1,741

Chilmark Homes

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  • 16 Shotnaigher Ln, Chilmark, MA 02535
    16 Shotnaigher Ln, Chilmark, MA 02535
    16 Shotnaigher Ln, Chilmark, MA 02535
    /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
  • 33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    /8

    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,393 Sq Ft
    • House for Rent

    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535

    THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

    Karen Overtoom Karen M. Overtoom R.E.

    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
  • 31 North Rd, Chilmark, MA 02535
    31 North Rd, Chilmark, MA 02535
    31 North Rd, Chilmark, MA 02535
    /22

    $1,000,000

    Sold Jun 03, 2026

    31 North Rd, Chilmark, MA 02535

    • 2 Beds
    • 1 Bath
    • 576 Sq Ft
    • Built 1970

    Last Sold Summary

    • 17% Below List Price
    • $1,736/SF
    • 9 Days On Market

    Current Estimated Value $1,101,183

    Last Listing Agent Russell Maloney Russell Maloney Real Estate

    31 North Rd, Chilmark, MA 02535
    • 1 Pond Mark, Chilmark, MA 02535
      1 Pond Mark, Chilmark, MA 02535
      /2

      Est $4,016,729

      Not Listed For Sale

      1 Pond Mark, Chilmark, MA 02535

      • 3 Beds
      • 3 Baths
      • 1,316 Sq Ft
      • Built 1955
      1 Pond Mark, 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
  • 5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    /8

    $16,000 Per Month

    • 7 Beds
    • 3.5 Baths
    • 4,000 Sq Ft
    • House for Rent

    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite.

    Karen Overtoom Karen M. Overtoom R.E.

    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
  • 94 Menemsha Inn Rd, Chilmark, MA 02535
    94 Menemsha Inn Rd, Chilmark, MA 02535
    94 Menemsha Inn Rd, Chilmark, MA 02535
    /44

    $8,178,500

    Sold Oct 27, 2025

    94 Menemsha Inn Rd, Chilmark, MA 02535

    • 6 Beds
    • 4.5 Baths
    • 4,104 Sq Ft
    • Built 2001

    Last Sold Summary

    • 3% Below List Price
    • $1,993/SF
    • 38 Days On Market

    Last Listing Agent Julianna Flanders Flanders Real Estate

    94 Menemsha Inn Rd, Chilmark, MA 02535
    • 5 Ocean View Farm Rd, Chilmark, MA 02535
      5 Ocean View Farm Rd, Chilmark, MA 02535
      5 Ocean View Farm Rd, Chilmark, MA 02535
      /12

      Est $2,452,473

      Not Listed For Sale

      5 Ocean View Farm Rd, Chilmark, MA 02535

      • 3 Beds
      • 1.5 Baths
      • 1,342 Sq Ft
      • Built 1971
      5 Ocean View Farm Rd, Chilmark, MA 02535

      Last Sold Summary

      • 3 Days On Market

  • 174 Middle Rd, Chilmark, MA 02535
    174 Middle Rd, Chilmark, MA 02535
    174 Middle Rd, Chilmark, MA 02535
    /40

    $1,795,000

    $104K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,061 Sq Ft

    174 Middle Rd, Chilmark, MA 02535

    Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

    Sheila Morse Island Real Estate

    174 Middle Rd, Chilmark, MA 02535
  • 224 N Rd Ch248, Chilmark, MA 02535
    224 N Rd Ch248, Chilmark, MA 02535
    224 N Rd Ch248, Chilmark, MA 02535
    /3

    $13,200 Per Month

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • House for Rent

    224 N Rd Ch248, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room.

    Karen Overtoom Karen M. Overtoom R.E.

    224 N Rd Ch248, Chilmark, MA 02535
  • 51 Squibnocket Farm Rd, Chilmark, MA 02535
    51 Squibnocket Farm Rd, Chilmark, MA 02535
    51 Squibnocket Farm Rd, Chilmark, MA 02535
    /10

    $10,500,000

    Sold Mar 12, 2026

    51 Squibnocket Farm Rd, Chilmark, MA 02535

    • 4 Beds
    • 2.5 Baths
    • 3,200 Sq Ft
    • Built 1981

    Last Sold Summary

    • 9% Below List Price
    • $3,281/SF

    Current Estimated Value $7,346,949

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

    51 Squibnocket Farm Rd, Chilmark, MA 02535
    • 27 Ocean View Farm Rd, Chilmark, MA 02535
      27 Ocean View Farm Rd, Chilmark, MA 02535
      /2

      Est $2,771,760

      Not Listed For Sale

      27 Ocean View Farm Rd, Chilmark, MA 02535

      • 4 Beds
      • 3 Baths
      • 2,450 Sq Ft
      • Built 1964
      27 Ocean View Farm Rd, Chilmark, MA 02535

  • 345 North Rd, Chilmark, MA 02535
    345 North Rd, Chilmark, MA 02535
    345 North Rd, Chilmark, MA 02535
    /25

    $1,550,000

    • 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
  • 17 Round Pond Rd Ch240, Chilmark, MA 02535
    17 Round Pond Rd Ch240, Chilmark, MA 02535
    17 Round Pond Rd Ch240, Chilmark, MA 02535
    /39

    $110,000 Per Month

    • 5 Beds
    • 5 Baths
    • 4,000 Sq Ft
    • House for Rent

    17 Round Pond Rd Ch240, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. See web site for pricing!! Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches and high speed internet wifi.

    Karen Overtoom Karen M. Overtoom R.E.

    17 Round Pond Rd Ch240, Chilmark, MA 02535
  • 31 N Slope Ln, Chilmark, MA 02535
    31 N Slope Ln, Chilmark, MA 02535
    31 N Slope Ln, Chilmark, MA 02535
    /34

    $2,475,000

    Sold Sep 05, 2025

    31 N Slope Ln, Chilmark, MA 02535

    • 4 Beds
    • 3.5 Baths
    • 2,300 Sq Ft
    • Built 1983

    Last Sold Summary

    • 15% Below List Price
    • $1,076/SF
    • 117 Days On Market

    Current Estimated Value $2,732,346

    Last Listing Agent Bill Rossi Studio Realty

    31 N Slope Ln, Chilmark, MA 02535
    • 276 South Rd, Chilmark, MA 02535
      276 South Rd, Chilmark, MA 02535
      276 South Rd, Chilmark, MA 02535
      /69

      Est $2,495,590

      Not Listed For Sale

      276 South Rd, Chilmark, MA 02535

      • 4 Beds
      • 2 Baths
      • 2,034 Sq Ft
      • Built 1981
      276 South Rd, Chilmark, MA 02535

      Last Sold Summary

      • 122 Days On Market

  • 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
  • 11 Hammett Ln, Chilmark, MA 02535
    11 Hammett Ln, Chilmark, MA 02535
    11 Hammett Ln, Chilmark, MA 02535
    /20

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • House for Rent

    11 Hammett Ln, Chilmark, MA 02535

    ** WEEKLY SUMMER RATE** Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    11 Hammett Ln, Chilmark, MA 02535
  • 122 Old Farm Rd, Chilmark, MA 02535
    122 Old Farm Rd, Chilmark, MA 02535
    122 Old Farm Rd, Chilmark, MA 02535
    /36

    $3,700,000

    Sold May 28, 2026

    122 Old Farm Rd, Chilmark, MA 02535

    • 5 Beds
    • 4 Baths
    • 3,413 Sq Ft
    • Built 1790

    Last Sold Summary

    • 38% Below List Price
    • $1,084/SF
    • 261 Days On Market

    Current Estimated Value $1,664,000

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

    122 Old Farm Rd, Chilmark, MA 02535
    • 2 Rockrose Path, Chilmark, MA 02535
      2 Rockrose Path, Chilmark, MA 02535
      2 Rockrose Path, Chilmark, MA 02535
      /37

      Est $2,222,524

      Not Listed For Sale

      2 Rockrose Path, Chilmark, MA 02535

      • 4 Beds
      • 3 Baths
      • 1,900 Sq Ft
      • Built 1978
      2 Rockrose Path, Chilmark, MA 02535

      Last Sold Summary

      • 414 Days On Market

  • 34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
    34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
    /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
  • 56 Chilmark Rd, Chilmark, MA 02535
    56 Chilmark Rd, Chilmark, MA 02535
    56 Chilmark Rd, Chilmark, MA 02535
    /23

    $24,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,637 Sq Ft
    • House for Rent

    56 Chilmark Rd, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Relax and enjoy this majestic estate you will call home during your stay. This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation

    Karen Overtoom Karen M. Overtoom R.E.

    56 Chilmark Rd, Chilmark, MA 02535
  • 0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
    /21

    $435,000

    Sold Aug 26, 2025

    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535

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

    Last Sold Summary

    • 3% Below List Price
    • 20 Days On Market

    Last Listing Agent Emma Bryant Landmarks at TODAY Real Estate

    0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
    • 23 Black Point Rd, Chilmark, MA 02535
      23 Black Point Rd, Chilmark, MA 02535
      23 Black Point Rd, Chilmark, MA 02535
      /20

      Est $2,915,065

      Not Listed For Sale

      23 Black Point Rd, Chilmark, MA 02535

      • 2 Beds
      • 2 Baths
      • 1,164 Sq Ft
      • Built 2004
      23 Black Point Rd, Chilmark, MA 02535

      Last Sold Summary

      • 13 Days On Market

  • 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
  • 44 Flanders Ln, Chilmark, MA 02535
    44 Flanders Ln, Chilmark, MA 02535
    44 Flanders Ln, Chilmark, MA 02535
    /19

    $24,000 Per Month

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • House for Rent

    44 Flanders Ln, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

    Karen Overtoom Karen M. Overtoom R.E.

    44 Flanders Ln, Chilmark, MA 02535
  • 60 Meetinghouse Rd, Chilmark, MA 02535
    60 Meetinghouse Rd, Chilmark, MA 02535
    60 Meetinghouse Rd, Chilmark, MA 02535
    /49

    $6,100,000

    Sold Mar 24, 2026

    60 Meetinghouse Rd, Chilmark, MA 02535

    • 6 Beds
    • 8 Baths
    • 5,660 Sq Ft
    • Built 2021

    Last Sold Summary

    • 6% Below List Price
    • $1,078/SF
    • 111 Days On Market

    Last Listing Agent Jim Feiner Feiner Real Estate

    60 Meetinghouse Rd, Chilmark, MA 02535
    • 3 Pepperbush Ln, Chilmark, MA 02535
      3 Pepperbush Ln, Chilmark, MA 02535
      3 Pepperbush Ln, Chilmark, MA 02535
      /21

      Not Listed For Sale

      3 Pepperbush Ln, Chilmark, MA 02535

      • 4 Beds
      • 2 Baths
      • 2,686 Sq Ft
      • Built 1977
      3 Pepperbush Ln, Chilmark, MA 02535

      Last Sold Summary

      • 0 Days On Market

  • 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
  • 29 Cemetery Rd Ch216, Chilmark, MA 02535
    29 Cemetery Rd Ch216, Chilmark, MA 02535
    29 Cemetery Rd Ch216, Chilmark, MA 02535
    /32

    $36,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,600 Sq Ft
    • House for Rent

    29 Cemetery Rd Ch216, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half

    Karen Overtoom Karen M. Overtoom R.E.

    29 Cemetery Rd Ch216, Chilmark, MA 02535
  • 15 Old Farm Rd, Chilmark, MA 02535
    15 Old Farm Rd, Chilmark, MA 02535
    15 Old Farm Rd, Chilmark, MA 02535
    /42

    $3,710,000

    Sold Mar 12, 2026

    15 Old Farm Rd, Chilmark, MA 02535

    • 3 Beds
    • 6 Baths
    • 3,171 Sq Ft
    • Built 2002

    Last Sold Summary

    • 13% Below List Price
    • $1,170/SF
    • 136 Days On Market

    Current Estimated Value $3,907,832

    Last Listing Agent Tina Miller Donnelly + Co.

    15 Old Farm Rd, Chilmark, MA 02535
    • 300 North Rd, Chilmark, MA 02535
      300 North Rd, Chilmark, MA 02535
      300 North Rd, Chilmark, MA 02535
      /69

      Est $3,183,104

      Not Listed For Sale

      300 North Rd, Chilmark, MA 02535

      • 2 Beds
      • 3 Baths
      • 2,515 Sq Ft
      • Built 1995
      300 North Rd, Chilmark, MA 02535

      Last Sold Summary

      • 193 Days On Market

  • 308 South Rd, Chilmark, MA 02535
    308 South Rd, Chilmark, MA 02535
    308 South Rd, Chilmark, MA 02535
    /39

    $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
  • 41 Cobbs Hill Rd, Chilmark, MA 02535
    41 Cobbs Hill Rd, Chilmark, MA 02535
    41 Cobbs Hill Rd, Chilmark, MA 02535
    /44

    $37,000,000

    Sold Jul 10, 2025

    41 Cobbs Hill Rd, Chilmark, MA 02535

    • 8 Beds
    • 5.5 Baths
    • 7,846 Sq Ft
    • Built 1993

    Last Sold Summary

    • 5% Below List Price
    • $4,716/SF
    • 39 Days On Market

    Last Listing Agent Brian Dougherty Corcoran Property Advisors

    41 Cobbs Hill Rd, Chilmark, MA 02535
    • 50 South Rd, Chilmark, MA 02535
      50 South Rd, Chilmark, MA 02535
      50 South Rd, Chilmark, MA 02535
      /29

      Est $2,331,715

      Not Listed For Sale

      50 South Rd, Chilmark, MA 02535

      • 5 Beds
      • 3 Baths
      • 2,427 Sq Ft
      • Built 1729
      50 South Rd, Chilmark, MA 02535

      Last Sold Summary

      • 111 Days On Market

  • 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
  • 23 Chockers Ln, Chilmark, MA 02535
    23 Chockers Ln, Chilmark, MA 02535
    23 Chockers Ln, Chilmark, MA 02535
    /3

    $5,750,000

    Sold Apr 10, 2026

    23 Chockers Ln, Chilmark, MA 02535

    • 2 Beds
    • 1.5 Baths
    • 1,446 Sq Ft
    • Built 1993

    Last Sold Summary

    • $3,976/SF
    • 0 Days On Market

    Current Estimated Value $5,280,715

    Last Listing Agent Julianna Flanders Flanders Real Estate

    23 Chockers Ln, Chilmark, MA 02535
    • 99 Hammett Rd, Chilmark, MA 02535
      99 Hammett Rd, Chilmark, MA 02535
      99 Hammett Rd, Chilmark, MA 02535
      /24

      Est $2,467,657

      Not Listed For Sale

      99 Hammett Rd, Chilmark, MA 02535

      • 4 Beds
      • 5.5 Baths
      • 2,405 Sq Ft
      • Built 2007
      99 Hammett Rd, Chilmark, MA 02535

      Last Sold Summary

      • 10 Days On Market

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

    $1,775,000

    Sold Nov 07, 2025

    3 Fulling Mill Rd, Chilmark, MA 02535

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 1976

    Last Sold Summary

    • 5% Below List Price
    • $1,027/SF
    • 170 Days On Market

    Current Estimated Value $1,884,275

    Last Listing Agent Jill Napior Tea Lane Associates

    3 Fulling Mill Rd, Chilmark, MA 02535

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