Homes for Sale in 02535

• 

  

  

  /30

  $6,595,000

  • 4 Beds
  • 4 Baths
  • 3,052 Sq Ft

  20 Eliot Ave, Chilmark, MA 02535

  Waterfront home on Stonewall Pond. Nestled along the serene shores of Stonewall Pond, this waterfront home is located in one is Chilmark’s most idyllic locations. This remarkable property offers an unparalleled living experience with breathtaking Atlantic Ocean views and exclusive access to Stonewall Beach. Step inside and be greeted by a seamless fusion of elegance and comfort. The interior

  Alyssa Halisky Wallace & Co. Sotheby's

  20 Eliot Ave, Chilmark, MA 02535
• 

  

  

  /38

  $4,195,000

  • 3 Beds
  • 4 Baths
  • 3,426 Sq Ft

  96 Hammett Ln, Chilmark, MA 02535

  This beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher soapstone counters and a butlers pantry with extra cupboards, shelving and a wine

  Brenda Galligan Karen M. Overtoom R.E.

  96 Hammett Ln, Chilmark, MA 02535
• 

  

  

  /36

  $5,450,000

  • 5 Beds
  • 4 Baths
  • 2,913 Sq Ft

  122 Old Farm Rd, Chilmark, MA 02535

  An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The original section of this 3000 sq ft home dates from the late 1700s and is on Chilmark's register of historic homes, but it has been expanded with new additions to create a thoroughly modern

  Mark Jenkins Wallace & Co. Sotheby's

  122 Old Farm Rd, Chilmark, MA 02535
• 

  

  

  /42

  $4,600,000

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

  15 Old Farm Rd, Chilmark, MA 02535

  CHILMARK BLISS- 15 Old Farm Rd, sits on over 3 beautiful acres, blends refined architecture with serene natural beauty. Reimagined in 2020 by Peter Breese and crafted by Doug Best, this timeless retreat offers open-concept living, anchored by a stunning kitchen, large pantry, screen porch, and a stone fireplace, with seamless indoor-outdoor flow. The main level includes a sunny primary suite

  Tina Miller Compass

  15 Old Farm Rd, Chilmark, MA 02535
• 

  

  

  /34

  $5,450,000

  • 5 Beds
  • 4.5 Baths
  • 2,913 Sq Ft

  124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535

  An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The original section of this 3000 sq ft home dates from the late 1700s and is on Chilmark's register of historic homes, but it has been expanded with new additions to create a thoroughly modern

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
• 

  

  /46

  $6,750,000

  • 3 Beds
  • 3 Baths
  • 3,432 Sq Ft

  44 Cencelle St, Chilmark, MA 02535

  This private 21-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
• 

  

  /49

  $6,490,000

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

  60 Meetinghouse Rd, Chilmark, MA 02535

  This spectacular and bright modern american farmhouse is perfectly sited to capture the varied scenic beauty that surrounds the farm. Built in 2021 with great attention to detail and materials, this home was created around gatherings and community with ample space for the extended family. The land has been lovingly curated into a place which can grow, generate and support those who want to have

  Jim Feiner Feiner Real Estate

  60 Meetinghouse Rd, Chilmark, MA 02535
• 

  

  /101

  $4,600,000

  • 4 Beds
  • 3 Baths
  • 2,704 Sq Ft

  370 Lighthouse Rd, Aquinnah, MA 02535

  Stunning waterview living with an active view that will never disappoint. Wake up every morning to breathtaking 180 degree water views in this beautifully appointed 4-bedroom, 3-bath coastal retreat. Perfectly situated to capture sunrise to sunset vistas, this home offers a blend of summer vibes with year-round living amenities. Step inside to find an open-concept living space filled with natural

  Jill Napior Tea Lane Associates

  370 Lighthouse Rd, Aquinnah, MA 02535
• 

  

  /34

  $4,350,000

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  131 State Rd, Chilmark, MA 02535

  Magical waterfront Quitsa pond cottage with private dock. This home has the most spectacular views including sunsets and an intimate relationship with the charming and timeless waterfront at Quitsa Pond. Designed with the setting in mind this sublime piece of architecture has wonderful spaces, fantastic detail and so much packed into a smaller home. Landscape design by Edwina von Gal accentuates

  Jim Feiner Feiner Real Estate

  131 State Rd, Chilmark, MA 02535
• 

  

  /31

  $3,950,000

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft

  29 Oxcart Rd, Aquinnah, MA 02535

  Waterfront beach house on Dogfish Bar in Aquinnah. Take in the beauty of this gem of a location with rolling dunes, waterviews and immense sunsets! This property is one of only a few homes on this stretch of private and preserved beach. This 2009 contemporary beach house offers a reverse floor plan with the entire top floor as the living area, kitchen & dining, and more windows than walls to

  Michelle Kelly Tea Lane Associates

  29 Oxcart Rd, Aquinnah, MA 02535
• 

  

  /32

  $2,250,000

  • 4 Beds
  • 3 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
• 

  

  /7

  $650,000

  • Land
  • 0.20 Acre
  • $3,250,000 per Acre

  00 Hancock Beach Lot Unit 73, Chilmark, MA 02535

  Spectacular Hancock beach lot on the Atlantic Ocean. Ownership of this lot allows you access to one of the world's most beautiful beaches, plenty of parking and away from the crowds. It is a most enjoyable spot to spend a relaxing day on the Vineyard, sunbathing, fishing, kayaking, canoeing, etc. as you also gain access to Chilmark Pond. Any property on the Vineyard would be greatly enhanced by

  Deb Hancock Hancock Real Estate

  00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
• 

  

  /50

  $3,250,000

  • 4 Beds
  • 3 Baths
  • 2,758 Sq Ft

  382 Lighthouse Rd, Aquinnah, MA 02535

  Spacious contemporary set high off Lighthouse Road with unobstructed, amazing water views of the Vineyard Sound and Elizabeth Islands. Open concept design with soaring ceilings and modern architecture. A retreat for all seasons this house is fully insulated, heated and has central air. A center island in the kitchen ensures the cook of the family does not miss out on the amazing sunsets. Ground

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

  382 Lighthouse Rd, Aquinnah, MA 02535
• 

  

  /41

  $3,600,000

  • 3 Beds
  • 4 Baths
  • 2,500 Sq Ft

  27 Clambelly Rd, Chilmark, MA 02535

  A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media

  Julianna Flanders Flanders Real Estate

  27 Clambelly Rd, Chilmark, MA 02535
• 

  

  /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
• 

  

  /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
• 

  

  /13

  $1,150,000

  • Land
  • 2.02 Acres
  • $569,307 per Acre

  00 Old Field Rd, Aquinnah, MA 02535

  The nearby roar of the Atlantic can be heard from this pristine two-acre building opportunity in Aquinnah, ideally located at the end of Old Field Road with easy access from Moshup Trail. A storybook walking path through woods and fields over an easement bordering a majestic beetlebung grove and over a bubbling stream, leads directly to the entrance of cherished Philbin Beach. A thoughtfully

  Katherine Donahue Sandpiper Realty Inc

  00 Old Field Rd, Aquinnah, 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
• 

  

  /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
• 

  

  /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
• 

  

  /10

  $350,000

  • Land
  • 0.00 Acre

  0 Moshup Trail Unit 32500206, Aquinnah, MA 02535

  Enjoy coveted access to one of Martha's Vineyard's most stunning sandy beaches, located just off Moshup Trail in Aquinnah. This secluded beach is shared with only seven other members, ensuring a peaceful and private coastal experience. Located near Aquinnah's iconic ''Painted House,'' the property includes use of a private gated parking area and a picturesque stretch of shoreline perfect for

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  0 Moshup Trail Unit 32500206, Aquinnah, MA 02535
• 

  

  /10

  $350,000

  • Land
  • 1.26 Acres
  • $277,778 per Acre

  0 Moshup Trail Unit 27 & 146 43498, Aquinnah, MA 02535

  Enjoy coveted access to one of Martha's Vineyard’s most stunning sandy beaches, located just off Moshup Trail in Aquinnah. This secluded beach is shared with only seven other members, ensuring a peaceful and private coastal experience. Located near Aquinnah’s iconic “Painted House,” the property includes use of a private gated parking area and a picturesque stretch of shoreline perfect for

  Alyssa Halisky Wallace & Co. Sotheby's

  0 Moshup Trail Unit 27 & 146 43498, Aquinnah, MA 02535
• 

  

  /41

  $1,850,000

  • 3 Beds
  • 4 Baths
  • 2,986 Sq Ft

  1 Harpoon Hollow, Aquinnah, MA 02535

  Custom built Red Oak Post and Beam country home, in the style of an Old English cottage mansion. The many unique and attractive features are sure to delight the most discerning buyer. A brick walk bordered by a lovely boxwood hedge leads to two separate entrances into the home. Throughout, this intriguing, creatively designed home, you will notice the high quality and attention to detail.

  Elaine Vanderhoop Beachcombers of MV

  1 Harpoon Hollow, Aquinnah, MA 02535
• 

  

  /20

  $949,900

  • Land
  • 0.00 Acre

  0 Jeffers Way Unit 73387831, Aquinnah, MA 02535

  This lovely parcel in Aquinnah offers a rare opportunity to own a pristine 3.8 acre parcel on Martha's Vineyard. This elevated, hilly lot is bordered by Classic New England stone walls and surrounded by mature trees, providing both privacy and a serene natural setting. The property is prepared for development, featuring an installed well, a 3-bedroom septic, electric and a completed archeological

  Brenda Galligan Karen M. Overtoom R.E.

  0 Jeffers Way Unit 73387831, Aquinnah, MA 02535
• 

  

  /8

  $1,695,000

  • Land
  • 0.00 Acre

  19A Locust Ln, Aquinnah, MA 02535

  This private 6.19 acres parcel has been approved for sub-division and not yet recorded. Potential to add acreage. Proposed lot lines and designated building envelope. Lovely rolling topography with mature trees. Septic & Well not installed

  Brenda Galligan Karen M. Overtoom R.E.

  19A Locust Ln, Aquinnah, MA 02535
• 

  

  /24

  $1,275,000

  • Land
  • 2.20 Acres
  • $579,545 per Acre

  0 Old Rd S Unit 58 43410, Aquinnah, MA 02535

  Oceanview parcel ready to build the home you've been dreaming of. Sited on gently sloping, extremely private 2.2 Acres, bordered on 3 sides by ancient stone walls. Second story Atlantic ocean views and the sound of the waves and breezes may be enjoyed all Summer. All systems in place: Title V, 4 BR septic, well with tested potable water and power is installed. Enjoy the unique views and amazing

  Elaine Vanderhoop Beachcombers of MV

  0 Old Rd S Unit 58 43410, Aquinnah, MA 02535
• 

  

  /47

  $2,500,000

  • 3 Beds
  • 3 Baths
  • 1,784 Sq Ft

  12 Lobsterville Rd, Aquinnah, MA 02535

  12 Lobsterville Rd in Aquinnah is a uniquely designed contemporary home set on 2.6 acres of lush grounds with large tracts of conservation land nearby. Open concept living, dining, kitchen on the second floor with unobstructed ocean views of Vineyard Sound. Spacious deck for sunset viewing and grassy lawn for sundown games. Walking distance to Lobsterville Beach and a short bike ride to the

  Tina Palmer Conroy & Company R.E., Inc.

  12 Lobsterville Rd, Aquinnah, 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
• 

  

  /21

  $949,900

  • Land
  • 3.80 Acres
  • $249,974 per Acre

  0 Jeffers Way Unit 165 43370, Aquinnah, MA 02535

  This lovely parcel in Aquinnah offers a rare opportunity to own a pristine 3.8 acre parcel on Martha's Vineyard. This elevated, hilly lot is bordered by Classic New England stone walls and surrounded by mature trees, providing both privacy and a serene natural setting. The property is prepared for development, featuring an installed well, a 3-bedroom septic, electric and a completed

  Brenda Galligan Karen M. Overtoom R.E.

  0 Jeffers Way Unit 165 43370, Aquinnah, MA 02535
• 

  

  /35

  $13,000,000

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /17

  $1,900,000

  • Land
  • 3.30 Acres
  • $575,758 per Acre

  32 Stonewall Rd Unit 2.1, Chilmark, MA 02535

  South shore beachy living in Stonewall Association with private parking and access to a lovely swim and surf beach in a beloved area of Chilmark. There are second floor water views over Squibnocket Point and the Atlantic Ocean. This lot is fully engineered and ready to be built on! Single-family dwelling, plus a detached bedroom and accessory buildings, permitted according to the Chilmark

  Jill Napior Tea Lane Associates

  32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
• 

  

  /4

  $1,695,000

  • Land
  • 6 Acres
  • $273,829 per Acre

  19A Locust Ln Unit part of lot 175.1, Aquinnah, MA 02535

  This private 6.19 acres parcel has been approved for sub-division and not yet recorded. Potential to add acreage. Proposed lot lines and designated building envelope. Lovely rolling topography with mature trees. Septic & Well not installed

  Brenda Galligan Karen M. Overtoom R.E.

  19A Locust Ln Unit part of lot 175.1, Aquinnah, MA 02535
• 

  

  /37

  $7,975,000

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

  25 Osprey Ln, Chilmark, MA 02535

  Spectacular views from one of the most sought after private enclaves on Chilmark's South Shore. This lovely home was built to take advantage of this magical location. Just steps to the shared dock on the shores of Upper Chilmark Pond and minutes to the extraordinary deeded Atlantic Beach front. The homeowners worked with world renowned architects, Crissman & Solomon, along with revolutionary

  Deb Hancock Hancock Real Estate

  25 Osprey Ln, Chilmark, MA 02535
• 

  

  /35

  $2,495,000

  • 4 Beds
  • 3 Baths
  • 2,968 Sq Ft

  9 Beetlebung Grove Way, Chilmark, MA 02535

  Beautifully sited on 3.4 acres, this distinctive Chilmark home offers a rare blend of privacy, comfort, and expansive living space, ideal for entertaining, both inside and outside. From the welcoming foyer, step into the dramatic vaulted living room, where wood-paneled ceilings, a gas fireplace, and abundant natural light from skylights and picture windows create a warm and inviting atmosphere.

  Stephanie Roache Donnelly + Co.

  9 Beetlebung Grove Way, Chilmark, MA 02535
• 

  

  /34

  $1,750,000

  • 5 Beds
  • 2 Baths
  • 1,440 Sq Ft

  393 Lighthouse Rd, Aquinnah, MA 02535

  Ranch style home & Guest camp situated on 1+/- acre lot. The Main House offers distant views of Lobersterville beach and the Vineyard Sound beyond. Located in the desirable Lighthouse Road area, which offers walkable/close-by beach access and quiet roads. The view can be enjoyed from the Kitchen/Living/Dining as well as the wrap-around deck. Enjoy the open concept main living area, two bedrooms,

  Julianna Flanders Flanders Real Estate

  393 Lighthouse Rd, Aquinnah, MA 02535
• 

  

  /41

  $2,950,000

  • 4 Beds
  • 3 Baths
  • 2,424 Sq Ft

  19 Old Woods Rd, Chilmark, MA 02535

  Tucked away in the heart of Chilmark, this nearly 3-acre property blends rustic Vineyard charm with unique creative potential. Chilmark was a very special place for the former owner, American artist Thomas Hart Benton, who summered on the Island for 50 years. Professor and Art Historian, Erika Doss, said “the years he spent in Chilmark honed the artistic style and subjects that led to his

  Cheri Mason Landvest MV

  19 Old Woods Rd, Chilmark, MA 02535
• 

  

  /37

  $3,400,000

  • 5 Beds
  • 2 Baths
  • 3,133 Sq Ft

  19 Old Woods Rd, Chilmark, MA 02535

  Nestled in the heart of Chilmark, this 12.5-acre property offers two charming dwellings, each with 3 bedrooms, set in a landscape of privacy and timeless Vineyard character. Built in 1950 and 1963 for American artist, Thomas Hart Benton, the homes were lovingly created as a compound for friends and family to return to year after year. Tucked down a quiet driveway, the two share a special legacy

  Cheri Mason Landvest MV

  19 Old Woods Rd, Chilmark, MA 02535
• 

  

  /11

  $1,250,000

  • Land
  • 6 Acres
  • $219,298 per Acre

  14 Ridge Rd Unit 94, Aquinnah, MA 02535

  Idyllic gently rolling parcel of mixed hardwoods, meadow and stone walls awaits your vision. A large level building envelope has been cleared. A house and an ADU are permitted by right and a barn(subject to town approval) will fit nicely on this secluded parcel with room for a horse to graze and access nearby Land Bank and Sheriffs Meadow conservation land .It is walking distance to Menemsha

  Jim Wallen Feiner Real Estate

  14 Ridge Rd Unit 94, Aquinnah, MA 02535

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