Dukes County MA Homes for Sale

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  /26

  $925,000

  • 2 Beds
  • 1.5 Baths
  • 1,208 Sq Ft

  4 Quail Run Unit 21, Oak Bluffs, MA 02557

  Welcome to this FULLY FURNISHED, private, 2-bedroom, end-unit townhouse offering 1,208 sq ft of effortless coastal living. With seasonal rentals already in place this opportunity is the defenition of TURN KEY. Thoughtfully designed with both comfort and style in mind, this coastal retreat blends relaxed island charm with modern convenience—perfect for year-round living or as an established rental

  Emma Bryant Studio Realty

  4 Quail Run Unit 21, Oak Bluffs, MA 02557
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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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  /12

  $1,495,000

  • 4 Beds
  • 4 Baths
  • 2,304 Sq Ft

  33 Alyssa Ln, Vineyard Haven, MA 02568

  Country Living so close to Town! Lovely 4 Bedroom 2,304sq ft. Colonial Cape perched on a rise on Alyssa Lane off West Spring Street. Open Kitchen with handcrafted side cabinets and Island with stool seating. Dining, sitting, entertainment area with sliders open to a generous front to back side deck. Living room with propane fired wood stove and half bath also on the first floor. Interior stairs

  Stephanie Burke Portfolio Properties

  33 Alyssa Ln, Vineyard Haven, MA 02568
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  /8

  $3,495,000

  • Land
  • 11.39 Acres
  • $306,848 per Acre

  0 Pocha Rd, Edgartown, MA 02539

  CHAPPAQUIDDICK -Dynamic views of Poucha Pond, barrier dunes, and the waters of the Atlantic are enjoyed from this 11+ acre building lot. The close to 1⁄2 mile of private pond frontage provides easy access for swimming, kayaking, paddle boarding and everything in between. Sheltered amongst 200 acres of conservation land, enjoy and explore the wonders of the natural habitat right in your backyard.

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  0 Pocha Rd, Edgartown, MA 02539
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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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  /32

  $1,625,000

  • 2 Beds
  • 2.5 Baths
  • 1,532 Sq Ft

  26 Union St Unit 7, Tisbury, MA 02568

  Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a tub/shower combination and direct access to a private deck complete with an outdoor shower, perfect

  Alyssa Halisky Wallace & Co. Sotheby's

  26 Union St Unit 7, Tisbury, MA 02568
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  /4

  $995,000

  $105K PRICE DROP

  • Land
  • 1 Acre
  • $995,000 per Acre

  25 Coffins Field Rd, Edgartown, MA 02539

  Per Board of Health approval, this 1.0-acre parcel is approved for the construction of a six-bedroom dwelling. Seller is offering a $40,000 credit at closing to assist the buyer with costs associated with the design, permitting, and installation of the septic system.The property is located in a centrally situated neighborhood and abuts conservation land, providing a private setting. Conveniently

  Casandra Hyland Sandpiper Realty, Inc.

  25 Coffins Field Rd, Edgartown, MA 02539
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  /2

  $12,500,000

  • Land
  • 38 Acres
  • $328,947 per Acre

  2 Old Farms Trail Unit 1, Edgartown, MA 02539

  Thirty-eight (38 acres) of available land in Edgartown! This is a truly extraordinary and increasingly rare opportunity to own thirty-eight (38) acres of contiguous land in Edgartown. Come create a landmark estate or private compound in one of Edgartown’s most sought-after locations. Perfectly positioned between the charm of Edgartown Historic Village and the sweeping sands of South Beach and

  Michele Casavant Vineyard Village Realty

  2 Old Farms Trail Unit 1, Edgartown, MA 02539
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  $2,399,000

  $176K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,910 Sq Ft

  76 Washque Ave, Edgartown, MA 02539

  This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick's most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird's-eye views capture the natural beauty that surrounds you. Thoughtfully renovated, the home blends

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  76 Washque Ave, Edgartown, MA 02539
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  /17

  $3,200,000

  • Land
  • 19.3 Acres
  • $165,803 per Acre

  32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575

  A Rare Offering in West Tisbury — Over 19 Acres of Opportunity An exceptional opportunity to own just over 19 acres in the heart of rural West Tisbury. This expansive parcel offers tremendous flexibility, with potential for multiple dwellings or subdivision into a thoughtfully designed niche development. Ideally situated near all island towns, the property is also just minutes from the pristine

  Jill Napior Tea Lane Associates

  32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
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  /25

  $1,550,000

  • 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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  /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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  /13

  $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. 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 International Realty

  7 Overview Ln, Oak Bluffs, MA 02557
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  /60

  $5,495,000

  • 3 Beds
  • 7 Baths
  • 3,608 Sq Ft

  385 Barnes Rd, Vineyard Haven, MA 02568

  SPECTACULAR WATERFRONT ESCAPE WITH POOL AND UNFORGETTABLE SUNSETS. Set along a coveted stretch of Lagoon frontage, this beautifully designed waterfront home captures the essence of relaxed luxury on Martha’s Vineyard. With 125 feet of private sandy beachfront and over 5,400 square feet of living space across three levels, the property is thoughtfully oriented to maximize light, views, and

  Stephanie Roache Donnelly + Co

  385 Barnes Rd, Vineyard Haven, MA 02568
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  /14

  $2,725,000

  • Land
  • 7.6 Acres
  • $358,553 per Acre

  34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535

  This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience —

  Peyton Wallace Studio Realty

  34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
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  /12

  $1,195,000

  • 3 Beds
  • 2 Baths
  • 1,472 Sq Ft

  0 Bayberry Hill Rd Unit 22602271, Gosnold, MA 02713

  Perched high above the harbor on one of New England's most secluded islands, Folly on Bayberry Hill is a classic Cuttyhunk retreat offering exceptional privacy, timeless coastal character, and sweeping panoramic water views.The home's elevated setting creates a remarkable sense of openness, light, and connection to the surrounding coastal landscape. Inside, approximately 1,472 square feet of

  Slater Anderson LandVest, Inc.

  0 Bayberry Hill Rd Unit 22602271, Gosnold, MA 02713
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  /8

  $3,495,000

  • Land
  • 11.39 Acres
  • $306,848 per Acre

  0 Pocha Road Extension Unit 1.1,1.2 43325, Edgartown, MA 02539

  CHAPPAQUIDDICK - Dynamic views of Poucha Pond, barrier dunes, and the waters of the Atlantic are enjoyed from this 11+ acre building lot. The close to 1⁄2 mile of private pond frontage provides easy access for swimming, kayaking, paddle boarding, and everything in between. Sheltered amongst 200 acres of conservation land, enjoy and explore the wonders of the natural habitat right in your

  Katherine Donahue Sandpiper Realty

  0 Pocha Road Extension Unit 1.1,1.2 43325, Edgartown, MA 02539
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  /65

  $45,000,000

  • 7 Beds
  • 13 Baths
  • 14,780 Sq Ft

  18 Point Inner Way, Chilmark, MA 02535

  A rare offering on the shores of Menemsha Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Thoughtfully designed with striking modern architecture, walls of glass, and seamless indoor-outdoor living, this one-of-a-kind compound captures breathtaking water views from nearly every room. Set on 4.9 acres with a private 115-foot deep-water dock, the

  Alyssa Halisky Wallace & Co. Sotheby's

  18 Point Inner Way, Chilmark, MA 02535
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  /15

  $1,495,000

  $2M PRICE DROP

  • Land
  • 3.01 Acres
  • $496,678 per Acre

  11 Beach Pebble Rd Unit 48.3, West Tisbury, MA 02568

  Over 3 acres in the West Tisbury section of Makonikey. This buildable lot is a short distance from the Lower Makonikey Association beach. The prime home site on this property was recently cleared to reveal beautifully contoured land with several ancient white oak trees. The property is situated in an area of several multimillion-dollar homes and will accommodate a house, a guesthouse, and a

  Cassie Courtney Wallace & Co. Sotheby's

  11 Beach Pebble Rd Unit 48.3, West Tisbury, MA 02568
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  /7

  $4,800,000

  • 4 Beds
  • 4.5 Baths
  • 3,816 Sq Ft

  7 Marthas Rd, Edgartown, MA 02539

  Welcome to this coastal chic farmhouse set in the heart of Katama, a few blocks from the Field Club, close to SOUTH BEACH and close to Edgartown Village. To be built is a four bedroom en-suite home with a heated saltwater POOL. This home sits upon a flat, beautiful parcel of land with mature trees. The facade of the home offers an inviting covered porch with free standing columns, a granite entry

  Michele Casavant Vineyard Village Realty

  7 Marthas Rd, Edgartown, MA 02539
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  /20

  $1,450,000

  • 3 Beds
  • 2 Baths
  • 1,749 Sq Ft

  10 Abels Neck Rd, Chilmark, MA 02535

  Nestled on a beautiful lot in the heart of Chilmark, this charming cottage is framed by mature blueberry bushes just off the deck — a true slice of island life. Perfectly positioned to enjoy the quiet calm of up-island living while remaining close to town, beaches, and all that the Vineyard has to offer. Step inside through sliding glass doors into a cozy living area, where an arched entryway

  Julianna Flanders Flanders Real Estate

  10 Abels Neck Rd, Chilmark, MA 02535
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  $1,575,000

  $325K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,056 Sq Ft

  20 Brook Hollow Rd, Vineyard Haven, MA 02568

  This spacious custom designed home is well sited to offer maximum privacy in the lush area of Long View. A short bike ride to Lambert's Cove beach, it's also about a 20-minute walk down a quiet private road. The home lays out well for family and extended guests with a roomy living room boasting vaulted ceilings and large windows. The house is designed to have an intimate relationship with the

  Jim Feiner Feiner Real Estate

  20 Brook Hollow Rd, Vineyard Haven, MA 02568
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  /45

  $1,765,000

  • 2 Beds
  • 2 Baths
  • 890 Sq Ft

  2 Great Rock Rd, Oak Bluffs, MA 02568

  Ready - Set - Go! This gorgeous centrally located private 1.5 acre wooded property is ready for you to complete. The Town approved this property to accommodate a 9 bedroom septic system, 20' x 40' in-ground pool, a 7 bedroom main house, garage and a 2 bedroom accessory dwelling unit. The town building and board of health departments approved the house and and septic plans attached. The property

  Susan Lemoie-Zarba Premier Properties

  2 Great Rock Rd, Oak Bluffs, MA 02568
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  /41

  $7,200,000

  • 5 Beds
  • 4.5 Baths
  • 4,389 Sq Ft

  2 Noras Ln, Edgartown, MA 02539

  Located in the highly sought-after Nora’s Meadow community in Edgartown, this exceptional coastal property offers privacy, acreage, and close proximity to downtown Edgartown, South Beach, and the Katama bike path. Set on 1.7 beautifully landscaped acres, this custom home, built in 2014, features over 4,000 square feet of living space across three levels. The open main living area includes a

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  2 Noras Ln, Edgartown, MA 02539
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  /5

  $995,000

  $105K PRICE DROP

  • Land
  • 43,472 Sq Ft
  • $996,994 per Acre

  25 Coffins Field Rd Unit 18, Edgartown, MA 02539

  Per Board of Health approval, this 1.0-acre parcel is approved for the construction of a six-bedroom dwelling. Seller is offering a $40,000 credit at closing to assist the buyer with costs associated with the design, permitting, and installation of the septic system. The property is located in a centrally situated neighborhood and abuts conservation land, providing a private setting. Conveniently

  Casandra Hyland Sandpiper Realty

  25 Coffins Field Rd Unit 18, Edgartown, MA 02539
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  /38

  $12,500,000

  • 5 Beds
  • 3.5 Baths
  • 3,700 Sq Ft

  18 Spruce Gate Rd, Chilmark, MA 02535

  Welcome to an extraordinary coastal retreat within the exclusive gates of Squibnocket Farm, a 450+ acre private community offering access to over two miles of oceanfront, pond frontage, and conservation land. Designed and built by Soikkeli & Company, this elegant home blends timeless New England farmhouse architecture with refined modern luxury. The chef’s kitchen features soapstone countertops,

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  18 Spruce Gate Rd, Chilmark, MA 02535
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  /37

  $3,195,000

  • 5 Beds
  • 4.5 Baths
  • 3,881 Sq Ft

  10 N Bog Rd, Edgartown, MA 02539

  Set on 2.2 private acres in Edgartown, this exceptional five-bedroom home with a heated saltwater pool offers the ideal blend of privacy, comfort, and convenience. Perfectly located just moments from Morning Glory Farm, South Beach, the bike path, and downtown Edgartown Village, the property provides easy access to some of the island’s most sought-after destinations while maintaining a peaceful,

  Michele Casavant Vineyard Village Realty

  10 N Bog 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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  /45

  $7,950,000

  • 4 Beds
  • 4.5 Baths
  • 7,766 Sq Ft

  2 Lexington Ave, Edgartown, MA 02539

  NEW CONSTRUCTION: Experience modern Katama luxury in this thoughtfully designed new construction by Morgan Studio, a husband-and-wife–led boutique design firm. A turn-key offering for elevated indoor-outdoor living, the residence features soaring ceilings, a fluid floor plan with multiple gathering spaces, abundant natural light through oversized windows, and exceptional materials and finishes

  Peyton Wallace Studio Realty

  2 Lexington Ave, Edgartown, MA 02539
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  /22

  $5,500,000

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft

  17 Chockers Ln, Chilmark, MA 02535

  Perfectly situated on Nashaquitsa Pond, this charming two-bedroom cottage offers sweeping views of Quitsa and Menemsha Pond from a rare vantage point few properties can match. The cottage includes private beach rights to Short Beach and dock access for a mooring. Inside, hand-painted floors and a warm, unpretentious interior reflect the authentic character of Old Vineyard — a property that has

  Julianna Flanders Flanders Real Estate

  17 Chockers Ln, Chilmark, MA 02535
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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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  /3

  $639,000

  • Land
  • 13,068 Sq Ft
  • $2,130,000 per Acre

  52 Heath Hen Ln, Vineyard Haven, MA 02568

  GOOD TO GO! This sunny 13,000-square-foot sunny lot is ready for your Vineyard home. The property comes with a complete six bedroom septic design prepared by Vineyard Land Surveying, allowing for both a main house and guest house. With key planning work already completed, this is an outstanding opportunity to move forward with confidence and begin the building process.Conveniently located just

  Tina Miller Donnelly + Co.

  52 Heath Hen Ln, Vineyard Haven, MA 02568
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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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  /2

  $2,700,000

  • 4 Beds
  • 4.5 Baths
  • 2,750 Sq Ft

  6 Laura's Way, Edgartown, MA 02568

  Welcome to the opportunity to own a brand-new, GORGEOUS, custom-built home in Edgartown, set on a one-acre plot with a detached 900 sq ft accessory dwelling. The main residence opens to an inviting two-story foyer, leading to an expansive, living room featuring a wall of glass sliders. The gourmet kitchen is a chef’s dream, boasting Bosch appliances, a large quartz-topped island with seating for

  Michele Casavant Vineyard Village Realty

  6 Laura's Way, Edgartown, MA 02568
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  /2

  $799,000

  • Land
  • 39,996 Sq Ft
  • $870,181 per Acre

  22 Bramble Path Unit 214, West Tisbury, MA 02568

  Flat building lot centrally located in West Tisbury. A perc test has been completed which supports a four bedroom Title Five septic system. It is the Buyers responsibility to install utilities, well and septic.

  Michele Casavant Vineyard Village Realty

  22 Bramble Path Unit 214, West Tisbury, MA 02568
• 

  

  /4

  $2,995,000

  • 4 Beds
  • 4.5 Baths
  • 3,024 Sq Ft

  9 Hagerty Dr, Tisbury, MA 02568

  West Chop Dream Home in the Making! Experience the charm of this brand-new Shingle Style Colonial, currently under construction. Featuring 4 spacious bedrooms, 4 full and one half bath. This thoughtfully designed home offers generous space. Venture outside into your private oasis, complete with an in-ground pool (36' x18') — perfect for sun-soaked afternoons and evening gatherings. Situated in a

  Lisa Gilberto C McManus Realty Group

  9 Hagerty Dr, Tisbury, MA 02568
• 

  

  /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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  /40

  $1,695,000

  • 4 Beds
  • 2 Baths
  • 1,342 Sq Ft

  58 Road To the Plains, Edgartown, MA 02539

  Turnkey Katama Home—Beautifully furnished and move-in ready, this updated coastal retreat offers relaxed Island living with a strong rental history and effortless ownership. Outdoor highlights include a 19-foot heated swim spa and Jacuzzi set on an expansive wood deck, an outdoor shower, bluestone fire pit patio, multiple lounging spaces, decks, and wooded privacy for serene entertaining. Inside,

  Stephanie Roache Donnelly + Co.

  58 Road To the Plains, Edgartown, MA 02539
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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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