3,640

Chilmark, MA Homes

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  • /23

    $1,695,000

    • 5 Beds
    • 5 Baths
    • 2,316 Sq Ft

    345 North Rd, Chilmark, MA 02535

    Abutting hundreds of acres of conservation land and walking trails leading to the second-highest point on Martha's Vineyard with views of the Elizabeth Islands, this classically-styled house with detached guest quarters offers 5 total bedrooms and 4 full baths plus an outdoor shower. The primary bedroom suite is a generous size and has its own small deck that overlooks the charming front yard.

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    345 North Rd, Chilmark, MA 02535
  • /8

    $8,000 per month

    • 4 Beds
    • 4.5 Baths
    • 3,600 Sq Ft
    • House for Rent

    56 Chilmark Rd, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! 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 land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and

    Karen Overtoom Karen M. Overtoom R.E.

    56 Chilmark Rd, Chilmark, MA 02535
  • /3

    $275,000 Sold Nov 19, 2024

    • Land
    • 1.80 Acres
    • $152,778 per Acre
    • 143 Days On Market

    0 Lamberts Cove Rd, Vineyard Haven, MA 02568

    Wooded parcel in Vineyard Haven located off scenic Lamberts Cove Road. Conveniently located to Tisbury Center and neighboring Vineyard Open Land Foundation's Cranberry Acres. A recent survey has been completed, identifying right of way and wetlands, all other engineering and permitting is the responsibility of the buyer. A License to Sell issued by the Dukes Probate and Family Court is a

    Katherine Donahue Sandpiper Realty Inc

    0 Lamberts Cove Rd, Vineyard Haven, MA 02568
    • /43

      Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,674 Sq Ft

      39 Sarita Walker Rd, Vineyard Haven, MA 02568

      39 Sarita Walker Rd, Vineyard Haven, MA 02568
  • /16

    $999,999

    • Land
    • 3.83 Acres
    • $261,096 per Acre

    25 N Vine Ln, West Tisbury, MA 02568

    Exceptional Opportunity in West Tisbury! Nestled on a dead end paved private road this exceptional land parcel offers the perfect blend of serenity and convenience. Just moments from the scenic Sepiessa and Tiah's Cove boat launches and the beaches at Long Point Nature Preserve this is an idyllic escape with quick access to Town Center. This tranquil plot of land is a blank canvas for you to

    Janna O'Loughlin Martha's Vineyard Seacoast Properties

    25 N Vine Ln, West Tisbury, MA 02568
  • /42

    $19,000 per month

    • 6 Beds
    • 6.5 Baths
    • 6,950 Sq Ft
    • House for Rent

    40 Sweet William Way, West Tisbury, MA 02575

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the

    Karen Overtoom Karen M. Overtoom R.E.

    40 Sweet William Way, West Tisbury, MA 02575
  • /35

    $1,995,000 Sold Nov 15, 2024

    • 1,995 Sq Ft
    • $1000/SF
    • 47 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2003

    159 Charles Neck Way, Vineyard Haven, MA 02568

    The Whale House: Coastal-Inspired Living Near Long Point - This beautifully appointed residence is an ideal sanctuary for family and friends to indulge in relaxation and seaside splendor. The first floor welcomes you with a sun-filled open layout. A Living Area adorned with a gas fireplace sets the stage for cozy gatherings. The well-appointed Kitchen boasts a prep counter/breakfast bar and

    Wendy Harman Compass

    159 Charles Neck Way, Vineyard Haven, MA 02568
    • /41

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,598 Sq Ft

      566 Scrubby Neck Rd, Vineyard Haven, MA 02568

      566 Scrubby Neck Rd, Vineyard Haven, MA 02568
  • /2

    $799,000

    • Land
    • 0.92 Acre
    • $868,478 per Acre

    22 Bramble Path, West Tisbury, MA 02568

    Flat building lot centrally located in West Tisbury. It is the Buyer's responsibility to conduct a perc test and install utilities, well and septic.

    Michele Casavant Vineyard Village Realty

    22 Bramble Path, West Tisbury, MA 02568
  • /39

    $46,000 per month

    • 6 Beds
    • 4.5 Baths
    • 3,800 Sq Ft
    • House for Rent

    99 Pond Road Wt104, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!! Beautiful bright sunny home with open concept living. Main floor features a gourmet kitchen with stainless appliances, breakfast bar and formal dining table to seat 10. Large glass sliders open up to expansive views of the deck, pool and pasture beyond. Also on the main level is a separate living area with large screen TV, powder room, and den with twin

    Karen Overtoom Karen M. Overtoom R.E.

    99 Pond Road Wt104, West Tisbury, MA 02575
  • /37

    $1,115,000 Sold Nov 07, 2024

    • 1,316 Sq Ft
    • $847/SF
    • 32 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1991

    43 Skiffs Ln, Vineyard Haven, MA 02568

    Nestled on a private road, follow the long gravel driveway to this 3-bedroom, 2-bathroom home offering tranquil living on 2.48 wooded acres. The fully-applianced kitchen and vinyl flooring throughout provide ease of maintenance, while the bedrooms offer cozy carpeting. The primary bedroom features an ensuite bathroom and generous closet space. Step out from the kitchen to the back deck and enjoy

    Chelsea Brennan Lamacchia Realty, Inc.

    43 Skiffs Ln, Vineyard Haven, MA 02568
    • /15

      Est $2,582,269 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 512 Sq Ft

      119 Old Thumb Point Rd, Vineyard Haven, MA 02568

      119 Old Thumb Point Rd, Vineyard Haven, MA 02568
  • /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
  • /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

      • 3 Beds
      • 2 Baths
      • 1,092 Sq Ft

      105 Charles Neck Way, Vineyard Haven, MA 02568

      105 Charles Neck Way, Vineyard Haven, MA 02568
  • /28

    $32,000 per month

    • 4 Beds
    • 4 Baths
    • 3,200 Sq Ft
    • House for Rent

    37 Mempremagog Ave Vh410, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in

    Karen Overtoom Karen M. Overtoom R.E.

    37 Mempremagog Ave Vh410, Tisbury, MA 02568
  • /26

    $950,000 Sold Oct 25, 2024

    • 1,182 Sq Ft
    • $804/SF
    • 8 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1977

    4 Elias Ln, Vineyard Haven, MA 02568

    This iconic West Tisbury property features a rustic post and beam farmhouse with endless charm. The inviting home highlights original wide-planked wood floors, cathedral ceiling, wood-burning stove and fireplace, and exposed brick. Enjoy the cozy kitchen, dining, and living area on the first floor, including a full bath and mudroom. The bedroom occupies the second floor with room for an

    Stephanie Roache Donnelly + Co.

    4 Elias Ln, Vineyard Haven, MA 02568
    • /31

      Est $1,234,831 Not Listed For Sale

      • 1 Bed
      • 1.5 Baths
      • 855 Sq Ft

      16 Elias Ln, Vineyard Haven, MA 02568

      16 Elias Ln, Vineyard Haven, MA 02568
  • /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
  • /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

    27 Ocean View Farm Rd, Chilmark, MA 02535
    • /24

      Est $1,778,847 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,856 Sq Ft

      280 Oak Ln, Vineyard Haven, MA 02568

      280 Oak Ln, Vineyard Haven, MA 02568
  • /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
  • /19

    $1,800,000 Sold Oct 17, 2024

    • 1,822 Sq Ft
    • $988/SF
    • 224 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1989

    7 Parsonage Woods Rd, West Tisbury, MA 02568

    This rare and cherished setting is truly in the heart of West Tisbury. With old growth cedar, oaks and evergreen trees this level 4.8 acre parcel includes a main house and timber barn, perfectly sited to enjoy serene views and southern exposure. Currently set up as a horse farm with a two stall barn, paddocks, full size arena, interconnecting grazing areas and multiple watering stations, it could

    7 Parsonage Woods Rd, West Tisbury, MA 02568
    • /16

      Est $1,278,011 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,408 Sq Ft

      35 Skiffs Ln, Vineyard Haven, MA 02568

      35 Skiffs Ln, Vineyard Haven, MA 02568
  • /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
  • /8

    $660,000 Sold Oct 04, 2024

    • Land
    • 1.60 Acres
    • $412,500 per Acre
    • 175 Days On Market

    87 Longview Rd, West Tisbury, MA 02575

    This lovely 1.60 acre wooded parcel is located in an outstanding neighborhood off Lambert's Cove Road with paved roads and easy access to beautiful Lambert's Cove Beach, less than a mile away. This lot is ready to build on. It has been staked, there is an approved septic design for 4 bedrooms, well has been installed and electric and cable are to the lot. This is the chance to build the house of

    Brenda Galligan Karen M. Overtoom R.E.

    87 Longview Rd, West Tisbury, MA 02575
    • /26

      Est $4,732,468 Not Listed For Sale

      • 8 Beds
      • 4 Baths
      • 4,800 Sq Ft

      48 Forest Rd, Vineyard Haven, MA 02568

      48 Forest Rd, Vineyard Haven, MA 02568
  • /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
  • /28

    $1,360,000 Sold Sep 24, 2024

    • 1,497 Sq Ft
    • $908/SF
    • 284 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1985

    46 Crow Hollow Rd, Vineyard Haven, MA 02568

    Welcome to a delightful Cape-style home nestled in this serene and picturesque area. This beautiful property offers the perfect blend of classic charm and modern comfort, making it an ideal retreat for those seeking the quintessential Vineyard experience. Situated on a peaceful, tree-lined cul-de-sac, this home has a tranquil and private setting, perfect for relaxing and enjoying the Island's

    Jennifer B. DaSilva Compass

    46 Crow Hollow Rd, Vineyard Haven, MA 02568
    • /33

      Est $1,596,642 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 770 Sq Ft

      2 Creek Hill, Chilmark, MA 02535

      2 Creek Hill, 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
  • /24

    $1,350,000 Sold Sep 05, 2024

    • 1,665 Sq Ft
    • $811/SF
    • 38 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1987

    188 Waldrons Bottom Rd, West Tisbury, MA 02575

    Welcome to 188 Waldrons Bottom Road near the south shore in West Tisbury. Nestled on a private 3-acre property with access to Long Point Beach, this home offers incredible potential for a serene lifestyle. This unique property currently has 1-bedroom (the property has a 2-bedroom septic), 1.5-bathroom home with a total of 1,665 square feet of living space. The main level features the library,

    Tina Miller Compass

    188 Waldrons Bottom Rd, West Tisbury, MA 02575
    • /18

      Est $4,089,275 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,316 Sq Ft

      1 Pond Mark, Chilmark, MA 02535

      1 Pond Mark, 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
  • /33

    $1,635,000 Sold Jul 10, 2024

    • 2,508 Sq Ft
    • $652/SF
    • 90 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1986

    163 Charles Neck Way, Vineyard Haven, MA 02568

    NEW PRICE! ENJOY YOUR ENTIRE SUMMER POOLSIDE OR AT THE BEACH! Welcome to this charming property near Long Point Wildlife Refuge and explore all it has to offer. Walk, bike, or drive from the house to the beach, and spend the day body surfing in the ocean, splashing with the little ones in the ponds, or walking the habitat. Afterward, take a dip in your 16 x 32 ft. in-ground swimming pool

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

    163 Charles Neck Way, Vineyard Haven, MA 02568
    • /12

      Est $2,285,195 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,342 Sq Ft

      5 Ocean View Farm Rd, Chilmark, MA 02535

      5 Ocean View Farm 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
  • /2

    $1,645,000 Sold Feb 21, 2025

    • 2,576 Sq Ft
    • $639/SF
    • 6 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1974

    49 Oak Ln, West Tisbury, MA 02575

    Private and serene on more than 2 acres, with over 2,500 s/f of living space, high ceilings, wide windows, 2 first-floor bedroom suites, and meadow views throughout - discover the perfect balance of sophistication and charm at 49 Oak Lane. When you consider the additional benefit of access to Lamberts Cove Beach, it truly is the ideal setting to enjoy your Vineyard lifestyle. The expanded first

    Dawn Bellante Sandpiper Realty Inc

    49 Oak Ln, West Tisbury, MA 02575
    • /39

      Est $8,210,723 Not Listed For Sale

      • 3 Beds
      • 5 Baths
      • 4,035 Sq Ft

      76 Menemsha Inn Rd, Chilmark, MA 02535

      76 Menemsha Inn Rd, Chilmark, MA 02535
  • /28

    $38,000 per month

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

    17 Otis Bassett Rd, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT MONTHLY. AUGUST WEEKLY IS $9,500. SEE OUR WEB SITE FOR WEEKLY PRICING!!!!!Are you looking for the perfect back yard Oasis? Well here it is!! Surrounding a large pool you will be able to relax on the expansive deck areas that include plenty of space for gathering. Inside is an amazing kitchen with every amenity you could want. Coffee lovers will appreciate a regular

    Karen Overtoom Karen M. Overtoom R.E.

    17 Otis Bassett Rd, West Tisbury, MA 02575

Showing Results 41 - 80, Page 2 of 18

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