1,739

Chilmark Homes

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  • /16

    $3,200,000

    • 4 Beds
    • 3 Baths
    • 2,346 Sq Ft

    6 Trails End, Chilmark, MA 02535

    Step into timeless mid-century modern style and comfort in this single-level, 4-bedroom, 3-bathroom home located in the heart of Chilmark. This home features an open layout with large glass panel doors that lead to a sun-drenched deck, heated in-ground pool, and grassy lawn. This home is offered completely furnished with a well-equipped kitchen, large living room with wood burning fireplace,

    Russell Maloney Russell Maloney Real Estate

    6 Trails End, Chilmark, MA 02535
  • /32

    $42,000 total monthly price

    • 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
  • /17

    $1,790,000 Sold Sep 23, 2025

    • Land
    • 3.3 Acres
    • $542,424 per Acre
    • 77 Days On Market

    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535

    South shore beachy living in Stonewall Association with private parking and access to a lovely swim and surf beach in a beloved area of Chilmark. There are second floor water views over Squibnocket Point and the Atlantic Ocean. This lot is fully engineered and ready to be built on! Single-family dwelling, plus a detached bedroom and accessory buildings, permitted according to the Chilmark

    Jill Napior Tea Lane Associates

    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
    • /69

      Est $2,333,534 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,034 Sq Ft

      276 South Rd, Chilmark, MA 02535

      276 South Rd, Chilmark, MA 02535
  • /36

    $12,500,000

    • 5 Beds
    • 3.5 Baths
    • 3,700 Sq Ft

    18 Spruce Gate Rd, Chilmark, MA 02535

    Welcome to an extraordinary ocean view coastal sanctuary set within the exclusive gates of Squibnocket Farm--a 450+ acre private community with access to over 2 miles of oceanfront, 1.5 miles of pond frontage, and 300+ acres of conservation land. Set on a peaceful, pastoral landscape abutting 17 acres of preserved land, this stately home was designed and built by Soikkeli & Company, one of the

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    18 Spruce Gate Rd, Chilmark, MA 02535
  • /35

    $22,000 total monthly price

    • 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
  • /3

    $105,000 Sold Sep 05, 2025

    • Land
    • 0.7 Acre
    • $150,000 per Acre
    • 29 Days On Market

    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
    • /37

      Est $2,004,371 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,900 Sq Ft

      2 Rockrose Path, Chilmark, MA 02535

      2 Rockrose Path, Chilmark, MA 02535
  • /7

    $400,000

    • Land
    • 0.2 Acre
    • $2,000,000 per Acre

    99 Cygnet Way Unit 103, Chilmark, MA 02535

    Escape the crowds at Lucy Vincent and Squibnocket and take advantage of this very rare opportunity to own a private, 17 member, Atlantic Ocean beach lot at Thumb Cove (abuts Hancock Beach). Included in the sale of this property is a deeded .2 acres of sandy beach, a deeded parking spot at Chilmark Pond and the right to launch boats from a dock in the pond. Sail, kayak, row, swim(!) or motor

    Russell Maloney Russell Maloney Real Estate

    99 Cygnet Way Unit 103, Chilmark, MA 02535
  • /39

    $110,000 total monthly price

    • 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
  • /34

    $2,475,000 Sold Sep 05, 2025

    • 2,300 Sq Ft
    • $1,076/SF
    • 117 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1983

    31 N Slope Ln, Chilmark, MA 02535

    Located on a private lane along North Road in the heart of Chilmark, this hilltop four bedroom home was perfectly sited to enjoy fantastic water views of Vineyard Sound toward the Elizabeth Islands. Built in 1983 and lived in seasonally, this home has been meticulously cared for. There is a new forced air HVAC system, and recently upgraded electrical. In addition, there are three working

    Bill Rossi Studio Realty

    31 N Slope Ln, Chilmark, MA 02535
    • /20

      Est $2,623,653 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,164 Sq Ft

      23 Black Point Rd, Chilmark, MA 02535

      23 Black Point Rd, Chilmark, MA 02535
  • /39

    $3,500,000

    • 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 total monthly price

    • 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
  • /22

    $435,000 Sold Aug 26, 2025

    • Land
    • 0.1 Acre
    • $4,350,000 per Acre
    • 18 Days On Market

    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535

    Stunning Quansoo Beach Lot available NOW. With this ownership you will gain access to gated parking and endless beach days along the Islands expansive South Shore and Tisbury Great Pond! Skip the lines and parking worries and enjoy the freedom to come and go as you please. If you have been dreaming of endless beach days, long walks on private shores... here is your chance. ***Note: This is not a

    Emma Kiley Bryant Landmarks at TODAY Real Estate

    0 Quansoo Beach Lot Unit 53 43599, 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
  • /19

    $2,675,000

    • 3 Beds
    • 1.5 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 total monthly price

    • 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
  • /21

    $435,000 Sold Aug 26, 2025

    • Land
    • 0.1 Acre
    • $4,350,000 per Acre
    • 20 Days On Market

    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535

    Stunning Quansoo Beach Lot available NOW. With this ownership you will gain access to gated parking and endless beach days along the Islands expansive South Shore and Tisbury Great Pond! Skip the lines and parking worries and enjoy the freedom to come and go as you please. If you have been dreaming of endless beach days, long walks on private shores... here is your chance. ***Note: This is not a

    Emma Bryant Landmarks at TODAY Real Estate

    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
    • /29

      Est $2,271,694 Not Listed For Sale

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

      50 South Rd, Chilmark, MA 02535

      50 South Rd, Chilmark, MA 02535
  • /40

    $1,895,000

    • 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
  • /29

    $34,000 total monthly price

    • 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
  • /7

    $650,000 Sold Aug 14, 2025

    • Land
    • 0.2 Acre
    • $3,250,000 per Acre
    • 7 Days On Market

    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535

    Spectacular Hancock beach lot on the Atlantic Ocean. Ownership of this lot allows you access to one of the world's most beautiful beaches, plenty of parking and away from the crowds. It is a most enjoyable spot to spend a relaxing day on the Vineyard, sunbathing, fishing, kayaking, canoeing, etc. as you also gain access to Chilmark Pond. Any property on the Vineyard would be greatly enhanced by

    Deb Hancock Hancock Real Estate

    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
    • /24

      Est $2,467,460 Not Listed For Sale

      • 4 Beds
      • 5.5 Baths
      • 2,405 Sq Ft

      99 Hammett Rd, Chilmark, MA 02535

      99 Hammett Rd, Chilmark, MA 02535
  • /77

    $2,995,000

    • 4 Beds
    • 3.5 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 two

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

    300 North Rd, Chilmark, MA 02535
  • /9

    $10,800 total monthly price

    • 4 Beds
    • 2 Baths
    • 702 Sq Ft
    • House for Rent

    141 N Rd Ch202, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a

    Karen Overtoom Karen M. Overtoom R.E.

    141 N Rd Ch202, Chilmark, MA 02535
  • /22

    $1,607,000 Sold Jul 10, 2025

    • 2,850 Sq Ft
    • $564/SF
    • 354 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1978

    10 N Abels Hill Rd, Chilmark, MA 02535

    A rare opportunity in the iconic Abel's Hill Association which offers private association beach access, three tennis courts and walking trails. This multi-level Chilmark home was designed and built as an homage to architect Frank Lloyd Wright's ethos of open living spaces with flowing sightlines from room to room. The main house has a pocket view to the Atlantic that opens in the fall and winter

    Elissa Lash Tea Lane Associates

    10 N Abels Hill Rd, Chilmark, MA 02535
    • /48

      Not Listed For Sale

      • 6 Beds
      • 5 Baths
      • 3,834 Sq Ft

      49 Tilton Rd, Chilmark, MA 02535

      49 Tilton Rd, Chilmark, MA 02535
  • /36

    $2,500,000

    • 4 Beds
    • 3 Baths
    • 2,350 Sq Ft

    16 South Rd, Chilmark, MA 02535

    Where Vineyard history meets pastoral beauty.Classic, lovingly restored 1800’s Chilmark farmhouse with multiple outbuildings, which includes a large barn with second floor loft, a run-in barn with two horse stalls, both overlook an expansive, pastoral fenced pasture for horses to run or field games to be played. This historic farmhouse home offers four bedrooms, three baths and has been updated

    Michele Casavant Vineyard Village Realty

    16 South Rd, Chilmark, MA 02535
  • /8

    $7,900 total monthly price

    • 3 Beds
    • 2.5 Baths
    • 2,107 Sq Ft
    • House for Rent

    2 Paddock Cir, Chilmark, MA 02535

    Karen Overtoom Karen M. Overtoom R.E.

    2 Paddock Cir, Chilmark, MA 02535
  • /44

    $37,000,000 Sold Jul 10, 2025

    • 7,846 Sq Ft
    • $4,716/SF
    • 39 Days On Market
    • 8 Beds
    • 5.5 Baths
    • Built 1993

    41 Cobbs Hill Rd, Chilmark, MA 02535

    One of the most exclusive estates across the Northeast, Blue Heron Farm on Martha's Vineyard is set on nearly 30 acres of lush landscaping along the shores of Tisbury Great Pond. The former summer residence of President Obama and family, chosen for its incredible privacy, serenity and significance, this multi-generational compound is protected by surrounding farmland and mature trees.

    Brian Dougherty Corcoran Property Advisors

    41 Cobbs Hill Rd, Chilmark, MA 02535
    • /21

      Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 4,967 Sq Ft

      27, 30, 31 Tower Lane; 34 Eben's Ln, Chilmark, MA 02535

      27, 30, 31 Tower Lane; 34 Eben's Ln, Chilmark, MA 02535
  • /33

    $1,985,000

    • Land
    • 3.58 Acres
    • $554,469 per Acre

    4 Cedar Ln Unit 2.2, Chilmark, MA 02535

    Premier Build-Ready Lot with Private Beach AccessGet to know Stonewall Association, one of Chilmark’s most sought-after enclaves on the South Shore. This sunny, build-ready parcel offers a rare opportunity to own land with deeded private access to Stonewall Beach—a beloved destination for swimming, surfing, excellent fishing and summer memories. Set on beautifully contoured land with

    Jill Napior Tea Lane Associates

    4 Cedar Ln Unit 2.2, Chilmark, MA 02535
  • /3

    $3,100,000 Sold Jul 03, 2025

    • 1,500 Sq Ft
    • $2,067/SF
    • 6 Beds
    • 3 Baths
    • Built 1975

    10 Basin Rd, Chilmark, MA 02535

    Unique compound in the heart of Menemsha - one of a kind!The cottage (520 sq.ft.), the chandlery buikding(5968 sq.ft.) and deli with an apartment(2172 sq.ft.) on just under an acre of land has tremendous potential for the right buyer!Special permits are required from the town to operate a business but they have approved a deli/restuarant, small stores and a commercial kitchen in the past.

    Julianna Flanders Flanders Real Estate

    10 Basin Rd, Chilmark, MA 02535
    • /14

      Not Listed For Sale

      34 Ebens Lane & 31 Tower Ln, Chilmark, MA 02535

      34 Ebens Lane & 31 Tower Ln, Chilmark, MA 02535
  • /35

    $2,850,000

    • 4 Beds
    • 3 Baths
    • 2,967 Sq Ft

    11 By the Woods, Chilmark, MA 02535

    Dreamlike Chilmark retreat on 4.5+/- acres overlooking the Chilmark Pond & Atlantic Ocean beyond. Uniquely designed with European and medieval history in mind. The House has 3 bedrooms, 3 bathrooms, an atrium dining area, a two-story library, a kitchen, and a pantry/wet bar. Charming garden and plantings surround the home.A must-see to appreciate all the special touches throughout the Main

    Julianna Flanders Flanders Real Estate

    11 By the Woods, Chilmark, MA 02535
  • /6

    $430,000 Sold Jun 30, 2025

    • Land
    • 1.4 Acres
    • $307,143 per Acre
    • 0 Days On Market

    0 Quansoo Beach Lot Unit 76 43513, Chilmark, MA 02535

    Not listed in LINK.

    LINK Email Cache LINK

    0 Quansoo Beach Lot Unit 76 43513, Chilmark, MA 02535
    • /13

      Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 816 Sq Ft

      70 State Rd, Aquinnah, MA 02535

      70 State Rd, Aquinnah, MA 02535
  • /16

    $1,295,000

    • 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 set on 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. There are so many outstanding possibilities for a future Buyer to build their dream home on this

    Elissa Lash Tea Lane Associates

    37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535
  • /6

    $430,000 Sold Jun 18, 2025

    • Land
    • 1.4 Acres
    • $307,143 per Acre
    • 0 Days On Market

    0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535

    Not listed in LINK.

    LINK Email Cache LINK

    0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535

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