Homes for Sale in 02535

• 

  

  

  /35

  $2,650,000

  • 4 Beds
  • 3 Baths
  • 2,967 Sq Ft

  11 By the Woods, Chilmark, MA 02535

  Dreamlike Chilmark retreat on 4.5+/- acres overlooking the Chilmark Pond & Atlantic Ocean beyond. Uniquely designed with European and medieval history in mind. The House has 3 bedrooms, 3 bathrooms, an atrium dining area, a two-story library, a kitchen, and a pantry/wet bar. Charming garden and plantings surround the home.A must-see to appreciate all the special touches throughout the Main

  Julianna Flanders Flanders Real Estate

  11 By the Woods, Chilmark, MA 02535
• 

  

  

  /10

  $330,000

  $20K PRICE DROP

  • Land
  • 1.26 Acres
  • $261,905 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 for 1 vehicle and a picturesque stretch of shoreline

  Alyssa Halisky Wallace & Co. Sotheby's

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

  

  

  /26

  $2,395,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,510 Sq Ft

  26 Bijahs Way, Chilmark, MA 02535

  This Chilmark 3 bedroom, 2 bath home has been meticulously maintained inside and out. A major addition and reconstruction of the original house was completed in 1991 & included a 22 x 43 addition, The completely new second floor added over 1,500 square feet & the work included new heating, plumbing, electrical, central AC, septic & well! Many nice features include spacious living spaces, a modern

  Brenda Galligan Karen M. Overtoom R.E.

  26 Bijahs Way, Chilmark, MA 02535
• 

  

  

  /39

  $3,295,000

  $100K PRICE DROP

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

  27 Clambelly Rd, Chilmark, MA 02535

  A place of serenity tucked in the woods of Chilmark. Beautifully designed & constructed home which was completely renovated in 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

  Julianna Flanders Flanders Real Estate

  27 Clambelly Rd, Chilmark, MA 02535
• 

  

  

  /53

  $9,875,000

  • 6 Beds
  • 5.5 Baths
  • 3,758 Sq Ft

  6 Wakeman Rd, Chilmark, MA 02535

  Set in a spectacular water view setting with private beach access, this exceptional coastal compound offers a rare blend of privacy, flexibility, and breathtaking scenery. The property is thoughtfully composed of a beautifully appointed main residence, a separate guest house, an artist’s studio, and a detached garage with an additional bedroom above — creating the ideal retreat for extended

  Jill Napior Tea Lane Associates

  6 Wakeman Rd, Chilmark, MA 02535
• 

  

  /15

  $1,975,000

  $300K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,176 Sq Ft

  9 Moshup Trail, Aquinnah, MA 02535

  Spectacular property in Aquinnah, featuring a newly installed and town-approved 6-bedroom septic system, ready to support your vision for expansion and renovation. Located on 4.7 acres filled with rolling meadows and stone walls, this property boasts a truly remarkable barn that was transported from Maine, and rebuilt on the Island. The grandfathered-in barn spans approximately 61' by 45' with

  Patrick McCarthy Grace Hagerty Real Estate Inc

  9 Moshup Trail, Aquinnah, MA 02535
• 

  

  /20

  $325,000

  $5K PRICE DROP

  • Land
  • 7,405 Sq Ft
  • $1,911,765 per Acre

  00 Moshup Trail, Aquinnah, MA 02535

  Tucked along the south shore of Aquinnah on Martha's Vineyard, this beach lot presents a chance to enjoy true oceanfront ownership. Accessed via Moshup Trail, this lot features a private gated entry with a pea stone parking area. A boardwalk, that winds through natural coastal vegetation, connects to a sandy trail that brings you over the bluff to the expansive shoreline. Secure your own stretch

  Sheila Morse Island Real Estate

  00 Moshup Trail, Aquinnah, MA 02535
• 

  

  /11

  $1,250,000

  • Land
  • 1.9 Acres
  • $657,895 per Acre

  15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535

  Nestled in a bucolic setting moments from the iconic Menemsha fishing village, this beautiful and fully engineered parcel is approved for a 6BR home. One of the few remaining Menemsha buildable lots makes this a rare opportunity. With room for a pool with a special permit!Surrounded by ancient stone walls on three sides and mature trees, the land has stunning sunset skies, lovely pastoral

  Jill Napior Tea Lane Associates

  15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
• 

  

  /7

  $2,500,000

  • Land
  • 1.4 Acres
  • $1,785,714 per Acre

  2 Other House Rd Unit 173, Chilmark, MA 02535

  Rare opportunity to build on Chilmark's south shore. This 1.4 acre parcel should allow for new construction of 3,100 square feet and 24 feet in height, by right, with building department approval. Views to the Atlantic Ocean and Chilmark Pond can be seen from the second floor. This parcel comes with a dock on the pond which provides access to a beautiful barrier beach on the Atlantic. Well in

  Russell Maloney Russell Maloney Real Estate

  2 Other House Rd Unit 173, Chilmark, MA 02535
• 

  

  /12

  $1,300,000

  $275K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 896 Sq Ft

  45 Quenames Rd, Chilmark, MA 02535

  Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two spacious bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with

  Dawn Bellante Sandpiper Realty, Inc.

  45 Quenames Rd, Chilmark, MA 02535
• 

  

  /37

  $3,050,000

  $300K PRICE DROP

  • 3 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 stunning settings, this coastal retreat captures sweeping views over the Atlantic and Noman’s Land. The main level offers an open living/dining/kitchen wrapped in windows and opening to a wraparound mahogany deck—ideal for sunrise coffee and sunset dinners. A Viking-equipped kitchen and a spacious ocean-facing primary suite complete this floor. The

  Jennifer O'hanlon Compass

  4 Nomans Watch Rd, Aquinnah, MA 02535
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  /42

  $4,995,000

  $655K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 5,402 Sq Ft

  205 South Rd, Chilmark, MA 02535

  CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a

  Tina Miller Donnelly + Co.

  205 South Rd, Chilmark, MA 02535
• 

  

  /3

  $375,000

  $75K PRICE DROP

  • Land
  • 8,712 Sq Ft
  • $1,875,000 per Acre

  00 Moshup Trail Unit 7-5, Aquinnah, MA 02535

  Spectacular, private beach lot located just off Moshup Trail. Gated entry, parking rights and a deeded 1/5 acre of beach on the Atlantic. This is not a buildable lot, no structures of any kind are permitted. Map 10, Lot 7-5

  Russell Maloney Russell Maloney Real Estate

  00 Moshup Trail Unit 7-5, Aquinnah, MA 02535
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  /38

  $3,795,000

  $400K PRICE DROP

  • 3 Beds
  • 3.5 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
• 

  

  /3

  $450,000

  • Land
  • 6,503 Sq Ft
  • $3,014,066 per Acre

  00 Moshup Trail Unit 14.2, Aquinnah, MA 02535

  Become one of only 21 members to access the exclusive Goff Beach, a gated community with parking. Traverse to the top of the sandy dune and overlook the sparkling ocean with wide sandy beach. A special opportunity rarely offered for sale. 0.15-acre parcel offers direct access to one of the most desirable stretches of shoreline on Martha’s Vineyard. Situated to the right of the Rainbow House, the

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

  00 Moshup Trail Unit 14.2, Aquinnah, MA 02535
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  /43

  $3,875,000

  $125K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,304 Sq Ft

  41 Moshup Trail, Aquinnah, MA 02535

  The Best of Aquinnah: Surf, Views, and Total Privacy. There is nothing quite like the south shore of Aquinnah, and this five-bedroom home puts you right in the heart of it. Tucked away along Moshup Trail, the property, lovingly referred to as "Surfside", is all about the Atlantic views and the effortless, barefoot lifestyle that comes with being this close to the water. The house is bright and

  Heidi Vanderhoop Tea Lane Associates

  41 Moshup Trail, Aquinnah, MA 02535
• 

  

  /34

  $1,499,000

  $100K PRICE DROP

  • 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
• 

  

  /32

  $5,200,000

  • 5 Beds
  • 3.5 Baths
  • 4,044 Sq Ft

  49 Gosnolds Way, Chilmark, MA 02535

  Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an

  Bonnie Pierce Wallace & Co. Sotheby's International Realty

  49 Gosnolds Way, Chilmark, MA 02535
• 

  

  /30

  $2,395,000

  $105K PRICE DROP

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

  16 South Rd, Chilmark, MA 02535

  Rare Chilmark compound with beach access, barn, horse stalls, and fenced pasture on 1.6 acres. Set just over the West Tisbury line, this restored 1885 farmhouse offers a compelling blend of authentic Vineyard character, modern comfort, and access to Chilmark’s coveted south shore beaches, including Lucy Vincent and Squibnocket. The property unfolds as a small country compound with a distinctly

  Michele Casavant Vineyard Village Realty

  16 South Rd, Chilmark, MA 02535
• 

  

  /34

  $1,600,000

  • 3 Beds
  • 3 Baths
  • 2,155 Sq Ft

  132 South Rd, Chilmark, MA 02535

  Nestled on a private, 1.9-acre lot along historic South Road in Chilmark, this charming New England retreat offers an exceptional sense of tranquility and classic Martha's Vineyard living. Built in 1950, Vineyard Home offers 2 bedrooms and 2 full bathrooms great light, cozy additional living spaces and fireplace. Multiple patios and gardens seamlessly connecting the living spaces to the

  Lisa Da Silva Compass

  132 South Rd, Chilmark, MA 02535
• 

  

  /14

  $1,275,000

  • Land
  • 3.91 Acres
  • $326,087 per Acre

  0 Cencelle Unit 57 & 56.1 (part of), Chilmark, MA 02535

  Set amid the rolling farmlands of Chilmark, this beautiful parcel offers an exceptional opportunity to create your own island retreat. Framed by stone walls, wooded surroundings, and open meadow views, the property combines privacy and natural beauty in a serene rural setting with glacial erratics and trails winding throughout. Elevated and peaceful, this is a rare opportunity to build a home

  Meg Bodnar Tea Lane Associates

  0 Cencelle Unit 57 & 56.1 (part of), Chilmark, MA 02535
• 

  

  /39

  $16,000,000

  • 2 Beds
  • 2 Baths
  • 1,041 Sq Ft

  0, 36, 38 Black Point Rd, 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 home sits on one lot with two detached studios alongside. Close to nature, this seasonal home

  Abby Rabinovitz Tea Lane Associates

  0, 36, 38 Black Point Rd, Chilmark, MA 02535
• 

  

  /15

  $1,195,000

  • Land
  • 5.7 Acres
  • $209,649 per Acre

  14 Ridge Rd Unit 94, Aquinnah, MA 02535

  Nearly 6 acres of land bordered by stonewalls on two sides. The property has been cleared, so you are able to see the level topography and mature trees. The location lends itself to a short walk to Lobsterville Beach or Red Beach on Menemsha Pond, where you can hop on your paddleboard or kayak or get to your mooring. There is fresh fish to catch off the beach or clams to gather from the Pond for

  Jill Napior Tea Lane Associates

  14 Ridge Rd Unit 94, Aquinnah, MA 02535
• 

  

  /24

  $3,225,000

  $270K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  12 E Pasture Rd, Aquinnah, MA 02535

  This elegant architectural home is set within a lovely rolling meadow on four and a half generous acres, surrounded by stone walls, blue sky, and tranquility at all times of year. 12 East Pasture is a peaceful retreat on the westernmost side of Martha's Vineyard, known for the beautiful beaches and quiet privacy. The house features multiple large windows and sliding glass doors, which flood the

  Elissa Lash Tea Lane Associates

  12 E Pasture Rd, Aquinnah, MA 02535
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  /46

  $2,490,000

  • 3 Beds
  • 3.5 Baths
  • 3,579 Sq Ft

  8 Jeffers Way, Aquinnah, MA 02535

  Tucked away on more than two acres along a private dirt road, this extensively updated post-and-beam home offers exceptional space and privacy in a peaceful Aquinnah setting. The property is surrounded by woodlands, open fields, streams, and ancient stone walls and is located approximately one mile from Aquinnah’s resident beaches.The four-bedroom, three-and-a-half-bath home offers

  Jennifer O'hanlon Compass LLC

  8 Jeffers Way, Aquinnah, MA 02535
• 

  

  /37

  $3,795,000

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

  96 Hammett Ln, Chilmark, MA 02535

  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
• 

  

  /7

  $349,000

  • Land
  • 1.26 Acres
  • $276,984 per Acre

  00 Moshup Trail Unit 27 & 146, Aquinnah, MA 02535

  Lovely beach lot off Moshup Trail in Aquinnah. Enjoy the sandy beach, Atlantic Ocean water and beauty of the South shore. This private beach lot is shared with only seven other members. Parking is located a short walk across the road from the beach access.Private parking limited to one car per member. This is not a buildable lot.

  Julianna Flanders Flanders Real Estate

  00 Moshup Trail Unit 27 & 146, Aquinnah, MA 02535
• 

  

  /29

  $3,950,000

  $400K PRICE DROP

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

  131 State Rd, Chilmark, MA 02535

  Magical waterfront Quitsa pond cottage with private dock will change your life living on the water. Every day is special when you have an intimate relationship with Quitsa Pond. Calm, safe and breathtaking, adventure is out the doorstep and the sunsets.... Designed with the setting in mind this sublime piece of architecture has wonderful spaces, fantastic detail and so much packed into a smaller

  Jim Feiner Feiner Real Estate

  131 State Rd, Chilmark, MA 02535
• 

  

  /3

  $785,000

  • Land
  • 3.8 Acres
  • $206,579 per Acre

  0 Jeffers Way Unit 165, Aquinnah, MA 02535

  Nestled within the serene landscape of Aquinnah, this 3.8-acre parcel offers a unique blend of natural beauty and historical significance. Bordered by ancient stone walls and mature vegetation, the elevated terrain provides a bucolic setting for a private residence. Already in place is a private well, 3-bedroom septic, and full engineering.

  Michele Casavant Vineyard Village Realty

  0 Jeffers Way Unit 165, Aquinnah, MA 02535
• 

  

  /10

  $1,325,000

  • Land
  • 4.28 Acres
  • $309,579 per Acre

  0 North Way, Chilmark, MA 02535

  Set just off North Road, this exceptional parcel offers a rare opportunity to build in a setting rich with natural beauty. Recently subdivided, this land combines privacy, character and thoughtful positioning. The lot is perfectly sited capturing serene woodland views and the natural contours of Middle Line Ridge. A 600ft stonewall lines the western property line, creating a timeless sense of

  Stacy Ickes Donnelly + Co.

  0 North Way, Chilmark, MA 02535
• 

  

  /42

  $7,500,000

  $1M PRICE DROP

  • 5 Beds
  • 7 Baths
  • 4,531 Sq Ft

  85 Reservoir Rd, Vineyard Haven, MA 02568

  Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone

  Alyssa Halisky Wallace & Co. Sotheby's

  85 Reservoir Rd, Vineyard Haven, MA 02568
• 

  

  /22

  $325,000

  $5K PRICE DROP

  • Land
  • 7,313 Sq Ft
  • $1,935,676 per Acre

  00 Moshup Trail Unit 6, Aquinnah, MA 02535

  Tucked along the south shore of Aquinnah on Martha’s Vineyard, this beach lot presents a chance to enjoy true oceanfront ownership. Accessed via Moshup Trail, this lot features a private gated entry with a pea stone parking area. A boardwalk, that winds through natural coastal vegetation, connects to a sandy trail that brings you over the bluff to the expansive shoreline. Secure your own stretch

  Diana Gilmore Island Real Estate

  00 Moshup Trail Unit 6, Aquinnah, MA 02535
• 

  

  /49

  $9,750,000

  • 7 Beds
  • 5 Baths
  • 3,617 Sq Ft

  23 Flanders Ln, Chilmark, MA 02535

  A rare offering of land, history, and sweeping water views — this exceptional 8.7+/- acre estate commands panoramic views of Menemsha Pond and Vineyard Sound from its rolling lawns and open meadows. Property includes parking and access to Menemsha Pond.Whether you're drawn by the storied architecture, the expansive land, or the irreplaceable Vineyard Sound vistas, this is a compound that

  Julianna Flanders Flanders Real Estate

  23 Flanders Ln, Chilmark, MA 02535
• 

  

  /46

  $3,400,000

  • 4 Beds
  • 2.5 Baths
  • 2,383 Sq Ft

  100 Gosnolds Way, Chilmark, MA 02535

  Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound & the Elizabeth Islands. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where you

  Julianna Flanders Flanders Real Estate

  100 Gosnolds Way, Chilmark, MA 02535
• 

  

  /46

  $3,900,000

  • 3 Beds
  • 4 Baths
  • 2,960 Sq Ft

  3 Bens Way, Chilmark, MA 02535

  Sited on 3.94 acres in the North Tabor Farm subdivision, this 3 bedroom, 4 bath farmhouse offers privacy in a quiet, wooded, agricultural setting abutting working pastures. Built in 1995, this home features elegant living room and dining rooms with 12 foot ceilings and large paned windows which flood the rooms with an abundance of natural light. Views are seen to the yard spaces and the heated,

  Russell Maloney Russell Maloney Real Estate

  3 Bens Way, Chilmark, MA 02535

Showing Results 41 - 75, Page 2 of 2