Dukes County MA Homes for Sale

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  $1,399,000

  • 0.5 Baths
  • 1,992 Sq Ft

  1 Mariners Way Unit A, Edgartown, MA 02539

  A standout commercial offering in Edgartown, combining striking contemporary design with exceptional flexibility. Located just outside the historic district and just shy of 2,000 square feet, this commercial condominium offers a beautifully finished, thoughtfully designed interior that feels anything but ordinary. Soaring ceilings, polished concrete floors, dramatic black architectural details

  Lesley Heidt Sandpiper Realty, Inc.

  1 Mariners Way Unit A, Edgartown, MA 02539
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  /26

  $2,735,000

  • 1 Bed
  • 1 Bath
  • 520 Sq Ft

  119 Old Thumb Point Rd, Vineyard Haven, MA 02568

  Beautifully sited on a knoll overlooking Deep Bottom Cove is a simple, yet totally charming, three season cottage with wonderful, protected water views and pond frontage. The cottage has seen some loving changes over the past 3 years: a dreamy screened porch has been added that the owner often uses as a sleeping porch; the beautiful, original wood floors have been restored; the galley kitchen has

  Candy DaRosa Feiner Real Estate

  119 Old Thumb Point Rd, Vineyard Haven, MA 02568
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  /56

  $4,995,000

  • 4 Beds
  • 4.5 Baths
  • 3,348 Sq Ft

  98 Edgartown Bay Rd, Edgartown, MA 02539

  COASTAL LUXURY IN KATAMA — EXCEPTIONAL LIVING NEAR SOUTH BEACH. Set in one of Katama’s most coveted locations, where the sound of the ocean drifts in and South Beach is within easy reach, this distinctive coastal contemporary was thoughtfully designed to maximize natural light, energy efficiency, and long-term flexibility.The reverse-style floor plan places the main gathering spaces on

  

  Wendy Harman

  Compass | Point B

  98 Edgartown Bay Rd, Edgartown, MA 02539
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  /25

  $1,599,000

  $26K PRICE DROP

  • 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. Also on

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  26 Union St Unit 7, Tisbury, MA 02568
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  /19

  $1,825,000

  • 7 Beds
  • 4 Baths
  • 2,597 Sq Ft

  4 Farm Way, Edgartown, MA 02539

  Two complete homes on one acre in Edgartown's Smith Hollow neighborhood — a rare find. Set at the end of a paved cul-de-sac, the property gives each house its own septic system, its own landscaped yard, and enough separation for real privacy.The main house has four bedrooms and two baths, along with a basement and a drive-under garage. The guest house features three bedrooms, two baths, a full

  Emma Kennedy Sandpiper Realty, Inc.

  4 Farm Way, Edgartown, MA 02539
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  /11

  $1,375,000

  • 5 Beds
  • 2 Baths
  • 1,952 Sq Ft

  234 County Rd, Oak Bluffs, MA 02557

  Surprisingly roomy Cape-style home, centrally located in Oak Bluffs and right across from the bike path. This five-bedroom house offers generously scaled living spaces throughout, including a large living room filled with natural light, an open stairway, a spacious dining room, and an updated kitchen. The first floor features a primary bedroom, a full bath with laundry, and a separate

  Emma Kennedy Sandpiper Realty, Inc.

  234 County Rd, Oak Bluffs, MA 02557
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  /31

  $7,495,000

  • 5 Beds
  • 4.5 Baths
  • 4,894 Sq Ft

  16 Witchwood Ln, Edgartown, MA 02539

  Situated down a long private driveway, this renovated 3.5-acre Katama estate offers a rare opportunity to acquire a turnkey property with a deep-water dock slip on Katama Bay. Impeccably executed throughout, the estate showcases exceptional craftsmanship, distinctive materials, top-of-the-line appliances, and an impressive array of amenities. Highlights include a finished lower level, expansive

  Jarrett Hurwitz Keller Williams Realty

  16 Witchwood Ln, Edgartown, MA 02539
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  /31

  $1,925,000

  • 3 Beds
  • 2 Baths
  • 1,553 Sq Ft

  4 Cormorant Cir, Edgartown, MA 02539

  Tucked at the end of a quiet cul-de-sac in the desirable Island Grove community, this charming three-bedroom, (plus bonus room), two-bathroom residence offers a private setting, association amenities and excellent proximity to Edgartown Village and Katama Beach.Located on arguably one of the most desirable lots in Island Grove and surrounded by conservation land, this half acre lot benefits

  Alexis Holden Tea Lane Associates

  4 Cormorant Cir, Edgartown, MA 02539
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  /34

  $2,150,000

  • 5 Beds
  • 3.5 Baths
  • 1,572 Sq Ft

  15 Pequot Ave, Oak Bluffs, MA 02557

  Oak Bluffs Copeland District -Just One Block from the Beach!Discover the perfect coastal getaway in this spacious 5-bedroom, 3½-bathroom home, ideally located just one block from the beach and within easy walking distance of the town center.Spend your days enjoying the sand and surf, then stroll into town for local shops, restaurants, cafés, and entertainment. Or just relax at home on the

  Lisa Lucier Anchor Realty of Martha's Vineyard

  15 Pequot Ave, Oak Bluffs, MA 02557
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  /6

  $7,200,000

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  111 Old Herring Creek Rd, Vineyard Haven, MA 02568

  Surrounded by hundreds of acres of conservation-minded land, this private 4.3-acre parcel presents a rare opportunity to create a truly exceptional architectural masterpiece. Perched atop a high ridge, a three-bedroom home currently exists that commands panoramic water views across the Elizabeth Islands and Lamberts Cove. A gently winding walking path leads approximately 150 feet downhill to a

  Thomas Leclair Landvest MV

  111 Old Herring Creek Rd, Vineyard Haven, MA 02568
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  $11,400,000

  • 4 Beds
  • 3.5 Baths
  • 2,480 Sq Ft

  104 Old Herring Creek Rd, Vineyard Haven, MA 02568

  An extraordinary opportunity to own one of the Cape’s most distinctive waterfront properties, this exceptional 5.3-acre estate parcel combines remarkable natural beauty, complete privacy, and an unparalleled coastal setting. At its heart is a beautifully renovated four-bedroom beach cottage, thoughtfully updated with modern amenities while preserving the character and intimacy of a classic

  Thomas Leclair Landvest MV

  104 Old Herring Creek Rd, Vineyard Haven, MA 02568
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  /41

  $2,550,000

  • 3 Beds
  • 3.5 Baths
  • 2,668 Sq Ft

  20 Meshacket Rd, Edgartown, MA 02539

  Incredible opportunity just a mile from downtown Edgartown. There are multiple options. This 3-bedroom/3.5-bath home is a garden oasis but also offers owners the option of running a significant business from the property with existing professional offices (reception, two offices, conference room, half bath, kitchenette). The property currently operates as a home business for an established law

  Mark Jenkins Wallace & Co. Sotheby's

  20 Meshacket Rd, Edgartown, MA 02539
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  /36

  $3,400,000

  • 5 Beds
  • 5 Baths
  • 3,095 Sq Ft

  62 Schoolhouse Rd, Edgartown, MA 02539

  Ideally situated between South Beach and Edgartown Village, this newly renovated Katama compound offers exceptional flexibility for personal use and rental income.The four-bedroom contemporary main house features a newly constructed, expansive great room with a cathedral ceiling and an abundance of windows that fill the space with natural light. The open floor plan flows from the updated kitchen

  Michele Casavant Vineyard Village Realty

  62 Schoolhouse Rd, Edgartown, MA 02539
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  /25

  $1,795,000

  • 4 Beds
  • 1.5 Baths
  • 1,871 Sq Ft

  487 Lamberts Cove Rd, Vineyard Haven, MA 02568

  This sweet four-bedroom home has fantastic energy and captures the effortless feeling of summer on Martha’s Vineyard. Set high on 2.4 acres along beloved Lamberts Cove Road, the property is just a short walk to Ice House, Lamberts Cove Beach, and Seth’s Pond. Designed for easy enjoyment, the home offers a warm and welcoming kitchen filled with sunshine, a spacious living room, and two fireplaces

  Jill Napior Tea Lane Associates

  487 Lamberts Cove Rd, Vineyard Haven, MA 02568
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  /37

  $1,150,000

  • 4 Beds
  • 3 Baths
  • 1,924 Sq Ft

  7 Fawndale Rd, Vineyard Haven, MA 02568

  Welcome to 7 Fawndale Road in Vineyard Haven. Located just 1 mile from Main St., this delightful property offers comfortable living and flexible spaces. The main level features offers single-story living featuring an open living and dining area with wood beams, a bay window, partial cathedral ceiling, skylight, and wood floors. The galley-style kitchen offers plenty of cabinetry and counter

  Michele Moore Island Real Estate

  7 Fawndale Rd, Vineyard Haven, MA 02568
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  /36

  $1,755,000

  • 3 Beds
  • 3 Baths
  • 2,815 Sq Ft

  68 Front St, Oak Bluffs, MA 02557

  Located on a quiet street in Oak Bluffs, this beautifully expanded Cape offers generous living spaces, along with an additional 700+ square feet of newly finished recreation space above the two-car garage, complete with a private entrance and second-floor deck. The inviting first floor is designed for comfortable living and entertaining, featuring a spacious kitchen with a center island and

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  68 Front St, Oak Bluffs, MA 02557
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  /42

  $2,200,000

  Open Wed 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 2,420 Sq Ft

  61 Canonicus Ave, Oak Bluffs, MA 02557

  Location, location, location: This 1999 home with all the comforts of the 21 st Century isnestled on a landscaped lot within mellow surroundings. And yet ... it’s located withinmere moments of town, beach, bike path, bus line, parks, recreation, Farm Pond and aLand Bank trail. The situation hardly gets better. The 3BR/2.5BA house features adeep wraparound farmer’s porch, Brazilian

  Kristin Buck Donnelly + Co

  61 Canonicus Ave, Oak Bluffs, MA 02557
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  /2

  $850,000

  • Land
  • 10,890 Sq Ft
  • $3,400,000 per Acre

  15 Roger's Way, Oak Bluffs, MA 02557

  Build Your Dream Home. Close to town and all that Oak Bluffs has to offer, Roger's Way is a small enclave offering a wonderful opportunity to create your own Vineyard retreat. A paved road leads to 15 Roger's Way, one of the last remaining lots in this desirable neighborhood. A three-bedroom septic system is already installed, and electric access is available at the edge of the property. Bring

  Michele Moore Island Real Estate

  15 Roger's Way, Oak Bluffs, MA 02557
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  /2

  $850,000

  • Land
  • 10,890 Sq Ft
  • $3,400,000 per Acre

  15 Roger's Way Unit 177.3, Oak Bluffs, MA 02557

  Build Your Dream Home.Close to town and all that Oak Bluffs has to offer, Roger’s Way is a small enclave offering a wonderful opportunity to create your own Vineyard retreat. A paved road leads to 15 Roger’s Way, one of the last remaining lots in this desirable neighborhood. A three-bedroom septic system is already installed, and electric access is available at the edge of the property. Bring

  Michele Moore Island Real Estate

  15 Roger's Way Unit 177.3, Oak Bluffs, MA 02557
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  $2,295,000

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

  125 Mayflower Ln, Vineyard Haven, MA 02568

  Nestled on an acre of beautifully landscaped grounds in a tranquil, park-like setting, this home is tucked away on a quiet lane within an established neighborhood. Located just a quarter mile from miles of Land Bank walking trails and less than two miles from Main Street, it offers the perfect opportunity to embrace the Vineyard lifestyle, just minutes from the vibrant center of Vineyard Haven.

  Courtney Marek Sandpiper Realty, Inc.

  125 Mayflower Ln, Vineyard Haven, MA 02568
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  $4,100,000

  • 5 Beds
  • 4 Baths
  • 3,654 Sq Ft

  148 Katama Rd, Edgartown, MA 02539

  A rare mixed-use property on Katama Road, set right between downtown Edgartown and South Beach! Two residential apartments above — a 2BR and a 3BR, each with their own walk-up deck, in-unit laundry and dedicated parking. Both are occupied month-tomonth under self-extending leases, giving a new owner flexibility. The first floor was home to an HVAC company for nearly a decade and is now vacant and

  Chelsea Brennan Lamacchia Realty, Inc.

  148 Katama Rd, Edgartown, MA 02539
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  /30

  $1,539,000

  • 3 Beds
  • 4.5 Baths
  • 1,951 Sq Ft

  8 Melrose, Oak Bluffs, MA 02557

  Incredible opportunity for workforce housing, live in one/rent the other, or multi generational family living. Main house has 4 levels of living space. Main floor living/kitchen/dining/full bath and laundry. 2nd floor has two bedrooms and full bath. 3rd floor is a large finished bonus room. The full walkout basement in the main house is finished with private entry, full bath, separate rooms and

  Jon Hartzband Martha's Vineyard Island-Wide Realty

  8 Melrose, Oak Bluffs, MA 02557
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  /36

  $1,850,000

  • 4 Beds
  • 2.5 Baths
  • 2,811 Sq Ft

  78 Vineyard Meadows Farm Rd, Vineyard Haven, MA 02568

  Situated down a long driveway, this distinctive West Tisbury property offers a rare combination of privacy, natural beauty, thoughtful design, and exceptional versatility. Designed with passive solar principles, the home takes full advantage of its orientation and abundant natural light. Exposed wood details throughout add warmth and character, complementing the home’s inviting, organic feel,

  Jarrett Hurwitz Keller Williams Realty

  78 Vineyard Meadows Farm Rd, Vineyard Haven, MA 02568
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  $1,649,000

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  43 N Slope Ln, Chilmark, MA 02535

  Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha's Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring

  

  Barbara O'Hara

  North Star Real Estate, LLC

  43 N Slope Ln, Chilmark, MA 02535
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  /25

  $1,295,000

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

  4 Periwinkle Ln, Oak Bluffs, MA 02557

  Stylish, thoughtfully designed ranch style home built in 2014 is bright and sunny. Tucked away in a private tranquil setting just a stroll to downtown, harbor, beaches, ferries, library, restaurants and shops, the home features solar panels, large living room with separate dining area, kitchen with stainless steel appliances, 3 bedrooms, 2 full baths with tiled floors, and laundry room.

  Perry Patterson MV Luxury Homes

  4 Periwinkle Ln, Oak Bluffs, MA 02557
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  $4,395,000

  • 3 Beds
  • 5.5 Baths
  • 4,046 Sq Ft

  267 Barnes Rd, Oak Bluffs, MA 02557

  Set along 163 feet of Lagoon frontage with its own sandy beach, 267 Barnes Road offers a contemporary take on waterfront living in Oak Bluffs. Set on 1.25 acres of beautifully maintained grounds, the 4,046-square-foot residence offers generous, light-filled spaces designed to capture the water views from nearly every room. From the moment you enter, the Lagoon is a constant presence, with

  Stephanie Roache Donnelly + Co

  267 Barnes Rd, Oak Bluffs, MA 02557
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  /31

  $1,649,900

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  43 N Slope Ln, Chilmark, MA 02535

  Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring

  

  Barbara O'Hara

  NorthStar Real Estate, LLC

  43 N Slope Ln, Chilmark, MA 02535
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  /21

  $1,475,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  7 Boylston Dr, Edgartown, MA 02539

  Well-maintained three-bedroom, two-bath home set on a quiet road in a convenient Edgartown location. The property is bordered by more than 100 acres of conservation land, offering a peaceful setting and added privacy while remaining close to Edgartown Village, beaches, bike paths, and everyday amenities.The home features comfortable living and dining spaces along with a beautifully

  Patrick McCarthy Grace Hagerty Real Estate Inc

  7 Boylston Dr, Edgartown, MA 02539
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  /35

  $1,625,000

  • 3 Beds
  • 2.5 Baths
  • 1,960 Sq Ft

  31 Dodgers Hole Rd, Edgartown, MA 02539

  Dodgers Hole - Delightful contemporary cape style home, centrally located, suitable for seasonal or year-round use. The privately sited half acre lot features a first floor primary bedroom with en-suite bath, a light filled eat-in kitchen, central A/C, full unfinished basement, a detached 18'x24' shed/garage, with a large rear deck and generous outdoor shower compliment the property. A four

  Sean Federowicz Landmarks at TODAY Real Estate

  31 Dodgers Hole Rd, Edgartown, MA 02539
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  $2,650,000

  • 3 Beds
  • 2.5 Baths
  • 2,874 Sq Ft

  10 Woodhaven Dr, Edgartown, MA 02539

  Edgartown - Room to Live. Space to Breathe. Tucked into more than an acre of peaceful woodland, 10 Woodhaven Drive is the kind of Vineyard home that invites you to settle in and stay awhile. Generous rooms, multiple gathering spaces and an easy connection to the outdoors create a home that feels equally suited to quiet Island weekends, a house full of summer guests or comfortable year-round

  Leslie C. Floyd Portfolio Properties

  10 Woodhaven Dr, Edgartown, MA 02539
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  /4

  $450,000

  • Land
  • 20,473 Sq Ft
  • $957,447 per Acre

  0 Old Country Ln Unit 73571746, Vineyard Haven, MA 02568

  Discover peace and privacy without sacrificing location. Nestled under a serene natural tree canopy, this central wooded parcel provides a quiet setting just minutes from local shops, dining, and beautiful beaches. Ready for your custom vision.

  Brenda Galligan Karen M. Overtoom R.E.

  0 Old Country Ln Unit 73571746, Vineyard Haven, MA 02568
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  /30

  $2,095,000

  • 4 Beds
  • 4 Baths
  • 2,876 Sq Ft

  18 Sylvan Ave, Vineyard Haven, MA 02568

  COMING SOON! Welcome to 18 Sylvan Avenue, a delightful, custom-crafted four-bedroom, four-bath, contemporary-style home set at the end of a quiet neighborhood road in Vineyard Haven. Surrounded by eight acres of conservation land, the property offers a peaceful setting with a spacious wraparound deck overlooking the natural landscape. It truly feels like its own private enclave, both inside and

  Madelyn Silvia Wallace & Co. Sotheby's International Realty

  18 Sylvan Ave, Vineyard Haven, MA 02568
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  /27

  $1,750,000

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

  14 Donaldbin Close, Edgartown, MA 02539

  Tucked into a quiet neighborhood and surrounded by mature trees, this home sits elevated on a 0.84-acre lot. With an open floorplan, the kitchen, dining, and living areas flow comfortably together, enhanced by vaulted ceilings, a stone gas fireplace, and French doors that bring in abundant natural light and provide easy access to the outdoors. A custom-designed open staircase serves as a focal

  Cheri Mason Landvest MV

  14 Donaldbin Close, Edgartown, MA 02539
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  /68

  $7,250,000

  • 4 Beds
  • 4.5 Baths
  • 3,501 Sq Ft

  8 Beach Plum Meadows, Edgartown, MA 02539

  BEACH PLUM MEADOWS: ARCHITECTURAL KATAMA COMPOUND NEAR SOUTH BEACH. Set on more than 1.6 acres in the coveted Beach Plum Meadows enclave, this distinctive property combines classic coastal architecture, private compound living, and distant views across the Katama plains to the Atlantic Ocean—all less than one mile from South Beach. The gambrel-style Main House features three light-filled levels

  

  Wendy Harman

  Compass | Point B

  8 Beach Plum Meadows, Edgartown, MA 02539
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  /31

  $2,045,000

  • 2 Beds
  • 2 Baths
  • 1,048 Sq Ft

  51 St, Oak Bluffs, MA 02557

  East Chop colonial style 2BR/2BA year-round home on East Chop PLUS a separate buildable lot behind the house. The house at 51 Winemack St has a 2-bedroom Title V septic that recently passed inspection, full basement, electric baseboard heat and large yard that allows for expansion potential of the house. Recent improvements include new roof, new shingle siding, and painted trim. The property is

  Perry Patterson MV Luxury Homes

  51 St, Oak Bluffs, MA 02557
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  /4

  $1,500,000

  • Land
  • 21,052 Sq Ft
  • $3,103,662 per Acre

  36 Pine St Unit 119.3, Edgartown, MA 02539

  Imagine creating your own Vineyard retreat on this almost half-acre parcel, ideally located within walking distance to downtown Edgartown. This property offers the opportunity to build a custom home within a designated building envelope, while a protected no-build area provides an added sense of privacy and separation from the neighboring property. The thoughtful placement of the building

  Bonnie Pierce Wallace & Co. Sotheby's

  36 Pine St Unit 119.3, Edgartown, MA 02539
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  /25

  $1,450,000

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  4 Lagrange Ave, Oak Bluffs, MA 02557

  New listing tucked away on a dead end road in Oak Bluffs ~Enjoy the best of Vineyard living from this beautifully renovated Oak Bluffs home, ideally located just a short walk from a private Lagoon beach—perfect for swimming, kayaking, paddleboarding and all your favorite water activities. The inviting living area features a dramatic vaulted ceiling and gas fireplace, creating a warm and spacious

  Marilyn Moses Ocean Park Realty Inc

  4 Lagrange Ave, Oak Bluffs, MA 02557
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  /9

  $1,950,000

  • Land
  • 41,556 Sq Ft
  • $2,044,025 per Acre

  171 Upper Main Street 9 Curtis Ln Unit 119.2, Edgartown, MA 02539

  A Rare Edgartown Opportunity — Privacy, Proximity & Possibility. Tucked away at the end of a private setting on Upper Main Street, this almost one acre parcel offers a rare opportunity to create your own Edgartown retreat within easy walking distance of downtown. Set well back from the road, the property provides a wonderful sense of privacy and seclusion while being remarkably close to the

  Bonnie Pierce Wallace & Co. Sotheby's

  171 Upper Main Street 9 Curtis Ln Unit 119.2, Edgartown, MA 02539
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  /11

  $1,175,000

  • 3 Beds
  • 1 Bath
  • 770 Sq Ft

  23 Hamblen Way, Edgartown, MA 02539

  Walk or Bike to Edgartown — Renovated & Move-In Ready. Fully furnished 3-bedroom home for year-round or vacation living, new roof & hot water heater, extensively renovated in 2014 (walls, windows, doors, insulation, gutters, siding). Open floor plan with cathedral ceilings and a wall of windows highlighting the beautiful views and natural light. Sliding doors open to a grill area and wide

  Dawn Bellante Sandpiper Realty, Inc.

  23 Hamblen Way, Edgartown, MA 02539
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  /15

  $6,250,000

  • Land
  • 21 Acres
  • $297,619 per Acre

  44 Cencelle St Unit 57, 58, 56.1, Chilmark, MA 02535

  This exceptional 21-acre estate offers sweeping ocean views, remarkable privacy, and a rare opportunity to create a truly special island retreat. Tucked among the rolling hills, open farmlands, and woodlands of Chilmark, the property combines a profound sense of seclusion with extraordinary natural beauty and the flexibility to shape the land to suit a variety of visions—including the potential

  Meg Bodnar Tea Lane Associates

  44 Cencelle St Unit 57, 58, 56.1, Chilmark, MA 02535

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