2,442

Dukes, MA Homes in ZIP Code 02535

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  • /32

    $2,250,000

    • 4 Beds
    • 3 Baths
    • 2,522 Sq Ft

    29 Old Nursery Ln, Chilmark, MA 02535

    Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and projects. Wood working area in the basement is a plus. Enjoy the outdoors via the screened porch, large

    Julianna Flanders Flanders Real Estate

    29 Old Nursery Ln, Chilmark, MA 02535
  • /26

    $50,700 per month

    • 4 Beds
    • 3 Baths
    • 2,346 Sq Ft
    • House for Rent

    6 Trails End Ch241, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,675. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set atop a hill you will find this wonderful 4 bedroom home with distant views and a wonderful lap pool. Enjoy your days on the large deck or take a swim in the pool. This great vacation home is tastefully decorated and is located on one level with plenty of space for

    Karen Overtoom Karen M. Overtoom R.E.

    6 Trails End Ch241, Chilmark, MA 02535
  • /32

    $1,050,000 Sold May 29, 2025

    • 1,701 Sq Ft
    • $617/SF
    • 28 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1960

    10 Rumpus Ridge Rd, Chilmark, MA 02535

    Discover this inviting two-unit property in the heart of Chilmark! Ideally situated near Chilmark General Store, Squibnocket, Menemsha, and the pristine shores of Lucy Vincent Beach, this home offers both convenience and charm. Thoughtfully updated for year-round comfort, the property features a new metal roof, new siding, solar panels, mini-split AC, and more. The main-level residence offers

    Peyton Wallace Studio Realty

    10 Rumpus Ridge Rd, Chilmark, MA 02535
    • /38

      Est $2,777,264 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,719 Sq Ft

      1 Mariners View Ln, Aquinnah, MA 02535

      1 Mariners View Ln, Aquinnah, MA 02535
  • /50

    $3,250,000

    • 4 Beds
    • 3 Baths
    • 2,758 Sq Ft

    382 Lighthouse Rd, Aquinnah, MA 02535

    Spacious contemporary set high off Lighthouse Road with unobstructed, amazing water views of the Vineyard Sound and Elizabeth Islands. Open concept design with soaring ceilings and modern architecture. A retreat for all seasons this house is fully insulated, heated and has central air. A center island in the kitchen ensures the cook of the family does not miss out on the amazing sunsets. Ground

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

    382 Lighthouse Rd, Aquinnah, MA 02535
  • /39

    $110,000 per month

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

    17 Round Pond Rd Ch240, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. See web site for pricing!! Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches and high speed internet wifi.

    Karen Overtoom Karen M. Overtoom R.E.

    17 Round Pond Rd Ch240, Chilmark, MA 02535
  • /52

    $9,525,000 Sold Apr 24, 2025

    • 5,808 Sq Ft
    • $1640/SF
    • 297 Days On Market
    • 6 Beds
    • 6 Baths
    • Built 2008

    2 Squibnocket Rd, Chilmark, MA 02535

    CHILMARK SOUTH SHORE WATER VIEWS. This Squibnocket gem is a Hutker Architect-designed family compound on 4.5 acres. With captivating water views in every direction, this home is the perfect launch pad for the ultimate up-Island lifestyle. Grab your surf or paddle board and head down the path to Squibnocket Beach for a morning surf or swim. Pack the cooler with lunch from the Chilmark Store for a

    Tina Miller Compass | Point B

    2 Squibnocket Rd, Chilmark, MA 02535
    • /33

      Est $3,617,342 Not Listed For Sale

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

      3 Oxcart Rd, Aquinnah, MA 02535

      3 Oxcart Rd, Aquinnah, MA 02535
  • /41

    $3,600,000

    • 3 Beds
    • 4 Baths
    • 2,500 Sq Ft

    27 Clambelly Rd, Chilmark, MA 02535

    A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media

    Julianna Flanders Flanders Real Estate

    27 Clambelly Rd, Chilmark, MA 02535
  • /19

    $24,000 per month

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • House for Rent

    44 Flanders Ln, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

    Karen Overtoom Karen M. Overtoom R.E.

    44 Flanders Ln, Chilmark, MA 02535
  • /42

    $9,725,000 Sold Apr 24, 2025

    • 5,808 Sq Ft
    • $1674/SF
    • 295 Days On Market
    • 6 Beds
    • 5.5 Baths
    • Built 2008

    2 Squibnocket Rd, Chilmark, MA 02535

    CHILMARK SOUTH SHORE WATER VIEW. This Squibnocket gem is a Hutker Arhictect-designed family compound, main house,& guest house on 4.5 acres. Live the ultimate up-Island life with captivating water views in every direction. The home is pristine and private, with many unique features. The chef's kitchen and dining area are serene, bright, and functional. Step up to what might be the best panorama

    Tina Miller Compass

    2 Squibnocket Rd, Chilmark, MA 02535
    • /33

      Est $1,600,453 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 770 Sq Ft

      2 Creek Hill, Chilmark, MA 02535

      2 Creek Hill, Chilmark, MA 02535
  • /3

    $110,000

    • Land
    • 0.70 Acre
    • $157,143 per Acre

    00 Eliot Ave Unit 17, Chilmark, MA 02535

    Enjoy access to beautiful Stonewall Beach located in Chilmark. It has great swimming and fishing!This is not a buildable lot.

    Julianna Flanders Flanders Real Estate

    00 Eliot Ave Unit 17, Chilmark, MA 02535
  • /31

    $40,000 per month

    • 6 Beds
    • 6 Baths
    • 3,960 Sq Ft
    • House for Rent

    384 Middle Rd Ch222, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four

    Karen Overtoom Karen M. Overtoom R.E.

    384 Middle Rd Ch222, Chilmark, MA 02535
  • /11

    $749,000 Sold Apr 14, 2025

    • 240 Sq Ft
    • $3121/SF
    • 0 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1980

    488 Lighthouse Rd, Aquinnah, MA 02535

    This is truly a once-in-a-lifetime opportunity…Step back in time, and away from any stress, into this magical beach shack in the dunes in Aquinnah with deeded walking path to Dog Fish Bar beach. As you follow a boardwalk toward the Sound, hidden away in the coastal brush, you’ll find this sweet little retreat with one cheery open room including kitchen, built-in bed and storage, and a

    Meg Bodnar Tea Lane Associates

    488 Lighthouse Rd, Aquinnah, MA 02535
    • /13

      Est $1,518,528 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 640 Sq Ft

      12 Harbor Hill Rd, Chilmark, MA 02535

      12 Harbor Hill Rd, Chilmark, MA 02535
  • /26

    $3,695,000

    • Land
    • 7 Acres
    • $551,493 per Acre

    32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, Chilmark, MA 02535

    Discover an exceptional opportunity with this rare combination of two abutting parcels spanning more than 6 acres in a coveted location offering water views and Atlantic Ocean private beach access. Surfers and fishermen delight in this location! The Stonewall Association is a beloved area of Chilmark in a supreme location for easy Chilmark living close to the Chilmark Store, the Chilmark

    Jill Napior Tea Lane Associates

    32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, Chilmark, MA 02535
  • /32

    $42,000 per month

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

    19 Lake Rd, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all with views, two livingrooms,

    Karen Overtoom Karen M. Overtoom R.E.

    19 Lake Rd, Chilmark, MA 02535
  • /2

    $1,600,000 Sold Feb 04, 2025

    • Land
    • 3.60 Acres
    • $444,444 per Acre
    • 0 Days On Market

    493 South Rd, Chilmark, MA 02535

    Lovely pastoral lot within walking distance of beach and center of town.Perc test completed, septic being designed and well to be drilled shortly.Includes conservation restricted lot which consists of 10.6 acres.Build the home of your dreams in this amazing location.

    Julianna Flanders Flanders Real Estate

    493 South Rd, Chilmark, MA 02535
    • /46

      Est $1,922,110 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,524 Sq Ft

      10 Mollys Way, Chilmark, MA 02535

      10 Mollys Way, Chilmark, MA 02535
  • /13

    $1,150,000

    • Land
    • 2.02 Acres
    • $569,307 per Acre

    00 Old Field Rd, Aquinnah, MA 02535

    The nearby roar of the Atlantic can be heard from this pristine two-acre building opportunity in Aquinnah, ideally located at the end of Old Field Road with easy access from Moshup Trail. A storybook walking path through woods and fields over an easement bordering a majestic beetlebung grove and over a bubbling stream, leads directly to the entrance of cherished Philbin Beach. A thoughtfully

    Katherine Donahue Sandpiper Realty Inc

    00 Old Field Rd, Aquinnah, MA 02535
  • /20

    $16,800 per month

    • 3 Beds
    • 2 Baths
    • 1,638 Sq Ft
    • House for Rent

    31 S Ridge Rd Ch218, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and

    Karen Overtoom Karen M. Overtoom R.E.

    31 S Ridge Rd Ch218, Chilmark, MA 02535
  • /32

    $3,000,000 Sold Jan 09, 2025

    • 3,500 Sq Ft
    • $857/SF
    • 194 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 2023

    4 Bartlett Woods, Chilmark, MA 02535

    NEW BRIGHT & AIRY CONTEMPORARY OFF SOUTH ROAD! The house newly completed in 2023 & the one car garage in 2024 are nicely situated on a 4.56 acre lot. The 4 bedroom residence offers 3500 sf of finished living on two levels. On the first level are 2 primary bedrooms, each with en suite bathrooms, and a spacious open floor plan for living, dining and kitchen. An office off the kitchen allows you to

    Kathryn Tate Kathryn Tate Gothard

    4 Bartlett Woods, Chilmark, MA 02535
    • /34

      Est $5,851,241 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 2,373 Sq Ft

      15 Red Valley Rd, Chilmark, MA 02535

      15 Red Valley Rd, Chilmark, MA 02535
  • /15

    $2,770,000

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    5 Ocean View Farm Rd, Chilmark, MA 02535

    Designed by the famous mid century architect Andrew Geller, this contemporary home is situated at the top of the parcel with ocean views and a glimpse of Chilmark pond. There is ample open space to accommodate family and friends and overlooks the large meadow which follows the stone wall to South Road. Access to walking trails, and Lucy Vincent Beach is a short distance away.

    Natalie Conroy Conroy & Company R.E., Inc.

    5 Ocean View Farm Rd, Chilmark, MA 02535
  • /32

    $36,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,600 Sq Ft
    • House for Rent

    29 Cemetery Rd Ch216, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half

    Karen Overtoom Karen M. Overtoom R.E.

    29 Cemetery Rd Ch216, Chilmark, MA 02535
  • /5

    $450,000 Sold Dec 12, 2024

    • 708 Sq Ft
    • $636/SF
    • 21 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1920

    1 Carroll Ln, Chilmark, MA 02535

    Discover the perfect blend of comfort and character in this delightful bungalow nestled in the heart of historic Chilmark. Surrounded by scenic landscapes and the serene beauty of Martha's Vineyard. This home will require substantial renovations and improvements or explore possibilities of a complete renovation. This property could be your idyllic escape and is less than a mile from Menemsha

    Nicholas Korba Landmarks at TODAY Real Estate

    1 Carroll Ln, Chilmark, MA 02535
    • /18

      Est $4,074,122 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,316 Sq Ft

      1 Pond Mark, Chilmark, MA 02535

      1 Pond Mark, Chilmark, MA 02535
  • /36

    $3,250,000

    • 4 Beds
    • 4 Baths
    • 2,515 Sq Ft

    300 North Rd, Chilmark, MA 02535

    Winding tree lined driveway off North Rd brings you to this commanding, custom designed residence built by a top tier island builder. This home is set on over 4 private acres of rolling meadows and big sky views. Main living space is all on one level which includes primary bedroom with en-suite bath, large living area with fireplace, bright sunroom or second living room, custom kitchen and

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

    300 North Rd, Chilmark, MA 02535
  • /33

    $22,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    2 Strikers Way Ch211, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable

    Karen Overtoom Karen M. Overtoom R.E.

    2 Strikers Way Ch211, Chilmark, MA 02535
  • /26

    $1,830,000 Sold Dec 05, 2024

    • 1,862 Sq Ft
    • $983/SF
    • 10 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1960

    82 South Rd, Chilmark, MA 02535

    This charming Chilmark home sits on over 3 acres and features an updated, move-in ready home, expansive outdoor living space with deck, lawn and firepit area, and a six-bedroom septic system for future expansion. The welcoming foyer opens into the dining room, kitchen and a large airy living room with vaulted ceiling and stone fireplace. Beyond the kitchen there are two bedrooms and a shared

    Meg Bodnar Tea Lane Associates

    82 South Rd, Chilmark, MA 02535
    • /21

      Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,686 Sq Ft

      3 Pepperbush Ln, Chilmark, MA 02535

      3 Pepperbush Ln, Chilmark, MA 02535
  • /40

    $1,899,000

    • 4 Beds
    • 3.5 Baths
    • 2,061 Sq Ft

    174 Middle Rd, Chilmark, MA 02535

    Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

    Sheila Morse Island Real Estate

    174 Middle Rd, Chilmark, MA 02535
  • /35

    $22,000 per month

    • 4 Beds
    • 2 Baths
    • 2,290 Sq Ft
    • House for Rent

    36 Henry Hough Lane Ch206, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four

    Karen Overtoom Karen M. Overtoom R.E.

    36 Henry Hough Lane Ch206, Chilmark, MA 02535
  • /56

    $3,725,000 Sold Nov 22, 2024

    • 4,875 Sq Ft
    • $764/SF
    • 21 Days On Market
    • 7 Beds
    • 6 Baths
    • Built 1996

    6 Beach Plum Way, Aquinnah, MA 02535

    Waterview compound with an updated, coastal move-in ready main house and a newer oversized guesthouse sited on 4 acres in the heart of Aquinnah. This exceptional property offers a rare package of two houses with a total of 7 bedrooms and 5.5 bathrooms, several decks on all levels for outdoor living and enjoying sunset skies above the meadow-like lawn, large yard with vegetable garden, mature

    Meg Bodnar Tea Lane Associates

    6 Beach Plum Way, Aquinnah, MA 02535
    • /29

      Est $2,277,215 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,427 Sq Ft

      50 South Rd, Chilmark, MA 02535

      50 South Rd, Chilmark, MA 02535
  • /10

    $350,000

    • Land
    • 0.00 Acre

    0 Moshup Trail Unit 32500206, Aquinnah, MA 02535

    Enjoy coveted access to one of Martha's Vineyard's most stunning sandy beaches, located just off Moshup Trail in Aquinnah. This secluded beach is shared with only seven other members, ensuring a peaceful and private coastal experience. Located near Aquinnah's iconic ''Painted House,'' the property includes use of a private gated parking area and a picturesque stretch of shoreline perfect for

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    0 Moshup Trail Unit 32500206, Aquinnah, MA 02535
  • /29

    $34,000 per month

    • 4 Beds
    • 2.5 Baths
    • 2,300 Sq Ft
    • House for Rent

    15 Loon Lane Ch203, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Modern 4 bedroom home completed in 2019, in Menemsha. Located on a quiet road with waterviews from the upstairs bedrooms also offers views of the famous Menemsha sunsets from the deck. Sustainably harvested flooring features silky smooth and buttery hard wood floors from

    Karen Overtoom Karen M. Overtoom R.E.

    15 Loon Lane Ch203, Chilmark, MA 02535
  • /48

    $7,650,000 Sold Nov 21, 2024

    • 3,834 Sq Ft
    • $1995/SF
    • 48 Days On Market
    • 6 Beds
    • 5 Baths
    • Built 1995

    49 Tilton Rd, Chilmark, MA 02535

    Unique opportunity to enjoy a remarkable, secure, elevated Chilmark north shore 4 acre waterfront property with dramatic 180 degree year round sunset water views over the one mile Spring Point sandy coastline to Great Rock Bight, Menemsha Hills, Aquinnah shore, Gay Head Lighthouse and the Elizabeth Islands stretching almost to Woods Hole. This wide expanse of the Vineyard Sound enjoys endless

    Robert Kenney Tea Lane Associates

    49 Tilton Rd, Chilmark, MA 02535

Showing Results 41 - 80, Page 2 of 18

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