    Sold Dec 12, 2025

    1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557

    • 2 Beds
    • 2.5 Baths
    • 2,128 Sq Ft
    • Built 2001

    Last Sold Summary

    • 9% Below List Price
    • $470/SF
    • 13 Days On Market

    Current Estimated Value $1,234,962

    Last Listing Agent Lisa Lucier Anchor Realty of Martha's Vineyard

    1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557
    • /19

      Est $2,336,593

      Not Listed For Sale

      30 Deacon Vincent Way, Edgartown, MA 02539

      • 3 Beds
      • 3 Baths
      • 2,784 Sq Ft
      • Built 2003
      30 Deacon Vincent Way, Edgartown, MA 02539

      Last Sold Summary

      • 208 Days On Market

      Last Listing Agent Tara Ledden Ledden Properties LLC

  • /53

    $1,700,000

    $145K PRICE DROP Under Contract
    • 5 Beds
    • 3 Baths
    • 2,552 Sq Ft

    10 Danls Way, West Tisbury, MA 02575

    Historic West Tisbury farmhouse with detached guest cottage on 1.27 acres in the heart of West Tisbury. Just moments from Alley's General Store, 7a Foods, North Tisbury Village, and a short drive to beaches and both up- and downd Island destinations. This property presents a rare opportunity for a family compound, multi-generational living, or investment with rental income potential.The

    Emma Bryant Studio Realty

    10 Danls Way, West Tisbury, MA 02575
  • /26

    $1,687,500

    Sold Jul 10, 2026

    103 Meadow View Rd, Oak Bluffs, MA 02557

    • 3 Beds
    • 2.5 Baths
    • 2,862 Sq Ft
    • Built 1988

    Last Sold Summary

    • 4% Below List Price
    • $590/SF
    • 31 Days On Market

    Current Estimated Value $1,734,954

    Last Listing Agent Alyson Parker Karen M. Overtoom R.E.

    103 Meadow View Rd, Oak Bluffs, MA 02557
    • /16

      Est $1,561,264

      Not Listed For Sale

      44 Jeremiah Rd, Edgartown, MA 02539

      • 2 Beds
      • 2 Baths
      • 1,380 Sq Ft
      • Built 1996
      44 Jeremiah Rd, Edgartown, MA 02539

      Last Sold Summary

      • 0 Days On Market

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

  • /30

    $1,800,000

    • 4 Beds
    • 4 Baths
    • 2,334 Sq Ft

    528 Main St, Vineyard Haven, MA 02568

    Expanded cottage with in-law suite, garage, and detached studio. On the way to West Chop, it is equidistant to Downtown Vineyard Haven, the flagpole at West Chop, Mink Meadows Golf Club, and Vineyard Haven Yacht Club. This 4 bedroom, 4 bathroom property offers a flexible floor plan, including a private inlaw wing complete with its own entrance, kitchen, living room, full bathroom, and

    Madelyn Silvia Wallace & Co. Sotheby's International Realty

    528 Main St, Vineyard Haven, MA 02568
  • /7

    $2,995,000

    Sold Sep 04, 2025

    9 Turkeyland Cove Rd Unit 10.31430, Edgartown, MA 02539

    • Land
    • 3.01 Acres
    • $995,017 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 389 Days On Market

    Last Listing Agent Wendy Harman Compass | Point B

    9 Turkeyland Cove Rd Unit 10.31430, Edgartown, MA 02539
    • /2

      Est $1,988,353

      Not Listed For Sale

      163 Charles Neck Way, Vineyard Haven, MA 02568

      • 5 Beds
      • 4 Baths
      • 2,508 Sq Ft
      • Built 1987
      163 Charles Neck Way, Vineyard Haven, MA 02568

  • /39

    $2,400,000

    Open Sat 12PM - 2PM
    • 7 Beds
    • 4 Baths
    • 2,232 Sq Ft

    220 North Rd, Chilmark, MA 02535

    Welcome to 220 North Road, Chilmark, an idyllic, up-island retreat featuring a 4-BR, post-and-beam, main house and 3-BR guest cottage. Set on three private acres, this verdant oasis is surrounded by preserves, walking trails and even an ancient way that leads directly from the property to Middle Line Woods Preserve, and then all the way to Tea Lane Farm. A two-thirds of an acre conservation

    David Lott Vineyard Open House Real Estate

    220 North Rd, Chilmark, MA 02535
  • /28

    $1,150,000

    Sold May 08, 2026

    18 Windsor Dr, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,294 Sq Ft
    • Built 1981

    Last Sold Summary

    • 15% Above List Price
    • $889/SF
    • 4 Days On Market

    Current Estimated Value $1,145,026

    Last Listing Agent Stephanie Roache Donnelly + Co.

    18 Windsor Dr, Edgartown, MA 02539
    • /30

      Est $2,937,173

      Not Listed For Sale

      23 Alex Way, Vineyard Haven, MA 02568

      • 3 Beds
      • 5 Baths
      • 2,926 Sq Ft
      • Built 2004
      23 Alex Way, Vineyard Haven, MA 02568

      Last Sold Summary

      • 109 Days On Market

      Last Listing Agent Elissa Lash Tea Lane Associates

  • /9

    $1,395,000

    $600K PRICE DROP
    • 0.5 Baths
    • 1,283 Sq Ft

    4 Lagoon Pond Rd, Vineyard Haven, MA 02568

    Located at the five corners, this rare commercial property presents an opportunity to set your future business venture up for success. This prime location captures the attention of every single vehicle disembarking the Vineyard Haven Ferry! There are 2.5 parking spots included. Please note that the bike shop business is not for sale. This offering is solely for the real estate. The sellers

    Jarrett Hurwitz Keller Williams Realty

    4 Lagoon Pond Rd, Vineyard Haven, MA 02568
  • /35

    $1,817,500

    Sold Feb 27, 2026

    32 Flamingo Dr, Edgartown, MA 02539

    • 5 Beds
    • 3 Baths
    • 2,432 Sq Ft
    • Built 1988

    Last Sold Summary

    • 9% Below List Price
    • $747/SF
    • 251 Days On Market

    Current Estimated Value $1,895,735

    Last Listing Agent Skip Dostal Martha's Vineyard R.E.

    32 Flamingo Dr, Edgartown, MA 02539
    • /25

      Not Listed For Sale

      7 Curtis Ln, Edgartown, MA 02539

      • 4 Beds
      • 2 Baths
      • 1,826 Sq Ft
      • Built 1940
      7 Curtis Ln, Edgartown, MA 02539

      Last Sold Summary

      • 44 Days On Market

      Last Listing Agent Jim Joyce Carroll & Vincent R.E.

  • /47

    $5,450,000

    • 4 Beds
    • 5.5 Baths
    • 3,300 Sq Ft

    8 Paddock Rd, Oak Bluffs, MA 02557

    Refined Vineyard Living in The Preserve - Set atop a knoll overlooking sweeping grassland and the pond, this exceptional residence embodies the perfect balance of classic coastal architecture and modern sophistication. Located within the prestigious enclave of The Preserve, the home offers a combination of privacy, elegance, and seamless indoor-outdoor living. At its core, an expansive great room

    Lesley Heidt Sandpiper Realty

    8 Paddock Rd, Oak Bluffs, MA 02557
  • /61

    $1,910,000

    Sold Apr 03, 2026

    28 Pine Tree Ln, Vineyard Haven, MA 02568

    • 5 Beds
    • 3.5 Baths
    • 3,250 Sq Ft
    • Built 1974

    Last Sold Summary

    • 15% Below List Price
    • $588/SF
    • 132 Days On Market

    Current Estimated Value $2,094,132

    Last Listing Agent Wendy Harman Compass | Point B

    28 Pine Tree Ln, Vineyard Haven, MA 02568
    • /20

      Est $1,354,941

      Not Listed For Sale

      225 Longview Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,730 Sq Ft
      • Built 1977
      225 Longview Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Michele Casavant Vineyard Village Realty

  • /29

    $10,950,000

    $2M PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,050 Sq Ft

    16 Shotnaigher Ln, Chilmark, MA 02535

    New to market this completely renovated water view home is located in a private enclave of upscale homes fronting on Squibnocket Pond in Chilmark. There are 360 degree views from this 3.6 acre hilltop site offering views of the pond, Atlantic Ocean and north to Menemsha Pond and the Vineyard Sound. Sunrise and Sunset! This home, completely renovated in 2022 features a state of the art gourmet

    Rebecca V Conroy Conroy & Company R.E., Inc.

    16 Shotnaigher Ln, Chilmark, MA 02535
  • /21

    $895,000

    Sold May 13, 2026

    22 Montgomery Square, Oak Bluffs, MA 02557

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

    Last Sold Summary

    • $961/SF
    • 7 Days On Market

    Current Estimated Value $905,359

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    22 Montgomery Square, Oak Bluffs, MA 02557
    • /2

      Est $2,295,585

      Not Listed For Sale

      59 Field View Ln, Vineyard Haven, MA 02568

      • 4 Beds
      • 4 Baths
      • 3,269 Sq Ft
      • Built 1975
      59 Field View Ln, Vineyard Haven, MA 02568

  • /58

    $2,895,000

    • 5 Beds
    • 4 Baths
    • 2,300 Sq Ft

    27 Spring St, Vineyard Haven, MA 02568

    Located in the William Street Historic District, this elegant Greek Revival home, built in 1842, has stood the test of time and has been thoughtfully expanded and renovated in recent years. This five-bedroom, four-bath residence combines historic character with modern comforts. The home features a gracious living room, dining room, office, and an inviting kitchen/breakfast room. There are five

    Alexis Holden Tea Lane Associates

    27 Spring St, Vineyard Haven, MA 02568
  • /7

    $600,000

    Sold Nov 04, 2025

    10 Putnam Way, Vineyard Haven, MA 02568

    • 3 Beds
    • 1 Bath
    • 1,168 Sq Ft
    • Built 1972

    Last Sold Summary

    • 22% Below List Price
    • $514/SF
    • 39 Days On Market

    Current Estimated Value $704,463

    Last Listing Agent Kathleen Dawson Donnelly + Co.

    10 Putnam Way, Vineyard Haven, MA 02568
    • /47

      Est $1,717,370

      Not Listed For Sale

      21 Coffins Field Rd, Edgartown, MA 02539

      • 5 Beds
      • 3 Baths
      • 1,822 Sq Ft
      • Built 2003
      21 Coffins Field Rd, Edgartown, MA 02539

      Last Sold Summary

      • 73 Days On Market

      Last Listing Agent Helena Kirschenbaum Studio Realty

  • /65

    $7,999,000

    • 7 Beds
    • 6.5 Baths
    • 7,133 Sq Ft

    9 Sutton's Way, Edgartown, MA 02539

    Nestled in an enviable Katama setting, this masterfully designed shingle-style farmhouse compound epitomizes the peak of casual Vineyard luxury across a manicured coastal landscape. From the sprawling covered entry porch, the front door opens into an impeccably choreographed layout where a grand entry hall flows seamlessly into an expansive great room, an elegant formal dining space and a

    Jennifer DaSilva Compass | Point B

    9 Sutton's Way, Edgartown, MA 02539
  • /20

    $1,225,000

    Sold Mar 16, 2026

    344 Greenwood Ave, Vineyard Haven, MA 02568

    • 4 Beds
    • 2 Baths
    • 1,566 Sq Ft
    • Built 1981

    Last Sold Summary

    • 6% Below List Price
    • $782/SF
    • 75 Days On Market

    Current Estimated Value $1,271,313

    Last Listing Agent Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    344 Greenwood Ave, Vineyard Haven, MA 02568
    • /50

      Not Listed For Sale

      29 Llewellyn Way, Edgartown, MA 02539

      • 5 Beds
      • 6 Baths
      • 5,195 Sq Ft
      • Built 2001
      29 Llewellyn Way, Edgartown, MA 02539

      Last Sold Summary

      • 81 Days On Market

      Last Listing Agent Stephanie Roache Donnelly + Co

  • /38

    $16,000,000

    • Land
    • 46 Acres
    • $347,826 per Acre

    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535

    Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach. Magical expansive views of meadows, pond and ocean. This estate-sized property abuts 140 acres of Sheriff’s Meadow conservation land, offering exceptional privacy. A simple 1041 square foot two bedroom seasonal home sits on one lot with two detached studios alongside. Close to nature, this home

    Abby Rabinovitz Tea Lane Associates

    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535
  • /41

    $1,900,000

    Sold May 01, 2026

    36 Smith Hollow Dr, Edgartown, MA 02539

    • 5 Beds
    • 2.5 Baths
    • 2,836 Sq Ft
    • Built 1985

    Last Sold Summary

    • 4% Below List Price
    • $670/SF
    • 172 Days On Market

    Current Estimated Value $1,917,498

    Last Listing Agent Katherine Donahue Sandpiper Realty

    36 Smith Hollow Dr, Edgartown, MA 02539
    • /42

      Not Listed For Sale

      49 William St, Vineyard Haven, MA 02568

      • 5 Beds
      • 4.5 Baths
      • 3,752 Sq Ft
      • Built 1836
      49 William St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 279 Days On Market

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

  • /24

    $429,000

    • 1 Bed
    • 1 Bath
    • 305 Sq Ft

    124 Skiff Ave Unit B-12, Vineyard Haven, MA 02568

    Welcome to Unit B-12 at the Causeway Condominiums, a turnkey studio offering comfortable, low-maintenance island living just a short walk to the charming village of Vineyard Haven. Thoughtfully designed to maximize space and functionality, this inviting residence features warm bamboo flooring throughout, a custom Murphy bed, and a beautifully crafted custom mahogany closet and storage system,

    Marilyn Moses Ocean Park Realty Inc

    124 Skiff Ave Unit B-12, Vineyard Haven, MA 02568
  • /27

    $1,735,000

    Sold Sep 29, 2025

    56 Bridle Path Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 4 Baths
    • 2,526 Sq Ft
    • Built 1996

    Last Sold Summary

    • 13% Below List Price
    • $687/SF
    • 2 Days On Market

    Current Estimated Value $2,166,208

    Last Listing Agent Tina Miller Donnelly + Co.

    56 Bridle Path Rd, Vineyard Haven, MA 02568
    • /34

      Est $7,523,454

      Not Listed For Sale

      93 Edgartown Bay Rd, Edgartown, MA 02539

      • 4 Beds
      • 4.5 Baths
      • 3,596 Sq Ft
      • Built 1978
      93 Edgartown Bay Rd, Edgartown, MA 02539

      Last Sold Summary

      • 95 Days On Market

      Last Listing Agent Jarrett Hurwitz Keller Williams Realty

  • /10

    $3,750,000

    $245K PRICE DROP
    • Land
    • 1.92 Acres
    • $1,956,182 per Acre

    98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568

    Farm Neck Golf Club – Undeveloped Water View Parcel with Membership A truly rare opportunity to acquire a 1.92-acre undeveloped parcel within the prestigious Farm Neck Golf Club community, one of the last remaining opportunities of its kind. This exceptional offering features sweeping water views over Sengekontacket Pond to the Vineyard Sound, creating a stunning backdrop for your future Martha’s

    Andrew McElhinney Compass LLC

    98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568

Showing Results 401 - 440, Page 11 of 18

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