51

Chilmark Homes for Sale

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  • 26 Harbor Hill Rd, Chilmark, MA 02535
    26 Harbor Hill Rd, Chilmark, MA 02535
    26 Harbor Hill Rd, Chilmark, MA 02535
    /40

    $7,000,000

    • 2 Beds
    • 3 Baths
    • 1,550 Sq Ft

    26 Harbor Hill Rd, Chilmark, MA 02535

    Martha's Vineyard has many wonderful properties but only a few are irreplaceable. Menemsha Harbor is authentic and irreplaceable and this property, Topmast, is the highest and most spacious lot with lovely yard and rare privacy. Topmast was designed and built by master craftsmen in 2016 with unusual quality and care and only occupied a few days each year so virtually brand new. Included close by

    Robert Kenney Tea Lane Associates

    26 Harbor Hill Rd, Chilmark, MA 02535
  • 21 & 25 Fulling Mill Rd, Chilmark, MA 02535
    21 & 25 Fulling Mill Rd, Chilmark, MA 02535
    21 & 25 Fulling Mill Rd, Chilmark, MA 02535
    /42

    $2,250,000

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

    21 & 25 Fulling Mill Rd, Chilmark, MA 02535

    Jessie Holtham Wallace & Co. Sotheby's International Realty

    21 & 25 Fulling Mill Rd, Chilmark, MA 02535
  • 34 Ebens Ln, Chilmark, MA 02535
    34 Ebens Ln, Chilmark, MA 02535
    34 Ebens Ln, Chilmark, MA 02535
    /8

    $2,725,000

    • Land
    • 7.6 Acres
    • $358,553 per Acre

    34 Ebens Ln, Chilmark, MA 02535

    This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience --

    Peyton Wallace Studio Realty LLC

    34 Ebens Ln, Chilmark, MA 02535
  • 21 Eliot Ave, Chilmark, MA 02535
    21 Eliot Ave, Chilmark, MA 02535
    21 Eliot Ave, Chilmark, MA 02535
    /40

    $5,250,000

    • 4 Beds
    • 3 Baths
    • 1,714 Sq Ft

    21 Eliot Ave, Chilmark, MA 02535

    An iconic retreat in Chilmark, this totally renovated beach house captures sweeping views of the Atlantic Ocean, Stonewall Beach, and Stonewall Pond. The design honors the timeless simplicity of its coastal setting with elegant, understated finishes that allow the extraordinary vistas to take center stage. Designed for effortless indoor-outdoor living, the home's light-filled spaces open to

    Mark Jenkins Wallace & Co. Sotheby's

    21 Eliot Ave, Chilmark, MA 02535
  • 28 Black Point Rd, Chilmark, MA 02535
    28 Black Point Rd, Chilmark, MA 02535
    28 Black Point Rd, Chilmark, MA 02535
    /55

    $2,950,000

    • 3 Beds
    • 3 Baths
    • 1,469 Sq Ft

    28 Black Point Rd, Chilmark, MA 02535

    Bright & Airy Black Point Retreat with Private Access to Black Point Beach. Nestled on 5.4 private acres just off Black Point Road in Chilmark, this beautifully maintained retreat offers tranquility and comfort where the sound of the ocean provides a constant backdrop and the shoreline is just moments away. Included with the property is a coveted beach lot (key) to this private south shore beach.

    Michele Moore Island Real Estate

    28 Black Point Rd, Chilmark, MA 02535
  • 132 South Rd, Chilmark, MA 02535
    132 South Rd, Chilmark, MA 02535
    132 South Rd, Chilmark, MA 02535
    /34

    $1,600,000

    • 3 Beds
    • 3 Baths
    • 2,155 Sq Ft

    132 South Rd, Chilmark, MA 02535

    Nestled on a private, 1.9-acre lot along historic South Road in Chilmark, this charming New England retreat offers an exceptional sense of tranquility and classic Martha's Vineyard living. Built in 1950, Vineyard Home offers 2 bedrooms and 2 full bathrooms great light, cozy additional living spaces and fireplace. Multiple patios and gardens seamlessly connecting the living spaces to the

    Lisa Da Silva Compass

    132 South Rd, Chilmark, MA 02535
  • 96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    /37

    $3,795,000

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

    96 Hammett Ln, Chilmark, MA 02535

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

    Brenda Galligan Karen M. Overtoom R.E.

    96 Hammett Ln, Chilmark, MA 02535
  • 8 Rumpus Ridge Rd, Chilmark, MA 02535
    8 Rumpus Ridge Rd, Chilmark, MA 02535
    8 Rumpus Ridge Rd, Chilmark, MA 02535
    /29

    $1,550,000

    • 4 Beds
    • 2 Baths
    • 1,757 Sq Ft

    8 Rumpus Ridge Rd, Chilmark, MA 02535

    Escape to your own getaway with mature landscaped gardens and privacy in the heart of Chilmark. Walk to the Chilmark Store, library, Chilmark Community Center, Beetlebung Farm and bank. Access to Chilmark beaches - Lucy Vincent and Squibnocket - and Menemsha Public Beach are a plus.This four bedroom, two bath home has hardwood floors throughout. The living room and eat-in kitchen separate the

    Julianna Flanders Flanders Real Estate

    8 Rumpus Ridge Rd, Chilmark, MA 02535
  • 139 Tea Ln, Chilmark, MA 02535
    139 Tea Ln, Chilmark, MA 02535
    139 Tea Ln, Chilmark, MA 02535
    /34

    $2,195,000

    • 3 Beds
    • 3 Baths
    • 2,363 Sq Ft

    139 Tea Ln, Chilmark, MA 02535

    Tucked away on a quiet country road in a serene Chilmark setting, this beautifully crafted home, built in 2023, offers modern comfort surrounded by natural beauty. The thoughtfully designed main level features an open, light-filled floor plan where the living, dining, kitchen, and family areas flow seamlessly together. A wall of glass doors opens to the outdoors, creating an effortless

    Meg Bodnar Tea Lane Associates

    139 Tea Ln, Chilmark, MA 02535
  • 63 Putnam Rd, Chilmark, MA 02535
    63 Putnam Rd, Chilmark, MA 02535
    63 Putnam Rd, Chilmark, MA 02535
    /42

    $4,995,000

    • 3 Beds
    • 2.5 Baths
    • 2,095 Sq Ft

    63 Putnam Rd, Chilmark, MA 02535

    Stylish Chilmark retreat with sweeping water views, private beach, tennis, and walking trails. Set within the coveted Spring Point community, this beautifully renovated island home captures a rare sense of place, with natural beauty, privacy, and effortless indoor-outdoor living. Thoughtfully updated in 2022, the home blends relaxed coastal sophistication with driftwood-colored hardwood floors, a

    Agent Photo

    Wendy Harman

    Compass

    63 Putnam Rd, Chilmark, MA 02535
  • 8 Snail Rd, Chilmark, MA 02535
    8 Snail Rd, Chilmark, MA 02535
    8 Snail Rd, Chilmark, MA 02535
    /31

    $15,400,000

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

    8 Snail Rd, Chilmark, MA 02535

    Horizon House sits atop one of Chilmark's most private and elevated parcels, offering protected and sweeping views of the Atlantic Ocean. Framed by meadow, mature trees, stone walls, and native terrain, the estate holds an extraordinary connection to both land and sea. The 4+ bedroom main house has been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects

    Brian Dougherty Corcoran Property Advisors

    8 Snail Rd, Chilmark, MA 02535
  • 49 Gosnolds Way, Chilmark, MA 02535
    49 Gosnolds Way, Chilmark, MA 02535
    49 Gosnolds Way, Chilmark, MA 02535
    /32

    $5,200,000

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

    49 Gosnolds Way, Chilmark, MA 02535

    Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an

    Bonnie Pierce Wallace & Co. Sotheby's International Realty

    49 Gosnolds Way, Chilmark, MA 02535
  • 49 Gosnold's Way, Chilmark, MA 02535
    49 Gosnold's Way, Chilmark, MA 02535
    49 Gosnold's Way, Chilmark, MA 02535
    /35

    $5,200,000

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

    49 Gosnold's Way, Chilmark, MA 02535

    Set high on the north shore with panoramic waterviews of Vineyard Sound and deeded private beach access, this secluded 9.8-acre property occupies a rare setting bordered by conservation land and the Menemsha Hills trail network.The spacious, meticulously maintained residence features a reverse floor plan that accentuates the natural light, soaring ceilings, and breathtaking views. The upper

    Bonnie Pierce Wallace & Co. Sotheby's

    49 Gosnold's Way, Chilmark, MA 02535
  • 35 S Bowl Rd, Chilmark, MA 02535
    35 S Bowl Rd, Chilmark, MA 02535
    35 S Bowl Rd, Chilmark, MA 02535
    /42

    $5,400,000

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

    35 S Bowl Rd, Chilmark, MA 02535

    Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by architects Jane and Christian Langmuir, this exceptional three-bedroom home is set on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace natural light and its surroundings, the residence blends natural materials with contemporary architectural details.The dramatic great room features a striking

    Tina Miller Donnelly + Co.

    35 S Bowl Rd, Chilmark, MA 02535
  • 15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
    15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
    15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
    /11

    $1,250,000

    • Land
    • 1.9 Acres
    • $657,895 per Acre

    15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535

    Nestled in a bucolic setting moments from the iconic Menemsha fishing village, this beautiful and fully engineered parcel is approved for a 6BR home. One of the few remaining Menemsha buildable lots makes this a rare opportunity. With room for a pool with a special permit!Surrounded by ancient stone walls on three sides and mature trees, the land has stunning sunset skies, lovely pastoral

    Jill Napior Tea Lane Associates

    15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
  • 17 Chockers Ln, Chilmark, MA 02535
    17 Chockers Ln, Chilmark, MA 02535
    17 Chockers Ln, Chilmark, MA 02535
    /22

    $5,500,000

    • 2 Beds
    • 1 Bath
    • 808 Sq Ft

    17 Chockers Ln, Chilmark, MA 02535

    Perfectly situated on Nashaquitsa Pond, this charming two-bedroom cottage offers sweeping views of Quitsa and Menemsha Pond from a rare vantage point few properties can match. The cottage includes private beach rights to Short Beach and dock access for a mooring. Inside, hand-painted floors and a warm, unpretentious interior reflect the authentic character of Old Vineyard — a property that has

    Julianna Flanders Flanders Real Estate

    17 Chockers Ln, Chilmark, MA 02535
  • 100 Gosnolds Way, Chilmark, MA 02535
    100 Gosnolds Way, Chilmark, MA 02535
    100 Gosnolds Way, Chilmark, MA 02535
    /46

    $3,400,000

    • 4 Beds
    • 2.5 Baths
    • 2,383 Sq Ft

    100 Gosnolds Way, Chilmark, MA 02535

    Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound & the Elizabeth Islands. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where you

    Julianna Flanders Flanders Real Estate

    100 Gosnolds Way, Chilmark, MA 02535
  • 6 Wakeman Rd, Chilmark, MA 02535
    6 Wakeman Rd, Chilmark, MA 02535
    6 Wakeman Rd, Chilmark, MA 02535
    /53

    $9,875,000

    • 6 Beds
    • 5.5 Baths
    • 3,758 Sq Ft

    6 Wakeman Rd, Chilmark, MA 02535

    Set in a spectacular water view setting with private beach access, this exceptional coastal compound offers a rare blend of privacy, flexibility, and breathtaking scenery. The property is thoughtfully composed of a beautifully appointed main residence, a separate guest house, an artist’s studio, and a detached garage with an additional bedroom above — creating the ideal retreat for extended

    Jill Napior Tea Lane Associates

    6 Wakeman Rd, Chilmark, MA 02535
  • 18 Point Inner Way, Chilmark, MA 02535
    18 Point Inner Way, Chilmark, MA 02535
    18 Point Inner Way, Chilmark, MA 02535
    /65

    $45,000,000

    • 7 Beds
    • 13 Baths
    • 14,780 Sq Ft

    18 Point Inner Way, Chilmark, MA 02535

    A rare offering on the shores of Menemsha Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Thoughtfully designed with striking modern architecture, walls of glass, and seamless indoor-outdoor living, this one-of-a-kind compound captures breathtaking water views from nearly every room. Set on 4.9 acres with a private 115-foot deep-water dock, the

    Alyssa Halisky Wallace & Co. Sotheby's

    18 Point Inner Way, Chilmark, MA 02535
  • 10 Abels Neck Rd, Chilmark, MA 02535
    10 Abels Neck Rd, Chilmark, MA 02535
    10 Abels Neck Rd, Chilmark, MA 02535
    /20

    $1,450,000

    • 3 Beds
    • 2 Baths
    • 1,749 Sq Ft

    10 Abels Neck Rd, Chilmark, MA 02535

    Nestled on a beautiful lot in the heart of Chilmark, this charming cottage is framed by mature blueberry bushes just off the deck — a true slice of island life. Perfectly positioned to enjoy the quiet calm of up-island living while remaining close to town, beaches, and all that the Vineyard has to offer. Step inside through sliding glass doors into a cozy living area, where an arched entryway

    Julianna Flanders Flanders Real Estate

    10 Abels Neck Rd, Chilmark, MA 02535
  • 61 Stonewall Rd, Chilmark, MA 02535
    61 Stonewall Rd, Chilmark, MA 02535
    61 Stonewall Rd, Chilmark, MA 02535
    /55

    $5,450,000

    • 5 Beds
    • 4 Baths
    • 3,513 Sq Ft

    61 Stonewall Rd, Chilmark, MA 02535

    Introducing a refined contemporary Chilmark beach house with water views and deeded access to Stonewall Beach on the Atlantic Ocean. The property is set within the storied Stonewall Road and Beach Association - where homes are held for generations and lifelong friendships take root - and offers a true sense of place and continuity. Built by South Mountain Company and thoughtfully renovated and

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    61 Stonewall Rd, Chilmark, MA 02535
  • 0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535
    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535
    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535
    /38

    $16,000,000

    • Land
    • 46 Acres
    • $347,826 per Acre

    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535

    Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach. Magical expansive views of meadows, pond and ocean. This estate-sized property abuts 140 acres of Sheriff’s Meadow conservation land, offering exceptional privacy. A simple 1041 square foot two bedroom seasonal home sits on one lot with two detached studios alongside. Close to nature, this home

    Abby Rabinovitz Tea Lane Associates

    0, 36, 38 Black Point Rd Unit 11, 9-02, 9-01, 058-, Chilmark, MA 02535
  • 0, 36, 38 Black Point Rd, Chilmark, MA 02535
    0, 36, 38 Black Point Rd, Chilmark, MA 02535
    0, 36, 38 Black Point Rd, Chilmark, MA 02535
    /39

    $16,000,000

    • 2 Beds
    • 2 Baths
    • 1,041 Sq Ft

    0, 36, 38 Black Point Rd, Chilmark, MA 02535

    Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach. Magical expansive views of meadows, pond and ocean. This estate-sized property abuts 140 acres of Sheriff's Meadow conservation land, offering exceptional privacy. A simple 1041 square foot two bedroom home sits on one lot with two detached studios alongside. Close to nature, this seasonal home

    Abby Rabinovitz Tea Lane Associates

    0, 36, 38 Black Point 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
    /46

    $6,250,000

    • 5 Beds
    • 2.5 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 an Island legacy family, this property is unique among Island estates for its combination of privacy yet convenience, seclusion yet expansive views. The property is only a

    Jill Napior Tea Lane Associates

    34 Edys Island Way, Chilmark, MA 02535
  • 44 Cencelle St, Chilmark, MA 02535
    44 Cencelle St, Chilmark, MA 02535
    44 Cencelle St, Chilmark, MA 02535
    /52

    $5,295,000

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

    44 Cencelle St, Chilmark, MA 02535

    This private 17-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
  • 26 Bijahs Way, Chilmark, MA 02535
    26 Bijahs Way, Chilmark, MA 02535
    26 Bijahs Way, Chilmark, MA 02535
    /26

    $2,395,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,510 Sq Ft

    26 Bijahs Way, Chilmark, MA 02535

    This Chilmark 3 bedroom, 2 bath home has been meticulously maintained inside and out. A major addition and reconstruction of the original house was completed in 1991 & included a 22 x 43 addition, The completely new second floor added over 1,500 square feet & the work included new heating, plumbing, electrical, central AC, septic & well! Many nice features include spacious living spaces, a modern

    Brenda Galligan Karen M. Overtoom R.E.

    26 Bijahs Way, Chilmark, MA 02535
  • 18 Spruce Gate Rd, Chilmark, MA 02535
    18 Spruce Gate Rd, Chilmark, MA 02535
    18 Spruce Gate Rd, Chilmark, MA 02535
    /38

    $12,500,000

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

    18 Spruce Gate Rd, Chilmark, MA 02535

    Welcome to an extraordinary coastal retreat within the exclusive gates of Squibnocket Farm, a 450+ acre private community offering access to over two miles of oceanfront, pond frontage, and conservation land. Designed and built by Soikkeli & Company, this elegant home blends timeless New England farmhouse architecture with refined modern luxury. The chef’s kitchen features soapstone countertops,

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    18 Spruce Gate Rd, Chilmark, MA 02535
  • 0 High Mark Rd Unit 66, Chilmark, MA 02535
    0 High Mark Rd Unit 66, Chilmark, MA 02535
    0 High Mark Rd Unit 66, Chilmark, MA 02535
    /9

    $1,900,000

    • Land
    • 15.05 Acres
    • $126,246 per Acre

    0 High Mark Rd Unit 66, Chilmark, MA 02535

    A rare opportunity to build a private retreat awaits at this 15 acre land parcel centrally located in Chilmark. Once part of the High Mark estate, the property features groves of mature trees planted more than 100 years ago, creating a wondrous, secluded and private setting rarely found anywhere on the island today.The parcel directly abuts the nearly 80 acres of conservation land at the

    Russell Maloney Russell Maloney Real Estate

    0 High Mark Rd Unit 66, 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

    $2,650,000

    • 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
  • 7 Black Point Rd, Chilmark, MA 02535
    7 Black Point Rd, Chilmark, MA 02535
    7 Black Point Rd, Chilmark, MA 02535
    /50

    $3,950,000

    $700K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,702 Sq Ft

    7 Black Point Rd, Chilmark, MA 02535

    Laid-back charm meets island character in this one-of-a-kind up-island beach house. Set on 5.5 acres of natural beauty, this four-bedroom, three-bath main house is full of updates, with bright, fun spaces and a relaxed summer-camp vibe. The creative layout on a single level connects sections of the house via breezy walkway, leading to a bedroom wing including a separate family room, off the

    Meg Bodnar Tea Lane Associates

    7 Black Point 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

    $2,250,000

    $250K PRICE DROP
    • 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. 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 full furnished with exception of some art and a few

    Patty Kendall Kendall & Kendall

    18 Allen Farm Rd, Chilmark, MA 02535
  • 345 North Rd, Chilmark, MA 02535
    345 North Rd, Chilmark, MA 02535
    345 North Rd, Chilmark, MA 02535
    /25

    $1,450,000

    $100K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 2,266 Sq Ft

    345 North Rd, Chilmark, MA 02535

    This versatile Chilmark property offers a rare combination of privacy, flexibility, and investment potential. The main residence features 4 bedrooms and 4 bathrooms, complemented by a detached 1-bedroom, 1-bath suite with an attached garage—ideal for guests, extended family, or rental income. Two separate parking areas provide ample space and convenience. Abutting over 200 acres of protected

    Jessica Campbell Flanders Real Estate

    345 North Rd, Chilmark, MA 02535
  • 146 Quenames Rd, Chilmark, MA 02535
    146 Quenames Rd, Chilmark, MA 02535
    146 Quenames Rd, Chilmark, MA 02535
    /78

    $35,000,000

    • 8 Beds
    • 8 Baths
    • 6,841 Sq Ft

    146 Quenames Rd, Chilmark, MA 02535

    Set on 60 acres along one of the most private and unspoiled stretches of Atlantic coastline in Chilmark, this exceptional estate offers a rare combination of scale, privacy, and enduring coastal beauty. With over 800 feet of direct ocean frontage, the property commands expansive views while maintaining a true sense of seclusion, an increasingly scarce offering on Martha’s Vineyard. A gated drive

    Grace Hagerty Grace Hagerty Real Estate Inc

    146 Quenames Rd, Chilmark, MA 02535
  • 27 Clambelly Rd, Chilmark, MA 02535
    27 Clambelly Rd, Chilmark, MA 02535
    27 Clambelly Rd, Chilmark, MA 02535
    /39

    $3,295,000

    $100K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 2,500 Sq Ft

    27 Clambelly Rd, Chilmark, MA 02535

    A place of serenity tucked in the woods of Chilmark. Beautifully designed & constructed home which was completely renovated in 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

    Julianna Flanders Flanders Real Estate

    27 Clambelly Rd, Chilmark, MA 02535
  • 205 South Rd, Chilmark, MA 02535
    205 South Rd, Chilmark, MA 02535
    205 South Rd, Chilmark, MA 02535
    /42

    $4,995,000

    $655K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 5,402 Sq Ft

    205 South Rd, Chilmark, MA 02535

    CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a

    Tina Miller Donnelly + Co.

    205 South Rd, Chilmark, MA 02535
  • 78 Hammett Rd, Chilmark, MA 02535
    78 Hammett Rd, Chilmark, MA 02535
    78 Hammett Rd, Chilmark, MA 02535
    /53

    $6,750,000

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

    78 Hammett Rd, Chilmark, MA 02535

    This magnificent Spring Point waterfront property, perched 50 ft above sea level and 425 ft back from the North Shore bluff, boasts beautiful views of the Vineyard Sound, Aquinnah coastline and the Elizabeth Islands -- and year dramatic year round sunsets. The property at the end of a well maintained wide dirt road 1 mile from North Rd is SECLUDED and TRANQUIL. It's a SHORT WALK TO THE BEACH,

    Robert Kenney Tea Lane Associates

    78 Hammett Rd, Chilmark, MA 02535
  • 16 South Rd, Chilmark, MA 02535
    16 South Rd, Chilmark, MA 02535
    16 South Rd, Chilmark, MA 02535
    /30

    $2,395,000

    $105K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,350 Sq Ft

    16 South Rd, Chilmark, MA 02535

    Rare Chilmark compound with beach access, barn, horse stalls, and fenced pasture on 1.6 acres. Set just over the West Tisbury line, this restored 1885 farmhouse offers a compelling blend of authentic Vineyard character, modern comfort, and access to Chilmark’s coveted south shore beaches, including Lucy Vincent and Squibnocket. The property unfolds as a small country compound with a distinctly

    Michele Casavant Vineyard Village Realty

    16 South Rd, Chilmark, MA 02535
  • 47 Quenames Rd, Chilmark, MA 02535
    47 Quenames Rd, Chilmark, MA 02535
    47 Quenames Rd, Chilmark, MA 02535
    /8

    $1,325,000

    $250K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 924 Sq Ft

    47 Quenames Rd, Chilmark, MA 02535

    On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural

    Dawn Bellante Sandpiper Realty, Inc.

    47 Quenames Rd, Chilmark, MA 02535
  • 45 Quenames Rd, Chilmark, MA 02535
    45 Quenames Rd, Chilmark, MA 02535
    45 Quenames Rd, Chilmark, MA 02535
    /12

    $1,300,000

    $275K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 896 Sq Ft

    45 Quenames Rd, Chilmark, MA 02535

    Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two spacious bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with

    Dawn Bellante Sandpiper Realty, Inc.

    45 Quenames Rd, Chilmark, MA 02535
  • 308 South Rd, Chilmark, MA 02535
    308 South Rd, Chilmark, MA 02535
    308 South Rd, Chilmark, MA 02535
    /36

    $7,350,000

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

    308 South Rd, Chilmark, MA 02535

    Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access.

    Rose Ryley Wallace & Co. Sotheby's International Realty

    308 South Rd, Chilmark, MA 02535

Showing Results 1 - 40, Page 1 of 2

Massachusetts Dukes County

Real Estate & Homes for Sale in Chilmark, Marthas Vineyard

Learn more about living in Chilmark

Chilmark Home Prices vs. Nearby Marthas Vineyard, MA Neighborhoods

Chilmark Chatham Village
Median Home Price
$4,995,000
$3,600,000
Median Sale Price
$4,017,500
+79% YoY
$2,510,000
+32% YoY
Median Single Family Price
$4,325,000
$4,050,000
Median Townhouse Price
--
$4,125,000
Median Condo Price
--
$552,500
Total Active Listings
59
41
Market Conditions
26 Months of Supply
Buyer's Market
7 Months of Supply
Buyer's Market

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 is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Chilmark has 1 park for recreational activities. It is sparse in population with 1.0 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% of residents renting and 80% 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.
Is Chilmark, MA a safe neighborhood?
Chilmark, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Chilmark?
The median home price in Chilmark is $4,995,000. If you put a 20% down payment of $999,000 and had a 30-year fixed mortgage with an interest rate of 6.66%, your estimated principal and interest payment would be $25,680 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $1M a year to afford the median home price in Chilmark. Learn how much home you can afford with our Home Affordability Calculator. 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, Vineyard Haven and Oak Bluffs.
Are home prices dropping in Chilmark?
Yes, home prices in Chilmark are down 35% in the last 12 months.
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