Dukes, MA Homes

• 

  

  

  /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
• 

  

  

  /10

  $11,000 per month

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

  15 Price's Way Ed322, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is an inviting and affordable home with air-conditioning. As you see from the pictures the sun is welcomed through many sliders and windows. Inside the furnishings are simple but well chosen. There is a splitter in the living area that cools the downstairs. The

  Karen Overtoom Karen M. Overtoom R.E.

  15 Price's Way Ed322, Edgartown, MA 02539
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  /37

  $1,835,000 Sold May 23, 2025

  • 2,391 Sq Ft
  • $767/SF
  • 59 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2001

  41 Smith Hollow Dr, Edgartown, MA 02539

  Discover this exquisite, contemporary home nestled in the heart of Edgartown's Smith Hollow, conveniently located just off the bike path and mere minutes from the lively Edgartown Village. Situated in a welcoming, family-oriented neighborhood, this stylish residence boasts a bright and airy open floor plan.The Great Room captivates with its soaring cathedral wood ceiling and robust timber accent

  Marilyn Moses Ocean Park Realty Inc

  41 Smith Hollow Dr, Edgartown, MA 02539
• 

  

  

  /23

  Est $2,907,034 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,252 Sq Ft

  5 Bold Meadow Cir, Edgartown, MA 02539

  5 Bold Meadow Cir, Edgartown, MA 02539
• 

  

  

  /32

  $4,075,000 Open Sun 1PM - 3PM

  • 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
• 

  

  /21

  $14,000 per month

  • 4 Beds
  • 2 Baths
  • 1,505 Sq Ft
  • House for Rent

  175 Meetinghouse Way Ed321, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This updated contemporary is located in Katama area and a short bike ride to South Beach. There are 4 bedrooms, 1 down and 3 up, and a beautiful kitchen/dining which opens to a large living room. The house has a nice deck on the front and owners have added a deck off the

  Karen Overtoom Karen M. Overtoom R.E.

  175 Meetinghouse Way Ed321, Edgartown, MA 02539
• 

  

  /33

  $1,790,000 Sold May 23, 2025

  • 1,674 Sq Ft
  • $1069/SF
  • 36 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1977

  8 Massasoit Rd, Edgartown, MA 02539

  This incredibly charming Katama Cape Cod-style home that has been completely refreshed top to bottom! An updated kitchen with high-end appliances, including a wine fridge, two brand new bathrooms, central AC, new heating system, and a new second floor deck are just some of the improvements. There are two bedrooms, one on each floor. The second floor has a comfortable lounge area, and a cozy loft

  Cheri Mason Landvest MV

  8 Massasoit Rd, Edgartown, MA 02539
• 

  

  /22

  Est $2,812,863 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,050 Sq Ft

  23 Majors Cove Ln, Edgartown, MA 02539

  23 Majors Cove Ln, Edgartown, MA 02539
• 

  

  /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
• 

  

  /28

  $29,300 per month

  • 3 Beds
  • 2.5 Baths
  • 1,871 Sq Ft
  • House for Rent

  76 Mattakesett Way Ed313, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,325. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This upside-down house was built in 2007. Sit out on the upper deck to panoramic ocean views or grill your favorite seafood while taking in the view. Watch the sun set to a new and beautiful aurora each night on either of the decks or while lazing on the porch swing.The

  Karen Overtoom Karen M. Overtoom R.E.

  76 Mattakesett Way Ed313, Edgartown, MA 02539
• 

  

  /13

  $1,195,000 Sold May 22, 2025

  • 1,110 Sq Ft
  • $1077/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  34 10th St S, Edgartown, MA 02539

  This charming 3 bedroom, 2 bathroom ranch-style Edgartown home offers comfortable single-level living with classic Vineyard appeal. The layout includes a dedicated living room, and an open kitchen and dining area. The primary suite features a private bath, while two additional bedrooms share a full bathroom. Outside, the property provides deck overlooking the yard for enjoying the outdoors.

  Rose Ryley Sandpiper Realty Inc

  34 10th St S, Edgartown, MA 02539
• 

  

  /7

  Est $4,090,508 Not Listed For Sale

  • 6 Beds
  • 7 Baths
  • 6,783 Sq Ft

  3 Duarte Cir, Edgartown, MA 02539

  3 Duarte Cir, Edgartown, MA 02539
• 

  

  /46

  $2,495,000

  • 5 Beds
  • 4 Baths
  • 3,873 Sq Ft

  50 Hidden Cove Rd, Edgartown, MA 02539

  Sengekontacket–Walk into a “turn-key” opportunity in the desirable Hidden Cove community, just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering an abundance of natural light that flows into the open living and entertaining spaces. The

  Sean Federowicz Landmarks at TODAY Real Estate

  50 Hidden Cove Rd, Edgartown, MA 02539
• 

  

  /17

  $48,000 per month

  • 4 Beds
  • 3.5 Baths
  • 2,675 Sq Ft
  • House for Rent

  9 Thaxter Lane Ed310, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Enjoy the pool with this Stunning custom designed and professionally decorated Tri Level contemporary home with open floor plan. Once inside you will be captivated by the dramatic open spaces, soaring ceiling and walls of glass. Located in a high end neighborhood within

  Karen Overtoom Karen M. Overtoom R.E.

  9 Thaxter Lane Ed310, Edgartown, MA 02539
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  /36

  $5,500,000 Sold May 20, 2025

  • 3,262 Sq Ft
  • $1686/SF
  • 295 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1984

  12 Tamarack Ln, Oak Bluffs, MA 02536

  This bright and sunny home has a spectacular waterview overlooking the Eighth Fairway of Farm Neck Golf Course, Sengekontacket Pond and Nantucket Sound. Professionaly designed landscaping with perennial beds and charming brick courtyard add to its ambiance. Included are Farm Neck Golf Club stockholder membership (meaning immediate entry into golf membership), tennis and dock & mooring privileges.

  Betsy Kessler Rutledge Properties

  12 Tamarack Ln, Oak Bluffs, MA 02536
• 

  

  /32

  Est $2,915,965 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,101 Sq Ft

  10 Codman Spring Rd, Edgartown, MA 02539

  10 Codman Spring Rd, Edgartown, MA 02539
• 

  

  /20

  $4,200,000

  • 4 Beds
  • 3.5 Baths
  • 3,716 Sq Ft

  1 Wilsons Ln, Edgartown, MA 02539

  NEWLY CONSTRUCTED gambrel home with a heated saltwater POOL, close to SOUTH BEACH and EDGARTOWN VILLAGE! The entry foyer presents with an oversized lounge area to the right and a spectacular great room ahead. The great room offers a cathedral ceiling and rear wall of two story windows with a gas fireplace. The great room opens to the dining room which features a wall of sliding glass doors

  Michele Casavant Vineyard Village Realty

  1 Wilsons Ln, 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
• 

  

  /18

  $1,850,000 Sold May 19, 2025

  • 1,428 Sq Ft
  • $1296/SF
  • 158 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1982

  18 Katama Dr, Edgartown, MA 02539

  Ocean views - Nestled on a quiet corner lot, this classic beach house offers a reverse floor plan and distant views of the Atlantic Ocean over the Katama Plain . The upper level features the common living space including the dining area, kitchen, living room with fireplace, and large powder room. The lower level is where you find the more private spaces, including the primary bedroom suite plus

  Bonnie Pierce Wallace & Co. Sotheby's International Realty

  18 Katama Dr, Edgartown, MA 02539
• 

  

  /19

  Est $1,353,179 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,520 Sq Ft

  46 Windsor Dr, Edgartown, MA 02539

  46 Windsor Dr, Edgartown, MA 02539
• 

  

  /42

  $2,500,000

  • 4 Beds
  • 3.5 Baths
  • 1 Sq Ft

  10 Wood Duck Way, Oak Bluffs, MA 02557

  Perched on a hill, this waterfront house encompasses three levels of living. Thoughtfully designed and well cared for, this home provides calming water views and direct access to Wiggy's freshwater Pond from almost every room. The main level boasts a kitchen fitted with high-end appliances and opens to the dining room, deck, and airy living room with exposed beams, a gas fireplace, and large

  Marcia Sullivan Garvey Donnelly + Co.

  10 Wood Duck Way, 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
• 

  

  /26

  $1,850,000 Sold May 14, 2025

  • 2,610 Sq Ft
  • $709/SF
  • 8 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1986

  137 Charles Neck Way, Vineyard Haven, MA 02568

  Fantastic opportunity to buy a two house compound in West Tisbury close to Long Point Beach access. A perfect investment, rental income generator or to host extended family and guests.Two well built houses on 1.6 acres, that have been impeccably maintained by the original owner. Offering a total of 5 bedrooms, 4 bathrooms, 2 outdoor showers and 2 garages. There is a charming garden shed and low

  Rebecca V Conroy Conroy & Company R.E., Inc.

  137 Charles Neck Way, Vineyard Haven, MA 02568
• 

  

  /30

  Est $2,453,061 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,404 Sq Ft

  10 Gerts Way, Edgartown, MA 02539

  10 Gerts Way, Edgartown, MA 02539
• 

  

  /39

  $2,650,000

  • 4 Beds
  • 6 Baths
  • 2,694 Sq Ft

  16 Mockingbird Dr, Edgartown, MA 02539

  Experience the ultimate Vineyard getaway in this custom Colonial that perfectly balances sophistication with Island charm. This thoughtfully designed property features soaring 9-foot ceilings, authentic Heart Pine flooring, and a show-stopping gourmet kitchen complete with professional-grade Viking appliances, handcrafted soapstone countertops, and a statement Carrara marble island. The spacious

  Emma Kennedy Sandpiper Realty Inc

  16 Mockingbird Dr, Edgartown, MA 02539
• 

  

  /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
• 

  

  /39

  $4,762,500 Sold May 14, 2025

  • 5,103 Sq Ft
  • $933/SF
  • 411 Days On Market

  • 6 Beds
  • 6 Baths
  • Built 2024

  69 Division Rd, Edgartown, MA 02539

  Welcome to BRAND NEW CONSTRUCTION!! This gorgeous home sits on a spacious lot in a new 5 home luxury private enclave with breathtaking views of the surrounding pastures. The property offers privacy, a serene and picturesque setting, perfect for those seeking tranquility and natural beauty yet a convenient 1.6 mile distance to Edgartown Village. With meticulous attention to detail, this home

  Jennifer DaSilva Compass | Point B

  69 Division Rd, Edgartown, MA 02539
• 

  

  /29

  Est $2,140,407 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  165 W Tisbury Rd, Edgartown, MA 02539

  165 W Tisbury Rd, Edgartown, MA 02539
• 

  

  /27

  $2,700,000

  • 4 Beds
  • 3 Baths
  • 2,001 Sq Ft

  2 Orchard Ln, Edgartown, MA 02539

  Welcome to this 4 bedroom home, with a pool, perched on the neighborhood hilltop. This tri-level cape offers an eat in kitchen featuring granite countertops, a Viking gas range, a double basin sink, a built in banquette and views of the front covered porch and hardscaped rear yard. The primary level presents with a living room, a separate bar area offering a wine refrigerator/dishwasher, a full

  Michele Casavant Vineyard Village Realty

  2 Orchard Ln, Edgartown, MA 02539
• 

  

  /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
• 

  

  /6

  $4,200,000 Sold May 09, 2025

  • 3,600 Sq Ft
  • $1167/SF
  • 11 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2024

  20 Mill Hill Rd, Edgartown, MA 02539

  NEW CONSTRUCTION, with POOL, walking distance to EDGARTOWN VILLAGE! Approx. 3,600 square feet of open living space. The Great Room has a dramatic Two Story wall of glass, (sliders and an oversized second story window) that overlooks the 14 x 30 foot IN GROUND POOL. In addition to the dramatic Great Room there is a first floor den/lounge area, a first floor primary-en-suite with views to the pool,

  Michele Casavant Vineyard Village Realty

  20 Mill Hill Rd, Edgartown, MA 02539
• 

  

  /14

  Est $2,001,334 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,519 Sq Ft

  2 Lexington Ave, Edgartown, MA 02539

  2 Lexington Ave, Edgartown, MA 02539
• 

  

  /32

  $2,999,000

  • 8 Beds
  • 7.5 Baths
  • 3,770 Sq Ft

  72 Chappaquiddick Ave, Edgartown, MA 02539

  WELCOME to this turn-key CHAPPY COMPOUND! This property offers it ALL, with its Six (6) Bedroom, Five (5) bath Primary Home, Two (2) bedroom, Two (2) bath GUEST HOUSE, expansive POOL HOUSE with a bath, kitchenette, large lounge area topped with a cathedral ceiling, a WORKOUT & GAME BARN, a POOL, a VOLLEY BALL COURT and a TENNIS COURT that doubles into TWO PICKLE BALL COURTS, and a BASKETBALL

  Michele Casavant Vineyard Village Realty

  72 Chappaquiddick Ave, Edgartown, MA 02539
• 

  

  /15

  $30,000 per month

  • 3 Beds
  • 3 Baths
  • 2,888 Sq Ft
  • House for Rent

  101 Peasepoint Way Ed324, Edgartown, MA 02539

  THIS IS A SUMMER RENTAL ONLY. This grand and stately home is located in Starbuck Point in Edgartown. The home is elegantly furnished with traditional charm . The Captain's house is surrounded by neatly manicured lawns and the ocean is at the end of the street. It is a five minute walk to the Edgartown Village and Harbor for shopping, dining or theater.

  Karen Overtoom Karen M. Overtoom R.E.

  101 Peasepoint Way Ed324, Edgartown, MA 02539
• 

  

  /19

  $1,110,000 Sold May 08, 2025

  • 1,275 Sq Ft
  • $871/SF
  • 45 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1972

  31 9th St N, Edgartown, MA 02539

  Nestled among the trees near the Sengekontacket Pond, this distinctive contemporary home offers privacy while being conveniently close to Downtown Edgartown and the picturesque trails at Felix Neck Sanctuary. Designed by architect Robert Orr, this multi-level residence showcases unique architectural details and striking angled ceilings.The main living area is bathed in natural light, surrounded

  Alyssa Halisky Wallace & Co. Sotheby's

  31 9th St N, Edgartown, MA 02539
• 

  

  /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
• 

  

  /29

  $2,700,000

  • 6 Beds
  • 4 Baths
  • 1,616 Sq Ft

  34 Massasoit Ave, Oak Bluffs, MA 02568

  Located on the corner of Circuit Ave and Massasoit this B1 property with mixed use capability has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms and plenty of room to build a commercial building facing Circuit Ave. The house spacious home with a large wrap around porch would be a great weekly rental property or for employee housing. Right in the heart of Oak Bluffs, walkable to

  Carleen Cordwell Anchor Realty of Martha's Vineyard

  34 Massasoit Ave, Oak Bluffs, MA 02568
• 

  

  /13

  $27,000 per month

  • 4 Beds
  • 3.5 Baths
  • 1,962 Sq Ft
  • House for Rent

  20 Bay Lot Circle Ed323, Edgartown, MA 02539

  THIS IS A SUMMER RENTAL ONLY. Vacation by the beach in a relaxed contemporary home offering fabulous panoramic views of Edgartown Harbor, Chappiquidick, Katama Bay and South Beach. Our Katama Bay home is located off of Edgartown Bay Road at the quiet cul-de-sac,close to the beaches and boat launch access. For those who love the ocean breezes and sandy beaches, there is great sunbathing,

  Karen Overtoom Karen M. Overtoom R.E.

  20 Bay Lot Circle Ed323, Edgartown, MA 02539
• 

  

  /6

  $700,500 Sold May 07, 2025

  • Land
  • 0.55 Acre
  • $1,273,636 per Acre

  • 0 Days On Market

  72 Windsor Dr Unit 99.71, Edgartown, MA 02539

  Level building lot ready for your new home ideas. Area of well cared for homes both year round and seasonal use. Bike path at end of street allows easy travel to all down island towns. Ask about a new home package or work with your own builder. Perc test has been done and confirmed it is a 4 bedroom lot with a standard septic design.

  Jim Joyce Carroll & Vincent R.E.

  72 Windsor Dr Unit 99.71, 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

Showing Results 81 - 120, Page 3 of 18