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Colonial Homes for Sale in Dukes County MA

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  • /31

    $1,699,999

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    43 N Slope Ln, Chilmark, MA 02535

    Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha's Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring

    Agent Photo

    Barbara O'Hara

    North Star Real Estate, LLC

    (508) 850-0854

    43 N Slope Ln, Chilmark, MA 02535
  • /42

    $2,325,000

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,630 Sq Ft

    81 Whalers Walk, Edgartown, MA 02539

    Experience the ease of summer living in your own Martha’s Vineyard beach house. Perched atop a rise with sweeping views, abundant natural light, and star-filled skies, this furnished, move-in-ready home with four levels of lifestyle. A dramatic 30-foot vaulted foyer leads to a fully renovated chef’s kitchen with Sub-Zero refrigeration, premium stainless appliances, stone counters, and a custom

    Dawn Bellante Sandpiper Realty, Inc.

    81 Whalers Walk, Edgartown, MA 02539
  • /30

    $8,950,000

    • 5 Beds
    • 7 Baths
    • 4,078 Sq Ft

    1 Field Club Dr, Edgartown, MA 02539

    Nestled within the prestigious Field Club, this exceptional five-bedroom compound captures the essence of refined island living, blending timeless elegance with modern sophistication. A welcoming foyer introduces a light-filled, open-concept main level designed for both comfort and entertaining. The gourmet kitchen is a standout, featuring high-end appliances, granite countertops, and custom

    Tom Wallace

    1 Field Club Dr, Edgartown, MA 02539
  • /26

    $7,850,000

    $150K PRICE DROP
    • 4 Beds
    • 6 Baths
    • 5,884 Sq Ft

    24 Katama Bay View Rd, Edgartown, MA 02539

    This classic New England home in Katama offers a refined blend of timeless architecture and modern comfort, set on a spacious, beautifully landscaped lot. The main house features three well-appointed bedrooms, including a light-filled primary suite and inviting guest rooms designed for comfort and privacy. The open-concept living area is ideal for entertaining, highlighted by a cozy fireplace and

    Tom Wallace

    24 Katama Bay View Rd, Edgartown, MA 02539
  • /28

    $1,790,000

    • 3 Beds
    • 2.5 Baths
    • 2,347 Sq Ft

    41 & 0 Cook St, Tisbury, MA 02568

    Enjoy the rare opportunity to own a beautifully maintained Vineyard Haven home together with an adjacent 16,000 sq. ft. buildable lot, totaling approximately .69 acres. Just moments from downtown, the ferry, shops, restaurants, and harbor, this offering combines convenience, privacy, and future potential.The updated home features 3 bedrooms, 2.5 bathrooms, wood floors throughout, central air, and

    Jennifer O'hanlon Compass

    41 & 0 Cook St, Tisbury, MA 02568
  • /39

    $3,250,000

    • 5 Beds
    • 3.5 Baths
    • 4,068 Sq Ft

    241 Daggett Ave, Vineyard Haven, MA 02568

    Built in 2016 by Squash Meadow Builders, this exceptional five bedroom Colonial sits moments from the sandy shores of Tashmoo Beach on Vineyard Sound. Spanning four levels, it blends timeless architecture with modern comfort. The main floor offers open living with gas fireplace, a gourmet kitchen with custom built-ins and bench seating, and a sunlit sunroom for relaxed coastal living. A private

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    241 Daggett Ave, Vineyard Haven, MA 02568
  • /7

    $2,300,000

    • 3 Beds
    • 2.5 Baths
    • 1,344 Sq Ft

    60 Crocker Dr, Edgartown, MA 02539

    South Beach! Katama Airfield! Look no further if you are hoping to find a great lot within close proximity to all Katama has to offer. Nestled in the heart of Katama, 60 Crocker Drive offers a discerning buyer a unique opportunity to renovate a house and guest house. Bring your creativity. With 2 pre-existing structures and a total of 3 bedrooms, you can renovate the existing structures or start

    Michele Moore Island Real Estate

    60 Crocker Dr, Edgartown, MA 02539
  • /24

    $1,999,000

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

    5 Pine Tree Ln, Vineyard Haven, MA 02568

    Blending 1920s charm with modern luxury, this beautifully renovated home is tucked into the coveted West Chop area of Vineyard Haven. Just steps from a neighborhood beach on the pristine shores of Vineyard Sound, it offers an elegant mix of historic character and contemporary comfort. A thoughtfully designed layout features generous living spaces centered around a chef’s kitchen with custom

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    5 Pine Tree Ln, Vineyard Haven, MA 02568
  • /42

    $16,900,000

    • 8 Beds
    • 7.5 Baths
    • 6,041 Sq Ft

    114 N Water St, Edgartown, MA 02539

    Edgartown Village Compound with Harbor Views: Positioned in the heart of Edgartown’s historic district, 114 North Water Street is a newly complete, move-in-ready property offering views of Edgartown Harbor. The offering includes eight bedrooms and seven-and-a-half baths across three thoughtfully designed structures: a six-bedroom, five-and-a-half bath main residence, a one-bedroom guest house

    Erin Hegarty Donnelly + Co.

    114 N Water St, Edgartown, MA 02539
  • /27

    $14,250,000

    $250K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 4,820 Sq Ft

    68 N Water St, Edgartown, MA 02539

    This expansive historic compound in the heart of Edgartown Village blends timeless charm with modern luxury. Just steps from top restaurants and shops, the home has been fully renovated by Stern McCafferty Architecture + Interiors, pairing contemporary design with classic architectural detail. Inside, open-plan living spaces create an effortless flow for entertaining, with a sleek kitchen and

    Tom Wallace

    68 N Water St, Edgartown, MA 02539
  • /28

    $2,395,000

    $100K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,968 Sq Ft

    105 Whalers Walk, Edgartown, MA 02539

    Fresh, stylish, and fun best describe this inviting four-bedroom Edgartown home with a newly completed pool! Thoughtfully renovated from top to bottom, the interior offers warm, functional living spaces where every detail has been carefully considered. The same level of attention carries outdoors to a true backyard oasis, complete with a heated saltwater pool, multiple patios, a pergola, and an

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    105 Whalers Walk, Edgartown, MA 02539
  • /38

    $3,199,000

    • 3 Beds
    • 3.5 Baths
    • 3,082 Sq Ft

    53 Stoney Hill Rd, Vineyard Haven, MA 02568

    This custom-built Martha’s Vineyard residence blends timeless elegance with contemporary luxury, offering exclusive access to Lambert’s Cove Beach.At its heart is a chef’s kitchen with bespoke cabinetry, honed Carrara marble, Wolf and Sub-Zero appliances, Miele dishwasher, and Hudson Valley lighting. An adjacent custom bar features Dolomite Italian granite, ideal for entertaining.The home boasts

    Jennifer B. DaSilva Compass

    53 Stoney Hill Rd, Vineyard Haven, MA 02568
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