1,732

Chilmark Homes

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  • 20 Eliot Ave, Chilmark, MA 02535
    20 Eliot Ave, Chilmark, MA 02535
    20 Eliot Ave, Chilmark, MA 02535
    /37

    $6,595,000

    • 4 Beds
    • 3.5 Baths
    • 3,052 Sq Ft

    20 Eliot Ave, Chilmark, MA 02535

    Waterfront home on Stonewall Pond with Ocean Views. Nestled along the serene shores of Stonewall Pond, this waterfront home is located in one is Chilmark's most idyllic locations. This remarkable property offers an unparalleled living experience with breathtaking Atlantic Ocean views and exclusive access to Stonewall Beach. Step inside and be greeted by a seamless fusion of elegance and comfort.

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    20 Eliot Ave, Chilmark, MA 02535
  • 27 Beach Plum Ln, Chilmark, MA 02535
    27 Beach Plum Ln, Chilmark, MA 02535
    27 Beach Plum Ln, Chilmark, MA 02535
    /21

    $7,000 per month

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

    27 Beach Plum Ln, Chilmark, MA 02535

    weekly rental The "Grapevine" is located on a private road next door to the Beach Plum Inn, It was completely rebuilt not to long ago it has 3 generous size bedrooms all with private baths, 2 of the bedrooms are located on the second floor, 1 bedroom is located on the first floor as well as the Open concept living with a chefs Kitchen, living room ,dining area and fireplace area. Walk out the

    Bryan Hummel Commonwealth Realty Group

    27 Beach Plum Ln, Chilmark, MA 02535
  • 0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
    /21

    $435,000 Sold Aug 26, 2025

    • Land
    • 0.10 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
    • 260 South Rd, Chilmark, MA 02535
      260 South Rd, Chilmark, MA 02535
      260 South Rd, Chilmark, MA 02535
      /79

      Not Listed For Sale

      • 6 Beds
      • 2.5 Baths
      • 2,604 Sq Ft

      260 South Rd, Chilmark, MA 02535

      260 South Rd, Chilmark, MA 02535
  • 15 Old Farm Rd, Chilmark, MA 02535
    15 Old Farm Rd, Chilmark, MA 02535
    15 Old Farm Rd, Chilmark, MA 02535
    /42

    $4,250,000

    • 3 Beds
    • 6 Baths
    • 3,171 Sq Ft

    15 Old Farm Rd, Chilmark, MA 02535

    CHILMARK BLISS – Refined Retreat | 15 Old Farm Road. Set on 3+ acres of manicured grounds, this 2020 Peter Breese–redesigned home blends elegance and tranquility. A serene pond, stream, and custom hardscape set the tone. Inside, a dramatic open kitchen/living area boasts high-end appliances, stone countertops, and a striking fireplace, with a pantry leading to a screened porch. The main-level

    Tina Miller Donnelly + Co.

    15 Old Farm Rd, Chilmark, MA 02535
  • 11 Hammett Ln, Chilmark, MA 02535
    11 Hammett Ln, Chilmark, MA 02535
    11 Hammett Ln, Chilmark, MA 02535
    /20

    $4,250 per month

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • House for Rent

    11 Hammett Ln, Chilmark, MA 02535

    Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime location off North Road

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    11 Hammett Ln, Chilmark, MA 02535
  • 0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    /22

    $435,000 Sold Aug 26, 2025

    • Land
    • 0.10 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
    • 68 Meeting House Rd, Chilmark, MA 02535
      68 Meeting House Rd, Chilmark, MA 02535
      68 Meeting House Rd, Chilmark, MA 02535
      /31

      Est $3,222,747 Not Listed For Sale

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

      68 Meeting House Rd, Chilmark, MA 02535

      68 Meeting House Rd, Chilmark, MA 02535
  • 122 Old Farm Rd, Chilmark, MA 02535
    122 Old Farm Rd, Chilmark, MA 02535
    122 Old Farm Rd, Chilmark, MA 02535
    /36

    $5,450,000

    • 5 Beds
    • 4 Baths
    • 3,413 Sq Ft

    122 Old Farm Rd, Chilmark, MA 02535

    An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

    Mark Jenkins Wallace & Co. Sotheby's

    122 Old Farm Rd, Chilmark, MA 02535
  • 5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    /8

    $16,000 per month

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

    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite.

    Karen Overtoom Karen M. Overtoom R.E.

    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
  • 00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
    /7

    $650,000 Sold Aug 14, 2025

    • Land
    • 0.20 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
    • 4 Tilton Rd, Chilmark, MA 02535
      4 Tilton Rd, Chilmark, MA 02535
      4 Tilton Rd, Chilmark, MA 02535
      /75

      Est $4,165,014 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,362 Sq Ft

      4 Tilton Rd, Chilmark, MA 02535

      4 Tilton Rd, Chilmark, MA 02535
  • 124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
    /34

    $5,450,000

    • 5 Beds
    • 4.5 Baths
    • 3,413 Sq Ft

    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535

    An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
  • 33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    /8

    $4,500 per month

    • 2 Beds
    • 2 Baths
    • 1,393 Sq Ft
    • House for Rent

    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535

    THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

    Karen Overtoom Karen M. Overtoom R.E.

    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
  • 10 N Abels Hill Rd, Chilmark, MA 02535
    10 N Abels Hill Rd, Chilmark, MA 02535
    10 N Abels Hill Rd, 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
    • 7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      /31

      Est $2,316,475 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,386 Sq Ft

      7 the Aerie, Chilmark, MA 02535

      7 the Aerie, Chilmark, MA 02535
  • 44 Cencelle St, Chilmark, MA 02535
    44 Cencelle St, Chilmark, MA 02535
    44 Cencelle St, Chilmark, MA 02535
    /46

    $6,750,000

    • 3 Beds
    • 3 Baths
    • 3,432 Sq Ft

    44 Cencelle St, Chilmark, MA 02535

    This private 21-acre Chilmark estate with ocean views, tucked away in the rolling hills and farmlands of Chilmark, offers sweeping ocean views to the south and a rare sense of seclusion and serenity. At the heart of the property is a striking modern style home, thoughtfully designed to bring the outdoors in. Expansive walls of glass flood the interior with natural light and frame panoramic views

    Meg Bodnar Tea Lane Associates

    44 Cencelle St, Chilmark, MA 02535
  • 56 Chilmark Rd, Chilmark, MA 02535
    56 Chilmark Rd, Chilmark, MA 02535
    56 Chilmark Rd, Chilmark, MA 02535
    /8

    $8,000 per month

    • 4 Beds
    • 4.5 Baths
    • 3,600 Sq Ft
    • House for Rent

    56 Chilmark Rd, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and

    Karen Overtoom Karen M. Overtoom R.E.

    56 Chilmark Rd, Chilmark, MA 02535
  • 41 Cobbs Hill Rd, Chilmark, MA 02535
    41 Cobbs Hill Rd, Chilmark, MA 02535
    41 Cobbs Hill Rd, 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
    • 2 Creek Hill, Chilmark, MA 02535
      2 Creek Hill, Chilmark, MA 02535
      2 Creek Hill, Chilmark, MA 02535
      /33

      Est $1,599,025 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 770 Sq Ft

      2 Creek Hill, Chilmark, MA 02535

      2 Creek Hill, Chilmark, MA 02535
  • 60 Meetinghouse Rd, Chilmark, MA 02535
    60 Meetinghouse Rd, Chilmark, MA 02535
    60 Meetinghouse Rd, Chilmark, MA 02535
    /49

    $6,490,000

    • 6 Beds
    • 8 Baths
    • 5,660 Sq Ft

    60 Meetinghouse Rd, Chilmark, MA 02535

    This spectacular and bright modern american farmhouse is perfectly sited to capture the varied scenic beauty that surrounds the farm. Built in 2021 with great attention to detail and materials, this home was created around gatherings and community with ample space for the extended family. The land has been lovingly curated into a place which can grow, generate and support those who want to have

    Jim Feiner Feiner Real Estate

    60 Meetinghouse Rd, Chilmark, MA 02535
  • 224 N Rd Ch248, Chilmark, MA 02535
    224 N Rd Ch248, Chilmark, MA 02535
    224 N Rd Ch248, Chilmark, MA 02535
    /3

    $13,200 per month

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • House for Rent

    224 N Rd Ch248, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room.

    Karen Overtoom Karen M. Overtoom R.E.

    224 N Rd Ch248, Chilmark, MA 02535
  • 10 Basin Rd, Chilmark, MA 02535
    10 Basin Rd, Chilmark, MA 02535
    10 Basin Rd, 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
    • 12 Harbor Hill Rd, Chilmark, MA 02535
      12 Harbor Hill Rd, Chilmark, MA 02535
      12 Harbor Hill Rd, Chilmark, MA 02535
      /13

      Est $1,547,093 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
  • 35 S Bowl Rd, Chilmark, MA 02535
    35 S Bowl Rd, Chilmark, MA 02535
    35 S Bowl Rd, Chilmark, MA 02535
    /29

    $6,000,000

    • 3 Beds
    • 2 Baths
    • 2,710 Sq Ft

    35 S Bowl Rd, Chilmark, MA 02535

    This exceptionally elegant and tranquil home in Seven Gates Farm combines contemporary architectural design with timeless high-end features for Vineyard casual, nature-inspired living. Extraordinary and rare, this move-in ready three-bedroom home with six-bedroom septic system sits on an oversized 5.3-acre parcel in Chilmark. This thoughtful layout has an easy flow, soothing tones with cypress

    Meg Bodnar Tea Lane Associates

    35 S Bowl Rd, Chilmark, MA 02535
  • 6 Trails End Ch241, Chilmark, MA 02535
    6 Trails End Ch241, Chilmark, MA 02535
    6 Trails End Ch241, 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
  • 0 Quansoo Beach Lot Unit 48 43513, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 48 43513, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 48 43513, Chilmark, MA 02535
    /6

    $430,000 Sold Jun 30, 2025

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

    0 Quansoo Beach Lot Unit 48 43513, Chilmark, MA 02535

    Not listed in LINK.

    LINK Email Cache LINK

    0 Quansoo Beach Lot Unit 48 43513, Chilmark, MA 02535
    • 10 Mollys Way, Chilmark, MA 02535
      10 Mollys Way, Chilmark, MA 02535
      10 Mollys Way, Chilmark, MA 02535
      /46

      Est $1,900,754 Not Listed For Sale

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

      10 Mollys Way, Chilmark, MA 02535

      10 Mollys Way, Chilmark, MA 02535
  • 308 South Rd, Chilmark, MA 02535
    308 South Rd, Chilmark, MA 02535
    308 South Rd, Chilmark, MA 02535
    /51

    $7,950,000

    • 4 Beds
    • 5 Baths
    • 3,490 Sq Ft

    308 South Rd, Chilmark, MA 02535

    Commanding Pondfront Retreat with Private Dock and South Shore Views. This exceptional Chilmark residence offers a rare blend of privacy, elegance, and modern comfort. Originally built by Tom Tate and renovated in 2018, it exudes contemporary sophistication while embracing its natural surroundings. A private dock on Chilmark Pond provides direct water access and stunning South Shore sunsets.

    Rose Ryley Sandpiper Realty Inc

    308 South Rd, Chilmark, MA 02535
  • 17 Round Pond Rd Ch240, Chilmark, MA 02535
    17 Round Pond Rd Ch240, Chilmark, MA 02535
    17 Round Pond Rd Ch240, Chilmark, 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
  • 0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535
    /6

    $430,000 Sold Jun 18, 2025

    • Land
    • 1.40 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
    • 15 Red Valley Rd, Chilmark, MA 02535
      15 Red Valley Rd, Chilmark, MA 02535
      15 Red Valley Rd, Chilmark, MA 02535
      /34

      Est $5,259,768 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
  • 146 Quansoo Rd, Chilmark, MA 02535
    146 Quansoo Rd, Chilmark, MA 02535
    146 Quansoo Rd, Chilmark, MA 02535
    /37

    $4,850,000

    • 5 Beds
    • 3 Baths
    • 3,440 Sq Ft

    146 Quansoo Rd, Chilmark, MA 02535

    Nestled along the beautiful and tranquil shoreline of Tisbury Great Pond and surrounded by a stunning natural environment of water, sand and sky, this is an unparallelled beach house experience on the south shore of Chilmark. The five-bedroom home consists of a three-bedroom main house connected by walkways to a two-bedroom guest wing with studio space above, all with spectacular water views

    Meg Bodnar Tea Lane Associates

    146 Quansoo Rd, Chilmark, MA 02535
  • 44 Flanders Ln, Chilmark, MA 02535
    44 Flanders Ln, Chilmark, MA 02535
    44 Flanders Ln, 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
  • 10 Rumpus Ridge Rd, Chilmark, MA 02535
    10 Rumpus Ridge Rd, Chilmark, MA 02535
    10 Rumpus Ridge Rd, 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
    • 1 Pond Mark, Chilmark, MA 02535
      1 Pond Mark, Chilmark, MA 02535
      1 Pond Mark, Chilmark, MA 02535
      /18

      Est $4,032,567 Not Listed For Sale

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

      1 Pond Mark, Chilmark, MA 02535

      1 Pond Mark, Chilmark, MA 02535
  • 49 Gosnold's Way, Chilmark, MA 02535
    49 Gosnold's Way, Chilmark, MA 02535
    49 Gosnold's Way, Chilmark, MA 02535
    /51

    $4,950,000 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 4,044 Sq Ft

    49 Gosnold's Way, Chilmark, MA 02535

    Perched high on the north shore with sweeping views of the Vineyard Sound, this expansive and private property is surrounded by Menemsha Hills conservation land and trails and offers broad water views, even from ground floor of house. The house is large and well maintained with an upside down floor plan allowing for high ceilings and bright spaces in the open plan kitchen/dining/living room, as

    Meg Bodnar Tea Lane Associates

    49 Gosnold's Way, Chilmark, MA 02535
  • 384 Middle Rd Ch222, Chilmark, MA 02535
    384 Middle Rd Ch222, Chilmark, MA 02535
    384 Middle Rd Ch222, 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
  • 2 Squibnocket Rd, Chilmark, MA 02535
    2 Squibnocket Rd, Chilmark, MA 02535
    2 Squibnocket Rd, Chilmark, MA 02535
    /52

    $9,525,000 Sold Apr 24, 2025

    • 5,808 Sq Ft
    • $1,640/SF
    • 297 Days On Market
    • 6 Beds
    • 5.5 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 Donnelly + Co

    2 Squibnocket Rd, Chilmark, MA 02535
    • 2 Rockrose Path, Chilmark, MA 02535
      2 Rockrose Path, Chilmark, MA 02535
      2 Rockrose Path, Chilmark, MA 02535
      /37

      Est $1,826,286 Not Listed For Sale

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

      2 Rockrose Path, Chilmark, MA 02535

      2 Rockrose Path, Chilmark, MA 02535

Showing Results 1 - 40, Page 1 of 18

Massachusetts Dukes County Marthas Vineyard Chilmark

Real Estate & Homes

Learn more about living in Chilmark

Home Trends in Chilmark, MA

On average, homes in Chilmark, Marthas Vineyard sell after 133 days on the market compared to the national average of 52 days. The median sale price for homes in Chilmark, Marthas Vineyard over the last 12 months is $2,300,000, down 34% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$2,300,000
Median Single Family Sale Price
$3,772,500
Average Price Per Sq Ft
$1,743
Number of Homes for Sale
25
Last 12 months Home Sales
25
Months of Supply
12.00
Median List Price
$3,895,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
-34%
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