2,459

Homes in ZIP Code 02535

Section Image
  • /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
  • /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
  • /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
    • /23

      Est $1,998,751

      Not Listed For Sale

      50 Campbell Rd, Vineyard Haven, MA 02568

      • 2 Beds
      • 2 Baths
      • 1,370 Sq Ft
      • Built 1994
      50 Campbell Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 16 Days On Market

  • /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
  • /4

    $6,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft
    • House for Rent

    836 State Rd, Aquinnah, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Windy Knoll is a 3BR, 2Bath home located in Aquinnah on a secluded lot off State Road with 160 degree views of the Atlantic Ocean. Approximately 1 mile to Philbin Beach similar distance to Moshup Beach and Lobsterville beach. Take the bike ferry over to Menemsha and enjoy sunset on the beach. Outdoor shower with multiple shower heads to wash off the

    Karen Overtoom Karen M. Overtoom R.E.

    836 State Rd, Aquinnah, 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
    • /6

      Est $2,952,719

      Not Listed For Sale

      71 Runner Rd, Vineyard Haven, MA 02568

      • 4 Beds
      • 3 Baths
      • 1,935 Sq Ft
      • Built 1982
      71 Runner Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 0 Days On Market

  • /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
  • /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
  • /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
    • /26

      Est $2,474,678

      Not Listed For Sale

      437 State Rd, Aquinnah, MA 02535

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft
      • Built 1955
      437 State Rd, Aquinnah, MA 02535

      Last Sold Summary

      • 357 Days On Market

  • /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
  • /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
  • /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
    • /79

      Est $1,517,332

      Not Listed For Sale

      76 State Rd, Aquinnah, MA 02535

      • 4 Beds
      • 2 Baths
      • 3,093 Sq Ft
      • Built 1856
      76 State Rd, Aquinnah, MA 02535

      Last Sold Summary

      • 190 Days On Market

  • /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
  • /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
  • /39

    $1,575,000

    Sold Jan 09, 2026

    453 Lighthouse Rd, Aquinnah, MA 02535

    • 3 Beds
    • 4 Baths
    • 2,308 Sq Ft
    • Built 1970

    Last Sold Summary

    • 12% Below List Price
    • $682/SF
    • 169 Days On Market

    Current Estimated Value $1,614,062

    Last Listing Agent We Close Deals Team Lamacchia Realty, Inc.

    453 Lighthouse Rd, Aquinnah, MA 02535
    • /33

      Est $3,328,850

      Not Listed For Sale

      3 Oxcart Rd, Aquinnah, MA 02535

      • 2 Beds
      • 2 Baths
      • 1,288 Sq Ft
      • Built 1970
      3 Oxcart Rd, Aquinnah, MA 02535

      Last Sold Summary

      • 4 Days On Market

  • /36

    $3,350,000

    • 4 Beds
    • 2.5 Baths
    • 2,686 Sq Ft

    4 Nomans Watch Rd, Aquinnah, MA 02535

    Perched on 2.7 acres in one of Aquinnah’s most breathtaking settings, this beautifully sited coastal retreat offers sweeping views over the Atlantic and Noman’s Land from its elevated position. Designed to embrace the light and scenery, the main level features an open living/dining/kitchen area wrapped in walls of windows—an airy, sun-soaked space where ocean views take center stage. The

    Jennifer O'hanlon Compass LLC

    4 Nomans Watch Rd, Aquinnah, 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
  • /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
    • /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

  • /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
  • /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
  • /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
    • /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

  • /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
  • /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
  • /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
    • /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

  • /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
  • /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
  • /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
    • /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

  • /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
  • /13

    $15,000 Per Month

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

    19 Lighthouse Road Aq605, Aquinnah, MA 02535

    This family-friendly, three-bedroom retreat on Lighthouse Road in Aquinnah offers all the comforts of home with stunning water views of the Vineyard Sound and the Elizabeth Islands. It is beautifully decorated and nicely furnished. The home features stylish post-and-beam architecture. The main level features cathedral ceilings, wrap-around picture windows and skylights. The main level opens out

    Karen Overtoom Karen M. Overtoom R.E.

    19 Lighthouse Road Aq605, Aquinnah, MA 02535
  • /28

    $6,650,000

    Sold Mar 17, 2026

    7 Clay Pit Ln, Aquinnah, MA 02535

    • 5 Beds
    • 4.5 Baths
    • 5,000 Sq Ft
    • Built 1999

    Last Sold Summary

    • 11% Below List Price
    • $1,330/SF
    • 98 Days On Market

    Current Estimated Value $7,336,095

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

    7 Clay Pit Ln, Aquinnah, 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 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home