19,928

Dukes, MA Homes

Section Image Section Image
  • /21

    $1,795,000

    • 3 Beds
    • 1 Bath
    • 1,033 Sq Ft

    9 Brunswick Ave, Oak Bluffs, MA 02557

    PRIME LOCATION! LESS THAN A 5-MINUTE WALK TO OAK BLUFFS HARBOR! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively updated inside and out. Enjoy peace of mind with a new septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts new flooring, insulation, fresh paint, a

    Agent Photo

    Alice Pierce

    Coldwell Banker Realty - Hingham

    (870) 917-0672

    9 Brunswick Ave, Oak Bluffs, MA 02557
  • /21

    $7,000 per month

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

    27 Beach Plum Ln, Chilmark, MA 02535

    weekly rental The "Grapevine" is located on a private road next door to the Beach Plum Inn, It was completely rebuilt not to long ago it has 3 generous size bedrooms all with private baths, 2 of the bedrooms are located on the second floor, 1 bedroom is located on the first floor as well as the Open concept living with a chefs Kitchen, living room ,dining area and fireplace area. Walk out the

    Bryan Hummel Commonwealth Realty Group

    27 Beach Plum Ln, Chilmark, MA 02535
  • /41

    $1,850,000 Sold Aug 04, 2025

    • 2,210 Sq Ft
    • $837/SF
    • 22 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1980

    26 Tia Anna Ln, Oak Bluffs, MA 02557

    Welcome to 26 Tia Anna Lane! This exquisite residence is immaculate, stylish, and fully renovated, ready to welcome its new owners! Situated on a beautifully landscaped 0.30-acre lot adorned with vibrant plantings, the home boasts pristine conditions both inside and out, featuring newer Hardi Plank siding. The inviting farmer's porch, complete with Mahogany decking, sets the tone for this

    Marilyn Moses Ocean Park Realty Inc

    26 Tia Anna Ln, Oak Bluffs, MA 02557
    • /3

      Est $1,671,734 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,329 Sq Ft

      18 Towanticut Ave, Oak Bluffs, MA 02557

      18 Towanticut Ave, Oak Bluffs, MA 02557
  • /42

    $3,395,000

    • 3 Beds
    • 3.5 Baths
    • 2,527 Sq Ft

    5 Katama Dr, Edgartown, MA 02539

    Modern Coastal Retreat In Katama: Freshly reimagined and impeccably styled, this modern coastal residence in the heart of Katama offers a rare opportunity to own a newly renovated home just one mile from South Beach. This appealing retreat has been elevated with curated finishes, high-end systems, and a designer-selected furnishing package that perfectly embodies the relaxed luxury of Vineyard

    Agent Photo

    Wendy Harman

    Compass

    (508) 274-5363

    5 Katama Dr, Edgartown, MA 02539
  • /21

    $9,500 per month

    • 4 Beds
    • 2 Baths
    • 1,579 Sq Ft
    • House for Rent

    155 Skiff Ave, Vineyard Haven, MA 02568

    Enjoy the serenity of a four bedroom, two full bathroom peaceful oasis complete with private in-ground pool. Close to lively dining and boutiques of downtown Vineyard Haven. Unwind at neighborhood beaches; Eastville, Owen Park, Tashmoo beaches all just a few minutes drive from your vacation retreat.This lovely home spread over 1600ft of living area provides first and second floor living and

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    155 Skiff Ave, Vineyard Haven, MA 02568
  • /20

    $1,525,000 Sold Jul 31, 2025

    • 1,411 Sq Ft
    • $1081/SF
    • 34 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1973

    467 Katama Rd Unit B2, Edgartown, MA 02539

    Mattakesett units continue to be in high demand and #B2 is the only unit currently on the market! Take advantage of all the Winnetu Resort amenities and a robust rental program which covers your fees and provides great revenue! This unit offers abundant views of the farm fields out front, open common space next to and behind, and is a short walk or bike to South Beach! There are 3 bedrooms, 2.5

    Cheri Mason Landvest MV

    467 Katama Rd Unit B2, Edgartown, MA 02539
    • /36

      Est $2,691,121 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,470 Sq Ft

      28 Woodhaven Dr, Edgartown, MA 02539

      28 Woodhaven Dr, Edgartown, MA 02539
  • /23

    $8,995,000

    • 11 Beds
    • 8.5 Baths
    • 6,289 Sq Ft

    1 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 this 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

    Agent Photo

    Wendy Harman

    Compass

    (508) 715-8610

    1 Louis Field Rd, Edgartown, MA 02539
  • /41

    $13,500 per month

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

    14 Bernard Cir, Vineyard Haven, MA 02568

    Unwind in the private luxury of this BRAND NEW contemporary chic 5 BED 5.5 BATH home perfectly situated close to downtown Vineyard Haven yet set amongst a rural and peaceful WEST CHOP adjacent neighborhood. Indulge and unwind in the PRIVATE HEATED SALTWATER IN-GROUND POOL surrounded by opulent outdoor living and dining area highlighted by covered al-fresco kitchen, BBQ grill and bar - fully

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    14 Bernard Cir, Vineyard Haven, MA 02568
  • /22

    $1,000,000 Sold Jul 31, 2025

    • 768 Sq Ft
    • $1302/SF
    • 96 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1960

    130 Wing Rd, Oak Bluffs, MA 02557

    This well-maintained property is beautifully landscaped with gardens and generous lawn areas, offering incredible potential for growth and development. Conveniently located close to downtown Oak Bluffs, this property offers easy access to essential amenities and tourist destinations, whether you're driving, biking or relying on public transportation to restaurants, shops, beaches, bike paths and

    Lynn Buder Sandpiper Realty Inc

    130 Wing Rd, Oak Bluffs, MA 02557
    • /21

      Est $1,121,552 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,176 Sq Ft

      10 Lagoon Rd, Oak Bluffs, MA 02557

      10 Lagoon Rd, Oak Bluffs, MA 02557
  • /41

    $9,495,000

    • 4 Beds
    • 6 Baths
    • 4,605 Sq Ft

    29 Slough Cove Rd, Edgartown, MA 02539

    LUXURIOUS COUNTRY ESTATE IN KATAMA. Sited at the end of a long private drive, amid a bucolic 1.5-acre meadow setting with stone retaining walls and lush perennial gardens, this elegant country estate, designed by noted architect Patrick Ahearn, offers the epitome of luxurious living in Katama. The home’s timeless and charming character is highlighted by thoughtful, top-notch architectural details

    Agent Photo

    Wendy Harman

    Compass

    (508) 274-5363

    29 Slough Cove Rd, Edgartown, MA 02539
  • /41

    $8,750 per month

    • 4 Beds
    • 2.5 Baths
    • 1,811 Sq Ft
    • House for Rent

    11 High Meadow Ln, Vineyard Haven, MA 02568

    Discover the perfect summer retreat in this beautifully updated Meadow View Farms home. Nestled on a private hilltop and minutes from beaches, bike paths, Farm Neck Gand Downtown Oak Bluffs, this home offers a serene escape close to the island’s best attractions. 4 spacious bedrooms, first floor primary ensuite, shared secondary floor full bath, plus additional half bath on main level. The

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    11 High Meadow Ln, Vineyard Haven, MA 02568
  • /44

    $1,650,000 Sold Jul 29, 2025

    • 2,320 Sq Ft
    • $711/SF
    • 35 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1960

    26 Manaquayak Rd, Vineyard Haven, MA 02568

    Large comfortable and charming expanded Cape in a lovely setting very close to Lambert's Cove Beach and James Pond Preserve with special walking access to Swimming on Ice House Pond in the Manaquayak Preserve as well as deeded walking access to swim and boat on Seth's Pond. The living room is open to the beautiful newly-renovated kitchen and has an often-used wood-burning fireplace. There is a

    Candy DaRosa Feiner Real Estate

    26 Manaquayak Rd, Vineyard Haven, MA 02568
    • /31

      Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,754 Sq Ft

      12 Fairway Dr, Vineyard Haven, MA 02568

      12 Fairway Dr, Vineyard Haven, MA 02568
  • /37

    $9,995,000

    • 6 Beds
    • 7.5 Baths
    • 7,205 Sq Ft

    25 Lelands Path, Edgartown, MA 02539

    Casual Elegance On Katama Bay - Welcome to 25 Leland’s Path on Katama Bay, a stunning property that embodies the perfect blend of casual elegance and serene waterfront living on Chappquiddick. This magnificent home offers over 7,200 square feet of living space, six bedrooms, all with en suite baths, and a three-room Owner's Suite with sweeping water views and a private second-floor deck. The

    Agent Photo

    Wendy Harman

    Compass

    (508) 274-5363

    25 Lelands Path, Edgartown, MA 02539
  • /14

    $8,400 per month

    • 4 Beds
    • 3 Baths
    • 2,148 Sq Ft
    • House for Rent

    39 Old Coach Rd, West Tisbury, MA 02568

    Summer weekly rental only! June weekly rate is $8,400 and July weekly rate is $10,000/week - Sunday to Saturday. Recently renovated 4 bedroom, 3 bathroom home that sits on a private 2 acre lot in West Tisbury MA! This large cape house has just been update with new stainless steel appliances, new kitchen cabinets and countertops. Other updates include, new bathroom vanities and hardware,

    Joseph D'Amico Dee Development Company

    39 Old Coach Rd, West Tisbury, MA 02568
  • /12

    $686,000 Sold Jul 23, 2025

    • 725 Sq Ft
    • $946/SF
    • 31 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1953

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

    Vineyard Haven Centrally located Causeway Condominiums just a short distance from town and ferries. Lovely grounds and a community swimming pool, a great place to live year-round or use as an investment property that's easy to manage. On ground level this spacious 2 bedroom condo with a tiled eat-in kitchen has a door accessing the back of condo. The tiled bathroom has been recently renovated and

    Carleen Cordwell Anchor Realty of Martha's Vineyard

    124 Skiff Ave Unit A-10, Vineyard Haven, MA 02568
    • /37

      Est $3,626,136 Not Listed For Sale

      • 3 Beds
      • 5 Baths
      • 4,417 Sq Ft

      149 Litchfield Rd, Edgartown, MA 02539

      149 Litchfield Rd, Edgartown, MA 02539
  • /42

    $5,995,000 Open House 8/17

    • 3 Beds
    • 6 Baths
    • 3,608 Sq Ft

    385 Barnes Rd, Vineyard Haven, MA 02568

    Indulge in luxurious living at this exquisite waterfront retreat featuring a private 125-foot sandy beach. Over 5,400 sq ft on three floors blend elegance with indoor-outdoor living. The grand foyer leads to dramatic interiors with high ceilings and floor-to-ceiling windows showcasing stunning water views. Highlights include a striking stone fireplace, custom built-ins, gourmet kitchen with stone

    Agent Photo

    Wendy Harman

    Compass

    (508) 274-5363

    385 Barnes Rd, Vineyard Haven, MA 02568
  • /27

    $21,700 per month

    • 5 Beds
    • 3 Baths
    • 2,168 Sq Ft
    • House for Rent

    97 3rd St N, Edgartown, MA 02539

    YOUR VINEYARD ESCAPE AWAITS! This sizable vintage rental with water views of Sengekontacket Pond and beyond is ideal for your island getaway. Boasting multiple levels of living and porches that take advantage of views, the main floor is awash in seaside tones. Display a raw bar on the center island and top off beverages in the kitchen before relaxing in the sunroom as you enjoy the painterly sky

    Fine Homes Group Keller Williams Realty Boston-Metro | Back Bay

    97 3rd St N, Edgartown, MA 02539
  • /8

    $175,000 Sold Jul 17, 2025

    • Land
    • 1.60 Acres
    • $109,375 per Acre
    • 14 Days On Market

    00 Oxcart Rd, Aquinnah, MA 02535

    Do you love to fish? Beach Lot! Amazing, private, beach on the North Shore. This is a private associate beach and not a buildable parcel. 1/16th ownership. $5,000 membership fee is due at closing

    Sheila Morse Island Real Estate

    00 Oxcart Rd, Aquinnah, MA 02535
    • /37

      Est $1,485,406 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,754 Sq Ft

      12 Fairway Dr, Oak Bluffs, MA 02557

      12 Fairway Dr, Oak Bluffs, MA 02557
  • /39

    $2,645,000

    • 3 Beds
    • 2 Baths
    • 1,350 Sq Ft

    31 The Blvd, Edgartown, MA 02539

    Waterfront Charmer on Sengekontacket Pond - Perched on the shoreline, this contemporary cottage is enveloped by stone walls, lush gardens, and stunning water views. Inside, a bright, airy living space features an open dining area and a well-appointed kitchen. The all-white interior is complemented by hardwood floors, vaulted ceilings, skylights, air conditioning, and ceiling fans. Three sliding

    Agent Photo

    Wendy Harman

    Compass

    (508) 301-9323

    31 The Blvd, Edgartown, MA 02539
  • /20

    $14,000 per month

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

    55 Samoset Ave, Oak Bluffs, MA 02557

    Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Formal dining for eight. A/C, WIFI and

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    55 Samoset Ave, Oak Bluffs, MA 02557
  • /32

    $899,000 Sold Jul 11, 2025

    • 955 Sq Ft
    • $941/SF
    • 6 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1871

    8 Rock Ave, Oak Bluffs, MA 02557

    Experience the charm of this exquisitely renovated Victorian Gingerbread Cottage, nestled within the historic Martha's Vineyard Camp Meeting Association. Just moments away from Oak Bluffs Harbor, ferry terminals, art galleries, restaurants, public beaches, and vibrant shopping areas, this cottage offers an unparalleled location next to all of Oak Bluffs' picturesque parks.This rare gem

    Marilyn Moses Ocean Park Realty Inc

    8 Rock Ave, Oak Bluffs, MA 02557
    • /40

      Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 4,500 Sq Ft

      1005 State Rd, West Tisbury, MA 02575

      1005 State Rd, West Tisbury, MA 02575
  • /27

    $1,695,000

    • 3 Beds
    • 2.5 Baths
    • 1,740 Sq Ft

    27 Chapde Ln, Tisbury, MA 02568

    Classic Style Meets Timeless Charm - Located at the end of a lightly traveled lane and surrounded by stunning gardens and stone retaining walls, this residence provides a modern and spacious environment for comfortable island living. The home welcomes you with an open and bright layout, featuring sleek finishes and an abundance of natural light. The gourmet kitchen is a chef's delight that

    Agent Photo

    Wendy Harman

    Compass

    (508) 691-8993

    27 Chapde Ln, Tisbury, MA 02568
  • /29

    $9,500 per month

    • 4 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • House for Rent

    29 Mercier Way, Edgartown, MA 02539

    **SUMMER RATE$ 9,500-$11,000 WEEKLY** Freshly remodeled 4 bed, 2 full bath coastal cape with all new furnishings, flawless finishes, large private yard, close to South Beach, bike path and downtown Edgartown. Large family room with vaulted ceiling and large TV , gorgeous kitchen with all new stainless appliances, vaulted ceilings, sky lights, custom blue stone countertop, island eatery, and wine

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    29 Mercier Way, Edgartown, MA 02539
  • /20

    $1,715,000 Sold Jul 11, 2025

    • 524 Sq Ft
    • $3273/SF
    • 72 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1915

    61 Hines Point Rd, Vineyard Haven, MA 02568

    Tucked away on the serene shores of Lagoon Pond in Vineyard Haven, this cozy one-bedroom cottage offers the perfect island escape. Located on exclusive Hines Point, the home features stunning water views, direct access to a private beach, and the calming sounds of the tide just steps from your door. Inside, the cottage is thoughtfully designed for comfort and simplicity, with an open living area

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    61 Hines Point Rd, Vineyard Haven, MA 02568
    • /58

      Est $7,101,577 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,945 Sq Ft

      394 Lighthouse Rd, Aquinnah, MA 02535

      394 Lighthouse Rd, Aquinnah, MA 02535
  • /42

    $5,750,000 Open Thu 3PM - 5PM

    • 4 Beds
    • 4.5 Baths
    • 3,643 Sq Ft

    4 Somerset Ln, Edgartown, MA 02539

    New Construction: Reimagined Island Living At Somerset. Located in Katama, Somerset is an exclusive five-home luxury enclave perfectly located between Edgartown Village and South Beach -- and developed by Stanmar, owners of the Winnetu Oceanside Resort. The home sites have been designed to maximize outdoor living and entertaining around a spacious and private yard with expansive lawns and room

    Agent Photo

    Wendy Harman

    Compass

    (508) 715-9594

    4 Somerset Ln, Edgartown, MA 02539
  • /30

    $28,500 per month

    • 9 Beds
    • 6.5 Baths
    • 3,500 Sq Ft
    • House for Rent

    9 Tuckernuck Ave, Oak Bluffs, MA 02557

    **PEAK SUMMER WEEKLY RATE** Water view Victorian fronting Waban Park, steps to Inkwell Beach. Newly restored 9-bed, 6+ bath Main and Guest House houses 18 guests. Internet, A/C and cable TV. Coastal chic interior with all new furnishings. Large open floor plan, ample gathering and relaxation spaces. Dining for 10, Wet Bar, gourmet kitchen, gas range, stainless appliances and distinctive design.

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    9 Tuckernuck Ave, Oak Bluffs, MA 02557
  • /22

    $1,607,000 Sold Jul 10, 2025

    • 2,850 Sq Ft
    • $564/SF
    • 354 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1978

    10 N Abels Hill Rd, Chilmark, MA 02535

    A rare opportunity in the iconic Abel's Hill Association which offers private association beach access, three tennis courts and walking trails. This multi-level Chilmark home was designed and built as an homage to architect Frank Lloyd Wright's ethos of open living spaces with flowing sightlines from room to room. The main house has a pocket view to the Atlantic that opens in the fall and winter

    Elissa Lash Tea Lane Associates

    10 N Abels Hill Rd, Chilmark, MA 02535
    • /38

      Est $1,036,460 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft

      287 County Rd, Vineyard Haven, MA 02568

      287 County Rd, Vineyard Haven, MA 02568
  • /32

    $985,000

    • 2 Beds
    • 1 Bath
    • 990 Sq Ft

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

    Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a semi-private rooftop deck (shared with unit 5 only). This spacious condo has a panoramic view of the town and surrounding waters sitting high above it all with outdoor seating and separate entrances from either condo. This solid deck adds a whole other dimension to this already desirable unit.The interior

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 514-5238

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
  • /20

    $4,250 per month

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • House for Rent

    11 Hammett Ln, Chilmark, MA 02535

    Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime location off North Road

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    11 Hammett Ln, Chilmark, MA 02535
  • /44

    $37,000,000 Sold Jul 10, 2025

    • 7,846 Sq Ft
    • $4716/SF
    • 39 Days On Market
    • 8 Beds
    • 5.5 Baths
    • Built 1993

    41 Cobbs Hill Rd, Chilmark, MA 02535

    One of the most exclusive estates across the Northeast, Blue Heron Farm on Martha's Vineyard is set on nearly 30 acres of lush landscaping along the shores of Tisbury Great Pond. The former summer residence of President Obama and family, chosen for its incredible privacy, serenity and significance, this multi-generational compound is protected by surrounding farmland and mature trees.

    Brian Dougherty Corcoran Property Advisors

    41 Cobbs Hill Rd, Chilmark, MA 02535
    • /17

      Est $1,551,966 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,298 Sq Ft

      19 Quantapog Rd, Vineyard Haven, MA 02568

      19 Quantapog Rd, Vineyard Haven, MA 02568

Showing Results 1 - 40, Page 1 of 18

How to Buy a Home How to Finance a Home How to Sell a Home