16

Chilmark, MA Homes for Sale under $2,000,000

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

    Agent Photo

    Barbara O'Hara

    NorthStar Real Estate LLC

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

    Agent Photo

    Barbara O'Hara

    NorthStar Real Estate, LLC

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

    Agent Photo

    Barbara O'Hara

    North Star Real Estate, LLC

    43 N Slope Ln, 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
  • 174 Middle Rd, Chilmark, MA 02535
    174 Middle Rd, Chilmark, MA 02535
    174 Middle Rd, Chilmark, MA 02535
    /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
  • 63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    /66

    $1,899,000

    $101K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,075 Sq Ft

    63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

    Set within the coveted Vineyard Meadow Farms community, this West Tisbury property presents a rare opportunity to own a thoughtfully configured compound in one of the island's most peaceful and sought-after settings. Privately sited on a generous parcel, the property is surrounded by natural beauty and offers a sense of calm that defines up-island living.The three-bedroom main residence is

    Valene Pires The Agency

    63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
  • 26 Flint Hill Rd, West Tisbury, MA 02575
    26 Flint Hill Rd, West Tisbury, MA 02575
    26 Flint Hill Rd, West Tisbury, MA 02575
    /13

    $1,575,000

    $70K PRICE DROP
    • Land
    • 3.32 Acres
    • $474,398 per Acre

    26 Flint Hill Rd, West Tisbury, MA 02575

    Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides— a setting no

    Dawn Bellante Sandpiper Realty, Inc.

    26 Flint Hill Rd, West Tisbury, MA 02575
  • 78 Vineyard Meadows Farm Rd, Vineyard Haven, MA 02568
    78 Vineyard Meadows Farm Rd, Vineyard Haven, MA 02568
    78 Vineyard Meadows Farm Rd, Vineyard Haven, MA 02568
    /36

    $1,850,000

    • 4 Beds
    • 2.5 Baths
    • 2,811 Sq Ft

    78 Vineyard Meadows Farm Rd, Vineyard Haven, MA 02568

    Situated down a long driveway, this distinctive West Tisbury property offers a rare combination of privacy, natural beauty, thoughtful design, and exceptional versatility. Designed with passive solar principles, the home takes full advantage of its orientation and abundant natural light. Exposed wood details throughout add warmth and character, complementing the home’s inviting, organic feel,

    Jarrett Hurwitz Keller Williams Realty

    78 Vineyard Meadows Farm Rd, Vineyard Haven, MA 02568
  • 0 State Rd Unit 29.3, Vineyard Haven, MA 02568
    0 State Rd Unit 29.3, Vineyard Haven, MA 02568
    0 State Rd Unit 29.3, Vineyard Haven, MA 02568
    /7

    $2,000,000

    • Land
    • 21,801 Sq Ft
    • $3,996,004 per Acre

    0 State Rd Unit 29.3, Vineyard Haven, MA 02568

    1/2 acre of commercial land in the State Road B-2 district. Possibilities are endless for the right business.Also available, next door, is a commercial building that currently has 10 rental units. $6,000,000.

    Peter Cronig Cronigs Real Estate

    0 State Rd Unit 29.3, Vineyard Haven, MA 02568
  • 60A Davis Look Rd Unit 46, West Tisbury, MA 02575
    60A Davis Look Rd Unit 46, West Tisbury, MA 02575
    60A Davis Look Rd Unit 46, West Tisbury, MA 02575
    /9

    $1,600,000

    • Land
    • 5.15 Acres
    • $310,680 per Acre

    60A Davis Look Rd Unit 46, West Tisbury, MA 02575

    Over five acres of privacy in one of the Island's most sought-after settings. This 5.15-acre parcel offers a rare opportunity to build a primary residence and accessory structure on old farmland surrounded by large, mature trees. Idyllic stonewalls run along some of the property lines.Large parcel size and building envelope ensures that the character of the neighborhood endures. Adjacent Land

    Julianna Flanders Flanders Real Estate

    60A Davis Look Rd Unit 46, West Tisbury, MA 02575
  • 174 Middle Rd, Chilmark, MA 02535
    174 Middle Rd, Chilmark, MA 02535
    174 Middle Rd, Chilmark, MA 02535
    /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
  • 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
  • 188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    /50

    $1,760,000

    $40K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,158 Sq Ft

    188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

    House & Guesthouse near Long Point Beach! The Island's coveted south shore is just minutes from this charming West Tisbury compound, where the connection to nature is seamless. The main house sits high atop the trees and overlooks a park-like, fenced-in backyard, perfect for kids and dogs. The yard also encompasses a sweet vegetable garden and storage shed. Inside, find an open floor plan with

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

    188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
  • 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
  • 150 Field View Ln, Vineyard Haven, MA 02568
    150 Field View Ln, Vineyard Haven, MA 02568
    150 Field View Ln, Vineyard Haven, MA 02568
    /20

    $1,600,000

    • 4 Beds
    • 2.5 Baths
    • 2,334 Sq Ft

    150 Field View Ln, Vineyard Haven, MA 02568

    A pastoral country road leads to this enchanting wood-shingled Cape-style home, offering three bedrooms and a welcoming blend of comfort and charm. The open-concept kitchen flows into a sunken living and dining area, creating an inviting space for everyday living and entertaining. A desirable first-floor bedroom and convenient first-floor laundry add to the home's thoughtful design. Upstairs you

    Sheila Morse Island Real Estate

    150 Field View Ln, Vineyard Haven, MA 02568
  • 26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575
    26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575
    26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575
    /13

    $1,575,000

    $70K PRICE DROP
    • Land
    • 3.32 Acres
    • $474,398 per Acre

    26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575

    Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides - a setting unlike

    Dawn Bellante-Holand Sandpiper Realty

    26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575
Massachusetts Dukes County

Real Estate & Homes in Chilmark, MA under $2,000,000

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