Dukes County, MA Homes

• 

  

  

  /30

  $2,240,000

  Sold Nov 06, 2025

  29 Pradas Way, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft
  • Built 1998

  Last Sold Summary

  • 6% Below List Price
  • $1,270/SF
  • 27 Days On Market

  Current Estimated Value $2,240,073

  Last Listing Agent Wendy Harman Compass | Point B

  29 Pradas Way, Edgartown, MA 02539
• 

  

  /2

  Est $1,034,662

  Not Listed For Sale

  90 Holly Tree Ln, Vineyard Haven, MA 02568

  • 2 Beds
  • 2 Baths
  • 1,081 Sq Ft
  • Built 1980

  90 Holly Tree Ln, Vineyard Haven, MA 02568
• 

  

  

  /31

  $1,575,000

  • 3 Beds
  • 4 Baths
  • 3,072 Sq Ft

  110 Clover Hill Dr, Vineyard Haven, MA 02568

  Minutes to downtown and the ferry, this updated year-round home checks every box buyers are asking for right now: space, flexibility, and a move-in ready setup in a highly convenient location. 3 bedrooms, 4 bathrooms, and over 3,000 sq ft of living space, including a private lower-level apartment ideal for guests, extended family, or income potential. The main level offers hardwood floors, a

  Jim Feiner Feiner Real Estate

  110 Clover Hill Dr, Vineyard Haven, MA 02568
• 

  

  /2

  $17,250,000

  Sold Oct 30, 2025

  81 S Water St, Edgartown, MA 02539

  • 7 Beds
  • 6 Baths
  • 4,388 Sq Ft
  • Built 1875

  Last Sold Summary

  • $3,931/SF
  • 0 Days On Market

  Last Listing Agent Gerrett Conover Landvest MV

  81 S Water St, Edgartown, MA 02539
• 

  

  

  /27

  Est $2,519,250

  Not Listed For Sale

  484 Main St, Vineyard Haven, MA 02568

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

  484 Main St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 14 Days On Market
• 

  

  /38

  $1,755,000

  $40K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,695 Sq Ft

  68 Front St, Oak Bluffs, MA 02557

  Nestled at the end of a quiet street, this charming and spacious Cape-style home offers both privacy and convenience, just a short distance from the Oak Bluffs School and town center, and walking distance to the Lagoon. Thoughtfully maintained, the sun-filled main level boasts an open floor plan with large windows that frame views of the surrounding property. The generously sized kitchen features

  Jayne Isford Ocean Park Realty Inc

  68 Front St, Oak Bluffs, MA 02557
• 

  

  /20

  $975,000

  Sold Sep 30, 2025

  32 Beach Rd, Oak Bluffs, MA 02557

  • 3 Beds
  • 2 Baths
  • 836 Sq Ft
  • Built 1920

  Last Sold Summary

  • 7% Below List Price
  • $1,166/SF
  • 29 Days On Market

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

  32 Beach Rd, Oak Bluffs, MA 02557
• 

  

  /26

  Est $3,877,354

  Not Listed For Sale

  137 Massasoit Ave, Vineyard Haven, MA 02568

  • 5 Beds
  • 3.5 Baths
  • 3,686 Sq Ft
  • Built 1988

  137 Massasoit Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 437 Days On Market
• 

  

  /33

  $1,995,000

  • 3 Beds
  • 2.5 Baths
  • 1,431 Sq Ft

  33 Vineyard Ave, Oak Bluffs, MA 02557

  Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha’s Vineyard. This fully renovated property features a 2BR/2BA primary home plus a separate 1BR/1BA suite—offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence showcases a light-filled interior, wood floors, beamwork, and refined finishes throughout. Open living flows to a gourmet kitchen

  Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

  33 Vineyard Ave, Oak Bluffs, MA 02557
• 

  

  /48

  $1,775,000

  Sold Nov 07, 2025

  3 Fulling Mill Rd, Chilmark, MA 02535

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • Built 1976

  Last Sold Summary

  • 5% Below List Price
  • $1,027/SF
  • 170 Days On Market

  Current Estimated Value $1,884,275

  Last Listing Agent Jill Napior Tea Lane Associates

  3 Fulling Mill Rd, Chilmark, MA 02535
• 

  

  /24

  Est $2,086,381

  Not Listed For Sale

  125 Massasoit Ave, Vineyard Haven, MA 02568

  • 5 Beds
  • 3 Baths
  • 1,830 Sq Ft
  • Built 1930

  125 Massasoit Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 1,036 Days On Market
• 

  

  /48

  $1,495,000

  Under Contract

  • 5 Beds
  • 4 Baths
  • 2,516 Sq Ft

  651 State Rd, Vineyard Haven, MA 02568

  Fabulous four-building farmhouse compound offered in the heart of West Tisbury. This cherished property features a well-maintained classic 1880 main house with 4 bedrooms and 3 baths, plus a fully separate guest cottage with 1 bedroom and 1 bath — offering immediate income potential through seasonal or year-round rental. A bunkhouse/office building provides flexible space ideal for a home office

  Jim Feiner Feiner Real Estate

  651 State Rd, Vineyard Haven, MA 02568
• 

  

  /36

  $1,950,000

  Sold Jul 02, 2025

  51 Black Brook Crossing Rd, West Tisbury, MA 02568

  • 4 Beds
  • 2.5 Baths
  • 2,691 Sq Ft
  • Built 1976

  Last Sold Summary

  • 6% Below List Price
  • $725/SF
  • 30 Days On Market

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

  51 Black Brook Crossing Rd, West Tisbury, MA 02568
• 

  

  /18

  Est $1,279,685

  Not Listed For Sale

  46 Lake Ave, Edgartown, MA 02539

  • 3 Beds
  • 1.5 Baths
  • 1,764 Sq Ft
  • Built 1870

  46 Lake Ave, Edgartown, MA 02539

  Last Sold Summary

  • 2 Days On Market
• 

  

  /21

  $2,250,000

  • 3 Beds
  • 2 Baths
  • 1,867 Sq Ft

  237 Lagoon Pond Rd, Vineyard Haven, MA 02568

  Ideally located at the beginning of Hines Point, this light-filled, well-maintained home offers a central setting with easy access to the Lagoon, the MV Museum, and town. Public water access is just a short walk away, making it easy to enjoy all the benefits of this special area.Set on a gentle rise overlooking the Lagoon, the home is filled with natural light and offers beautiful water

  Alison Rich Carroll & Vincent R.E.

  237 Lagoon Pond Rd, Vineyard Haven, MA 02568
• 

  

  /26

  $3,250,000

  Sold May 15, 2026

  99 Cooke St, Edgartown, MA 02539

  • 4 Beds
  • 4 Baths
  • 1,590 Sq Ft
  • Built 1999

  Last Sold Summary

  • 17% Below List Price
  • $2,044/SF
  • 42 Days On Market

  Current Estimated Value $3,633,506

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

  99 Cooke St, Edgartown, MA 02539
• 

  

  /26

  Est $2,474,678

  Not Listed For Sale

  437 State Rd, Aquinnah, MA 02535

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 1955

  437 State Rd, Aquinnah, MA 02535

  Last Sold Summary

  • 357 Days On Market
• 

  

  /36

  $2,400,000

  • 5 Beds
  • 4 Baths
  • 3,328 Sq Ft

  159 Lake St, Vineyard Haven, MA 02568

  Tucked back from the road on scenic Lake Street, this one-of-a-kind home offers privacy and charm on a beautifully landscaped 0.7 acre lot accented by mature trees and a classic stone wall. Inside, rich wood detailing, exposed beams, and high ceilings create a warm and inviting atmosphere. The home’s four-level design provides exceptional character and flexibility. The main level features a

  Alyssa Halisky Wallace & Co. Sotheby's

  159 Lake St, Vineyard Haven, MA 02568
• 

  

  /22

  $1,164,000

  Sold Aug 12, 2025

  110 Daggett Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1921

  Last Sold Summary

  • 22% Below List Price
  • $705/SF
  • 106 Days On Market

  Current Estimated Value $1,168,815

  Last Listing Agent Kate Burnside Portfolio Properties

  110 Daggett Ave, Vineyard Haven, MA 02568
• 

  

  /79

  Est $1,517,332

  Not Listed For Sale

  76 State Rd, Aquinnah, MA 02535

  • 4 Beds
  • 2 Baths
  • 3,093 Sq Ft
  • Built 1856

  76 State Rd, Aquinnah, MA 02535

  Last Sold Summary

  • 190 Days On Market
• 

  

  /35

  $1,369,000

  $26K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,783 Sq Ft

  51 Summer St, Vineyard Haven, MA 02568

  Rare under-$1.4M value story in Vineyard Haven. In a Martha’s Vineyard price range where buyers are often choosing between smaller homes, dated interiors, limited bath count, or properties needing immediate improvements, 51 Summer Street offers a cleaner path. This updated 4-bedroom, 2.5-bath home features 1,783 square feet of well-planned living space in a convenient Vineyard Haven setting near

  Janet Scott eXp Realty

  51 Summer St, Vineyard Haven, MA 02568
• 

  

  /12

  $1,987,500

  Sold Feb 19, 2026

  131 N Water St Unit 51, Edgartown, MA 02539

  • 1 Bed
  • 1 Bath
  • 862 Sq Ft
  • Built 2011

  Last Sold Summary

  • 3% Below List Price
  • $2,306/SF
  • 0 Days On Market

  Current Estimated Value $2,107,188

  Last Listing Agent Kim Naylor Donnelly + Co

  131 N Water St Unit 51, Edgartown, MA 02539
• 

  

  /33

  Est $3,328,850

  Not Listed For Sale

  3 Oxcart Rd, Aquinnah, MA 02535

  • 2 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 1970

  3 Oxcart Rd, Aquinnah, MA 02535

  Last Sold Summary

  • 4 Days On Market
• 

  

  /47

  $1,975,000

  • 3 Beds
  • 2.5 Baths
  • 1,902 Sq Ft

  81 Leland Ave, Vineyard Haven, MA 02568

  Close to town with exceptional indoor / outdoor flow & privacy.Consider this beautifully designed home just minutes from town. The first floor features a bright, open kitchen + dining area flowing into a welcoming living room with a fireplace. From there, step onto a spacious deck—ideal for al fresco dining and lounging—complete with direct access to a hot tub and nearby outdoor

  Jill Napior Tea Lane Associates

  81 Leland Ave, Vineyard Haven, MA 02568
• 

  

  /29

  $2,000,000

  Sold Feb 11, 2026

  34 Massasoit Ave, Oak Bluffs, MA 02557

  • 6 Beds
  • 3.5 Baths
  • 1,616 Sq Ft
  • Built 1900

  Last Sold Summary

  • $1,238/SF
  • 0 Days On Market

  Current Estimated Value $1,589,429

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

  34 Massasoit Ave, Oak Bluffs, MA 02557
• 

  /2

  Est $2,091,325

  Not Listed For Sale

  15 Kane Ln Unit 9, Edgartown, MA 02539

  • 4 Beds
  • 3 Baths
  • 1,319 Sq Ft
  • Built 1975

  15 Kane Ln Unit 9, Edgartown, MA 02539
• 

  

  /6

  $2,795,000

  • Land
  • 3.05 Acres
  • $916,393 per Acre

  Lot 4B Browns Farm Ln Unit 10, Edgartown, MA 02539

  Tucked off Meetinghouse Way, this 3-acre parcel offers an opportunity to create something lasting on the Vineyard. Open pasture sweeps across the property's core, framed by bordering woodland that lends a sense of privacy without sacrificing the light and openness that makes the setting so appealing. Just under 2.5 miles from the Village and South Beach, the location balances seclusion with easy

  Courtney Marek Sandpiper Realty

  Lot 4B Browns Farm Ln Unit 10, Edgartown, MA 02539
• 

  

  /24

  $4,325,000

  Sold Dec 05, 2025

  18 Homeward Way, Chilmark, MA 02535

  • 5 Beds
  • 2.5 Baths
  • 3,885 Sq Ft
  • Built 1986

  Last Sold Summary

  • 8% Below List Price
  • $1,113/SF
  • 8 Days On Market

  Current Estimated Value $4,570,969

  Last Listing Agent Bill Rossi Studio Realty

  18 Homeward Way, Chilmark, MA 02535
• 

  

  /37

  Est $4,079,643

  Not Listed For Sale

  119 S Water St, Edgartown, MA 02539

  • 4 Beds
  • 2.5 Baths
  • 1,949 Sq Ft
  • Built 1850

  119 S Water St, Edgartown, MA 02539

  Last Sold Summary

  • 37 Days On Market
• 

  

  /50

  $4,650,000

  • 4 Beds
  • 3.5 Baths
  • 3,702 Sq Ft

  7 Black Point Rd, Chilmark, MA 02535

  Laid-back charm meets island character in this one-of-a-kind up-island beach house. Set on 5.5 acres of natural beauty, this four-bedroom, three-bath main house is full of updates, with bright, fun spaces and a relaxed summer-camp vibe. The creative layout on a single level connects sections of the house via breezy walkway, leading to a bedroom wing including a separate family room, off the

  Meg Bodnar Tea Lane Associates

  7 Black Point Rd, Chilmark, MA 02535
• 

  

  /30

  $946,500

  Sold Mar 11, 2026

  22 Clark Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1967

  Last Sold Summary

  • 4% Below List Price
  • $939/SF
  • 82 Days On Market

  Current Estimated Value $943,219

  Last Listing Agent Helena Kirschenbaum Studio Realty

  22 Clark Ave, Vineyard Haven, MA 02568
• 

  

  /41

  Est $4,207,588

  Not Listed For Sale

  109 School St, Edgartown, MA 02539

  • 6 Beds
  • 4 Baths
  • 3,193 Sq Ft
  • Built 1900

  109 School St, Edgartown, MA 02539

  Last Sold Summary

  • 168 Days On Market
• 

  

  /42

  $1,275,000

  $520K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,033 Sq Ft

  9 Brunswick Ave, Oak Bluffs, MA 02557

  PRIME LOCATION! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively UPDATED inside and out. Enjoy peace of mind with a NEW septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts NEW flooring, insulation, fresh paint, a stylishly renovated kitchen, and efficient new

  Alice Pierce Coldwell Banker Realty - Martha's Vineyard

  9 Brunswick Ave, Oak Bluffs, MA 02557
• 

  

  /7

  $600,000

  Sold Jun 23, 2025

  27 7th St N Unit 198, Edgartown, MA 02539

  • Land
  • 21,780 Sq Ft
  • $1,200,000 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 4 Days On Market

  Last Listing Agent Stephanie Roache Donnelly + Co

  27 7th St N Unit 198, Edgartown, MA 02539
• 

  /2

  Est $1,765,706

  Not Listed For Sale

  45 North St, Edgartown, MA 02539

  • 1 Bed
  • 1 Bath
  • 948 Sq Ft
  • Built 2006

  45 North St, Edgartown, MA 02539
• 

  

  /12

  $1,295,000

  $30K PRICE DROP

  • 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 READY TO BUILD. The land has 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, NHESP has been completed and there are no restrictions on the lot, there's a

  Elissa Lash Tea Lane Associates

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

  /2

  $14,750,000

  Sold Mar 27, 2026

  23 Edgartown Bay Rd, Edgartown, MA 02539

  • 6 Beds
  • 4.5 Baths
  • 4,744 Sq Ft
  • Built 1990

  Last Sold Summary

  • $3,109/SF
  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK

  23 Edgartown Bay Rd, Edgartown, MA 02539
• 

  

  /45

  Est $4,262,404

  Not Listed For Sale

  106 Peases Point Way S, Edgartown, MA 02539

  • 4 Beds
  • 4.5 Baths
  • 3,345 Sq Ft
  • Built 2022

  106 Peases Point Way S, Edgartown, MA 02539

  Last Sold Summary

  • 85 Days On Market
• 

  

  /42

  $21,500,000

  • 10 Beds
  • 14 Baths
  • 7,598 Sq Ft

  56 N Summer St, Edgartown, MA 02539

  A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest on Martha’s Vineyard. Originally built in 1835 and masterfully renovated, it blends historic character with refined modern luxury just moments from Edgartown Harbor, dining, and shopping. Spanning two lots, the property features 10 bedrooms and 14 baths, designed for elegant

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  56 N Summer St, Edgartown, MA 02539
• 

  

  /46

  $1,150,000

  Sold Apr 14, 2026

  185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

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

  Last Sold Summary

  • 11% Below List Price
  • $657/SF
  • 85 Days On Market

  Current Estimated Value $1,208,482

  Last Listing Agent Candy DaRosa Feiner Real Estate

  185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

Showing Results 641 - 680, Page 17 of 18