20,059

Dukes County, MA Homes

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  • /29

    $10,950,000

    • 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
  • /8

    $18,000 total monthly price

    • 3 Beds
    • 2.5 Baths
    • House for Rent

    71 Bartmus Luce Road Wt154, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard Views available. It is a short

    Karen Overtoom Karen M. Overtoom R.E.

    71 Bartmus Luce Road Wt154, West Tisbury, MA 02575
  • /31

    $3,750,000 Sold Oct 31, 2025

    29 Oxcart Rd, Aquinnah, MA 02535

    • 3 Beds
    • 2 Baths
    • 1,274 Sq Ft
    • Built 2009

    Last Sold Summary

    • 11% Below List Price
    • $2,943/SF
    • 380 Days On Market

    Last Listing Agent Michelle Kelly Tea Lane Associates

    29 Oxcart Rd, Aquinnah, MA 02535
    • /14

      Est $1,887,286 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,519 Sq Ft

      2 Lexington Ave, Edgartown, MA 02539

      2 Lexington Ave, Edgartown, MA 02539
  • /26

    $1,445,000

    • 4 Beds
    • 2.5 Baths
    • 1,738 Sq Ft

    22 Oklahoma Ave, Vineyard Haven, MA 02568

    3 BEDROOM HOUSE + 1 BEDROOM APARTMENT! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This move-in ready property features a 3 BR, 1.5 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset your mortgage. The main house features a stunning solarium or sunroom, a cheerful

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's

    22 Oklahoma Ave, Vineyard Haven, MA 02568
  • /23

    $36,000 total monthly price

    • 3 Beds
    • 3 Baths
    • 2,556 Sq Ft
    • House for Rent

    74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Less than 5 miles from the center of town, the property is a 3 bedroom uniquely-designed guest house which provides the space needed for a large family or visiting guests. Most of the living/entertaining space is on the second floor. The kitchen has granite countertops,

    Karen Overtoom Karen M. Overtoom R.E.

    74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539
  • /42

    $15,725,000 Sold Oct 22, 2025

    111 N Water St, Edgartown, MA 02539

    • 6 Beds
    • 4.5 Baths
    • 3,606 Sq Ft
    • Built 1850

    Last Sold Summary

    • 5% Below List Price
    • $4,361/SF
    • 41 Days On Market

    Last Listing Agent Wendy Harman Compass

    111 N Water St, Edgartown, MA 02539
    • /26

      Est $2,032,807 Not Listed For Sale

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

      82 South Rd, Chilmark, MA 02535

      82 South Rd, Chilmark, MA 02535
  • /42

    $3,995,000

    • 3 Beds
    • 4 Baths
    • 3,426 Sq Ft

    96 Hammett Ln, Chilmark, MA 02535

    Beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher, soapstone counters and a butlers pantry with extra cupboards, shelving and a wine

    Brenda Galligan Karen M. Overtoom R.E.

    96 Hammett Ln, Chilmark, MA 02535
  • /28

    $29,300 total monthly price

    • 3 Beds
    • 2.5 Baths
    • 1,871 Sq Ft
    • House for Rent

    76 Mattakesett Way Ed313, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,325. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This upside-down house was built in 2007. Sit out on the upper deck to panoramic ocean views or grill your favorite seafood while taking in the view. Watch the sun set to a new and beautiful aurora each night on either of the decks or while lazing on the porch swing.The

    Karen Overtoom Karen M. Overtoom R.E.

    76 Mattakesett Way Ed313, Edgartown, MA 02539
  • /42

    $865,000 Sold Apr 17, 2025

    4 Quail Run Rd Unit 17, Edgartown, MA 02539

    • 2 Beds
    • 2 Baths
    • 1,208 Sq Ft
    • Built 1972

    Last Sold Summary

    • 1% Below List Price
    • $716/SF
    • 2 Days On Market

    Last Listing Agent Wendy Harman Compass

    4 Quail Run Rd Unit 17, Edgartown, MA 02539
    • /18

      Est $1,890,232 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,461 Sq Ft

      29 Brook Hollow Rd, Vineyard Haven, MA 02568

      29 Brook Hollow Rd, Vineyard Haven, MA 02568
  • /12

    $899,000

    • 2 Beds
    • 2 Baths
    • 1,232 Sq Ft

    8 Hitchings Cir, Oak Bluffs, MA 02557

    Nestled in a quiet Oak Bluffs neighborhood, less than a mile from the harbor, beaches, shops, and restaurants, this Cape-style home offers the perfect balance of convenience and tranquility. The interior features an open kitchen and living room, plenty of space for guests, and a full unfinished basement. The two bedroom Title V septic system has passed inspection. Outside, the property features a

    Peyton Wallace Studio Realty

    8 Hitchings Cir, Oak Bluffs, MA 02557
  • /10

    $11,000 total monthly price

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    15 Price's Way Ed322, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is an inviting and affordable home with air-conditioning. As you see from the pictures the sun is welcomed through many sliders and windows. Inside the furnishings are simple but well chosen. There is a splitter in the living area that cools the downstairs. The

    Karen Overtoom Karen M. Overtoom R.E.

    15 Price's Way Ed322, Edgartown, MA 02539
  • /30

    $1,525,000 Sold Jun 18, 2025

    54 Lake St, Vineyard Haven, MA 02568

    • 4 Beds
    • 3 Baths
    • 2,016 Sq Ft
    • Built 1967

    Last Sold Summary

    • 12% Below List Price
    • $756/SF
    • 110 Days On Market

    Current Estimated Value $1,536,350

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

    54 Lake St, Vineyard Haven, MA 02568
    • /25

      Est $1,670,503 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,287 Sq Ft

      101 Dunham Ave, Vineyard Haven, MA 02568

      101 Dunham Ave, Vineyard Haven, MA 02568
  • /21

    $1,999,999

    • 4 Beds
    • 3 Baths
    • 2,730 Sq Ft

    5 Pine Tree Ln, Vineyard Haven, MA 02568

    Nestled at 5 Pinetree Lane, Vineyard Haven, MA, this single-family residence in Dukes County presents a unique opportunity to own a piece of classic American architecture. Built in 1927, this home offers a blend of vintage charm and comfortable living. The residence features three full bathrooms, providing convenience and privacy for all occupants. Imagine mornings where everyone can prepare for

    Kristin Francoeur Gibson Sotheby's International Realty

    5 Pine Tree Ln, Vineyard Haven, MA 02568
  • /25

    $80,000 total monthly price

    • 4 Beds
    • 4.5 Baths
    • 3,800 Sq Ft
    • House for Rent

    7 Mill Hill Farms Rd Ed315, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $20,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Gorgeous new 4 bedroom 4 bath home. Top of the line finishes and appliances. Gourmet kitchen, screened in porch with fireplace and TV. Pool with swim up bar, hot tub and grilling area. This is a cream of the crop Katama house is a short distance to downtown Edgartown and

    Karen Overtoom Karen M. Overtoom R.E.

    7 Mill Hill Farms Rd Ed315, Edgartown, MA 02539
  • /18

    $3,350,000 Sold Jun 05, 2025

    25 Simpson's Ln, Edgartown, MA 02539

    • 6 Beds
    • 6 Baths
    • 3,156 Sq Ft
    • Built 1900

    Last Sold Summary

    • 4% Below List Price
    • $1,061/SF
    • 138 Days On Market

    Last Listing Agent Greg Hartel Hartel Realty

    25 Simpson's Ln, Edgartown, MA 02539
    • /35

      Est $2,756,695 Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 2,728 Sq Ft

      89 Main St, Vineyard Haven, MA 02568

      89 Main St, Vineyard Haven, MA 02568
  • /14

    $799,000

    • 2 Beds
    • 1 Bath
    • 624 Sq Ft

    60R Carol Ln, Oak Bluffs, MA 02557

    Charming Ranch-Style Cottage nestled on an 8,438 sq ft lot, this cozy ranch-style cottage offers easy, single-story living, ideal for those seeking the simplicity and charm of island life. The bright and open-concept kitchen and living area features a breakfast bar, creating a warm and welcoming space for everyday living or entertaining. The home includes two comfortable bedrooms and one full

    Nora Jardin Island Real Estate

    60R Carol Ln, Oak Bluffs, MA 02557
  • /28

    $38,000 total monthly price

    • 4 Beds
    • 3.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    17 Otis Bassett Rd, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT MONTHLY. AUGUST WEEKLY IS $9,500. SEE OUR WEB SITE FOR WEEKLY PRICING!!!!!Are you looking for the perfect back yard Oasis? Well here it is!! Surrounding a large pool you will be able to relax on the expansive deck areas that include plenty of space for gathering. Inside is an amazing kitchen with every amenity you could want. Coffee lovers will appreciate a regular

    Karen Overtoom Karen M. Overtoom R.E.

    17 Otis Bassett Rd, West Tisbury, MA 02575
  • /43

    $1,675,000 Sold Apr 04, 2025

    7 N Bog Rd, Edgartown, MA 02539

    • 3 Beds
    • 3 Baths
    • 2,094 Sq Ft
    • Built 1994

    Last Sold Summary

    • 27% Below List Price
    • $800/SF
    • 276 Days On Market

    Last Listing Agent Robin Perschel Feiner Real Estate

    7 N Bog Rd, Edgartown, MA 02539
    • /48

      Est $1,489,010 Not Listed For Sale

      • 6 Beds
      • 5.5 Baths
      • 2,417 Sq Ft

      152 Main St, Vineyard Haven, MA 02568

      152 Main St, Vineyard Haven, MA 02568
  • /21

    $749,900

    • Land
    • 1 Acre
    • $749,900 per Acre

    0 W End Rd Unit 73450428, Gosnold, MA 02713

    A rare opportunity to build your Island dream retreat on an elevated 1 acre lot with water-views on picturesque Cuttyhunk Island! This buildable lot offers sweeping views and the perfect quiet setting to design your coastal getaway or inherit house plans already drawn up for the perfect fit. Enjoy the serenity of Island living surrounded by natural beauty, gentle sea breezes and panoramic vistas.

    Amanda Defazio William Raveis R.E. & Home Services

    0 W End Rd Unit 73450428, Gosnold, MA 02713
  • /36

    $56,800 total monthly price

    • 5 Beds
    • 4 Baths
    • 3,000 Sq Ft
    • House for Rent

    2 Nonamessett Rd, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING.Newly renovated architect designed home with every amenity. Cook's gourmet kitchen, open plan living/dining room, second living room, lots of outdoor patio and deck space, Set in a private 7 acre property with wildflower meadow. Relax around the beautiful in ground pool

    Karen Overtoom Karen M. Overtoom R.E.

    2 Nonamessett Rd, Edgartown, MA 02539
  • /2

    $880,000 Sold Oct 17, 2025

    5 Johns Way, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 1,365 Sq Ft
    • Built 1987

    Last Sold Summary

    • $645/SF
    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    5 Johns Way, Oak Bluffs, MA 02557
    • /36

      Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,780 Sq Ft

      52 Marthas Rd, Edgartown, MA 02539

      52 Marthas Rd, Edgartown, MA 02539
  • /78

    $7,950,000

    • 6 Beds
    • 6.5 Baths
    • 6,927 Sq Ft

    6 Janes Cove Rd, Edgartown, MA 02539

    Waterfront on Edgartown Great Pond with delightful water views, this newly-renovated Coastal Colonial is set on a very private 9.2 acre lot on Janes Cove. You know you are somewhere very special the moment you enter through the gates. As you travel along the cobblestone lined driveway flanked by lush lawns, the gorgeous home rises before you. Stunning the day it was originally completed, it has

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    6 Janes Cove Rd, Edgartown, MA 02539
  • /21

    $14,000 total monthly price

    • 4 Beds
    • 2 Baths
    • 1,505 Sq Ft
    • House for Rent

    175 Meetinghouse Way Ed321, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This updated contemporary is located in Katama area and a short bike ride to South Beach. There are 4 bedrooms, 1 down and 3 up, and a beautiful kitchen/dining which opens to a large living room. The house has a nice deck on the front and owners have added a deck off the

    Karen Overtoom Karen M. Overtoom R.E.

    175 Meetinghouse Way Ed321, Edgartown, MA 02539
  • /2

    $1,100,000 Sold Jun 17, 2025

    17 Front St, Oak Bluffs, MA 02557

    • 2 Beds
    • 2 Baths
    • 2,912 Sq Ft
    • Built 1989

    Last Sold Summary

    • $378/SF
    • 0 Days On Market

    Current Estimated Value $1,240,624

    Last Listing Agent LINK Email Cache LINK

    17 Front St, Oak Bluffs, MA 02557
    • /31

      Est $1,444,063 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,999 Sq Ft

      48 Puritan Dr, Vineyard Haven, MA 02568

      48 Puritan Dr, Vineyard Haven, MA 02568
  • /38

    $840,000

    • 3 Beds
    • 2.5 Baths
    • 2,679 Sq Ft

    12 Beach Plum Path, East Falmouth, MA 02536

    Set on a quiet dead-end street in Locustfield Estates, this 2021 Cape offers an easy, flexible layout with a first-floor primary suite and two bedrooms plus a den upstairs. The open main level features a gas fireplace and a granite kitchen with a center island and counter-height seating. The finished lower level adds an office and game room for extra space to work or unwind. Owned Tesla solar

    Pamela Heylin Berkshire Hathaway HomeServices Robert Paul Properties

    12 Beach Plum Path, East Falmouth, MA 02536
  • /32

    $100,000 total monthly price

    • 5 Beds
    • 4 Baths
    • 4,500 Sq Ft
    • House for Rent

    60 Witchwood Lane Ed317, Edgartown, MA 02539

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $25,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gorgeous waterfront home is well equipped with gourmet kitchen, stone fireplace, numerous sitting areas, and multiple decks each with water views over the Edgartown Harbor. Both the main and upper level have beautiful master suites and also washers & dryers. Easy

    Karen Overtoom Karen M. Overtoom R.E.

    60 Witchwood Lane Ed317, Edgartown, MA 02539
  • /2

    $1,100,000 Sold Oct 29, 2025

    11 Quammox Rd, Edgartown, MA 02539

    • 2 Beds
    • 1 Bath
    • 685 Sq Ft
    • Built 1940

    Last Sold Summary

    • $1,606/SF
    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    11 Quammox Rd, Edgartown, MA 02539
    • /14

      Est $1,527,262 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,717 Sq Ft

      13 Saddle Club Rd, Edgartown, MA 02539

      13 Saddle Club Rd, Edgartown, MA 02539
  • /28

    $2,400,000 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,372 Sq Ft

    46 Bold Meadow Rd, Edgartown, MA 02539

    Welcome to 46 Bold Meadow, a beautifully crafted, move-in-ready 4-bedroom, 3.5-bathroom home nestled in Edgartown's desirable Bold Meadow neighborhood. This thoughtfully designed home showcases quality construction throughout, featuring well-appointed living spaces that balance comfort with functionality. The house features a beautiful front porch that opens into the hall, leading to a study and

    Julianna Flanders Flanders Real Estate

    46 Bold Meadow Rd, Edgartown, MA 02539
  • /26

    $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
  • /2

    $1,390,000 Sold Jul 22, 2025

    57 Colonial Dr, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,299 Sq Ft
    • Built 1984

    Last Sold Summary

    • $1,070/SF
    • 0 Days On Market

    Current Estimated Value $1,117,614

    Last Listing Agent LINK Email Cache LINK

    57 Colonial Dr, Vineyard Haven, MA 02568
    • /20

      Est $1,752,668 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,240 Sq Ft

      11 Pine Tree Ln, Vineyard Haven, MA 02568

      11 Pine Tree Ln, Vineyard Haven, MA 02568

Showing Results 241 - 280, Page 7 of 18

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