1,726

Chilmark Homes

Section Image
  • /3

    $110,000

    • Land
    • 0.70 Acre
    • $157,143 per Acre

    00 Eliot Ave Unit 17, Chilmark, MA 02535

    Enjoy access to beautiful Stonewall Beach located in Chilmark. It has great swimming and fishing!This is not a buildable lot.

    Julianna Flanders Flanders Real Estate

    00 Eliot Ave Unit 17, 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
  • /26

    $1,830,000 Sold Dec 05, 2024

    • 1,862 Sq Ft
    • $983/SF
    • 10 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1960

    82 South Rd, Chilmark, MA 02535

    This charming Chilmark home sits on over 3 acres and features an updated, move-in ready home, expansive outdoor living space with deck, lawn and firepit area, and a six-bedroom septic system for future expansion. The welcoming foyer opens into the dining room, kitchen and a large airy living room with vaulted ceiling and stone fireplace. Beyond the kitchen there are two bedrooms and a shared

    Meg Bodnar Tea Lane Associates

    82 South Rd, Chilmark, MA 02535
    • /21

      Not Listed For Sale

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

      3 Pepperbush Ln, Chilmark, MA 02535

      3 Pepperbush Ln, Chilmark, MA 02535
  • /26

    $3,695,000

    • Land
    • 7 Acres
    • $551,493 per Acre

    32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, Chilmark, MA 02535

    Discover an exceptional opportunity with this rare combination of two abutting parcels spanning more than 6 acres in a coveted location offering water views and Atlantic Ocean private beach access. Surfers and fishermen delight in this location! The Stonewall Association is a beloved area of Chilmark in a supreme location for easy Chilmark living close to the Chilmark Store, the Chilmark

    Jill Napior Tea Lane Associates

    32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, 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
  • /48

    $7,650,000 Sold Nov 21, 2024

    • 3,834 Sq Ft
    • $1995/SF
    • 48 Days On Market
    • 6 Beds
    • 5 Baths
    • Built 1995

    49 Tilton Rd, Chilmark, MA 02535

    Unique opportunity to enjoy a remarkable, secure, elevated Chilmark north shore 4 acre waterfront property with dramatic 180 degree year round sunset water views over the one mile Spring Point sandy coastline to Great Rock Bight, Menemsha Hills, Aquinnah shore, Gay Head Lighthouse and the Elizabeth Islands stretching almost to Woods Hole. This wide expanse of the Vineyard Sound enjoys endless

    Robert Kenney Tea Lane Associates

    49 Tilton Rd, Chilmark, MA 02535
    • /29

      Est $2,277,215 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,427 Sq Ft

      50 South Rd, Chilmark, MA 02535

      50 South Rd, Chilmark, MA 02535
  • /15

    $2,770,000

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

    5 Ocean View Farm Rd, Chilmark, MA 02535

    Designed by the famous mid century architect Andrew Geller, this contemporary home is situated at the top of the parcel with ocean views and a glimpse of Chilmark pond. There is ample open space to accommodate family and friends and overlooks the large meadow which follows the stone wall to South Road. Access to walking trails, and Lucy Vincent Beach is a short distance away.

    Natalie Conroy Conroy & Company R.E., Inc.

    5 Ocean View Farm Rd, 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
  • /23

    $2,300,000 Sold Nov 08, 2024

    • 2,229 Sq Ft
    • $1032/SF
    • 11 Days On Market
    • 6 Beds
    • 4 Baths
    • Built 1989

    51 Blueberry Ridge Ln, Chilmark, MA 02535

    Rare opportunity to purchase a compound on large 8 acre parcel in Chilmark. Main House is 4 bedrooms, 2 1/2 baths on two levels. Oak floors, fieldstone fireplace and large screened in three season porch. Lower level offers a one car garage, workshop, large laundry room and storage room.The "Dinghy" is a detached cottage with 2 bedroom & full bath. The third building is a charming "pool house"

    Rebecca V Conroy Conroy & Company R.E., Inc.

    51 Blueberry Ridge Ln, Chilmark, MA 02535
    • /24

      Est $2,378,026 Not Listed For Sale

      • 4 Beds
      • 6 Baths
      • 2,405 Sq Ft

      99 Hammett Rd, Chilmark, MA 02535

      99 Hammett Rd, Chilmark, MA 02535
  • /36

    $3,250,000

    • 4 Beds
    • 4 Baths
    • 2,515 Sq Ft

    300 North Rd, Chilmark, MA 02535

    Winding tree lined driveway off North Rd brings you to this commanding, custom designed residence built by a top tier island builder. This home is set on over 4 private acres of rolling meadows and big sky views. Main living space is all on one level which includes primary bedroom with en-suite bath, large living area with fireplace, bright sunroom or second living room, custom kitchen and

    Rebecca V Conroy Conroy & Company R.E., Inc.

    300 North Rd, 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

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.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

    Karen Overtoom Karen M. Overtoom R.E.

    2 Strikers Way Ch211, Chilmark, MA 02535
  • /22

    $1,500,000 Sold Nov 05, 2024

    • 1,008 Sq Ft
    • $1488/SF
    • 361 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2010

    5 Meetinghouse Rd, Chilmark, MA 02535

    CHARMING CHILMARK- This sweet, sunny home comes with deeded access to Chilmark Pond and South Shore Beach. Kayak, paddleboard, sail, or motor across the pond to one of Chilmark's most pristine private beaches. The location is also convenient, being centrally located and close to West Tisbury Center, Grey Barn, the Yoga Barn, Chilmark Center, Beetlebung Farm, Chilmark Store, and Chilmark Tavern.

    Tina Miller Compass

    5 Meetinghouse Rd, Chilmark, MA 02535
    • /7

      Not Listed For Sale

      • 6 Beds
      • 7 Baths
      • 4,900 Sq Ft

      45 Beach Rd, Chilmark, MA 02535

      45 Beach Rd, Chilmark, MA 02535
  • /40

    $1,899,000

    • 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
  • /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
  • /19

    $2,200,000 Sold Oct 25, 2024

    • 2,450 Sq Ft
    • $898/SF
    • 182 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1964

    27 Ocean View Farm Rd, Chilmark, MA 02535

    27 Ocean View Farm Road is a unique house with the main living spaces designed by architect Elizabeth Carlhian in 1964 along with a connected, yet private bed and bath suite designed by architects Modigliani/Noyes in 1987. A covered breezeway between the two spaces frames the ocean views while providing cover from the weather. Taken together the house consists of 4 bedrooms and 3 baths sited high

    Russell Maloney Russel Maloney Real Estate

    27 Ocean View Farm Rd, Chilmark, MA 02535
    • /21

      Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 4,967 Sq Ft

      27, 30, 31 Tower Lane; 34 Eben's Ln, Chilmark, MA 02535

      27, 30, 31 Tower Lane; 34 Eben's Ln, Chilmark, MA 02535
  • /36

    $2,500,000

    • 4 Beds
    • 3 Baths
    • 2,350 Sq Ft

    16 South Rd, Chilmark, MA 02535

    Where Vineyard history meets pastoral beauty.Classic, lovingly restored 1800’s Chilmark farmhouse with multiple outbuildings, which includes a large barn with second floor loft, a run-in barn with two horse stalls, both overlook an expansive, pastoral fenced pasture for horses to run or field games to be played. This historic farmhouse home offers four bedrooms, three baths and has been

    Michele Casavant Vineyard Village Realty

    16 South Rd, 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
  • /34

    $6,100,000 Sold Oct 16, 2024

    • 3,859 Sq Ft
    • $1581/SF
    • 38 Days On Market
    • 6 Beds
    • 5 Baths
    • Built 1941

    391 Middle Rd, Chilmark, MA 02535

    This iconic property and location is truly a once-in-a-lifetime opportunity. Exceptional house and guest house that is ready to move into . The exterior resonates with what is beloved about Chilmark but the interior is contemporary and fresh. The main house has views overlooking the Keith farm and the Atlantic Ocean beyond, old stone walls and open meadows. A new owner will have the gratification

    Jill Napior Tea Lane Associates

    391 Middle Rd, Chilmark, MA 02535
    • /14

      Not Listed For Sale

      34 Ebens Lane & 31 Tower Ln, Chilmark, MA 02535

      34 Ebens Lane & 31 Tower Ln, Chilmark, MA 02535
  • /26

    $1,985,000

    • Land
    • 3.58 Acres
    • $554,469 per Acre

    4 Cedar Ln Unit 2.2, Chilmark, MA 02535

    Premier Build-Ready Lot with Private Beach AccessGet to know Stonewall Association, one of Chilmark’s most sought-after enclaves on the South Shore. This sunny, build-ready parcel offers a rare opportunity to own land with deeded private access to Stonewall Beach—a beloved destination for swimming, surfing, excellent fishing and summer memories. Set on beautifully contoured land with southern

    Jill Napior Tea Lane Associates

    4 Cedar Ln Unit 2.2, 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
  • /6

    $430,000 Sold Oct 10, 2024

    • Land
    • 0.60 Acre
    • $716,667 per Acre
    • 0 Days On Market

    0 Beach Lot Quansoo Unit 42634, Chilmark, MA 02535

    Not listed in LINK.

    LINK Email Cache LINK

    0 Beach Lot Quansoo Unit 42634, Chilmark, MA 02535
    • /13

      Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 816 Sq Ft

      70 State Rd, Aquinnah, MA 02535

      70 State Rd, Aquinnah, MA 02535
  • /35

    $14,000,000

    • 5 Beds
    • 5 Baths
    • 3,758 Sq Ft

    6 Wakeman Rd, Chilmark, MA 02535

    A 1930s-built home that has been remarkably updated to retain its historic charm while incorporating sophisticated and modern amenities. The house overlooks the Chilmark Great Pond and the Atlantic Ocean beyond. The Main House includes 3 bedrooms, 3 beautifully renovated bathrooms, a walk-in closet, a Pantry, a Library/Media room, a full basement, Outdoor showers, and a screened-in porch. The

    Julianna Flanders Flanders Real Estate

    6 Wakeman Rd, Chilmark, MA 02535
  • /13

    $14,000 per month

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • House for Rent

    88 Quenames Rd, Chilmark, MA 02535

    THIS IS A SUMMER RENTAL ONLY. This bright and cheerful, wooded retreat is truly tranquil, yet just a little over a mile from West Tisbury village, with its General Store (Alley's), Farmer's Market, Artisan's Festivals and Flea Market. This home has been recently updated by its new owners. They have chosen the loveliest colors and simple, appropriate cottage touches. There is a new expansive deck

    Karen Overtoom Karen M. Overtoom R.E.

    88 Quenames Rd, Chilmark, MA 02535
  • /29

    $1,680,000 Sold Oct 09, 2024

    • 1,200 Sq Ft
    • $1400/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1954

    7 Flanders Ln, Chilmark, MA 02535

    Sweet, renovated cottage in Menemsha. Classic Vineyard home that is move-in ready! You'll find a renovated kitchen, central A/C, new bathrooms and fresh interior which still maintains the cottage charm of the original house. Open living room through to kitchen with all three bedrooms on the main level. The house is at the beginning of Flanders Lane just 1/4 mile from the Village of Menemsha

    Meg Bodnar Tea Lane Associates

    7 Flanders Ln, Chilmark, MA 02535
    • /6

      Not Listed For Sale

      0 Beach Lot Quansoo #136, Chilmark, MA 02535

      0 Beach Lot Quansoo #136, Chilmark, MA 02535
  • /25

    $3,600,000

    • 3 Beds
    • 3 Baths
    • 4,382 Sq Ft

    88 & 90 Quenames Rd, Chilmark, MA 02535

    Make your own Chilmark dream come true!12.6 +/- acres of prime land allows you to create your own familycompound or Island Farm. Enjoy the peacefulness of the Chilmarkwith room to expand. Two separate buildable lots provides you uniqueoptions. The Main house has three bedrooms, three bathrooms, twostudies, multiple living spaces and a large three-car garage

    Julianna Flanders Flanders Real Estate

    88 & 90 Quenames Rd, Chilmark, MA 02535
  • /12

    $12,500 per month

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • House for Rent

    138 South Rd, Chilmark, MA 02535

    THIS IS A SUMMER RENTAL ONLY. This newly remodeled 3 bedroom 2 bath has a spacious master bedroom suite, cozy sun room and updated kitchen. It has a great yard with garden landscaping, a perfect spot for outdoor dining. 1.5 miles from Alley's store. 3.3 miles to Lucy Vincent Beach.The bathrooms are fully remodeled. An easy, comfortable house in a central location. Three ceiling fans and 3

    Karen Overtoom Karen M. Overtoom R.E.

    138 South Rd, Chilmark, MA 02535
  • /29

    $1,895,000 Sold Sep 06, 2024

    • 1,108 Sq Ft
    • $1710/SF
    • 44 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1994

    5 Oyster Ln, Chilmark, MA 02535

    Bounded by discernible ancient ways, bridle paths and exquisite ancient woodlands, this charming custom built home is perfectly sited on 4.5 acres. Sculpted manicured walking paths meander throughout the property and provide access to fruit , vegetable and lush flower gardens. Perfect for entertaining on the amply-sized, mahogany deck, the home is augmented by a shaded and moss-lined, bluestone

    Rebecca V Conroy Conroy & Company R.E., Inc.

    5 Oyster Ln, Chilmark, MA 02535
    • /13

      Not Listed For Sale

      0 Gosnold's Way, Chilmark, MA 02535

      0 Gosnold's Way, Chilmark, MA 02535
  • /6

    $2,950,000

    • Land
    • 2.36 Acres
    • $1,250,000 per Acre

    18 Allen Farm Rd Unit 20-2, Chilmark, MA 02535

    This private and serene 2.36 acre property is located one mile from Lucy Vincent Beach. There is a large building envelope located between the eighty and one hundred foot contour with exciting architectural options. The land has open woodlands, a small pasture and a fenced garden area. A charming cottage on the property is offered fully furnished and has everything you need to enjoy your stays

    Patty Kendall Kendall & Kendall

    18 Allen Farm Rd Unit 20-2, 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
  • /37

    $1,550,000 Sold Sep 05, 2024

    • 1,900 Sq Ft
    • $816/SF
    • 414 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1978

    2 Rockrose Path, Chilmark, MA 02535

    A great opportunity in Chilmark with a water view out to the Atlantic Ocean. Built and owned by one family for 45 years, this home was sited to embrace the south shore views. The main floor has a light and open living, kitchen, dining room while the second floor has three bedrooms and two full baths. This level has very strong views. There is a walk out ground level with a bedroom, bath, storage

    Jill Napior Tea Lane Associates

    2 Rockrose Path, Chilmark, MA 02535
    • /3

      Not Listed For Sale

      0 Black Point Road Beach Lot 7, Chilmark, MA 02535

      0 Black Point Road Beach Lot 7, Chilmark, MA 02535

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