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Chilmark Homes for Sale

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  • 20 Eliot Ave, Chilmark, MA 02535
    20 Eliot Ave, Chilmark, MA 02535
    20 Eliot Ave, Chilmark, MA 02535
    /30

    $6,595,000

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

    20 Eliot Ave, Chilmark, MA 02535

    Waterfront home on Stonewall Pond. 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. The interior

    Alyssa Halisky Wallace & Co. Sotheby's

    20 Eliot Ave, Chilmark, MA 02535
  • 96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    /38

    $4,195,000

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

    96 Hammett Ln, Chilmark, MA 02535

    This 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
  • 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
    • 2,913 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 original section of this 3000 sq ft home dates from the late 1700s and is on Chilmark's register of historic homes, but it has been expanded with new additions to create a thoroughly modern

    Mark Jenkins Wallace & Co. Sotheby's

    122 Old Farm 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

    $4,600,000

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

    15 Old Farm Rd, Chilmark, MA 02535

    CHILMARK BLISS- 15 Old Farm Rd, sits on over 3 beautiful acres, blends refined architecture with serene natural beauty. Reimagined in 2020 by Peter Breese and crafted by Doug Best, this timeless retreat offers open-concept living, anchored by a stunning kitchen, large pantry, screen porch, and a stone fireplace, with seamless indoor-outdoor flow. The main level includes a sunny primary suite

    Tina Miller Compass

    15 Old Farm 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
    • 2,913 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 original section of this 3000 sq ft home dates from the late 1700s and is on Chilmark's register of historic homes, but it has been expanded with new additions to create a thoroughly modern

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    124 Old Farm Rd Unit 122, 116, 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
  • 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
  • 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

    • 5 Beds
    • 4 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
  • 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
  • 29 Old Nursery Ln, Chilmark, MA 02535
    29 Old Nursery Ln, Chilmark, MA 02535
    29 Old Nursery Ln, Chilmark, MA 02535
    /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
  • 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

    • Land
    • 0.20 Acre
    • $3,250,000 per Acre

    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
  • 27 Clambelly Rd, Chilmark, MA 02535
    27 Clambelly Rd, Chilmark, MA 02535
    27 Clambelly Rd, Chilmark, 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
  • 00 Eliot Ave Unit 17, Chilmark, MA 02535
    00 Eliot Ave Unit 17, Chilmark, MA 02535
    00 Eliot Ave Unit 17, 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
  • 32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, Chilmark, MA 02535
    32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, Chilmark, MA 02535
    32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, 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
  • 5 Ocean View Farm Rd, Chilmark, MA 02535
    5 Ocean View Farm Rd, Chilmark, MA 02535
    5 Ocean View Farm 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
  • 300 North Rd, Chilmark, MA 02535
    300 North Rd, Chilmark, MA 02535
    300 North Rd, 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
  • 174 Middle Rd, Chilmark, MA 02535
    174 Middle Rd, Chilmark, MA 02535
    174 Middle Rd, 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
  • 4 Cedar Ln Unit 2.2, Chilmark, MA 02535
    4 Cedar Ln Unit 2.2, Chilmark, MA 02535
    4 Cedar Ln Unit 2.2, Chilmark, MA 02535
    /26

    $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 southern

    Jill Napior Tea Lane Associates

    4 Cedar Ln Unit 2.2, Chilmark, MA 02535
  • 6 Wakeman Rd, Chilmark, MA 02535
    6 Wakeman Rd, Chilmark, MA 02535
    6 Wakeman Rd, Chilmark, MA 02535
    /35

    $13,000,000

    • 5 Beds
    • 5 Baths
    • 3,758 Sq Ft

    6 Wakeman Rd, Chilmark, MA 02535

    A 1930s-built home that has been remarkably updated to retain its historic charm while incorporating sophisticated and modern amenities. The house overlooks the Chilmark Great Pond and the Atlantic Ocean beyond. The Main House includes 3 bedrooms, 3 beautifully renovated bathrooms, a walk-in closet, a Pantry, a Library/Media room, a full basement, Outdoor showers, and a screened-in porch. The

    Julianna Flanders Flanders Real Estate

    6 Wakeman Rd, Chilmark, MA 02535
  • 88 & 90 Quenames Rd, Chilmark, MA 02535
    88 & 90 Quenames Rd, Chilmark, MA 02535
    88 & 90 Quenames Rd, Chilmark, MA 02535
    /25

    $3,600,000

    • 3 Beds
    • 3 Baths
    • 4,382 Sq Ft

    88 & 90 Quenames Rd, Chilmark, MA 02535

    Make your own Chilmark dream come true!12.6 +/- acres of prime land allows you to create your own familycompound or Island Farm. Enjoy the peacefulness of the Chilmarkwith room to expand. Two separate buildable lots provides you uniqueoptions. The Main house has three bedrooms, three bathrooms, twostudies, multiple living spaces and a large three-car garage

    Julianna Flanders Flanders Real Estate

    88 & 90 Quenames Rd, Chilmark, MA 02535
  • 18 Allen Farm Rd Unit 20-2, Chilmark, MA 02535
    18 Allen Farm Rd Unit 20-2, Chilmark, MA 02535
    18 Allen Farm Rd Unit 20-2, Chilmark, MA 02535
    /6

    $2,950,000

    • Land
    • 2.36 Acres
    • $1,250,000 per Acre

    18 Allen Farm Rd Unit 20-2, Chilmark, MA 02535

    This private and serene 2.36 acre property is located one mile from Lucy Vincent Beach. There is a large building envelope located between the eighty and one hundred foot contour with exciting architectural options. The land has open woodlands, a small pasture and a fenced garden area. A charming cottage on the property is offered fully furnished and has everything you need to enjoy your stays

    Patty Kendall Kendall & Kendall

    18 Allen Farm Rd Unit 20-2, Chilmark, MA 02535
  • 32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
    32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
    /17

    $1,900,000

    • Land
    • 3.30 Acres
    • $575,758 per Acre

    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
  • 25 Osprey Ln, Chilmark, MA 02535
    25 Osprey Ln, Chilmark, MA 02535
    25 Osprey Ln, Chilmark, MA 02535
    /37

    $7,975,000

    • 4 Beds
    • 5 Baths
    • 3,777 Sq Ft

    25 Osprey Ln, Chilmark, MA 02535

    Spectacular views from one of the most sought after private enclaves on Chilmark's South Shore. This lovely home was built to take advantage of this magical location. Just steps to the shared dock on the shores of Upper Chilmark Pond and minutes to the extraordinary deeded Atlantic Beach front. The homeowners worked with world renowned architects, Crissman & Solomon, along with revolutionary

    Deb Hancock Hancock Real Estate

    25 Osprey Ln, Chilmark, MA 02535
  • 9 Beetlebung Grove Way, Chilmark, MA 02535
    9 Beetlebung Grove Way, Chilmark, MA 02535
    9 Beetlebung Grove Way, Chilmark, MA 02535
    /35

    $2,495,000

    • 4 Beds
    • 3 Baths
    • 2,968 Sq Ft

    9 Beetlebung Grove Way, Chilmark, MA 02535

    Beautifully sited on 3.4 acres, this distinctive Chilmark home offers a rare blend of privacy, comfort, and expansive living space, ideal for entertaining, both inside and outside. From the welcoming foyer, step into the dramatic vaulted living room, where wood-paneled ceilings, a gas fireplace, and abundant natural light from skylights and picture windows create a warm and inviting atmosphere.

    Stephanie Roache Donnelly + Co.

    9 Beetlebung Grove Way, Chilmark, MA 02535
  • 19 Old Woods Rd, Chilmark, MA 02535
    19 Old Woods Rd, Chilmark, MA 02535
    19 Old Woods Rd, Chilmark, MA 02535
    /41

    $2,950,000

    • 4 Beds
    • 3 Baths
    • 2,424 Sq Ft

    19 Old Woods Rd, Chilmark, MA 02535

    Tucked away in the heart of Chilmark, this nearly 3-acre property blends rustic Vineyard charm with unique creative potential. Chilmark was a very special place for the former owner, American artist Thomas Hart Benton, who summered on the Island for 50 years. Professor and Art Historian, Erika Doss, said “the years he spent in Chilmark honed the artistic style and subjects that led to his

    Cheri Mason Landvest MV

    19 Old Woods Rd, Chilmark, MA 02535
  • 19 Old Woods Rd, Chilmark, MA 02535
    19 Old Woods Rd, Chilmark, MA 02535
    19 Old Woods Rd, Chilmark, MA 02535
    /37

    $3,400,000

    • 5 Beds
    • 2 Baths
    • 3,133 Sq Ft

    19 Old Woods Rd, Chilmark, MA 02535

    Nestled in the heart of Chilmark, this 12.5-acre property offers two charming dwellings, each with 3 bedrooms, set in a landscape of privacy and timeless Vineyard character. Built in 1950 and 1963 for American artist, Thomas Hart Benton, the homes were lovingly created as a compound for friends and family to return to year after year. Tucked down a quiet driveway, the two share a special legacy

    Cheri Mason Landvest MV

    19 Old Woods Rd, Chilmark, MA 02535
  • 11 By the Woods, Chilmark, MA 02535
    11 By the Woods, Chilmark, MA 02535
    11 By the Woods, 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 House,

    Julianna Flanders Flanders Real Estate

    11 By the Woods, Chilmark, MA 02535
  • 78 Hammett Rd, Chilmark, MA 02535
    78 Hammett Rd, Chilmark, MA 02535
    78 Hammett Rd, Chilmark, MA 02535
    /63

    $5,975,000

    • 5 Beds
    • 4 Baths
    • 4,050 Sq Ft

    78 Hammett Rd, Chilmark, MA 02535

    Wonderful elevated Chilmark north shore 3.8 acre secure waterfront property with dramatic year round sunset water views to the Gay Head Lighthouse and Elizabeth Islands. The Vineyard Sound expanse enjoys peaceful sailing, fishing and other boating activity to enhance the ocean splendor. The 5 bedroom 3 1/2 bath 4,050 sq ft home is literally in move-in condition. Architect designed and built by

    Robert Kenney Tea Lane Associates

    78 Hammett 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
    /23

    $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
  • 18 Spruce Gate Rd, Chilmark, MA 02535
    18 Spruce Gate Rd, Chilmark, MA 02535
    18 Spruce Gate Rd, Chilmark, MA 02535
    /52

    $12,500,000

    • 5 Beds
    • 4 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

    18 Spruce Gate Rd, Chilmark, MA 02535
  • 18 Allen Farm Rd, Chilmark, MA 02535
    18 Allen Farm Rd, Chilmark, MA 02535
    18 Allen Farm Rd, Chilmark, MA 02535
    /13

    $2,950,000

    • 1 Bed
    • 1 Bath
    • 726 Sq Ft

    18 Allen Farm Rd, Chilmark, MA 02535

    Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1 + bedroom cottage with screened porch, brick patio and outside shower. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, especially for solar designs. The cottage is offered fully furnished,

    Patty Kendall Kendall & Kendall

    18 Allen Farm Rd, 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
  • 34 Edys Island Way, Chilmark, MA 02535
    34 Edys Island Way, Chilmark, MA 02535
    34 Edys Island Way, Chilmark, MA 02535
    /42

    $7,450,000

    • 5 Beds
    • 3 Baths
    • 2,269 Sq Ft

    34 Edys Island Way, Chilmark, MA 02535

    Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by anIsland legacy family, this property is unique among Island estates for its combination of privacy yet convenience and seclusion yet expansive views. To the

    Jill Napior Tea Lane Associates

    34 Edys Island Way, Chilmark, MA 02535
  • 37 Bijah's Way, Chilmark, MA 02535
    37 Bijah's Way, Chilmark, MA 02535
    37 Bijah's Way, Chilmark, MA 02535
    /16

    $1,325,000

    • Land
    • 4.40 Acres
    • $301,136 per Acre

    37 Bijah's Way, 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, Chilmark, MA 02535
  • 8 Snail Rd, Chilmark, MA 02535
    8 Snail Rd, Chilmark, MA 02535
    8 Snail Rd, Chilmark, MA 02535
    /60

    $14,000,000

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

    8 Snail Rd, Chilmark, MA 02535

    This exceptional Martha's Vineyard estate promises unmatched privacy and breathtaking views of the Atlantic Ocean and Chilmark Pond. Masterfully designed by acclaimed architect Rick Sundberg and built by renowned island builder Andrew Flake, this three-parcel property seamlessly blends modern sophistication with the timeless charm of the Vineyard. Upon entering, you are greeted by soaring

    Alyssa Halisky Wallace & Co. Sotheby's

    8 Snail Rd, Chilmark, MA 02535
  • 3 Fulling Mill Rd, Chilmark, MA 02535
    3 Fulling Mill Rd, Chilmark, MA 02535
    3 Fulling Mill Rd, Chilmark, MA 02535
    /48

    $1,875,000

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

    3 Fulling Mill Rd, Chilmark, MA 02535

    Tucked away in a prime location just off Middle Road is this bright modern home offering the perfect blend of comfort and style. The main level features a large bedroom or first-floor office and a full bath, while the upper floor boasts two additional bedrooms and a beautifully appointed bathroom with a steam shower and double vanity. The open concept living and dining areas flow effortlessly

    Jill Napior Tea Lane Associates

    3 Fulling Mill Rd, Chilmark, MA 02535
  • 31 N Slope Ln, Chilmark, MA 02535
    31 N Slope Ln, Chilmark, MA 02535
    31 N Slope Ln, Chilmark, MA 02535
    /34

    $2,895,000

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

    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
  • 16 Shotnaigher Ln, Chilmark, MA 02535
    16 Shotnaigher Ln, Chilmark, MA 02535
    16 Shotnaigher Ln, Chilmark, MA 02535
    /29

    $12,750,000

    • 4 Beds
    • 4 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
  • 25 Fulling Mill Rd, Chilmark, MA 02535
    25 Fulling Mill Rd, Chilmark, MA 02535
    25 Fulling Mill Rd, Chilmark, MA 02535
    /31

    $2,450,000

    • 4 Beds
    • 3 Baths
    • 1,918 Sq Ft

    25 Fulling Mill Rd, Chilmark, MA 02535

    Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to

    Thomas Wallace Wallace & Co. Sotheby's International Realty

    25 Fulling Mill Rd, Chilmark, MA 02535
  • 345 North Rd, Chilmark, MA 02535
    345 North Rd, Chilmark, MA 02535
    345 North Rd, Chilmark, MA 02535
    /23

    $1,625,000

    • 5 Beds
    • 5 Baths
    • 2,316 Sq Ft

    345 North Rd, Chilmark, MA 02535

    Abutting hundreds of acres of conservation land and walking trails leading to the second-highest point on Martha's Vineyard with views of the Elizabeth Islands, this classically-styled house with detached guest quarters offers 5 total bedrooms and 4 full baths plus an outdoor shower. The primary bedroom suite is a generous size and has its own small deck that overlooks the charming front yard.

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    345 North Rd, Chilmark, MA 02535

Showing Results 1 - 40, Page 1 of 2

Massachusetts Dukes County Marthas Vineyard Chilmark

Real Estate & Homes for Sale in Chilmark, Marthas Vineyard

Why Live in Chilmark
Chilmark, located in the up-island region of Martha’s Vineyard, is characterized by its serene, rural landscape and expansive rolling hills reminiscent of Ireland. This quiet town is known for its privacy, with homes set on large lots of at least three acres, often at the end of private dirt roads. The area lacks a downtown district and gastropubs, offering instead the tranquility of mighty-waved beaches like Lucy Vincent Beach, exclusive to town residents. The neighborhood is home to gray-shingled Cape Cod-style houses and vast family compounds, reflecting its reputation for high property values, though it maintains one of the lowest property tax rates on the island. Menemsha, a quaint fishing village within Chilmark, features markets selling fresh seafood and offers scenic hikes along Menemsha Hills. Residents enjoy local amenities such as the Chilmark General Store, known for its pizza and locally sourced goods, and the Yard, a performing arts venue. Chilmark School serves younger children with a unique multi-age classroom approach, while older students attend Martha’s Vineyard Regional High School, which provides a range of educational programs. The town is about a 30-minute drive from Edgartown and Oak Bluffs, with Martha’s Vineyard Airport just 15 minutes away, offering both year-round and seasonal flights.
Learn more about living in Chilmark

Frequently Asked Questions

Is Chilmark a good place to live?
Chilmark is a good place to live. Chilmark is considered very car-dependent and somewhat bikeable. Chilmark has 1 park for recreational activities. It is sparse in population with 0.1 people per acre and a median age of 56. The average household income is $161,487 which is above the national average. College graduates make up 64.4% of residents. A majority of residents in Chilmark are home owners, with 20.4% of residents renting and 79.6% of residents owning their home. A local real estate agent serving Chilmark can help you decide if this neighborhood is the right one for you. Learn more on our Chilmark neighborhood guide.
How much do you need to make to afford a house in Chilmark?
The median home price in Chilmark is $435,000. If you put a 20% down payment of $87,000 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $2,250 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $96K a year to afford the median home price in Chilmark. The average household income in Chilmark is $161K.
What are the best public schools in Chilmark?
The best public schools that serve Chilmark are:
What are the most popular zip codes in Chilmark, Marthas Vineyard, MA?
The most popular zip codes in Chilmark, Marthas Vineyard, MA include 02535, 02568, 02575, 02539 and 02536.
What are the most popular neighborhoods near Chilmark, Marthas Vineyard, MA?
The most popular neighborhoods near Chilmark, Marthas Vineyard, MA are West Tisbury, Aquinnah, Edgartown, Oak Bluffs and Vineyard Haven.

Home Trends in Chilmark, MA

On average, homes in Chilmark, Marthas Vineyard sell after 72 days on the market compared to the national average of 70 days. The median sale price for homes in Chilmark, Marthas Vineyard over the last 12 months is $419,485, up 30% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$419,485
Median Single Family Sale Price
$421,000
Median Townhouse Sale Price
$372,390
Median 2 Bedroom Sale Price
$353,000
Average Price Per Sq Ft
$252
Number of Homes for Sale
6
Last 12 months Home Sales
74
Months of Supply
1.00
Median List Price
$435,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
30%
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