Dukes County MA Homes for Sale

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  /42

  $6,275,000

  • 4 Beds
  • 5.5 Baths
  • 4,136 Sq Ft

  10 Tilton Way, Edgartown, MA 02539

  This Greek Revival style home blends timeless architecture with a bright, modern open floor plan, all presented in impeccable condition. A welcoming front foyer leads into a beautifully appointed kitchen featuring high-end appliances, a large center island, and seamless flow into the dining and living areas. The living room is anchored by a fireplace and filled with natural light throughout.

  Gerrett Conover Landvest MV

  10 Tilton Way, Edgartown, MA 02539
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  /33

  $2,300,000

  • 4 Beds
  • 3.5 Baths
  • 2,428 Sq Ft

  35 Nat's Farm Ln, West Tisbury, MA 02568

  Nestled within the prestigious Nats Farm Association, this beautifully crafted West Tisbury home offers a quintessential Martha’s Vineyard retreat. The first floor features a bright, open layout with a well-appointed kitchen, dining area, and inviting living room, ideal for gatherings. The spacious primary suite is located on the main level and includes a private office and a spa-like bath with

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  35 Nat's Farm Ln, West Tisbury, MA 02568
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  /40

  $1,395,000

  • 4 Beds
  • 3 Baths
  • 1,305 Sq Ft

  46 Kennebec Ave, Oak Bluffs, MA 02557

  This exquisite Victorian home, lovingly preserved by the same family for over a generation, stands in outstanding condition and is perfectly situated in the vibrant heart of Oak Bluffs Center. Enjoy the convenience of being just steps away from the Public Beach, Steamship Authority, Oak Bluffs Harbor, a supermarket, and a variety of charming restaurants and shops that contribute to Oak Bluffs'

  Michael Schweikert Ocean Park Realty Inc

  46 Kennebec Ave, Oak Bluffs, MA 02557
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  /38

  $1,495,000

  • 1 Bed
  • 2.5 Baths
  • 1,254 Sq Ft

  20 Union St Unit C, Tisbury, MA 02568

  Welcome to 20 Union Court, Unit C at the Old Stone Bank Condominiums - a unique community in the heart of downtown Vineyard Haven. This two-level condo offers a truly special Vineyard lifestyle. Enter through the inviting porch into an open floor plan filled with character, thoughtful details, and sun-lit rooms that create a warm and welcoming atmosphere throughout. This home features a

  Michele Moore Island Real Estate

  20 Union St Unit C, Tisbury, MA 02568
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  /25

  $7,300,000

  • 5 Beds
  • 5.5 Baths
  • 3,539 Sq Ft

  65 Carl's Way, West Tisbury, MA 02568

  Stylized Private Waterfront Retreat close to townperched along the tranquil shores of the beloved Tisbury Great Pond, this stunning Hutker-designed waterfront home is a seamless blend of coastal elegance and timeless island charm. Designed to capture the essence of Vineyard living, the home features intimate water views, sun-drenched interiors, and carefully curated finishes

  Jill Napior Tea Lane Associates

  65 Carl's Way, West Tisbury, MA 02568
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  /31

  $7,250,000

  • 5 Beds
  • 6.5 Baths
  • 5,454 Sq Ft

  54 Fuller St, Edgartown, MA 02539

  This stately Greek Revival home lies on beautiful Fuller Street and a short walk to the beach. This 5-bedroom / 5.5-bath home features a beautiful foyer with arches and paneling leading past a grand staircase to a beautiful family room, kitchen and screened porch overlooking the backyard. There is an ensuite ground first floor bedroom and office off the hall as well as a side mudroom entry and

  Gerrett Conover Landvest MV

  54 Fuller St, Edgartown, MA 02539
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  /27

  $1,850,000

  • 4 Beds
  • 2 Baths
  • 1,833 Sq Ft

  22 Old Harbor Ln, Oak Bluffs, MA 02557

  Quintessential Waterview Farm! Built as a year-round home with the charm of the original cottages, this well-loved retreat awaits its next chapter. The sunny, open floor plan offers two bedrooms and a full bath on each level, with generous gathering spaces throughout. A skylit kitchen is tucked into a corner of the main living area, where a curved wall of glass opens to a deck and private yard.

  Lisa Stewart Sandpiper Realty, Inc.

  22 Old Harbor Ln, Oak Bluffs, MA 02557
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  /25

  $1,550,000 Open House 5/23

  • 5 Beds
  • 5 Baths
  • 2,266 Sq Ft

  345 North Rd, Chilmark, MA 02535

  This versatile Chilmark property offers a rare combination of privacy, flexibility, and investment potential. The main residence features 4 bedrooms and 4 bathrooms, complemented by a detached 1-bedroom, 1-bath suite with an attached garage—ideal for guests, extended family, or rental income. Two separate parking areas provide ample space and convenience. Abutting over 200 acres of protected

  Jessica Campbell Flanders Real Estate

  345 North Rd, Chilmark, MA 02535
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  /78

  $35,000,000

  • 8 Beds
  • 8 Baths
  • 6,841 Sq Ft

  146 Quenames Rd, Chilmark, MA 02535

  Set on 60 acres along one of the most private and unspoiled stretches of Atlantic coastline in Chilmark, this exceptional estate offers a rare combination of scale, privacy, and enduring coastal beauty. With over 800 feet of direct ocean frontage, the property commands expansive views while maintaining a true sense of seclusion, an increasingly scarce offering on Martha’s Vineyard. A gated drive

  Grace Hagerty Grace Hagerty Real Estate Inc

  146 Quenames Rd, Chilmark, MA 02535
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  /26

  $7,850,000

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

  24 Katama Bay View Rd, Edgartown, MA 02539

  This classic New England home in Katama offers a refined blend of timeless architecture and modern comfort, set on a spacious, beautifully landscaped lot. The main house features three well-appointed bedrooms, including a light-filled primary suite and inviting guest rooms designed for comfort and privacy. The open-concept living area is ideal for entertaining, highlighted by a cozy fireplace and

  Tom Wallace

  24 Katama Bay View Rd, Edgartown, MA 02539
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  /52

  $1,800,000

  • 4 Beds
  • 3 Baths
  • 3,158 Sq Ft

  188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

  Long Point Beach - House plus ADU! The crashing surf of the south shore, the tranquil waters of Long Cove Pond, the walking trails of the Wildlife Refuge - all minutes from this charming West Tisbury property, appropriately referred to as "Pinch Me" by the current owners. Here, the connection to nature is seamless. The main house sits high atop the trees and overlooks a sprawling lawn from two

  Idalyn Macchia Gilstad Wallace & Co. Sotheby's

  188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
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  /27

  $14,250,000

  • 6 Beds
  • 5.5 Baths
  • 4,820 Sq Ft

  68 N Water St, Edgartown, MA 02539

  This expansive historic compound in the heart of Edgartown Village blends timeless charm with modern luxury. Just steps from top restaurants and shops, the home has been fully renovated by Stern McCafferty Architecture + Interiors, pairing contemporary design with classic architectural detail. Inside, open-plan living spaces create an effortless flow for entertaining, with a sleek kitchen and

  Tom Wallace

  68 N Water St, Edgartown, MA 02539
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  /18

  $799,000

  • 2 Beds
  • 1 Bath
  • 623 Sq Ft

  1 Pease Ave, Oak Bluffs, MA 02557

  Tucked away on a quiet no-thru street near the Tabernacle and Trinity Park, this meticulously maintained year-round Martha’s Vineyard Camp Meeting Association cottage blends charm and convenience. Thoughtful 2023 updates—including a new kitchen with stainless steel appliances, refreshed bathroom, upgraded insulation and electrical, three mini-splits, onsite laundry, spiral staircase, and new

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  1 Pease Ave, Oak Bluffs, MA 02557
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  /37

  $1,395,000

  • 3 Beds
  • 2.5 Baths
  • 1,783 Sq Ft

  51 Summer St, Vineyard Haven, MA 02568

  Beautifully renovated and full of charm, this Vineyard Haven home combines stylish design with modern function in one of the island’s most sought-after neighborhoods. Every space has been thoughtfully planned to offer flexibility, comfort, and light, while maintaining the relaxed character that defines Martha’s Vineyard living. The result is a home that feels spacious yet inviting—with elegant

  Janet Scott eXp Realty

  51 Summer St, Vineyard Haven, MA 02568
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  /6

  $2,300,000

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  60 Crocker Dr, Edgartown, MA 02539

  Nestled in the heart of Katama, 60 Crocker Drive offers a discerning buyer a unique opportunity to renovate a house and guest house. Bring your creativity. With 2 pre-existing structures and a total of 3 bedrooms, you can renovate the existing structures or start from scratch to make it your own. The main house is a reverse-style home with a garage underneath. The guest house is an A-frame home.

  Sheila Morse Island Real Estate

  60 Crocker Dr, Edgartown, MA 02539
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  /14

  $5,100,000

  • Land
  • 2.34 Acres
  • $2,182,285 per Acre

  7 Overview Ln Unit 47, Oak Bluffs, MA 02557

  A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy exclusive

  Alyssa Halisky Wallace & Co. Sotheby's

  7 Overview Ln Unit 47, Oak Bluffs, MA 02557
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  /14

  $5,100,000

  • Land
  • 2.34 Acres
  • $2,179,487 per Acre

  7 Overview Ln, Oak Bluffs, MA 02557

  A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association on Martha's Vineyard. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck,

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  7 Overview Ln, Oak Bluffs, MA 02557
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  /7

  $2,000,000

  • Land
  • 21,801 Sq Ft
  • $3,996,004 per Acre

  0 State Rd Unit 29.3, Vineyard Haven, MA 02568

  1/2 acre of commercial land in the State Road B-2 district. Possibilities are endless for the right business. Also available, next door, is a commercial building that currently has 10 rental units. $6,000,000.

  Peter Cronig Cronigs Real Estate

  0 State Rd Unit 29.3, Vineyard Haven, MA 02568
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  /34

  $1,599,000

  • 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
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  /28

  $2,495,000

  • 4 Beds
  • 3 Baths
  • 1,968 Sq Ft

  105 Whalers Walk, Edgartown, MA 02539

  Fresh, stylish, and fun best describe this inviting four-bedroom Edgartown home with a newly completed pool! Thoughtfully renovated from top to bottom, the interior offers warm, functional living spaces where every detail has been carefully considered. The same level of attention carries outdoors to a true backyard oasis, complete with a heated saltwater pool, multiple patios, a pergola, and an

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  105 Whalers Walk, Edgartown, MA 02539
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  /18

  $1,195,000

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  10 Winthrop Ave, Oak Bluffs, MA 02557

  Oak Bluffs- Fully renovated and just completed, this three-bedroom, two-bath home is ready for immediate occupancy! Ideally located just moments from downtown Oak Bluffs and the vibrant harborfront, you’ll enjoy easy access to shops, dining, beaches, and ferry connections. Featuring modern updates throughout, this home offers the perfect blend of comfort and convenience.

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  10 Winthrop Ave, Oak Bluffs, MA 02557
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  /48

  $3,950,000

  • 3 Beds
  • 4.5 Baths
  • 3,314 Sq Ft

  20 Edson Forrest Rd, West Tisbury, MA 02575

  Exquisite home befitting its stunning location on four serene acres surrounded by conservation and agricultural lands and overlooking a neighbor's private pond. This special spot is authentic up-island character at its best. A full restoration of this this three-bedroom house (with six-bedroom septic) in 2022 created a luxury home with a thoughtful layout, 2 story expansion, and exceptional

  Meg Bodnar Tea Lane Associates

  20 Edson Forrest Rd, West Tisbury, MA 02575
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  /26

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  17 Mariner Rd, Vineyard Haven, MA 02568

  This home has been patiently awaiting its next chapter in Vineyard living. Built in 1983, it offers a functional center-entrance layout with efficient use of space and modern systems already in place. The generously sized lot, both wide and deep, presents an excellent opportunity to expand the home's footprint and tailor it to your vision. Located in the Spring Hill neighborhood of single-family

  Karl Olsen Carlson & Company, LLC

  17 Mariner Rd, Vineyard Haven, MA 02568
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  /4

  $1,325,000

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

  0 N Road 15 Belhaven Way Unit 4-2, 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 N Road 15 Belhaven Way Unit 4-2, Chilmark, MA 02535
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  /21

  $2,250,000

  • 3 Beds
  • 2 Baths
  • 1,867 Sq Ft

  237 Lagoon Pond Rd, Vineyard Haven, MA 02568

  Ideally located at the beginning of Hines Point, this light-filled, well-maintained home offers a central setting with easy access to the Lagoon, the MV Museum, and town. Public water access is just a short walk away, making it easy to enjoy all the benefits of this special area.Set on a gentle rise overlooking the Lagoon, the home is filled with natural light and offers beautiful water

  Alison Rich Carroll & Vincent R.E.

  237 Lagoon Pond Rd, Vineyard Haven, MA 02568
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  /3

  $1,325,000

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

  0/15 N 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.

  0/15 N Way, Chilmark, MA 02535
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  /21

  $1,700,000

  • Land
  • 37,026 Sq Ft
  • $2,000,000 per Acre

  4 Wilson's Landing, Edgartown, MA 02539

  Build your dream home in Katama just 2 miles to the parking area at South Beach, and the same distance to the heart of vibrant Edgartown village. This wooded parcel of vacant land is almost an acre in size and will support SEVEN bedrooms once tied into town sewer. Swimming pool and Accessory Dwelling Unit are allowed "by right" (certain restrictions apply to ADUs; an unrestricted 900 sq ft

  Bonnie Pierce Wallace & Co. Sotheby's International Realty

  4 Wilson's Landing, Edgartown, MA 02539
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  /13

  $1,645,000

  • Land
  • 3.32 Acres
  • $495,482 per Acre

  26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575

  Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides - a setting unlike

  Dawn Bellante-Holand Sandpiper Realty

  26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575
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  /64

  $2,579,000

  • 4 Beds
  • 2 Baths
  • 1,399 Sq Ft

  34 Windemere Rd, Oak Bluffs, MA 02557

  Set along the shimmering edge of The Lagoon and Brush Pond, this rare offering captures the essence of classic island living, with expansive water views, on a little known enclave of only 9 homes. The house dates back to 1910 and was thoughtfully renovated in 2019, blending a timeless Vineyard location with all the modern comforts one would want. The house is perfectly sited to take full

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  34 Windemere Rd, Oak Bluffs, MA 02557
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  /22

  $325,000

  • 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
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  /2

  $1,150,000

  • Land
  • 2 Acres
  • $575,000 per Acre

  834 State Rd Unit 133, Aquinnah, MA 02535

  Gorgeous hilltop water view property looks out over the Atlantic Ocean. This building site is optimal for a passive or active solar home with ideal south-west orientation for panels and maximizing light. Great breezes come from the southwest keeping down the mosquito interactions. The driveway approaches from the rear. This parcel also offers the ability to create a pond in a depression near the

  Jim Feiner Feiner Real Estate

  834 State Rd Unit 133, Aquinnah, MA 02535
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  /55

  $2,180,000

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

  25 Pennacook Ave, Oak Bluffs, MA 02557

  A unique offering in the heart of the historic Copeland District of downtown Oak Bluffs. This cherished main residence and guest house, embody the timeless charm that defines this beloved community. Just minutes from Circuit Ave, the ferries and harbor, and a block from Inkwell Beach. This home invites you to experience the essence of Oak Bluffs! The main house, dating back to the 1850s, has been

  Nya Clarke Martha's Vineyard Island-Wide Realty

  25 Pennacook Ave, Oak Bluffs, MA 02557
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  /6

  $1,125,000

  • Land
  • 10,018 Sq Ft
  • $4,891,304 per Acre

  15 Chapman La, Edgartown, MA 02539

  Opportunity Abounds - This conforming parcel offers a great opportunity to build with close proximity to Edgartown Village! This adjoining lot offers ability to connect to Town Water and Sewer creating the perfect setting for your custom dream home or next investment. Located just moments from shops, restaurants, parks, and everyday conveniences, this is a chance to enjoy all the benefits of

  

  Wendy Harman

  Compass

  (508) 625-9227

  15 Chapman La, Edgartown, MA 02539
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  /39

  $3,395,000

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

  27 Clambelly Rd, Chilmark, MA 02535

  A place of serenity tucked in the woods of Chilmark. 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
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  /20

  $325,000

  • 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
• 

  

  /41

  $2,295,000

  • 4 Beds
  • 3.5 Baths
  • 3,016 Sq Ft

  3 Hidden Cove Rd, Oak Bluffs, MA 02557

  Hidden Cove Gem with Serene Pond Views And Coveted Water Access - Located in the desirable Hidden Cove enclave—a 65+ acre water-access community—this inviting contemporary home offers privacy and high-end finishes with direct access to Sengekontacket Pond and Nantucket Sound. Community amenities include a private boat dock, walking trails, pickleball and tennis, all near Oak Bluffs. The

  

  Wendy Harman

  Compass

  (508) 456-9911

  3 Hidden Cove Rd, Oak Bluffs, MA 02557
• 

  

  /10

  $3,995,000

  • Land
  • 1.92 Acres
  • $2,083,985 per Acre

  98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568

  Farm Neck Golf Club – Undeveloped Water View Parcel with Membership A truly rare opportunity to acquire a 1.92-acre undeveloped parcel within the prestigious Farm Neck Golf Club community, one of the last remaining opportunities of its kind. This exceptional offering features sweeping water views over Sengekontacket Pond to the Vineyard Sound, creating a stunning backdrop for your future Martha’s

  Andrew McElhinney Compass LLC

  98 Farm Neck Way Unit 51, Oak Bluffs, MA 02568
• 

  

  /32

  $3,125,000

  • 3 Beds
  • 2 Baths
  • 1,569 Sq Ft

  309 Barnes Rd, Oak Bluffs, MA 02557

  Your Vineyard summer begins the moment you arrive. This rare, fully furnished waterfront retreat offers 175' of private shorefront on Lagoon Pond — one of Martha's Vineyard's most coveted settings. Taken to the studs in 2022 and reimagined by architect Ramsay Gourd, this bright coastal escape features soaring vaulted ceilings, white shiplap, and painted beams. Glass sliders open to bluestone

  Dawn Bellante Sandpiper Realty, Inc.

  309 Barnes Rd, Oak Bluffs, MA 02557
• 

  

  /34

  $1,250,000

  • 3 Beds
  • 3 Baths
  • 1,682 Sq Ft

  261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

  END UNIT WITH PRIVATE DRIVEWAY IN TASHMOO WOODS. This well-maintained 3-bedroom, 3-bath end-unit condo offers a rare combination of privacy, space, and access to one of Vineyard Haven’s most sought-after communities. As an end unit with its own private driveway, this home offers added separation and a more single-family feel—along with a one-car garage and additional storage for bikes and beach

  Jennifer O'hanlon Compass LLC

  261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
• 

  

  /36

  $1,625,000

  • 4 Beds
  • 3 Baths
  • 1,514 Sq Ft

  26 Sea Glen Rd, Oak Bluffs, MA 02557

  Nestled in a desirable neighborhood, this beautifully maintained cape style home offers a rare blend of charm, flexibility and convenience in a serene island setting. Thoughtfully appointed throughout, the home welcomes you with an open living room that flows effortlessly into a bright dining area, where French doors open to a private stone patio—creating an inviting connection between indoor

  Jennifer DaSilva Compass | Point B

  26 Sea Glen Rd, Oak Bluffs, MA 02557

Showing Results 41 - 80, Page 2 of 7