Chilmark Homes for Sale

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  /31

  $1,649,900

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

  43 N Slope Ln, Chilmark, MA 02535

  Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring

  

  Barbara O'Hara

  NorthStar Real Estate, LLC

  43 N Slope Ln, Chilmark, MA 02535
• Explore Chilmark

• 

  

  

  /27

  $1,649,000

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

  43 N Slope Ln, Chilmark, MA 02535

  Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha's Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring

  

  Barbara O'Hara

  North Star Real Estate, LLC

  43 N Slope Ln, Chilmark, MA 02535
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  /27

  $1,699,999

  $100K PRICE DROP

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

  43 N Slope Ln, Chilmark, MA 02535

  Set on a private 3.5-acre wooded parcel surrounded by conservation land, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees and protected open space, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully

  

  Barbara O'Hara

  NorthStar Real Estate LLC

  43 N Slope Ln, Chilmark, MA 02535
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  /32

  $2,150,000

  $100K PRICE DROP

  • 4 Beds
  • 2.5 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
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  /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
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  /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
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  /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
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  /40

  $1,695,000

  $100K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,702 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
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  /43

  $14,500,000

  $2M PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,705 Sq Ft

  64 Squibnocket Farm Rd, Chilmark, MA 02535

  Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within

  Thomas Wallace Wallace & Co. Sotheby's

  64 Squibnocket Farm Rd, Chilmark, MA 02535
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  /8

  $1,225,000

  $350K 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
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  /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
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  /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
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  /52

  $4,975,000

  $320K PRICE DROP

  • 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
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  /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
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  /39

  $2,400,000

  • 7 Beds
  • 4 Baths
  • 2,232 Sq Ft

  220 North Rd, Chilmark, MA 02535

  Welcome to 220 North Road, Chilmark, an idyllic, up-island retreat featuring a 4-BR, post-and-beam, main house and 3-BR guest cottage. Set on three private acres, this verdant oasis is surrounded by preserves, walking trails and even an ancient way that leads directly from the property to Middle Line Woods Preserve, and then all the way to Tea Lane Farm. A two-thirds of an acre conservation

  David Lott Vineyard Open House Real Estate

  220 North Rd, Chilmark, MA 02535
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  /15

  $6,250,000

  • Land
  • 21 Acres
  • $297,619 per Acre

  44 Cencelle St Unit 57, 58, 56.1, Chilmark, MA 02535

  This exceptional 21-acre estate offers sweeping ocean views, remarkable privacy, and a rare opportunity to create a truly special island retreat. Tucked among the rolling hills, open farmlands, and woodlands of Chilmark, the property combines a profound sense of seclusion with extraordinary natural beauty and the flexibility to shape the land to suit a variety of visions—including the potential

  Meg Bodnar Tea Lane Associates

  44 Cencelle St Unit 57, 58, 56.1, Chilmark, MA 02535
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  /29

  $10,950,000

  $2M PRICE DROP

  • 4 Beds
  • 3.5 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
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  /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
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  /25

  $1,375,000

  $175K 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

  Jessica Campbell Flanders Real Estate

  345 North Rd, Chilmark, MA 02535
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  /42

  $4,995,000

  $405K PRICE DROP

  • 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
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  /14

  $2,725,000

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

  34 Ebens Ln Unit 20 and 22, 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

  34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
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  /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
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  /56

  $16,250,000

  • 6 Beds
  • 8 Baths
  • 8,648 Sq Ft

  25 Brickyard Rd, Chilmark, MA 02535

  Perched on an elevated 10.69-acre site off picturesque North Road in Chilmark, this exceptional private compound pairs natural beauty with architectural distinction. Designed by renowned architect Patrick Ahearn and built by Rosbeck Builders, the 7,691-square-foot residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, with spectacular sunsets.

  Peyton Wallace Studio Realty LLC

  25 Brickyard Rd, Chilmark, MA 02535
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  /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
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  /79

  $5,300,000

  • 5 Beds
  • 3.5 Baths
  • 2,210 Sq Ft

  8 Wauwompauque Trail, Chilmark, MA 02535

  Abels Hill opportunity! Coastal living at its finest in this contemporary Abels Hill retreat, where south-facing ocean views and exceptional amenities define the lifestyle. Situated within one of Chilmark's most sought-after communities, the property enjoys exclusive access to the Atlantic Ocean, Chilmark Pond, and private association tennis courts.The property features a beautifully designed

  Jill Napior Tea Lane Associates

  8 Wauwompauque Trail, 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
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  /78

  $32,500,000

  $3M PRICE DROP

  • 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

  Grace Hagerty Grace Hagerty Real Estate Inc

  146 Quenames Rd, Chilmark, MA 02535
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  /34

  $2,095,000

  $100K PRICE DROP

  • 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
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  /31

  $2,250,000

  $200K PRICE DROP

  • 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

  25 Fulling Mill Rd, Chilmark, MA 02535
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  /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
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  /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
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  /40

  $1,695,000

  $204K PRICE DROP

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

  174 Middle Rd, Chilmark, MA 02535

  Nestled in Chilmark, this four-bedroom home blends classic Vineyard charm with modern comfort. The sunlit eat-in kitchen features dual ovens, granite countertops, and custom cherry built-ins, flowing seamlessly to a living room with a Vermont Castings wood stove and access to a covered porch and spacious deck. The first-floor primary suite offers two en-suite baths and two walk-in closets, while

  Sheila Morse Island Real Estate

  174 Middle Rd, Chilmark, MA 02535
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  /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
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  /12

  $1,245,000

  $80K PRICE DROP

  • Land
  • 4.4 Acres
  • $282,955 per Acre

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

  FRESHLY BRUSH CUT and EASY to WALK! This quiet and lovely four-and-a-half-acre lot in Chilmark is READY-TO-BUILD. The land has 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, NHESP has been completed and there are no

  Elissa Lash Tea Lane Associates

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

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /7

  $2,500,000

  • Land
  • 1.4 Acres
  • $1,785,714 per Acre

  2 Other House Rd Unit 173, Chilmark, MA 02535

  Rare opportunity to build on Chilmark's south shore. This 1.4 acre parcel should allow for new construction of 3,100 square feet and 24 feet in height, by right, with building department approval. Views to the Atlantic Ocean and Chilmark Pond can be seen from the second floor. This parcel comes with a dock on the pond which provides access to a beautiful barrier beach on the Atlantic. Well in

  Russell Maloney Russell Maloney Real Estate

  2 Other House Rd Unit 173, Chilmark, MA 02535

Showing Results 1 - 40, Page 1 of 2

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

Chilmark, Marthas Vineyard, MA Home Prices vs. Nearby Neighborhoods

	Chilmark	Aquinnah	Chatham Village
Median Home Price	$4,222,500	$3,350,000	$3,950,000
Median Sale Price	$4,337,500 +58% YoY	$2,385,000 -25% YoY	$2,520,000 +7% YoY
Avg. Price per Square Foot	$1,939	$1,191	$1,151
Median Single Family Price	$3,705,000	$3,050,000	$3,595,000
Total Active Listings	51 listings	10 listings	35 listings
Market Conditions	20 Months of Supply Buyer's Market	11 Months of Supply Buyer's Market	4 Months of Supply Seller'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 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.

How much do you need to make to afford a house in Chilmark?

The median home price in Chilmark is $4,222,500. If you put a 20% down payment of $844,500 and had a 30-year fixed mortgage with an interest rate of 6.76%, your estimated principal and interest payment would be $21,930 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $940K 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:

• Martha's Vineyard Regional High School has a B+ Niche grade, a student teacher ratio of 9:1 and an average review score of 3.6.
• Chilmark Elementary School has a B+ Niche grade and a student teacher ratio of 7:1.
• West Tisbury Elementary School has a B Niche grade and a student teacher ratio of 7:1.

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 47% in the last 12 months.