Dukes, MA Homes in ZIP Code 02568

• 

  

  

  /54

  $1,830,000

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

  12 & 14 Maple Ave, Oak Bluffs, MA 02557

  Two Historic Oak Bluffs Cottages - Prime Location - Deeded Separately Perched atop a gentle hill, surrounded by lush, established gardens in one of the island's most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history--just a short distance to the harbor, downtown, and the beloved Winston's takeout. Built at a time when automobiles

  Leslie Floyd Portfolio Properties

  12 & 14 Maple Ave, Oak Bluffs, MA 02557
• 

  

  

  /22

  $10,000 per month

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft
  • House for Rent

  21 Leona Lane Wt115, West Tisbury, MA 02575

  THIS IS A SUMMER RENTAL ONLY. This very charming post & beam home is the perfect getaway for those who appreciate West Tisbury's rural character. The home is very nicely furnished and equipped, has a lovely, big yard, and the location, adjacent to the bike path, is central to up-Island shopping and the fantastic sandy beaches of Lambert's Cove and Long Point Reservation. There is no land line

  Karen Overtoom Karen M. Overtoom R.E.

  21 Leona Lane Wt115, West Tisbury, MA 02575
• 

  

  

  /38

  $1,875,000 Sold Apr 01, 2025

  • 3,841 Sq Ft
  • $488/SF
  • 24 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1994

  83 Dolan Ave, Vineyard Haven, MA 02568

  Beautiful Cape style home renovated over the years with an open floor plan, five bedrooms including a first-floor primary with en-suite, and a nicely finished walk-out lower level. There is a 7-bedroom septic system for additional bedrooms and a special permit for the apartment. Manicured yard with mature plantings providing excellent privacy. In-ground heated pool with blue stone patio and lots

  Courtney Marek Sandpiper Realty

  83 Dolan Ave, Vineyard Haven, MA 02568
• 

  

  

  /17

  Est $1,422,592 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
• 

  

  

  /44

  $6,395,000

  • 6 Beds
  • 6 Baths
  • 7,000 Sq Ft

  400 Barnes Rd, Vineyard Haven, MA 02568

  Experience the quiet elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime Oak Bluffs location. Tucked behind a long private drive and surrounded by 234 acres of Southern Woodlands conservation land offering biking and hiking, this expansive property offers unparalleled privacy just minutes from Featherstone Center for the Arts, Farm Neck Golf Club and the island’s

  Jennifer DaSilva Compass | Point B

  400 Barnes Rd, Vineyard Haven, MA 02568
• 

  

  /15

  $21,000 per month

  • 6 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • House for Rent

  12 John Wesley Ave Ob519, Oak Bluffs, MA 02557

  THIS IS A SUMMER RENTAL ONLY. EAST CHOP LOCATION!! Located across from the historic Baptist Temple Town Park. This charming 1885 Victorian cottage is original to days gone by and a significant part of the Vineyard Highlands. Six bedrooms and two full bathrooms allow for friends and family to visit along with a cozy, bright vintage kitchen. This is a house of distinctive "Carpenter Gothic"

  Karen Overtoom Karen M. Overtoom R.E.

  12 John Wesley Ave Ob519, Oak Bluffs, MA 02557
• 

  

  /34

  $980,000 Sold Mar 26, 2025

  • 1,608 Sq Ft
  • $609/SF
  • 191 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1969

  11 Fairway Dr, Oak Bluffs, MA 02557

  In the well established residential neighborhood of Sea Glen, turn in onto the second street on the right. At the soft curve of the road, just on the other side of the low natural stone wall, the land gently slopes down toward the house where you will find this understated rustic one level home nestled in the midst of lovely seasonal flower beds surrounding the house with mature trees along the

  Sandra Grymes Portfolio Real Estate, Inc.

  11 Fairway Dr, Oak Bluffs, MA 02557
• 

  

  /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
• 

  

  /52

  $3,950,000

  • 5 Beds
  • 7 Baths
  • 4,372 Sq Ft

  139 Main St, Vineyard Haven, MA 02568

  Nestled just two blocks from Vineyard Haven’s working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses—now gracefully combined into a single half-acre parcel—this home offers rare space, privacy, and timeless character in one of the island’s most approachable villages.From the moment you step through the welcoming

  Leslie C. Floyd Portfolio Real Estate, Inc.

  139 Main St, Vineyard Haven, MA 02568
• 

  

  /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
• 

  

  /34

  $1,136,250 Sold Mar 19, 2025

  • 1,152 Sq Ft
  • $986/SF
  • 239 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1999

  41 Towanticut Ave, Oak Bluffs, MA 02557

  What a wonderful opportunity to own a Contemporary Ranch style home on this beautiful Island of Martha’s Vineyard. It is well maintained with three bedrooms, two full baths, central a/c, and a full unfinished basement. Ideal location in a very quiet neighborhood, just a short distance to bike path, Town, ferry, restaurants, beaches, shops all that you could ask for. Living room is light, bright

  JoJo Lambert Island Home Realty Inc.

  41 Towanticut Ave, Oak Bluffs, MA 02557
• 

  

  /30

  Est $1,535,358 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft

  88 Hopps Farm Rd, Vineyard Haven, MA 02568

  88 Hopps Farm Rd, Vineyard Haven, MA 02568
• 

  

  /84

  $1,350,000

  • 3 Beds
  • 3 Baths
  • 1,900 Sq Ft

  145 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

  Enjoy effortless island living in this beautifully renovated 3-bedroom, 2.5-bath condo, tucked within a quiet and well-maintained association. Thoughtfully updated with modern finishes and quality craftsmanship, this spacious unit offers comfort, style, and functionality. The open-concept living area features a cozy wood pellet fireplace, perfect for cooler evenings, and flows seamlessly into a

  Emily Flake Viewpoints

  145 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568
• 

  

  /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
• 

  

  /22

  $1,115,000 Sold Mar 14, 2025

  • 1,286 Sq Ft
  • $867/SF
  • 212 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1955

  496 Lamberts Cove Rd, Vineyard Haven, MA 02568

  Two peaceful acres on coveted Lamberts Cove Road with access to Lamberts Cove Beach and proximity to West Tisbury Center and Conservation Land. This property boasts mature plantings, various trees, and much Mother Nature offers, including a small pond. The home has been completely renovated and enjoys hardwood floors, skylights, a wood stove, and other special features such as antique

  Stephanie Roache Donnelly + Co

  496 Lamberts Cove Rd, Vineyard Haven, MA 02568
• 

  

  /22

  Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,250 Sq Ft

  33 Summer St, Vineyard Haven, MA 02568

  33 Summer St, Vineyard Haven, MA 02568
• 

  

  /21

  $1,675,000

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft

  111 Charles Neck Way, Vineyard Haven, MA 02568

  Tucked away on 1.6 wooded acres in West Tisbury, this classic Cape-style home offers both privacy and convenience, with easy access to the charm of Up-Island and the amenities of Down-Island. Located on a paved road near Long Point Beach, it also includes coveted access to Lambert's Cove Beach. The bright, open interior features a living and dining area with a wood-burning fireplace, a kitchen

  Emma Kennedy Sandpiper Realty Inc

  111 Charles Neck Way, Vineyard Haven, MA 02568
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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
• 

  

  /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
• 

  

  /44

  Est $4,915,949 Not Listed For Sale

  • 6 Beds
  • 7 Baths
  • 5,034 Sq Ft

  59 Hagerty Dr, Vineyard Haven, MA 02568

  59 Hagerty Dr, Vineyard Haven, MA 02568
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /15

  Est $1,197,123 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 966 Sq Ft

  73 Leonard Cir, Vineyard Haven, MA 02568

  73 Leonard Cir, Vineyard Haven, MA 02568
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /33

  Est $1,896,538 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,508 Sq Ft

  163 Charles Neck Way, Vineyard Haven, MA 02568

  163 Charles Neck Way, Vineyard Haven, MA 02568
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /41

  Est $4,069,861 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 4,521 Sq Ft

  89 Pond Rd, Vineyard Haven, MA 02568

  89 Pond Rd, 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
• 

  

  /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
• 

  

  /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
• 

  

  /20

  Est $1,337,713 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,730 Sq Ft

  225 Longview Rd, Vineyard Haven, MA 02568

  225 Longview Rd, Vineyard Haven, MA 02568
• 

  

  /114

  $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
• 

  

  /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
• 

  

  /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
• 

  /2

  Est $2,311,716 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,269 Sq Ft

  59 Field View Ln, Vineyard Haven, MA 02568

  59 Field View Ln, Vineyard Haven, MA 02568

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