Dukes County MA Homes for Sale

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  /9

  $1,900,000

  • Land
  • 15.05 Acres
  • $126,246 per Acre

  0 High Mark Rd Unit 66, Chilmark, MA 02535

  A rare opportunity to build a private retreat awaits at this 15 acre land parcel centrally located in Chilmark. Once part of the High Mark estate, the property features groves of mature trees planted more than 100 years ago, creating a wondrous, secluded and private setting rarely found anywhere on the island today.The parcel directly abuts the nearly 80 acres of conservation land at the

  Russell Maloney Russell Maloney Real Estate

  0 High Mark Rd Unit 66, Chilmark, MA 02535
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  /34

  $2,250,000

  • 4 Beds
  • 4 Baths
  • 2,340 Sq Ft

  11 Oak Ln, Vineyard Haven, MA 02568

  Welcome to 11 Oak Lane, a rare West Tisbury offering that lives as a true Martha's Vineyard family compound, an income-producing investment, or both. Set on 2.7 private acres, the property has been meticulously maintained and recently updated from the systems up, giving you the flexibility to gather generations under one address, live in one home and rent the other, or simply enjoy an exceptional

  Patrick McCarthy Grace Hagerty Real Estate Inc

  11 Oak Ln, Vineyard Haven, MA 02568
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  /4

  $799,900

  • Land
  • 1.4 Acres
  • $571,357 per Acre

  90 Charles Neck Way, West Tisbury, MA 02568

  Spacious 1.4-acre corner lot in Vineyard Meadow Farms. This private parcel sits on a paved road with no unwanted through traffic and is centrally located to all Island towns. Enjoy a peaceful neighborhood and easy access to Long Point Wild Refuge Beach and the Nature Preserve conservation land, featuring 632 acres of Trustees of the Reservations beach and trails. Pack a lunch and spend a relaxing

  Kimberly Rocci Keller Williams Realty Colonial Partners

  90 Charles Neck Way, West Tisbury, MA 02568
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  /29

  $3,150,000

  • 4 Beds
  • 3.5 Baths
  • 2,791 Sq Ft

  8 Atwood Cir, Edgartown, MA 02539

  This charming and historic home is ideally situated at the head of Atwood Circle, a private neighborhood just off Dunham Road, and only a short stroll to town. Recently renovated, the residence blends classic character with modern comfort. The main level features a spacious living room, a cozy den with fireplace, a dining area, and an updated kitchen—perfect for both everyday living and

  Gerrett Conover Landvest MV

  8 Atwood Cir, Edgartown, MA 02539
• 

  

  

  /25

  $599,000

  • 2 Beds
  • 1 Bath
  • 725 Sq Ft

  124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568

  JUST COMPLETED ~ fully renovated exterior including a new roof, siding, shutters, trim, all new windows, doors, stairways, and decks. Outstanding move-in-ready, year-round two-bedroom ground-level condo with dedicated parking in an ideal Vineyard Haven location close to the ferry, Main Street shops, and restaurants.The beautifully maintained common grounds feature colorful landscaping, picnic

  Stephanie Roache Donnelly + Co

  124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
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  /22

  $1,100,000

  • 2 Beds
  • 1 Bath
  • 1,118 Sq Ft

  4 5th St N, Edgartown, MA 02539

  An exciting rare find off the Edgartown / Tisbury road directly across from the bike path. The first floor open plan includes a fire place, family room and kitchen with a walk out to the wrap around porch. Two pleasant bedrooms and a full bath are on the first floor. The upper level loft opens to the living room visually expanding the living space. The house has the benefit of a full basement

  Doug Burke Signal House Group at Compass

  4 5th St N, Edgartown, MA 02539
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  /6

  $2,795,000

  • Land
  • 3.05 Acres
  • $916,393 per Acre

  Lot 4B Browns Farm Ln Unit 10, Edgartown, MA 02539

  Tucked off Meetinghouse Way, this 3-acre parcel offers an opportunity to create something lasting on the Vineyard. Open pasture sweeps across the property's core, framed by bordering woodland that lends a sense of privacy without sacrificing the light and openness that makes the setting so appealing. Just under 2.5 miles from the Village and South Beach, the location balances seclusion with easy

  Courtney Marek Sandpiper Realty

  Lot 4B Browns Farm Ln Unit 10, Edgartown, MA 02539
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  /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
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  /31

  $1,488,000

  • 5 Beds
  • 4 Baths
  • 2,884 Sq Ft

  39 Ferro Way, Vineyard Haven, MA 02568

  Tucked away on a quiet cul-de-sac, this beautifully maintained single-family home offers the perfect blend of privacy and convenience. Built in 2020, the property features 5 spacious bedrooms and 4 full bathrooms across 2,884 square feet of thoughtfully designed living space.Set on a generous 15,593 sq ft lot, the home provides ample outdoor space with exciting potential for a guest house,

  Emily Flake Viewpoints

  39 Ferro Way, Vineyard Haven, MA 02568
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  /20

  $8,900,000

  • 4 Beds
  • 8 Baths
  • 7,767 Sq Ft

  4 Jacobs Neck Rd, Edgartown, MA 02539

  Extraordinary Privacy in Boldwater, Edgartown. Over 10 acres of pristine acreage abutting extensive conservation land. Dwellings built by master craftsmen with a variety of potential options to combine with your vision of the perfect Vineyard compound for your family and friends to enjoy for generations. Deeded pond and beach access along with association tennis courts and common land are

  Deb Hancock Hancock Real Estate

  4 Jacobs Neck Rd, Edgartown, MA 02539
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  /7

  $2,795,000

  • Land
  • 3.05 Acres
  • $916,393 per Acre

  Lot 4A Browns Farm Ln Unit Portion of 10, Edgartown, MA 02539

  Located off Meetinghouse Way, this 3-acre parcel offers something truly special: room to breathe. Open pasture rolls across the heart of the property, while bordering woodland creates a setting that feels private yet open and airy. The location is less than 2.5 miles from Main Street and South Beach, offering convenient access to both town amenities and the sand and surf of the south shore.

  Courtney Marek Sandpiper Realty

  Lot 4A Browns Farm Ln Unit Portion of 10, Edgartown, MA 02539
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  /24

  $1,625,000

  • 3 Beds
  • 2.5 Baths
  • 1,962 Sq Ft

  109 Litchfield Rd, Edgartown, MA 02539

  CHAPPAQUIDDICK – Set back from the road on an oversized parcel, this spacious three-bedroom home offers both privacy and convenience, making it ideal for every season. A detached workshop provides exceptional versatility, offering ample space for storing boating and beach gear, fishing equipment, or serving as a creative workspace. Distant second-story water views and proximity to conservation

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  109 Litchfield Rd, Edgartown, MA 02539
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  /20

  $19,900,000

  • 5 Beds
  • 7 Baths
  • 6,577 Sq Ft

  33 Boldwater Rd, Edgartown, MA 02539

  Exceptional Waterfront Retreat on Edgartown Great Pond. A very special offering with lovely sandy pond beach and deeded ocean beach access. Located in a private but convenient area - only 12 minutes to the airport or Edgartown village. This is a rare opportunity to purchase a meticulously crafted stone house and guest house with pool in a naturalized setting that redefines the conventions of

  Deb Hancock Hancock Real Estate

  33 Boldwater Rd, Edgartown, MA 02539
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  /41

  $8,900,000

  • 8 Beds
  • 9 Baths
  • 8,170 Sq Ft

  150 E Chop Dr, Oak Bluffs, MA 02568

  BIG BLUFF- Recognized for its architectural significance and featured in leading design publications, this home stands as one of the Vineyard’s most notable coastal residences. Set along the prestigious shoreline of East Chop, this estate represents a rare convergence of architectural pedigree, craftsmanship, and irreplaceable setting. Designed by Hutker Architects, built by J.G. Early, and

  Andrew McElhinney Compass LLC

  150 E Chop Dr, Oak Bluffs, MA 02568
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  /37

  $2,495,000

  • 6 Beds
  • 2.5 Baths
  • 2,577 Sq Ft

  16 Atlantic Ave, Oak Bluffs, MA 02557

  Oak Bluffs | East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The stately five-bedroom main residence is rich in character and nostalgic charm, thoughtfully updated to enhance comfort for year-round living. Tucked privately at the rear of the

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  16 Atlantic Ave, Oak Bluffs, MA 02557
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  /6

  $2,795,000

  • Land
  • 0 Sq Ft

  Lot 4B Browns Farm Ln, Edgartown, MA 02539

  Tucked off Meetinghouse Way, this 3-acre parcel offers an opportunity to create something lasting on the Vineyard. Open pasture sweeps across the property's core, framed by bordering woodland that lends a sense of privacy without sacrificing the light and openness that makes the setting so appealing. Just under 2.5 miles from the Village and South Beach, the location balances seclusion with easy

  Courtney Marek

  Lot 4B Browns Farm Ln, Edgartown, MA 02539
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  /3

  $1,650,000

  • Land
  • 1.57 Acres
  • $1,050,955 per Acre

  63 Division Rd Unit 46, Edgartown, MA 02539

  LOT #4 - The last lot available in this 5-lot Edgartown subdivision! Division Road is located between Meshacket and Meetinghouse Way, less than 1 mile from the center of town. This concept was thoughtfully and creatively developed in an effort to create a new and upcoming neighborhood. The new residences will be able to accommodate up to 7 bedrooms, and offer the opportunity to create your own

  Cheri Mason Landvest MV

  63 Division Rd Unit 46, Edgartown, MA 02539
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  /34

  $11,250,000

  • 7 Beds
  • 8 Baths
  • 10,142 Sq Ft

  14 Trapps Pond Rd, Edgartown, MA 02539

  Located on nearly 2-acres in the exclusive and newly created Trapps Pond Preserve, is this grand luxuriously appointed home. This is one of four homes being built and will be the first to be completed. Every room in the house is on a scale not often afforded in a Vineyard home, with 10 ft coffered ceilings and open/flowing floor plan. There is an abundance of light streaming in from the oversized

  Gerrett Conover Landvest MV

  14 Trapps Pond Rd, Edgartown, MA 02539
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  /47

  $4,650,000

  • 4 Beds
  • 3.5 Baths
  • 3,702 Sq Ft

  7 Black Point Rd, Chilmark, MA 02535

  Laid-back charm meets island character in this one-of-a-kind up-island beach house. Set on 5.5 acres of natural beauty, this four-bedroom, three-bath main house is full of updates, with bright, fun spaces and a relaxed summer-camp vibe. The creative layout on a single level connects sections of the house via breezy walkway, leading to a bedroom wing including a separate family room, off the

  Meg Bodnar Tea Lane Associates

  7 Black Point Rd, Chilmark, MA 02535
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  /6

  $2,795,000

  • Land
  • 0 Sq Ft

  Lot 4A Browns Farm Ln, Edgartown, MA 02539

  Located off Meetinghouse Way, this 3-acre parcel offers something truly special: room to breathe. Open pasture rolls across the heart of the property, while bordering woodland creates a setting that feels private yet open and airy. The location is less than 2.5 miles from Main Street and South Beach, offering convenient access to both town amenities and the sand and surf of the south shore.

  Courtney Marek

  Lot 4A Browns Farm Ln, Edgartown, MA 02539
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  /15

  $950,000

  • 2 Beds
  • 1 Bath
  • 1,074 Sq Ft

  22 Firehouse Ln, Oak Bluffs, MA 02557

  Tucked away on a quiet side street just 0.7 miles from Circuit Avenue, this charming Oak Bluffs cottage offers the rare combination of privacy and proximity to town. The original two-bedroom, one-bath home was thoughtfully expanded to include a bright great room that opens directly to a large fenced yard — ideal for outdoor dining, pets, or simply enjoying Vineyard summers. The property is

  Jennifer O'hanlon Compass LLC

  22 Firehouse Ln, Oak Bluffs, MA 02557
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  /30

  $1,245,000

  • 3 Beds
  • 2 Baths
  • 1,752 Sq Ft

  66 Barnes Rd, Vineyard Haven, MA 02568

  Oak Bluffs~ Classic Cape charm meets modern efficiency in this move-in-ready 3-bedroom home. Thoughtfully maintained and beautifully presented, the home features sun-filled living spaces, an updated kitchen, and comfortable bedrooms designed for easy everyday living. Enjoy year-round comfort with energy-efficient mini-split systems providing both heating and air conditioning, offering

  Marilyn Moses Ocean Park Realty Inc

  66 Barnes Rd, Vineyard Haven, MA 02568
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  /10

  $1,275,000

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft

  34 10th St S, Edgartown, MA 02539

  Welcome to easy Edgartown living in this charming 3-bedroom, 2-bath ranch offering comfort, convenience, and classic Vineyard appeal. Designed for effortless single-level living, the home features a spacious living room, an open kitchen and dining area, and a thoughtful layout ideal for both everyday life and entertaining. The private primary suite includes its own bath, while two additional

  Chrissie Teague Insight Realty Group, Inc.

  34 10th St S, Edgartown, MA 02539
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  /41

  $4,800,000

  • 4 Beds
  • 3.5 Baths
  • 3,715 Sq Ft

  9 Martha's Way, Edgartown, MA 02539

  Welcome to this NEWLY CONSTRUCTED gorgeous gambrel home with a POOL that is close to SOUTH BEACH and EDGARTOWN VILLAGE! This home sits upon a flat, beautiful parcel of land with mature trees. The facade of the home presents an inviting covered porch with free standing columns, a granite entry step, mahogany decking and shiplapped ceiling. Attention to architectural detail presents at moment one.

  Michele Casavant Vineyard Village Realty

  9 Martha's Way, Edgartown, MA 02539
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  /31

  $1,995,000

  • 3 Beds
  • 2.5 Baths
  • 1,431 Sq Ft

  33 Vineyard Ave, Oak Bluffs, MA 02557

  Welcome to 33 Vineyard Ave a completely renovated two-bedroom, two bathroom primary residence and attached one bedroom, one bathroom secondary suite offering a move-in ready, flexible living investment opportunity nestled in the heart of Oak Bluffs. This property offers perfect proximity to Downtown Oak Bluffs with fast access to harbor front, restaurants, shopping, historic parks, multiple

  Allison Parry Douglas Elliman MV

  33 Vineyard Ave, Oak Bluffs, MA 02557
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  /37

  $15,000,000

  • 7 Beds
  • 9 Baths
  • 6,462 Sq Ft

  14 Cow Bay Rd, Edgartown, MA 02539

  Set within the prestigious Cow Bay Association, one of the island’s most exclusive and sought-after enclaves, this extraordinary 1.5-acre estate embodies the pinnacle of refined coastal living. Accessed via private road through protected land, the property includes access to over 2,000 feet of private shoreline, beach cabanas, Trapps Pond and potential mooring. Despite its remarkable seclusion,

  Gerrett Conover Landvest MV

  14 Cow Bay Rd, Edgartown, MA 02539
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  /13

  $2,500,000

  • 1 Bed
  • 1 Bath
  • 726 Sq Ft

  18 Allen Farm Rd, Chilmark, MA 02535

  Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1+ bedroom cottage with screened porch. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, especially for solar designs. The cottage is offered full furnished with exception of some art and a few

  Patty Kendall Kendall & Kendall

  18 Allen Farm Rd, Chilmark, MA 02535
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  /36

  $2,400,000

  • 5 Beds
  • 4 Baths
  • 3,328 Sq Ft

  159 Lake St, Vineyard Haven, MA 02568

  Tucked back from the road on scenic Lake Street, this one-of-a-kind home offers privacy and charm on a beautifully landscaped 0.7 acre lot accented by mature trees and a classic stone wall. Inside, rich wood detailing, exposed beams, and high ceilings create a warm and inviting atmosphere. The home’s four-level design provides exceptional character and flexibility. The main level features a

  Alyssa Halisky Wallace & Co. Sotheby's

  159 Lake St, Vineyard Haven, MA 02568
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  /24

  $3,495,000

  • 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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  /33

  $3,200,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  24 Beetle Swamp Rd, Edgartown, MA 02539

  Bucolic Sweetened Water Farm has the agrarian feel of up island yet it's close to the heart and vibe of Edgartown. 24 Beetle Swamp Rd is a custom built home, a Vineyard gem constructed by local craftsmen over time with pastoral views. The current main house has 3 bedrooms and two bathrooms, however the lot can support up to 6 bedrooms according to the Edgartown board of health and building

  Kathleen Dawson Donnelly + Co.

  24 Beetle Swamp Rd, Edgartown, MA 02539
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  /29

  $2,950,000

  • 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
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  /46

  $5,450,000

  • 4 Beds
  • 5.5 Baths
  • 3,300 Sq Ft

  8 Paddock Rd, Oak Bluffs, MA 02557

  Refined Vineyard Living in The Preserve - Set atop a knoll overlooking sweeping grassland and the pond, this exceptional residence embodies the perfect balance of classic coastal architecture and modern sophistication. Located within the prestigious enclave of The Preserve, the home offers a combination of privacy, elegance, and seamless indoor-outdoor living. At its core, an expansive great room

  Lesley Heidt Sandpiper Realty

  8 Paddock Rd, Oak Bluffs, MA 02557
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  /49

  $4,589,000

  • 4 Beds
  • 4 Baths
  • 3,299 Sq Ft

  31 North St, Edgartown, MA 02539

  Nothing was left untouched with this total renovation, and the downtown location of this home is superb. The Vineyard decorators team turned this home around with all new windows, new flooring, 4 full new timeless tiled bathrooms, all Viking appliances, beverage fridge, 6 burner stove, Miele coffee maker, warming drawer for your parties you will be having in this gourmet kitchen. With Sonos sound

  Jim Joyce Carroll & Vincent R.E.

  31 North St, Edgartown, MA 02539
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  /3

  $525,000

  • Land
  • 10,240 Sq Ft
  • $2,233,092 per Acre

  Lot 1 Dolan Ave Unit 7, Tisbury, MA 02568

  A level parcel in a convenient Vineyard Haven location offering ease and opportunity. Set within an established neighborhood, it’s just a short stroll or bike ride to public beach access at the end of Owen Little Way. Only one mile from the vibrant shops and restaurants of Main Street, and less than two miles from the sandy shores of Lake Tashmoo beach, the setting provides the perfect balance of

  Katie Donahue Sandpiper Realty

  Lot 1 Dolan Ave Unit 7, Tisbury, MA 02568
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  /41

  $1,850,000

  • 5 Beds
  • 3 Baths
  • 2,068 Sq Ft

  4 Hye Ln, Edgartown, MA 02539

  Pristine and superbly maintained, this three-bedroom home and two-bedroom guest house has tremendous upside potential and a substantial rental history. This property is tied to town sewer and will allow for up to 7 bedrooms. One additional bedroom in the main house is possible within the existing footprint with appropriate town approvals. There is an additional 668 sq. ft. of finished space in

  Buder Team Sandpiper Realty, Inc.

  4 Hye Ln, Edgartown, MA 02539
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  /54

  $2,000,000

  • 5 Beds
  • 3.5 Baths
  • 2,075 Sq Ft

  63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

  Set within the coveted Vineyard Meadow Farms community, this West Tisbury property presents a rare opportunity to own a thoughtfully configured compound in one of the island’s most peaceful and sought-after settings. Privately sited on a generous parcel, the property is surrounded by natural beauty and offers a sense of calm that defines up-island living.The three-bedroom main residence is

  Valene Pires The Agency

  63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
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  /8

  $330,000

  • Land
  • 1.26 Acres
  • $261,905 per Acre

  0 Moshup Trail Unit 73508205, 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 International Realty

  0 Moshup Trail Unit 73508205, Aquinnah, MA 02535
• 

  

  /30

  $8,950,000

  • 5 Beds
  • 7 Baths
  • 4,078 Sq Ft

  1 Field Club Dr, Edgartown, MA 02539

  Nestled within the prestigious Field Club, this exceptional five-bedroom compound captures the essence of refined island living, blending timeless elegance with modern sophistication. A welcoming foyer introduces a light-filled, open-concept main level designed for both comfort and entertaining. The gourmet kitchen is a standout, featuring high-end appliances, granite countertops, and custom

  Tom Wallace

  1 Field Club Dr, Edgartown, MA 02539
• 

  

  /3

  $525,000

  • Land
  • 10,454 Sq Ft
  • $2,187,500 per Acre

  Lot 1 Dolan Ave, Tisbury, MA 02568

  A level parcel in a convenient Vineyard Haven location offering ease and opportunity. Set within an established neighborhood, it’s just a short stroll or bike ride to public beach access at the end of Owen Little Way. Only one mile from the vibrant shops and restaurants of Main Street, and less than two miles from the sandy shores of Lake Tashmoo beach, the setting provides the perfect balance of

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  Lot 1 Dolan Ave, Tisbury, MA 02568
• 

  

  /48

  $1,495,000

  • 5 Beds
  • 4 Baths
  • 2,516 Sq Ft

  651 State Rd, Vineyard Haven, MA 02568

  Fabulous four-building farmhouse compound offered in the heart of West Tisbury. This cherished property features a well-maintained classic 1880 main house with 4 bedrooms and 3 baths, plus a fully separate guest cottage with 1 bedroom and 1 bath — offering immediate income potential through seasonal or year-round rental. A bunkhouse/office building provides flexible space ideal for a home office

  Jim Feiner Feiner Real Estate

  651 State Rd, Vineyard Haven, MA 02568

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