19,924

Dukes, MA Homes

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  • 16 Atlantic Ave, Oak Bluffs, MA 02557
    16 Atlantic Ave, Oak Bluffs, MA 02557
    16 Atlantic Ave, Oak Bluffs, MA 02557
    /39

    $2,495,000

    • 5 Beds
    • 2.5 Baths
    • 2,577 Sq Ft

    16 Atlantic Ave, Oak Bluffs, MA 02557

    East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The main residence is a stately four-bedroom, classic summer home, rich in character and nostalgic charm. At the rear of the property, a one-bedroom guest house provides privacy and, perhaps most

    Katherine Donahue Sandpiper Realty Inc

    16 Atlantic Ave, Oak Bluffs, MA 02557
  • 100 Connie's Way Vh401, Tisbury, MA 02568
    100 Connie's Way Vh401, Tisbury, MA 02568
    100 Connie's Way Vh401, Tisbury, MA 02568
    /34

    $25,000 per month

    • 4 Beds
    • 3.5 Baths
    • 2,334 Sq Ft
    • House for Rent

    100 Connie's Way Vh401, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,250. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

    Karen Overtoom Karen M. Overtoom R.E.

    100 Connie's Way Vh401, Tisbury, MA 02568
  • 25 Oxcart Rd, Aquinnah, MA 02535
    25 Oxcart Rd, Aquinnah, MA 02535
    25 Oxcart Rd, Aquinnah, MA 02535
    /39

    $2,750,000 Sold Jun 10, 2025

    • 1,008 Sq Ft
    • $2728/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1953

    25 Oxcart Rd, Aquinnah, MA 02535

    Vineyard Sound waterfront! This is what summer on the Vineyard is all about. Contemporary beach house set in the dunes on 4.6 acres amongst beach plum bushes and windswept beach grass. Open concept interior with a wall of windows facing the Vineyard Sound and Elizabeth Islands. Two guest rooms on the main level and a top floor primary bedroom with deck for star gazing and glorious sunsets. A

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

    25 Oxcart Rd, Aquinnah, MA 02535
    • 8 Old Purchase Way, Edgartown, MA 02539
      8 Old Purchase Way, Edgartown, MA 02539
      8 Old Purchase Way, Edgartown, MA 02539
      /21

      Est $1,585,977 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,583 Sq Ft

      8 Old Purchase Way, Edgartown, MA 02539

      8 Old Purchase Way, Edgartown, MA 02539
  • 18 Allen Farm Rd, Chilmark, MA 02535
    18 Allen Farm Rd, Chilmark, MA 02535
    18 Allen Farm Rd, Chilmark, MA 02535
    /13

    $2,950,000

    • 1 Bed
    • 1 Bath
    • 726 Sq Ft

    18 Allen Farm Rd, Chilmark, MA 02535

    Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1 + bedroom cottage with screened porch, brick patio and outside shower. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, especially for solar designs. The cottage is offered fully furnished,

    Patty Kendall Kendall & Kendall

    18 Allen Farm Rd, Chilmark, MA 02535
  • 6 Trails End Ch241, Chilmark, MA 02535
    6 Trails End Ch241, Chilmark, MA 02535
    6 Trails End Ch241, Chilmark, MA 02535
    /26

    $50,700 per month

    • 4 Beds
    • 3 Baths
    • 2,346 Sq Ft
    • House for Rent

    6 Trails End Ch241, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,675. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set atop a hill you will find this wonderful 4 bedroom home with distant views and a wonderful lap pool. Enjoy your days on the large deck or take a swim in the pool. This great vacation home is tastefully decorated and is located on one level with plenty of space for

    Karen Overtoom Karen M. Overtoom R.E.

    6 Trails End Ch241, Chilmark, MA 02535
  • 97 Snake Hollow, Vineyard Haven, MA 02568
    97 Snake Hollow, Vineyard Haven, MA 02568
    97 Snake Hollow, Vineyard Haven, MA 02568
    /31

    $1,750,000 Sold Jun 06, 2025

    • 1,850 Sq Ft
    • $946/SF
    • 226 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1981

    97 Snake Hollow, Vineyard Haven, MA 02568

    Nestled in a private neighborhood in Vineyard Haven conveniently located to the ferry and town for plenty of shopping and dining, this renovated home is move-in ready and sited on 1.5 generous acres. There are two entrances to the home. The most operational is off the side deck where you enter the fabulous must-have mudroom. Offering separation from the main part of the home is a dramatic

    Stephanie Roache Donnelly + Co.

    97 Snake Hollow, Vineyard Haven, MA 02568
    • 26 Chappaquiddick Ave, Vineyard Haven, MA 02568
      26 Chappaquiddick Ave, Vineyard Haven, MA 02568
      26 Chappaquiddick Ave, Vineyard Haven, MA 02568
      /16

      Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,275 Sq Ft

      26 Chappaquiddick Ave, Vineyard Haven, MA 02568

      26 Chappaquiddick Ave, Vineyard Haven, MA 02568
  • 111 Eastville Ave, Oak Bluffs, MA 02557
    111 Eastville Ave, Oak Bluffs, MA 02557
    111 Eastville Ave, Oak Bluffs, MA 02557
    /44

    $2,748,000

    • 6 Beds
    • 4 Baths
    • 2,400 Sq Ft

    111 Eastville Ave, Oak Bluffs, MA 02557

    JUST REDUCED!! Steps to the beach- Minutes to downtown Oak Bluffs and Vineyard Haven. This is a perfect location.FULLY FURNISHED, TURNKEY, with an impressive rental history. Situated on an oversized lot that is two parcels away from the beach. This home offers six bedrooms and four

    Ed Charter Arrowhead Homes

    111 Eastville Ave, Oak Bluffs, MA 02557
  • 17 Round Pond Rd Ch240, Chilmark, MA 02535
    17 Round Pond Rd Ch240, Chilmark, MA 02535
    17 Round Pond Rd Ch240, Chilmark, MA 02535
    /39

    $110,000 per month

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

    17 Round Pond Rd Ch240, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. See web site for pricing!! Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches and high speed internet wifi.

    Karen Overtoom Karen M. Overtoom R.E.

    17 Round Pond Rd Ch240, Chilmark, MA 02535
  • 6 Martha's Park Rd, Oak Bluffs, MA 02557
    6 Martha's Park Rd, Oak Bluffs, MA 02557
    6 Martha's Park Rd, Oak Bluffs, MA 02557
    /42

    $2,400,000 Sold Jun 05, 2025

    • 3,200 Sq Ft
    • $750/SF
    • 49 Days On Market
    • 3 Beds
    • 4.5 Baths
    • Built 2014

    6 Martha's Park Rd, Oak Bluffs, MA 02557

    Must see stunning “reverse” layout (kitchen and main living spaces upstairs for the views) contemporary home with breathtaking water views and a thoughtfully designed layout in the exclusive Harthaven community! This spacious property features open kitchen concept with marble counter tops and stainless steel appliances, comfortable living areas, a bonus room (with full bathroom), food prep,

    Jennifer B. DaSilva Compass

    6 Martha's Park Rd, Oak Bluffs, MA 02557
    • 1 Gray Gull Cir, Edgartown, MA 02539
      1 Gray Gull Cir, Edgartown, MA 02539
      1 Gray Gull Cir, Edgartown, MA 02539
      /27

      Est $2,201,793 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,428 Sq Ft

      1 Gray Gull Cir, Edgartown, MA 02539

      1 Gray Gull Cir, Edgartown, MA 02539
  • 10 Wood Duck Way, Oak Bluffs, MA 02557
    10 Wood Duck Way, Oak Bluffs, MA 02557
    10 Wood Duck Way, Oak Bluffs, MA 02557
    /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
  • 44 Flanders Ln, Chilmark, MA 02535
    44 Flanders Ln, Chilmark, MA 02535
    44 Flanders Ln, Chilmark, MA 02535
    /19

    $24,000 per month

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • House for Rent

    44 Flanders Ln, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

    Karen Overtoom Karen M. Overtoom R.E.

    44 Flanders Ln, Chilmark, MA 02535
  • 25 Simpson's Ln, Edgartown, MA 02539
    25 Simpson's Ln, Edgartown, MA 02539
    25 Simpson's Ln, Edgartown, MA 02539
    /18

    $3,350,000 Sold Jun 05, 2025

    • 3,156 Sq Ft
    • $1061/SF
    • 138 Days On Market
    • 6 Beds
    • 6 Baths
    • Built 1900

    25 Simpson's Ln, Edgartown, MA 02539

    Nestled in the heart of Edgartown, is this historic residence known as The Lightkeeper’s Inn. This property has five bedrooms, five baths and a separate one bedroom, one bath cottage, on .20 acre. Beautifully decorated in ole Vineyard style, the residence has the island feel of old time Martha’s Vineyard. This 5BD/5BA home sits in the heart of Edgartown close to the waterfront. Known as The

    Greg Hartel Hartel Realty

    25 Simpson's Ln, Edgartown, MA 02539
    • 7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      7 the Aerie, Chilmark, MA 02535
      /31

      Est $2,432,400 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,386 Sq Ft

      7 the Aerie, Chilmark, MA 02535

      7 the Aerie, Chilmark, MA 02535
  • 79 David Ave, Vineyard Haven, MA 02568
    79 David Ave, Vineyard Haven, MA 02568
    79 David Ave, Vineyard Haven, MA 02568
    /37

    $2,725,000 Open Fri 11AM - 1PM

    • 5 Beds
    • 4.5 Baths
    • 4,982 Sq Ft

    79 David Ave, Vineyard Haven, MA 02568

    BEAUTIFUL CUSTOM-BUILT RETREAT- LAMBERT'S COVE This impressive property offers the perfect blend of privacy and convenient access to downtown and the picturesque James Pond Reserve at Lambert's Cove Beach. Step inside to discover over 4,900 sq ft of recently renovated living space. The home boasts 5 bedrooms and 4.5 bathrooms, including a stunning chef's kitchen that will ignite your culinary

    Tina Miller Compass

    79 David Ave, Vineyard Haven, MA 02568
  • 384 Middle Rd Ch222, Chilmark, MA 02535
    384 Middle Rd Ch222, Chilmark, MA 02535
    384 Middle Rd Ch222, Chilmark, MA 02535
    /31

    $40,000 per month

    • 6 Beds
    • 6 Baths
    • 3,960 Sq Ft
    • House for Rent

    384 Middle Rd Ch222, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four

    Karen Overtoom Karen M. Overtoom R.E.

    384 Middle Rd Ch222, Chilmark, MA 02535
  • 5 Vincent Rd, Vineyard Haven, MA 02568
    5 Vincent Rd, Vineyard Haven, MA 02568
    5 Vincent Rd, Vineyard Haven, MA 02568
    /3

    $1,695,000 Sold May 30, 2025

    • 1,296 Sq Ft
    • $1308/SF
    • 2 Beds
    • 2 Baths
    • Built 1960

    5 Vincent Rd, Vineyard Haven, MA 02568

    NOT LISTED IN LINK

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    5 Vincent Rd, Vineyard Haven, MA 02568
    • 5 Bold Meadow Cir, Edgartown, MA 02539
      5 Bold Meadow Cir, Edgartown, MA 02539
      5 Bold Meadow Cir, 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
  • 6 Church St, Aquinnah, MA 02535
    6 Church St, Aquinnah, MA 02535
    6 Church St, Aquinnah, MA 02535
    /33

    $2,395,000

    • 3 Beds
    • 3 Baths
    • 1,862 Sq Ft

    6 Church St, Aquinnah, MA 02535

    This beautifully renovated contemporary home is perched on a hillside, offering views of the Atlantic Ocean. Upon entering the home has a light and airy atmosphere with cathedral ceilings and a wall of windows connecting you with the outdoors. The main level consists of an open-concept kitchen, living, and dining area with soaring ceilings and sliding glass doors that overlook the treetops of

    Heidi Vanderhoop Tea Lane Associates

    6 Church St, Aquinnah, MA 02535
  • 19 Lake Rd, Chilmark, MA 02535
    19 Lake Rd, Chilmark, MA 02535
    19 Lake Rd, Chilmark, MA 02535
    /32

    $42,000 per month

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

    19 Lake Rd, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all with views, two livingrooms,

    Karen Overtoom Karen M. Overtoom R.E.

    19 Lake Rd, Chilmark, MA 02535
  • 14 Galway Rd, Vineyard Haven, MA 02568
    14 Galway Rd, Vineyard Haven, MA 02568
    14 Galway Rd, Vineyard Haven, MA 02568
    /15

    $1,150,000 Sold May 30, 2025

    • 1,338 Sq Ft
    • $859/SF
    • 48 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1966

    14 Galway Rd, Vineyard Haven, MA 02568

    Welcome to 14 Galway Road, West Tisbury. The home and property have been lovingly maintained and used by the same family since the home was built. It offers an open eat-in kitchen/living room design with a masonry fireplace. On the first floor are two bedrooms, one full bathroom, a linen closet, and hidden washer and dryer along the hallway. The stairway brings you to a second floor which

    Michele Casavant Vineyard Village Realty

    14 Galway Rd, Vineyard Haven, MA 02568
    • 23 Majors Cove Ln, Edgartown, MA 02539
      23 Majors Cove Ln, Edgartown, MA 02539
      23 Majors Cove Ln, 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
  • 26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575
    26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575
    26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575
    /13

    $2,650,000

    • 4 Beds
    • 3 Baths
    • 2,299 Sq Ft

    26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575

    Discover the rare opportunity to build your dream home in one of the island’s most sought-after locations off Lamberts Cove Road. This parcel offers year-round waterfront living with the ultimate blend of privacy, beach access, and design potential, without the usual coastal erosion concerns. Approved architectural plans by Moskow Linn Architects are in place for a four-bedroom main residence, a

    Jill Napior Tea Lane Associates

    26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575
  • 31 S Ridge Rd Ch218, Chilmark, MA 02535
    31 S Ridge Rd Ch218, Chilmark, MA 02535
    31 S Ridge Rd Ch218, Chilmark, MA 02535
    /20

    $16,800 per month

    • 3 Beds
    • 2 Baths
    • 1,638 Sq Ft
    • House for Rent

    31 S Ridge Rd Ch218, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and

    Karen Overtoom Karen M. Overtoom R.E.

    31 S Ridge Rd Ch218, Chilmark, MA 02535
  • 10 Rumpus Ridge Rd, Chilmark, MA 02535
    10 Rumpus Ridge Rd, Chilmark, MA 02535
    10 Rumpus Ridge Rd, Chilmark, MA 02535
    /32

    $1,050,000 Sold May 29, 2025

    • 1,701 Sq Ft
    • $617/SF
    • 28 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1960

    10 Rumpus Ridge Rd, Chilmark, MA 02535

    Discover this inviting two-unit property in the heart of Chilmark! Ideally situated near Chilmark General Store, Squibnocket, Menemsha, and the pristine shores of Lucy Vincent Beach, this home offers both convenience and charm. Thoughtfully updated for year-round comfort, the property features a new metal roof, new siding, solar panels, mini-split AC, and more. The main-level residence offers

    Peyton Wallace Studio Realty

    10 Rumpus Ridge Rd, Chilmark, MA 02535
    • 225 Bigelow Rd, Vineyard Haven, MA 02568
      225 Bigelow Rd, Vineyard Haven, MA 02568
      225 Bigelow Rd, Vineyard Haven, MA 02568
      /32

      Est $4,888,183 Not Listed For Sale

      • 5 Beds
      • 8 Baths
      • 5,305 Sq Ft

      225 Bigelow Rd, Vineyard Haven, MA 02568

      225 Bigelow Rd, Vineyard Haven, MA 02568
  • 71 Netock Ave, Oak Bluffs, MA 02557
    71 Netock Ave, Oak Bluffs, MA 02557
    71 Netock Ave, Oak Bluffs, MA 02557
    /19

    $2,295,000

    • 4 Beds
    • 5 Baths
    • 2,820 Sq Ft

    71 Netock Ave, Oak Bluffs, MA 02557

    On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated 4-bed home w/separate, office or studio space, ensconced in professionally landscaped grounds. Blending modern comfort w/timeless island charm, house features wide plank white oak floors, beautiful ceiling height & natural light, open-concept living-dining space w/new kitchen, 1st-floor primary bedroom w/ensuite bath,

    Ellen Valentgas Sotheby's International Realty

    71 Netock Ave, Oak Bluffs, MA 02557
  • 29 Cemetery Rd Ch216, Chilmark, MA 02535
    29 Cemetery Rd Ch216, Chilmark, MA 02535
    29 Cemetery Rd Ch216, Chilmark, MA 02535
    /32

    $36,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,600 Sq Ft
    • House for Rent

    29 Cemetery Rd Ch216, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half

    Karen Overtoom Karen M. Overtoom R.E.

    29 Cemetery Rd Ch216, Chilmark, MA 02535
  • 9 Hollow Way, Edgartown, MA 02539
    9 Hollow Way, Edgartown, MA 02539
    9 Hollow Way, Edgartown, MA 02539
    /74

    $3,284,500 Sold May 23, 2025

    • 3,085 Sq Ft
    • $1065/SF
    • 657 Days On Market
    • 6 Beds
    • 6 Baths
    • Built 2024

    9 Hollow Way, Edgartown, MA 02539

    EDGARTOWN - NEW CONSTRUCTION with POOL - 6 Bedrooms...in Two Structures.....Plus a 31'6" x 14' heated saltwater pool! 5 Bedroom Main House with 4.5 Bathrooms. Detached 1 bedroom w/Full Bathroom over a Two (2) car garage. Main house has a lovely open floor plan with a large kitchen w/Bosch Stainless Steel Appliances, beautiful Soapstone Island and Carrara Marble counters, a dining room,

    Alisan Lohan-Conway Alisan Lohan-Conway Properties

    9 Hollow Way, Edgartown, MA 02539
    • 3 Duarte Cir, Edgartown, MA 02539
      3 Duarte Cir, Edgartown, MA 02539
      3 Duarte Cir, 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
  • 27 Watcha Path, Edgartown, MA 02539
    27 Watcha Path, Edgartown, MA 02539
    27 Watcha Path, Edgartown, MA 02539
    /41

    $2,590,000 Pending

    • 4 Beds
    • 4 Baths
    • 3,052 Sq Ft

    27 Watcha Path, Edgartown, MA 02539

    STYLISH VINEYARD LIVING WITH EXCEPTIONAL OUTDOOR AMENITIES. This beautifully landscaped coastal-style home is set on three acres just off the bike path, offering easy access to all Island towns. The highlight? A heated salt water pool surrounded by expansive decking and outdoor gathering spaces—an ideal setup for Vineyard summers. Thoughtfully updated by the current owners, the home features four

    Jen O'Hanlon Compass | The O'Hanlon Group

    27 Watcha Path, Edgartown, MA 02539
  • 2 Strikers Way Ch211, Chilmark, MA 02535
    2 Strikers Way Ch211, Chilmark, MA 02535
    2 Strikers Way Ch211, Chilmark, MA 02535
    /33

    $22,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    2 Strikers Way Ch211, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable

    Karen Overtoom Karen M. Overtoom R.E.

    2 Strikers Way Ch211, Chilmark, MA 02535
  • 41 Smith Hollow Dr, Edgartown, MA 02539
    41 Smith Hollow Dr, Edgartown, MA 02539
    41 Smith Hollow Dr, Edgartown, MA 02539
    /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
    • 10 Codman Spring Rd, Edgartown, MA 02539
      10 Codman Spring Rd, Edgartown, MA 02539
      10 Codman Spring Rd, Edgartown, MA 02539
      /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
  • 7 Upper Meadow Ln, Oak Bluffs, MA 02557
    7 Upper Meadow Ln, Oak Bluffs, MA 02557
    7 Upper Meadow Ln, Oak Bluffs, MA 02557
    /28

    $1,950,000

    • 4 Beds
    • 2.5 Baths
    • 3,268 Sq Ft

    7 Upper Meadow Ln, Oak Bluffs, MA 02557

    Tucked at the end of a quiet cul-de-sac in the desirable Meadow View Farms neighborhood, this spacious Colonial offers over 3,200 square feet of comfortable and inviting living space. This home is ideal for those who love to host lively gatherings while providing comfortable accommodations for all. Inside, you'll find four well-sized bedrooms and two and a half baths, including a generous primary

    Lesley Heidt Sandpiper Realty Inc

    7 Upper Meadow Ln, Oak Bluffs, MA 02557
  • 36 Henry Hough Lane Ch206, Chilmark, MA 02535
    36 Henry Hough Lane Ch206, Chilmark, MA 02535
    36 Henry Hough Lane Ch206, Chilmark, MA 02535
    /35

    $22,000 per month

    • 4 Beds
    • 2 Baths
    • 2,290 Sq Ft
    • House for Rent

    36 Henry Hough Lane Ch206, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four

    Karen Overtoom Karen M. Overtoom R.E.

    36 Henry Hough Lane Ch206, Chilmark, MA 02535
  • 8 Massasoit Rd, Edgartown, MA 02539
    8 Massasoit Rd, Edgartown, MA 02539
    8 Massasoit Rd, 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
    • 46 Windsor Dr, Edgartown, MA 02539
      46 Windsor Dr, Edgartown, MA 02539
      46 Windsor 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

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