1,741

Chilmark Homes

Section Image Section Image
  • 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
  • 2 Strikers Way Ch211, Chilmark, MA 02535
    2 Strikers Way Ch211, Chilmark, MA 02535
    2 Strikers Way Ch211, Chilmark, MA 02535
    /33

    $22,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    2 Strikers Way Ch211, Chilmark, MA 02535

    SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable drip coffee maker with glass carafe. There is a coffee grinder provided in the

    Karen Overtoom Karen M. Overtoom R.E.

    2 Strikers Way Ch211, 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

    $105,000

    Sold Sep 05, 2025

    00 Eliot Ave Unit 17, Chilmark, MA 02535

    • Land
    • 30,492 Sq Ft
    • $150,000 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 29 Days On Market

    Last Listing Agent Julianna Flanders Flanders Real Estate

    00 Eliot Ave Unit 17, Chilmark, MA 02535
    • 260 South Rd, Chilmark, MA 02535
      260 South Rd, Chilmark, MA 02535
      260 South Rd, Chilmark, MA 02535
      /79

      Not Listed For Sale

      260 South Rd, Chilmark, MA 02535

      • 6 Beds
      • 2.5 Baths
      • 2,604 Sq Ft
      • Built 1688
      260 South Rd, Chilmark, MA 02535

      Last Sold Summary

      • 109 Days On Market

  • 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

    43 N Slope Ln, Chilmark, MA 02535
  • 15 Loon Lane Ch203, Chilmark, MA 02535
    15 Loon Lane Ch203, Chilmark, MA 02535
    15 Loon Lane Ch203, Chilmark, MA 02535
    /29

    $34,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,300 Sq Ft
    • House for Rent

    15 Loon Lane Ch203, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Modern 4 bedroom home completed in 2019, in Menemsha. Located on a quiet road with waterviews from the upstairs bedrooms also offers views of the famous Menemsha sunsets from the deck. Sustainably harvested flooring features silky smooth and buttery hard wood floors from

    Karen Overtoom Karen M. Overtoom R.E.

    15 Loon Lane Ch203, Chilmark, MA 02535
  • 00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
    /7

    $650,000

    Sold Aug 14, 2025

    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535

    • Land
    • 8,712 Sq Ft
    • $3,250,000 per Acre

    Last Sold Summary

    • 7 Days On Market

    Last Listing Agent Deb Hancock Hancock Real Estate

    00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
    • 2 Squibnocket Rd, Chilmark, MA 02535
      2 Squibnocket Rd, Chilmark, MA 02535
      2 Squibnocket Rd, Chilmark, MA 02535
      /52

      Not Listed For Sale

      2 Squibnocket Rd, Chilmark, MA 02535

      • 6 Beds
      • 5.5 Baths
      • 5,808 Sq Ft
      • Built 2008
      2 Squibnocket Rd, Chilmark, MA 02535

      Last Sold Summary

      • 297 Days On Market

  • 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
    • 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
  • 31 S Ridge Rd Ch218, Chilmark, MA 02535
    31 S Ridge Rd Ch218, Chilmark, MA 02535
    31 S Ridge Rd Ch218, Chilmark, MA 02535
    /20

    $16,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,638 Sq Ft
    • House for Rent

    31 S Ridge Rd Ch218, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and

    Karen Overtoom Karen M. Overtoom R.E.

    31 S Ridge Rd Ch218, Chilmark, MA 02535
  • 25 Osprey Ln, Chilmark, MA 02535
    25 Osprey Ln, Chilmark, MA 02535
    25 Osprey Ln, Chilmark, MA 02535
    /9

    $7,289,000

    Sold Oct 15, 2025

    25 Osprey Ln, Chilmark, MA 02535

    • 4 Beds
    • 5 Baths
    • 3,777 Sq Ft
    • Built 1988

    Last Sold Summary

    • 9% Below List Price
    • $1,930/SF
    • 77 Days On Market

    Last Listing Agent Deb Hancock Hancock Real Estate

    25 Osprey Ln, Chilmark, MA 02535
    • 82 South Rd, Chilmark, MA 02535
      82 South Rd, Chilmark, MA 02535
      82 South Rd, Chilmark, MA 02535
      /26

      Est $2,011,420

      Not Listed For Sale

      82 South Rd, Chilmark, MA 02535

      • 3 Beds
      • 2 Baths
      • 1,862 Sq Ft
      • Built 1960
      82 South Rd, Chilmark, MA 02535

      Last Sold Summary

      • 10 Days On Market

  • 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
  • 27 Beach Plum Ln, Chilmark, MA 02535
    27 Beach Plum Ln, Chilmark, MA 02535
    27 Beach Plum Ln, Chilmark, MA 02535
    /21

    $6,800 Per Month

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

    27 Beach Plum Ln, Chilmark, MA 02535

    Some August and September Availability 2026 weekly rental rate negotiable, cost $400-$975 per night depending on season and month 3 night min stay The "Grapevine" is located on a private road , It was completely rebuilt .The house has 3 generous size bedrooms all with private baths, 2 of the bedrooms are located on the second floor, 1 bedroom is located on the first floor as well as the Open

    Bryan Hummel Commonwealth Realty Group

    27 Beach Plum Ln, Chilmark, MA 02535
  • 0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    /22

    $435,000

    Sold Aug 26, 2025

    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535

    • Land
    • 4,356 Sq Ft
    • $4,350,000 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 18 Days On Market

    Last Listing Agent Emma Bryant Studio Realty

    0 Quansoo Beach Lot Unit 53 43599, Chilmark, MA 02535
    • 51 Blueberry Ridge Ln, Chilmark, MA 02535
      51 Blueberry Ridge Ln, Chilmark, MA 02535
      51 Blueberry Ridge Ln, Chilmark, MA 02535
      /23

      Not Listed For Sale

      51 Blueberry Ridge Ln, Chilmark, MA 02535

      • 6 Beds
      • 3.5 Baths
      • 2,229 Sq Ft
      • Built 1989
      51 Blueberry Ridge Ln, Chilmark, MA 02535

      Last Sold Summary

      • 11 Days On Market

  • 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
  • 2 Paddock Cir, Chilmark, MA 02535
    2 Paddock Cir, Chilmark, MA 02535
    2 Paddock Cir, Chilmark, MA 02535
    /8

    $7,900 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,107 Sq Ft
    • House for Rent

    2 Paddock Cir, Chilmark, MA 02535

    Karen Overtoom Karen M. Overtoom R.E.

    2 Paddock Cir, Chilmark, MA 02535
  • 6 Tabor Hills, Chilmark, MA 02535
    6 Tabor Hills, Chilmark, MA 02535
    6 Tabor Hills, Chilmark, MA 02535
    /45

    $2,100,000

    Sold Nov 25, 2025

    6 Tabor Hills, Chilmark, MA 02535

    • 4 Beds
    • 3 Baths
    • 2,544 Sq Ft
    • Built 1993

    Last Sold Summary

    • 11% Below List Price
    • $825/SF
    • 48 Days On Market

    Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

    6 Tabor Hills, Chilmark, MA 02535
    • 391 Middle Rd, Chilmark, MA 02535
      391 Middle Rd, Chilmark, MA 02535
      391 Middle Rd, Chilmark, MA 02535
      /34

      Not Listed For Sale

      391 Middle Rd, Chilmark, MA 02535

      • 6 Beds
      • 4.5 Baths
      • 3,859 Sq Ft
      • Built 1941
      391 Middle Rd, Chilmark, MA 02535

      Last Sold Summary

      • 38 Days On Market

  • 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

    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
  • 384 Middle Rd Ch222, Chilmark, MA 02535
    384 Middle Rd Ch222, Chilmark, MA 02535
    384 Middle Rd Ch222, Chilmark, MA 02535
    /31

    $40,000 Per Month

    • 6 Beds
    • 6 Baths
    • 3,960 Sq Ft
    • House for Rent

    384 Middle Rd Ch222, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four

    Karen Overtoom Karen M. Overtoom R.E.

    384 Middle Rd Ch222, Chilmark, MA 02535
  • 99 Cygnet Way Unit 103, Chilmark, MA 02535
    99 Cygnet Way Unit 103, Chilmark, MA 02535
    99 Cygnet Way Unit 103, Chilmark, MA 02535
    /7

    $375,000

    Sold Apr 06, 2026

    99 Cygnet Way Unit 103, Chilmark, MA 02535

    • Land
    • 8,712 Sq Ft
    • $1,875,000 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 120 Days On Market

    Last Listing Agent Russell Maloney Russell Maloney Real Estate

    99 Cygnet Way Unit 103, Chilmark, MA 02535
    • 1 Carroll Ln, Chilmark, MA 02535
      1 Carroll Ln, Chilmark, MA 02535
      /2

      Est $762,619

      Not Listed For Sale

      1 Carroll Ln, Chilmark, MA 02535

      • 2 Beds
      • 1 Bath
      • 708 Sq Ft
      • Built 1920
      1 Carroll Ln, Chilmark, MA 02535

  • 64 Squibnocket Farm Rd, Chilmark, MA 02535
    64 Squibnocket Farm Rd, Chilmark, MA 02535
    64 Squibnocket Farm Rd, Chilmark, MA 02535
    /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
  • 6 Trails End Ch241, Chilmark, MA 02535
    6 Trails End Ch241, Chilmark, MA 02535
    6 Trails End Ch241, Chilmark, MA 02535
    /26

    $50,700 Per Month

    • 4 Beds
    • 3 Baths
    • 2,346 Sq Ft
    • House for Rent

    6 Trails End Ch241, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,675. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set atop a hill you will find this wonderful 4 bedroom home with distant views and a wonderful lap pool. Enjoy your days on the large deck or take a swim in the pool. This great vacation home is tastefully decorated and is located on one level with plenty of space for

    Karen Overtoom Karen M. Overtoom R.E.

    6 Trails End Ch241, Chilmark, MA 02535
  • 00 Quenames Rd Unit 30-02, Chilmark, MA 02535
    00 Quenames Rd Unit 30-02, Chilmark, MA 02535
    /2

    $900,000

    Sold Sep 17, 2025

    00 Quenames Rd Unit 30-02, Chilmark, MA 02535

    • Land
    • 3.05 Acres
    • $295,082 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 83 Days On Market

    Last Listing Agent Candy DaRosa Feiner Real Estate

    00 Quenames Rd Unit 30-02, Chilmark, MA 02535
    • 7 Flanders Ln, Chilmark, MA 02535
      7 Flanders Ln, Chilmark, MA 02535
      7 Flanders Ln, Chilmark, MA 02535
      /29

      Est $1,788,009

      Not Listed For Sale

      7 Flanders Ln, Chilmark, MA 02535

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1954
      7 Flanders Ln, Chilmark, MA 02535

      Last Sold Summary

      • 4 Days On Market

  • 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
  • 19 Lake Rd, Chilmark, MA 02535
    19 Lake Rd, Chilmark, MA 02535
    19 Lake Rd, Chilmark, MA 02535
    /32

    $42,000 Per Month

    • 5 Beds
    • 2.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    19 Lake Rd, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all with views, two livingrooms,

    Karen Overtoom Karen M. Overtoom R.E.

    19 Lake Rd, Chilmark, MA 02535
  • 0 North Rd Unit 40 43533, Aquinnah, MA 02535
    0 North Rd Unit 40 43533, Aquinnah, MA 02535
    /2

    $60,000

    Sold Jul 01, 2025

    0 North Rd Unit 40 43533, Aquinnah, MA 02535

    • Land
    • 0 Sq Ft

    Last Sold Summary

    Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

    0 North Rd Unit 40 43533, Aquinnah, MA 02535
    • 12 Harbor Hill Rd, Chilmark, MA 02535
      12 Harbor Hill Rd, Chilmark, MA 02535
      12 Harbor Hill Rd, Chilmark, MA 02535
      /13

      Est $1,591,801

      Not Listed For Sale

      12 Harbor Hill Rd, Chilmark, MA 02535

      • 1 Bed
      • 1 Bath
      • 640 Sq Ft
      • Built 1955
      12 Harbor Hill Rd, Chilmark, MA 02535

      Last Sold Summary

      • 0 Days On Market

  • 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
  • 36 Henry Hough Lane Ch206, Chilmark, MA 02535
    36 Henry Hough Lane Ch206, Chilmark, MA 02535
    36 Henry Hough Lane Ch206, Chilmark, MA 02535
    /35

    $22,000 Per Month

    • 4 Beds
    • 2 Baths
    • 2,290 Sq Ft
    • House for Rent

    36 Henry Hough Lane Ch206, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four

    Karen Overtoom Karen M. Overtoom R.E.

    36 Henry Hough Lane Ch206, Chilmark, MA 02535
  • 49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    /9

    $1,500,000

    Sold Oct 20, 2025

    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535

    • Land
    • 3.9 Acres
    • $384,615 per Acre

    Last Sold Summary

    Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

    49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
    • 15 Red Valley Rd, Chilmark, MA 02535
      15 Red Valley Rd, Chilmark, MA 02535
      15 Red Valley Rd, Chilmark, MA 02535
      /34

      Est $5,582,783

      Not Listed For Sale

      15 Red Valley Rd, Chilmark, MA 02535

      • 5 Beds
      • 4 Baths
      • 2,373 Sq Ft
      • Built 1954
      15 Red Valley Rd, Chilmark, MA 02535

      Last Sold Summary

      • 31 Days On Market

  • 9 Ridge Hill Rd, Chilmark, MA 02535
    9 Ridge Hill Rd, Chilmark, MA 02535
    9 Ridge Hill Rd, Chilmark, MA 02535
    /48

    $5,850,000

    • 6 Beds
    • 6.5 Baths
    • 3,608 Sq Ft

    9 Ridge Hill Rd, Chilmark, MA 02535

    Set on three beautifully landscaped acres, this exceptional six-bedroom property offers a seamless blend of modern farmhouse design and timeless Vineyard appeal. The estate features a five-bedroom, five and a half bathroom main residence, along with a one-bedroom guest suite above a two-car barn and 16' x 40' swimming pool. This thoughtfully designed post and beam main home was featured in

    Alexis Holden Tea Lane Associates

    9 Ridge Hill Rd, Chilmark, MA 02535
  • 141 N Rd Ch202, Chilmark, MA 02535
    141 N Rd Ch202, Chilmark, MA 02535
    141 N Rd Ch202, Chilmark, MA 02535
    /9

    $10,800 Per Month

    • 4 Beds
    • 2 Baths
    • 702 Sq Ft
    • House for Rent

    141 N Rd Ch202, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a

    Karen Overtoom Karen M. Overtoom R.E.

    141 N Rd Ch202, Chilmark, MA 02535
  • 10 N Abels Hill Rd, Chilmark, MA 02535
    10 N Abels Hill Rd, Chilmark, MA 02535
    10 N Abels Hill Rd, Chilmark, MA 02535
    /22

    $1,607,000

    Sold Jul 10, 2025

    10 N Abels Hill Rd, Chilmark, MA 02535

    • 4 Beds
    • 3 Baths
    • 2,850 Sq Ft
    • Built 1978

    Last Sold Summary

    • 39% Below List Price
    • $564/SF
    • 354 Days On Market

    Current Estimated Value $2,176,121

    Last Listing Agent Elissa Lash Tea Lane Associates

    10 N Abels Hill Rd, Chilmark, MA 02535
    • 10 Rumpus Ridge Rd, Chilmark, MA 02535
      10 Rumpus Ridge Rd, Chilmark, MA 02535
      10 Rumpus Ridge Rd, Chilmark, MA 02535
      /32

      Est $1,626,890

      Not Listed For Sale

      10 Rumpus Ridge Rd, Chilmark, MA 02535

      • 4 Beds
      • 2 Baths
      • 1,701 Sq Ft
      • Built 1960
      10 Rumpus Ridge Rd, Chilmark, MA 02535

      Last Sold Summary

      • 28 Days On Market

Showing Results 1 - 40, Page 1 of 18

Massachusetts Dukes County Marthas Vineyard Chilmark

Real Estate & Homes

Learn more about living in Chilmark

Home Prices in Chilmark, MA

The median home sale price in Chilmark, Marthas Vineyard is $4,325,000, up 101% year-over-year. Homes in Chilmark sell in 103 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$4,325,000
Median Single Family Sale Price
$4,500,000
Median 2 Bedroom Sale Price
$1,522,500
Median 1 Bedroom Sale Price
$2,250,000
Average Price Per Sq Ft
$2,157
Number of Homes for Sale
40
Last 12 months Home Sales
25
Months of Supply
19.20
Median List Price
$5,097,500
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
101%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group