Dukes, MA Homes

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  /34

  $1,590,000

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

  46 Kennebec Ave, Oak Bluffs, MA 02557

  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' allure as a premier summer destination on Martha's Vineyard. This delightful three-season cottage has been carefully modernized over the years, offering a rare investment opportunity. Located

  Michael Schweikert Ocean Park Realty, Inc.

  46 Kennebec Ave, Oak Bluffs, MA 02557
• 

  

  

  /19

  $17,600 per month

  • 4 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • House for Rent

  50 Carls Way, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Looking for that perfect setting with a water view? This is the one!!This cute cape is privately set with a water view and direct water access to Town Pond. You can dock your canoes and kyacks here and access Tisbury Great Pond and then right out to the beach. There are

  Karen Overtoom Karen M. Overtoom R.E.

  50 Carls Way, West Tisbury, MA 02575
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  /15

  $975,000 Sold May 02, 2025

  • 1,056 Sq Ft
  • $923/SF
  • 55 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2018

  15 14th St N, Edgartown, MA 02539

  Great STARTER HOME in EDGARTOWN! The house itself was modular built BRAND NEW just under 7 years ago, so everything is plum, level, well insulated and updated. Featuring 2 beds and 2 baths on the first level, with a unfinished full walk-out basement and unfinished upstairs office space. Lots of room to spread out inside. Just under 1/4 acre lot near Edgartown Vineyard Haven Road, only a 5 minute

  Mike Sawyer Sawyer Realty Group

  15 14th St N, Edgartown, MA 02539
• 

  

  

  /18

  Est $1,863,909 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,461 Sq Ft

  29 Brook Hollow Rd, Vineyard Haven, MA 02568

  29 Brook Hollow Rd, Vineyard Haven, MA 02568
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  /8

  $875,000

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568

  Bright first-floor, three-bedroom, two bath condo in the popular Vineyard Haven Causeway Harborview association. Easy access to downtown shops, restaurants, harbor, ferry, and beaches. Building amenities include a shared pool, convenient storage, and on-site laundry facilities. The perfect blend of convenience and comfort for year-round living or as your ideal summer retreat.

  Emma Kennedy Sandpiper Realty Inc

  124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
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  /10

  $17,600 per month

  • 4 Beds
  • 3.5 Baths
  • 2,676 Sq Ft
  • House for Rent

  40 Summer Cir, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and living room surrounded by windows and decks with an outdoor table and extra seating. An "upside down" house with the living

  Karen Overtoom Karen M. Overtoom R.E.

  40 Summer Cir, West Tisbury, MA 02575
• 

  

  /19

  $1,095,000 Sold May 02, 2025

  • 1,945 Sq Ft
  • $563/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1966

  31 Davis St, Vineyard Haven, MA 02568

  Ideal location within close proximity to the lagoon, post office, Steamship Authority, and all the downtown area has to offer. This cape home is perched on a hill and a great distance from the road. The features include a large living room with brick fireplace, kitchen with breakfast bar, separate dining area, first floor bedroom, study and full bathroom. The second-floor features two bedrooms,

  Sheila Morse Island Real Estate

  31 Davis St, Vineyard Haven, MA 02568
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  /25

  Est $1,519,332 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,287 Sq Ft

  101 Dunham Ave, Vineyard Haven, MA 02568

  101 Dunham Ave, Vineyard Haven, MA 02568
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  /40

  $1,899,000

  • 4 Beds
  • 3.5 Baths
  • 2,061 Sq Ft

  174 Middle Rd, Chilmark, MA 02535

  Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

  Sheila Morse Island Real Estate

  174 Middle Rd, Chilmark, MA 02535
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  /34

  $12,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • House for Rent

  267 Great Plains Road Wt117, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Large spacious home with open concept living and dining area. This house has gorgeous hardwood floors throughout, separate media room, and loads of natural sunlight. It also features an exceptionally large master bedroom with en-suite bath, and private deck. There is

  Karen Overtoom Karen M. Overtoom R.E.

  267 Great Plains Road Wt117, West Tisbury, MA 02575
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  /26

  $1,665,000 Sold May 02, 2025

  • 2,408 Sq Ft
  • $691/SF
  • 300 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1986

  33 Clay Ave, Oak Bluffs, MA 02557

  East Chop - Tucked away on a quiet tree-lined street, you will find this contemporary three-bedroom home. A distinctive floor plan provides ample living spaces on all three levels. The expansive outdoor deck and large yard expand the living space and are the perfect places to enjoy the quiet setting. The unique layout and five-bedroom septic allows easy reconfiguration. A fantastic opportunity to

  Katherine Donahue Sandpiper Realty Inc

  33 Clay Ave, Oak Bluffs, MA 02557
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  /48

  Est $1,457,177 Not Listed For Sale

  • 6 Beds
  • 5.5 Baths
  • 2,417 Sq Ft

  152 Main St, Vineyard Haven, MA 02568

  152 Main St, Vineyard Haven, MA 02568
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  /30

  $1,850,000

  • 4 Beds
  • 3 Baths
  • 2,291 Sq Ft

  63 Saddle Club Rd, Edgartown, MA 02539

  Welcoming and Picturesque from outside to inside! Thru the door, into the entryway you immediately sense comfort and well-being in this beautifully cared for 4-bedroom home. Open floor plan stars a chef’s kitchen outfitted with premium luxury appliances, granite counters, and loads of cabinets along with a dining area perfect for family and friend gatherings. Family room, along with a

  Martha Smith C McManus Realty Group

  63 Saddle Club Rd, Edgartown, MA 02539
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  /18

  $10,000 per month

  • 3 Beds
  • 2 Baths
  • 1,439 Sq Ft
  • House for Rent

  24 Nat's Farm Lane Wt113, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Charming three bedroom home located in a private neighborhood close to bike path, walking trails and public tennis courts. Just a short drive to Lambert's Cove Beach, West Tisbury Village and down island restaurants and shops.Amenities include High definition TV, wifi

  Karen Overtoom Karen M. Overtoom R.E.

  24 Nat's Farm Lane Wt113, West Tisbury, MA 02575
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  /13

  $2,050,000 Sold May 01, 2025

  • 1,007 Sq Ft
  • $2036/SF
  • 0 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 2016

  16 Red Coat Hill Rd, Vineyard Haven, MA 02568

  Exquisite West Tisbury Property: A Unique Opportunity.Discover the allure of a truly exceptional property nestled on 4.85 stunning acres in the serene locale of West Tisbury. This opportunity is not one to be missed, as it combines elegance, foresight, and sustainability in perfect harmony.The home is adorned with beautiful beams throughout, with nickelboard and shiplap covering the walls and

  Joe Holland Vineyard Dream Realty LLC

  16 Red Coat Hill Rd, Vineyard Haven, MA 02568
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  /11

  Est $1,016,321 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,180 Sq Ft

  36 Park Ave, Vineyard Haven, MA 02568

  36 Park Ave, Vineyard Haven, MA 02568
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  /59

  $6,495,000

  • 6 Beds
  • 6 Baths
  • 3,998 Sq Ft

  15 Tamarack Ln, Oak Bluffs, MA 02557

  FARM NECK: The original 1780 Farm House was tastefully restored in 1985 to honor the land and legacy of Farm Neck. This serene 3.7 acre oasis of rolling greenery with a variety of mature trees and lots of natural privacy has an up Island feel with the down Island convenience to fine dining, shopping, ferry, airport, bike paths and includes Stockholder Membership in the popular Farm Neck Golf

  Alan Schweikert Ocean Park Realty Inc

  15 Tamarack Ln, Oak Bluffs, MA 02557
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  /9

  $19,000 per month

  • 6 Beds
  • 2.5 Baths
  • 2,155 Sq Ft
  • House for Rent

  17 Umbagog Ave Wt109, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three story home is located in a very desirable area off of Lambert's Cove Road, Makonikey, with access to a private association beach and walking trails. There are four plus bedrooms and bright and open living spaces that lead out to a deck and a screened-in porch.

  Karen Overtoom Karen M. Overtoom R.E.

  17 Umbagog Ave Wt109, West Tisbury, MA 02575
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  /32

  $1,100,000 Sold May 01, 2025

  • 1,680 Sq Ft
  • $655/SF
  • 172 Days On Market

  • 2 Beds
  • 4 Baths
  • Built 2003

  10 Nunes Way, Oak Bluffs, MA 02557

  On approximately .40 of an acre this 21 year old home has much to offer. In a very convenient location close to theFarm Neck golf course, O.B. elementary school, and a land bank conservation property - the 72 acre Tradewinds Field Reserve dog park. Two decks provide summertime fun and the walk out basement with bath offers an opportunity to finish off more living space. An excellent floor plan

  Neal Stiller Cronigs Real Estate

  10 Nunes Way, Oak Bluffs, MA 02557
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  /36

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,780 Sq Ft

  52 Marthas Rd, Edgartown, MA 02539

  52 Marthas Rd, Edgartown, MA 02539
• 

  

  /39

  $3,299,000

  • 3 Beds
  • 3.5 Baths
  • 3,082 Sq Ft

  53 Stoney Hill Rd, Vineyard Haven, MA 02568

  Nestled in one of the island’s most sought-after locations, this exceptional property offers refined coastal living with access to the famed Lambert’s Cove Beach yet a short drive to VH.Thoughtfully designed, it features 3 spacious bedrooms each with an en suite bath, providing comfort and privacy for all. Primary suite is a true retreat with a brand new luxurious bathroom. At the heart of the

  Jennifer B. DaSilva Compass

  53 Stoney Hill Rd, Vineyard Haven, MA 02568
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  /36

  $56,800 per month

  • 5 Beds
  • 4 Baths
  • 3,000 Sq Ft
  • House for Rent

  2 Nonamessett Rd, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING.Newly renovated architect designed home with every amenity. Cook's gourmet kitchen, open plan living/dining room, second living room, lots of outdoor patio and deck space, Set in a private 7 acre property with wildflower meadow. Relax around the beautiful in ground pool

  Karen Overtoom Karen M. Overtoom R.E.

  2 Nonamessett Rd, Edgartown, MA 02539
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  /35

  $900,000 Sold Apr 30, 2025

  • 1,092 Sq Ft
  • $824/SF
  • 1 Day On Market

  • 1 Bed
  • 1.5 Baths
  • Built 2008

  53 Anthiers Way, Edgartown, MA 02539

  This unique and beautifully handcrafted home in Edgartown is a rare find. It features 1 bedroom, 1.5 bathrooms, and a 3-bedroom septic system, offering the potential for additional bedrooms with town approval. The custom woodwork and fireplace create a warm and inviting atmosphere, while the open-concept kitchen and dining area showcase handmade wood countertops and rustic charm--making it the

  Valentina Globa eXp Realty, LLC

  53 Anthiers Way, Edgartown, MA 02539
• 

  

  /31

  Est $1,461,908 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,999 Sq Ft

  48 Puritan Dr, Vineyard Haven, MA 02568

  48 Puritan Dr, Vineyard Haven, MA 02568
• 

  

  /29

  $4,500,000

  • 5 Beds
  • 6 Baths
  • 5,598 Sq Ft

  71 Stoney Hill Rd, Vineyard Haven, MA 02568

  A combination of luxury, comfort, and natural beauty, this expansive custom, 6,000+ square foot, five bedroom, post and beam home is sited on more than seven acres of land, surrounded by more than 200 acres of Land Bank property. From the moment you step inside, you'll be captivated by the attention to detail and the high-end finishes throughout. The open concept layout allows for seamless flow

  Sheila Morse Island Real Estate

  71 Stoney Hill Rd, Vineyard Haven, MA 02568
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  /25

  $80,000 per month

  • 4 Beds
  • 4.5 Baths
  • 3,800 Sq Ft
  • House for Rent

  7 Mill Hill Farms Rd Ed315, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $20,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Gorgeous new 4 bedroom 4 bath home. Top of the line finishes and appliances. Gourmet kitchen, screened in porch with fireplace and TV. Pool with swim up bar, hot tub and grilling area. This is a cream of the crop Katama house is a short distance to downtown Edgartown and

  Karen Overtoom Karen M. Overtoom R.E.

  7 Mill Hill Farms Rd Ed315, Edgartown, MA 02539
• 

  

  /50

  $3,000,000 Sold Apr 29, 2025

  • 3,311 Sq Ft
  • $906/SF

  • 3 Beds
  • 3 Baths
  • Built 2000

  34 S Pond Rd, Vineyard Haven, MA 02568

  Stunning Deep Bottom Pond property with an oversized 3.77-acre lot surrounded by Mother Nature’s beauty, with exclusive association access to Tisbury Great Pond and private tennis courts. This beautiful home is lovingly maintained and ready for immediate occupancy. Through the welcoming grand foyer, a cathedral-ceiling living room with a fabulous wood-burning fireplace, and slider doors leading

  Stephanie Roache Donnelly + Co

  34 S Pond Rd, Vineyard Haven, MA 02568
• 

  

  /14

  Est $1,503,222 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,717 Sq Ft

  13 Saddle Club Rd, Edgartown, MA 02539

  13 Saddle Club Rd, Edgartown, MA 02539
• 

  

  /40

  $2,095,000

  • 4 Beds
  • 4 Baths
  • 3,927 Sq Ft

  44 Tiffany Dr, Oak Bluffs, MA 02557

  Nestled within the desirable Lagoon Estates development and set on a beautifully wooded 1.38-acre lot abutting Land Bank property, this expansive and sun-filled home offers versatile living space and a flexible floor plan. The main house features generously sized rooms enhanced by large windows that flood the interior with natural light. The kitchen boasts white cabinetry, a wall-mounted

  Nora Jardin Island Real Estate

  44 Tiffany Dr, Oak Bluffs, MA 02557
• 

  

  /23

  $36,000 per month

  • 3 Beds
  • 3 Baths
  • 2,556 Sq Ft
  • House for Rent

  74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Less than 5 miles from the center of town, the property is a 3 bedroom uniquely-designed guest house which provides the space needed for a large family or visiting guests. Most of the living/entertaining space is on the second floor. The kitchen has granite countertops,

  Karen Overtoom Karen M. Overtoom R.E.

  74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539
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  /56

  $7,926,400 Sold Apr 28, 2025

  • 4,520 Sq Ft
  • $1754/SF
  • 205 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1990

  32 Boldwater Rd, Edgartown, MA 02539

  Spectacular 20.8 acre Boldwater Association waterfront estate on Edgartown Great Pond with breathtaking views over 1,000 ft wide low brushy pond front terrain and across the 3/4 mile wide Lyles Bay, dreamy Swan Neck Point, the 1.5 mile wide main pond and barrier beach to the ocean beyond. The handful of well pruned trees on the property enhance the water views. The sophisticated and charming

  Robert Kenney Tea Lane Associates

  32 Boldwater Rd, Edgartown, MA 02539
• 

  

  /20

  Est $1,926,271 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,240 Sq Ft

  11 Pine Tree Ln, Vineyard Haven, MA 02568

  11 Pine Tree Ln, Vineyard Haven, MA 02568
• 

  

  /22

  $1,749,000

  • 3 Beds
  • 2 Baths
  • 1,324 Sq Ft

  76 Norton Orchard Rd, Edgartown, MA 02539

  Conveniently located near downtown Edgartown and the Edgartown Golf Course, this well-maintained three-bedroom, two-bathroom home offers endless potential. The first floor includes a comfortable living room, dining area, kitchen, and a full bathroom. Upstairs, you will find three bedrooms and another full bathroom. There is an unfinished basement which has the laundry and utilities. The property

  Jarrett Hurwitz Keller Williams Realty

  76 Norton Orchard Rd, Edgartown, MA 02539
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  /21

  $8,000 per month

  • 1 Bed
  • 1 Bath
  • 936 Sq Ft
  • House for Rent

  10 James Pond Way, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a

  Karen Overtoom Karen M. Overtoom R.E.

  10 James Pond Way, West Tisbury, MA 02575
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  /52

  $9,525,000 Sold Apr 24, 2025

  • 5,808 Sq Ft
  • $1640/SF
  • 297 Days On Market

  • 6 Beds
  • 6 Baths
  • Built 2008

  2 Squibnocket Rd, Chilmark, MA 02535

  CHILMARK SOUTH SHORE WATER VIEWS. This Squibnocket gem is a Hutker Architect-designed family compound on 4.5 acres. With captivating water views in every direction, this home is the perfect launch pad for the ultimate up-Island lifestyle. Grab your surf or paddle board and head down the path to Squibnocket Beach for a morning surf or swim. Pack the cooler with lunch from the Chilmark Store for a

  Tina Miller Compass | Point B

  2 Squibnocket Rd, Chilmark, MA 02535
• 

  

  /17

  Est $1,726,442 Not Listed For Sale

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

  55 Pinehurst Rd, Edgartown, MA 02539

  55 Pinehurst Rd, Edgartown, MA 02539
• 

  

  /57

  $6,900,000

  • 7 Beds
  • 6 Baths
  • 4,730 Sq Ft

  180 Pilot Hill Farm Rd, Vineyard Haven, MA 02568

  A storybook sanctuary in Pilot Hill. For the first time in 37 years, one of the rarest and most beautiful properties within Pilot Hill Farm is being offered for sale.Set on nearly eight acres, this unique estate includes a thoughtfully renovated antique farmhouse and several distinctive outbuildings: a pool, guest house, an art studio, and a carriage house with room for three cars, plus a

  Alexis Holden Tea Lane Associates

  180 Pilot Hill Farm Rd, Vineyard Haven, MA 02568
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  /26

  $50,000 per month

  • 4 Beds
  • 3 Baths
  • 3,237 Sq Ft
  • House for Rent

  29 Naushon Rd Wt142, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfortable single level 4 BR 3 bath home has central air and heat. Enjoy summer star-studded skies from your patio or through skylights in each bedroom.

  Karen Overtoom Karen M. Overtoom R.E.

  29 Naushon Rd Wt142, West Tisbury, MA 02575
• 

  

  /42

  $9,725,000 Sold Apr 24, 2025

  • 5,808 Sq Ft
  • $1674/SF
  • 295 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 2008

  2 Squibnocket Rd, Chilmark, MA 02535

  CHILMARK SOUTH SHORE WATER VIEW. This Squibnocket gem is a Hutker Arhictect-designed family compound, main house,& guest house on 4.5 acres. Live the ultimate up-Island life with captivating water views in every direction. The home is pristine and private, with many unique features. The chef's kitchen and dining area are serene, bright, and functional. Step up to what might be the best panorama

  Tina Miller Compass

  2 Squibnocket Rd, Chilmark, MA 02535
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  /47

  Est $2,356,806 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 3,627 Sq Ft

  24 Peacegate Way, Vineyard Haven, MA 02568

  24 Peacegate Way, Vineyard Haven, MA 02568

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