Dukes, MA Homes

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  /20

  $1,050,000

  • 3 Beds
  • 2 Baths
  • 836 Sq Ft

  32 Beach Rd, Oak Bluffs, MA 02557

  Tucked along a main road in Oak Bluffs, this small yet cozy year-round cottage offers a charming Vineyard lifestyle with surprising touches of serenity. While compact in size, the home lives larger than expected with its inviting layout, warm interiors, and thoughtful use of space. A standout feature: peeks of the Lagoon and Vineyard Haven harbor, offering glimmers of coastal beauty to brighten

  Bonnie Pierce Wallace & Co. Sotheby's

  32 Beach Rd, Oak Bluffs, MA 02557
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  /16

  $30,000 per month

  • 4 Beds
  • 2.5 Baths
  • 1,988 Sq Ft
  • House for Rent

  45A Buttonwood Farm Wt121, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. This stunning sanctuary offers a unique balance of simplicity and sophistication. There is a lot of room for family and friends to enjoy both indoors and out. Nestled about midway between Tisbury and West Tisbury, here you will find yourself close to two of Martha's Vineyard's town centers. Enjoy ping pong in the retro style game room or a fire in the fire pit. This

  Karen Overtoom Karen M. Overtoom R.E.

  45A Buttonwood Farm Wt121, West Tisbury, MA 02575
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  /19

  $2,100,000 Sold Mar 14, 2025

  • 2,784 Sq Ft
  • $754/SF
  • 208 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2003

  30 Deacon Vincent Way, Edgartown, MA 02539

  Explore this colonial style home in the ideal Edgartown Estates neighborhood. The upside-down layout maximizes lush tree views and privacy. The main living area awaits—a bright cathedral-ceilinged room that seamlessly blends kitchen, dining, and lounging spaces. Two separate decks with sliding doors off dining and living area perfect for summer gatherings with a fireplace to anchor the open

  Tara Ledden Ledden Properties LLC

  30 Deacon Vincent Way, Edgartown, MA 02539
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  /32

  Est $1,847,458 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  261 W Tisbury Rd, Edgartown, MA 02539

  261 W Tisbury Rd, Edgartown, MA 02539
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  /14

  $3,995,000

  • 4 Beds
  • 4 Baths
  • 3,270 Sq Ft

  160 Katama Rd, Edgartown, MA 02539

  Gorgeous post-and-beam home built by a respected contractor. This spacious house plus detached guest quarters is on the outskirts of the village conveniently located on the way to South Beach. The property is at the end of a long driveway off Katama Road and is private and quiet. Upon arrival, you are greeted by beautiful landscaping with large beds of hydrangeas. There are 3 bedrooms in the main

  Bonnie Pierce Wallace & Co. Sotheby's

  160 Katama Rd, Edgartown, MA 02539
• 

  

  /11

  $12,500 per month

  • 4 Beds
  • 1.5 Baths
  • 1,413 Sq Ft
  • House for Rent

  11 Wamsutta Ave Ob540, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. This antique Vineyard home is thoughtfully styled with classic country-chic interior decor. The wraparound porch has plenty of room to enjoy people watching or sipping ice cold tea, perfect for a hot summer day. Alternatively, you can enjoy peering down the street from the master bedroom which opens up to a charming porch with plenty of room for two to enjoy

  Karen Overtoom Karen M. Overtoom R.E.

  11 Wamsutta Ave Ob540, Oak Bluffs, MA 02557
• 

  

  /19

  $1,265,000 Sold Mar 11, 2025

  • 1,682 Sq Ft
  • $752/SF
  • 357 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2010

  62 Lagoon Pond Rd Unit B, Vineyard Haven, MA 02568

  A must see property located in the heart of Vineyard Haven. This three-bedroom, two bath, colonial style condo boasts expansive living spread over three floors. Completed in 2019, this energy efficient 1682 sq ft home includes a 5 KW solar PV system. The open layout of the first floor includes a modern, galley style kitchen with stainless steel appliances and extensive counter space. The three

  Allison Fisher Snowden Donnelly + Co

  62 Lagoon Pond Rd Unit B, Vineyard Haven, MA 02568
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  /12

  Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 2,892 Sq Ft

  9 Dunes Rd, Edgartown, MA 02539

  9 Dunes Rd, Edgartown, MA 02539
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  /33

  $8,995,000

  • 11 Beds
  • 9 Baths
  • 9,678 Sq Ft

  5 Louis Field Rd, Edgartown, MA 02539

  SWEETENED WATER FARM ESTATE. Located just one mile from the heart of historic Edgartown Village, this compound in Sweetened Water Farm presents a rare opportunity to become the next steward of an extraordinary Martha’s Vineyard estate. Privately sited on 4.6 acres of exquisitely cultivated gardens, this remarkable property has been featured in several publications celebrating the island’s most

  Wendy Harman Compass | Point B

  5 Louis Field Rd, Edgartown, MA 02539
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  /9

  $6,500 per month

  • 3 Beds
  • 3 Baths
  • 1,645 Sq Ft
  • House for Rent

  23 Ocean Ave Unit OB539, Edgartown, MA 02539

  THIS IS A SUMMER WEEKLY RENTAL ONLY. PRICES ARE WEEKLY NOT MONTHLY. Victorian Cottage located on Ocean Park in the heart of Oak Bluffs with fully equipped and updated kitchen, five bedrooms and three baths, cozy living spaces and multiple amenities will accommodate your family and friends. Smell the sea air and watch the waves break from your front porch. This charming beach house is steps away

  Karen Overtoom Karen M. Overtoom R.E.

  23 Ocean Ave Unit OB539, Edgartown, MA 02539
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  /25

  $917,500 Sold Mar 10, 2025

  • 1,898 Sq Ft
  • $483/SF
  • 140 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1983

  40 Hidden Cove Rd Unit 15, Oak Bluffs, MA 02557

  NEW PRICE. Enjoy the fabulous amenities in the well-established Hidden Cove community, including the heated pool, tennis courts, and a boat launch for easy access to Sengekontacket. This is what a vacation home is all about! This unit offers abundant natural light, a comfortable floor plan, and pleasant meadow views with a peek of water. The kitchen, dining, and living rooms are on the main floor

  Stephanie Roache Donnelly + Co

  40 Hidden Cove Rd Unit 15, Oak Bluffs, MA 02557
• 

  

  /18

  Est $1,136,676 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1 Sq Ft

  10 Canterbury Ln, Vineyard Haven, MA 02568

  10 Canterbury Ln, Vineyard Haven, MA 02568
• 

  

  /39

  $1,695,000

  • 3 Beds
  • 4 Baths
  • 3,027 Sq Ft

  110 Clover Hill Dr, Vineyard Haven, MA 02568

  Located just six minutes from Downtown Vineyard Haven and the ferry, this updated home offers flexible living with three bedrooms and four bathrooms and many additional interior/exterior living areas to enjoy. It has a private entry studio apartment a large fenced in yard and a detached garage for boat or car storage. The main level features hardwood floors, a modern kitchen with granite

  Janna O'Loughlin Portfolio Real Estate, Inc.

  110 Clover Hill Dr, Vineyard Haven, MA 02568
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  /11

  $21,000 per month

  • 3 Beds
  • 2 Baths
  • 1,481 Sq Ft
  • House for Rent

  24 Deer Run Rd Unit OB521, Vineyard Haven, MA 02568

  THIS IS A SUMMER RENTAL ONLY. Centrally located to Edgartown, Vineyard Haven and Oak Bluffs. Just a short drive will take you to any of the town beaches and the Sailing Camp Park is a quick bike ride away. The home is located on over a 1/2 acre of landscaped property in a beautiful, private, neighborhood, with private roads great for biking and is wonderful for families, friends or even a

  Karen Overtoom Karen M. Overtoom R.E.

  24 Deer Run Rd Unit OB521, Vineyard Haven, MA 02568
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  /24

  $917,500 Sold Mar 10, 2025

  • 1,898 Sq Ft
  • $483/SF
  • 138 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1983

  40 Hidden Cove Rd Unit 15, Edgartown, MA 02539

  NEW PRICE. Enjoy the fabulous amenities in the well-established Hidden Cove community, including the heated pool, tennis courts, and a boat launch for easy access to Sengekontacket. This is what a vacation home is all about! This unit offers abundant natural light, a comfortable floor plan, and pleasant meadow views with a peek of water. The kitchen, dining, and living rooms are on the main floor

  Stephanie Roache Donnelly + Co.

  40 Hidden Cove Rd Unit 15, Edgartown, MA 02539
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  /32

  Est $1,319,395 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,118 Sq Ft

  58 Hagerty Dr, Vineyard Haven, MA 02568

  58 Hagerty Dr, Vineyard Haven, MA 02568
• 

  

  /41

  $1,850,000

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

  4 Hye Ln, Edgartown, MA 02539

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

  Lynn Buder Sandpiper Realty Inc

  4 Hye Ln, Edgartown, MA 02539
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  /14

  $20,000 per month

  • 3 Beds
  • 1 Bath
  • 1,629 Sq Ft
  • House for Rent

  67 New York Ave Unit OB536, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. 1900 Oak Bluffs Victorian. Ten minute walk to Nancy’s restaurant/downtown OB and 1/2 mile walk to Jetty beach in East Chop. The house was purchased empty in 2018 so all furnishings are new and the house is freshly painted. On the second floor, there are 3 bedrooms and a full bathroom, which connects to hall and master bedroom. Two bedrooms include queen beds and

  Karen Overtoom Karen M. Overtoom R.E.

  67 New York Ave Unit OB536, Oak Bluffs, MA 02557
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  /25

  $917,500 Sold Mar 10, 2025

  • 1,898 Sq Ft
  • $483/SF
  • 139 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1983

  40 Hidden Cove Rd, Edgartown, MA 02539

  NEW PRICE. Enjoy the fabulous amenities in the well-established Hidden Cove community, including the heated pool, tennis courts, and a boat launch for easy access to Sengekontacket. This is what a vacation home is all about! This unit offers abundant natural light, a comfortable floor plan, and pleasant meadow views with a peek of water. The kitchen, dining, and living rooms are on the main floor

  Stephanie Roache Donnelly + Co.

  40 Hidden Cove Rd, Edgartown, MA 02539
• 

  

  /35

  Est $3,432,477 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,407 Sq Ft

  5 Hillman Dr, Edgartown, MA 02539

  5 Hillman Dr, Edgartown, MA 02539
• 

  

  /4

  $425,000

  • Land
  • 0.23 Acre
  • $1,847,826 per Acre

  0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568

  Lovely untouched piece of land waiting for you to create your own special island retreat. Property, being sold "AS IS", is nestled on a quiet dead end road off of DeBettencourt Place in Oak Bluffs. Conveniently located within walking distance to downtown OB, OB Ferry, beaches, parks, arts district and more... Included on the "Sea View Bluffs Subdivision Plan of Land" and recorded with Dukes

  Rosemary Byrd Ocean Park Realty Inc

  0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568
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  /16

  $40,000 per month

  • 4 Beds
  • 3 Baths
  • 2,748 Sq Ft
  • House for Rent

  38 Farm Pond Ob524, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. Gracious 4 bedroom home with private beach access and tennis. This home has a reverse design that has been fully renovated and thoughtfully decorated. There is a large deck overlooking gardens and a peep of the water. A separate studio is attached by the deck. You are a short distance from town, less than a mile to the public beach and a minutes to a beautiful

  Karen Overtoom Karen M. Overtoom R.E.

  38 Farm Pond Ob524, Oak Bluffs, MA 02557
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  /38

  $2,860,000 Sold Mar 10, 2025

  • 3,752 Sq Ft
  • $762/SF
  • 290 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1836

  49 William St, Vineyard Haven, MA 02568

  Welcome to the timeless elegance of the Captain Swain House, nestled on the prestigious historic William Street in Vineyard Haven. This distinguished Greek Revival main residence and barn-style guest house seamlessly merges historical charm with modern luxury. Step into this meticulously updated 4-bedroom home and you will find a gourmet kitchen, a welcoming dining room, wet-bar and a screened

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  49 William St, Vineyard Haven, MA 02568
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  /42

  Est $4,296,903 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,467 Sq Ft

  8 Jennifer Way, Edgartown, MA 02539

  8 Jennifer Way, Edgartown, MA 02539
• 

  

  /31

  $4,075,000 Open Wed 11AM - 1PM

  • 4 Beds
  • 3.5 Baths
  • 2,861 Sq Ft

  39 Sengekontacket Rd, Edgartown, MA 02539

  Spectacular waterfront home with stunning water views from every room and completely renovated in 2014. Situated in a private location in the Sengekontacket Association, this is an exceptional property in a rare setting. In addition to the breathtaking water view of Major's Cove and of Felix Neck throughout the home, the front of the property faces serene pastoral views. This home offers four

  Jayne Isford Ocean Park Realty, Inc.

  39 Sengekontacket Rd, Edgartown, MA 02539
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  /11

  $25,000 per month

  • 3 Beds
  • 3 Baths
  • 2,300 Sq Ft
  • House for Rent

  61 Roadto Greatneck, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. This lovely new build house features 3 bedrooms, and 3 bathrooms. There is a full gourmet kitchen, open to the dining, living and patio area. French doors off the living area open up to a beautiful blue stone patio complete with breath taking water views. All three bedrooms are located on the upstairs level including the master suite. Lambert's Cove Beach Access.

  Karen Overtoom Karen M. Overtoom R.E.

  61 Roadto Greatneck, West Tisbury, MA 02575
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  /47

  $4,650,000 Sold Mar 06, 2025

  • 4,084 Sq Ft
  • $1139/SF
  • 572 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2005

  5 Armstrong Ln, Edgartown, MA 02539

  This custom Gambrel-style home sits high atop Manaca Hill on Chappaquiddick Island with views of Edgartown Harbor and Katama Bay. The first-floor features hardwood floors throughout, tall ceilings and lots of windows to maximize the views. Enjoy the spacious open kitchen with top of the line appliances, a large center island and soapstone countertops. Perfect for entertaining, the area opens up

  Thomas Leclair Landvest MV

  5 Armstrong Ln, Edgartown, MA 02539
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  /17

  Est $1,462,380 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft

  2 Pond View Farm Rd, Vineyard Haven, MA 02568

  2 Pond View Farm Rd, Vineyard Haven, MA 02568
• 

  

  /21

  $650,000

  • 2 Beds
  • 1 Bath
  • 725 Sq Ft

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

  Outstanding year-round, two-bedroom condo on the ground level with dedicated parking, and close to the ferry, shops, and restaurants on Main Street, Vineyard Haven. The common grounds feature colorful landscaping, picnic tables, grills, and a swimming pool with a distant peek at the Lagoon. This unit has been delightfully renovated, featuring new hardwood floors, an updated bathroom, updated

  Stephanie Roache Donnelly + Co.

  124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
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  /12

  $17,000 per month

  • 4 Beds
  • 3.5 Baths
  • 2,300 Sq Ft
  • House for Rent

  196 Vineyard Meadow Farms Wt130, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. Well appointed Farmhouse Colonial, on two private acres on private road. Conveniently located in Vineyard Meadow Farms abutting the entrance to Long Point Beach, considered by many to be the best beach on the Island. Home was built for families in mind, with three bedrooms upstairs, master with queen bed and ensuite bathroom. In addition there are two bedrooms, each

  Karen Overtoom Karen M. Overtoom R.E.

  196 Vineyard Meadow Farms Wt130, West Tisbury, MA 02575
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  /13

  $776,500 Sold Mar 05, 2025

  • 768 Sq Ft
  • $1011/SF
  • 17 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1968

  32 Clark Ave, Vineyard Haven, MA 02568

  This two bedroom year-round home will afford you all the opportunities Vineyard Haven has to offer. This private lot is bursting with lilacs, forsythia, wisteria, raspberry canes, a mock orange bush and a peach tree. The home boasts natural light, cathedral ceilings, a comfortable kitchen and living area with two bedrooms and one full bath. There is a mudroom and a handsome, fully enclosed front

  Diana Gilmore Island Real Estate

  32 Clark Ave, Vineyard Haven, MA 02568
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  /41

  Est $2,042,201 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,803 Sq Ft

  7 Tar Barrel Rd, Aquinnah, MA 02535

  7 Tar Barrel Rd, Aquinnah, MA 02535
• 

  

  /37

  $6,250,000

  • 6 Beds
  • 9 Baths
  • 5,732 Sq Ft

  31 Lamberts Cove Rd, Vineyard Haven, MA 02568

  Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation

  Idalyn Macchia Gilstad Wallace & Co. Sotheby's

  31 Lamberts Cove Rd, Vineyard Haven, MA 02568
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  /21

  $13,000 per month

  • 4 Beds
  • 3 Baths
  • 2,500 Sq Ft
  • House for Rent

  14 Pulpit Rock Rd, Oak Bluffs, MA 02557

  PRICES ARE WEEKLY NOT MONTHLY. Located in Waterview Farms, this four bedroom home features a private beach on Sengekontacket Pond, private dock access to Land Bank boat launch and several walking trails. Just minutes to Farm Neck Golf Course, beaches and town.

  Karen Overtoom Karen M. Overtoom R.E.

  14 Pulpit Rock Rd, Oak Bluffs, MA 02557
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  /17

  $1,300,000 Sold Mar 03, 2025

  • 1,241 Sq Ft
  • $1048/SF
  • 4 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2018

  22 Briarwood Ln, Vineyard Haven, MA 02568

  This Recently Constructed Carriage House in Vineyard Haven is the epitome of thoughtful planning with custom details and exceptional finishes throughout. The sunny second level has an open floor living and kitchen area with vaulted ceilings. Highlights include a farmer’s sink, quartz countertops, pull out kitchen cabinets and self-closing drawers. There are two bedrooms, one is ensuite and the

  Carol Shore Donnelly + Co

  22 Briarwood Ln, Vineyard Haven, MA 02568
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  /22

  Est $1,105,440 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,025 Sq Ft

  10 Saddle Club Rd, Edgartown, MA 02539

  10 Saddle Club Rd, Edgartown, MA 02539
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  /32

  $3,150,000

  • 4 Beds
  • 3.5 Baths
  • 2,566 Sq Ft

  28 Marthas Rd, Edgartown, MA 02539

  Nestled on a generous corner lot in one of Edgartown’s sought-after neighborhoods, this beautifully maintained 4BD, 3.5BA home offers the perfect blend of comfort, convenience, and classic Vineyard charm. The home features a spacious and versatile floor plan, ideal for both year-round living and summer getaways. The light-filled living areas, anchored by a floor to ceiling wood burning fireplace,

  Stacy Ickes Donnelly + Co.

  28 Marthas Rd, Edgartown, MA 02539
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  /26

  $18,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • House for Rent

  40 Lighthouse Rd, Aquinnah, MA 02535

  Great water view property in Aquinnah - this immaculate contemporary has that unique combination of a beautifully designed and constructed, year-round home, AND an outstanding view of the Sound and Elizabeth Islands. Not only is the water view property packed with many custom details, but the home's layout is perfect for relaxed living - with a fantastic kitchen open to the dining and living

  Karen Overtoom Karen M. Overtoom R.E.

  40 Lighthouse Rd, Aquinnah, MA 02535
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  /10

  $550,000 Sold Feb 28, 2025

  • Land
  • 0.33 Acre
  • $1,666,667 per Acre

  • 70 Days On Market

  0 Shawanue Ave Unit 42704, Oak Bluffs, MA 02557

  Secluded lot in a prime Oak Bluffs location, offering both privacy and convenience. Just moments from public access points to the sandy shores of Lagoon Pond and the vibrant downtown area, this property provides the perfect setting for your dream home. With engineering plans already in place for a 2-bedroom residence, you have the opportunity to create a custom-built home tailored to your vision.

  Alyssa Halisky Wallace & Co. Sotheby's

  0 Shawanue Ave Unit 42704, Oak Bluffs, MA 02557
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  /32

  Est $1,221,911 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,429 Sq Ft

  10 Elm St, Vineyard Haven, MA 02568

  10 Elm St, Vineyard Haven, MA 02568

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