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5-Bedroom Homes for Sale in Dukes County MA

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  • 1 Louis Field Rd, Edgartown, MA 02539
    1 Louis Field Rd, Edgartown, MA 02539
    1 Louis Field Rd, 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
  • 25 Lelands Path, Edgartown, MA 02539
    25 Lelands Path, Edgartown, MA 02539
    25 Lelands Path, Edgartown, MA 02539
    /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
  • 34 Massasoit Ave, Oak Bluffs, MA 02568
    34 Massasoit Ave, Oak Bluffs, MA 02568
    34 Massasoit Ave, Oak Bluffs, MA 02568
    /34

    $2,700,000

    • 6 Beds
    • 2.5 Baths
    • 1,666 Sq Ft

    34 Massasoit Ave, Oak Bluffs, MA 02568

    This is the last B1 undeveloped commercial property on Circuit Avenue's main strip. Previous development plans included mixed use with commercial store front and condos above. Located on the corner of Circuit Ave and Massasoit this property has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms, perfect for a weekly rental or employee housing. Right in the heart of Oak Bluffs walk to

    Agent Photo

    Lisa Lucier

    Anchor Realty of MV

    (508) 348-7972

    34 Massasoit Ave, Oak Bluffs, MA 02568
  • 111 N Water St, Edgartown, MA 02539
    111 N Water St, Edgartown, MA 02539
    111 N Water St, Edgartown, MA 02539
    /42

    $16,975,000

    • 6 Beds
    • 4.5 Baths
    • 3,606 Sq Ft

    111 N Water St, Edgartown, MA 02539

    Historic captain’s home circa 1850, brilliantly renovated by architect Patrick Ahearn in 2002, on coveted North Water Street. Enjoy sweeping 180 Edgartown Harbor views from bright, sunlit living spaces with heart pine floors and custom millwork. An open-concept first floor flows to an 18x29' mahogany deck, perfect for al fresco dining and entertaining. The rare double-wide lot offers a lawn

    Agent Photo

    Wendy Harman

    Compass

    (508) 274-5363

    111 N Water St, Edgartown, MA 02539
  • 400 Barnes Rd, Vineyard Haven, MA 02568
    400 Barnes Rd, Vineyard Haven, MA 02568
    400 Barnes 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 Tamarack Ln, Oak Bluffs, MA 02557
    15 Tamarack Ln, Oak Bluffs, MA 02557
    15 Tamarack Ln, Oak Bluffs, MA 02557
    /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
  • 180 Pilot Hill Farm Rd, Vineyard Haven, MA 02568
    180 Pilot Hill Farm Rd, Vineyard Haven, MA 02568
    180 Pilot Hill Farm 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
  • 33 Goethals Way, Vineyard Haven, MA 02568
    33 Goethals Way, Vineyard Haven, MA 02568
    33 Goethals Way, Vineyard Haven, MA 02568
    /35

    $12,500,000

    • 5 Beds
    • 2.5 Baths
    • 2,794 Sq Ft

    33 Goethals Way, Vineyard Haven, MA 02568

    A rare opportunity -- a Vineyard harbor front property with a Victorian gambrel cottage restored to its original grandeur of a century ago, an expansive front yard, 180 degree commanding views of the active harbor, private sandy beach, and unmatched serenity. You have the opportunity to own one of the finest estates gracing the Vineyard Haven harbor front -- so admired by all visitors to the

    Lynn Buder Sandpiper Realty Inc

    33 Goethals Way, Vineyard Haven, MA 02568
  • 31 Lamberts Cove Rd, Vineyard Haven, MA 02568
    31 Lamberts Cove Rd, Vineyard Haven, MA 02568
    31 Lamberts Cove Rd, Vineyard Haven, MA 02568
    /37

    $6,250,000

    • 6 Beds
    • 9 Baths
    • 5,732 Sq Ft

    31 Lamberts Cove Rd, Vineyard Haven, MA 02568

    Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's

    31 Lamberts Cove Rd, Vineyard Haven, MA 02568
  • 122 Old Farm Rd, Chilmark, MA 02535
    122 Old Farm Rd, Chilmark, MA 02535
    122 Old Farm Rd, Chilmark, MA 02535
    /36

    $5,450,000

    • 5 Beds
    • 4 Baths
    • 2,913 Sq Ft

    122 Old Farm Rd, Chilmark, MA 02535

    An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The original section of this 3000 sq ft home dates from the late 1700s and is on Chilmark's register of historic homes, but it has been expanded with new additions to create a thoroughly modern

    Mark Jenkins Wallace & Co. Sotheby's

    122 Old Farm Rd, Chilmark, MA 02535
  • 124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
    /34

    $5,450,000

    • 5 Beds
    • 4.5 Baths
    • 2,913 Sq Ft

    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535

    An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The original section of this 3000 sq ft home dates from the late 1700s and is on Chilmark's register of historic homes, but it has been expanded with new additions to create a thoroughly modern

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
  • 150 E Chop Dr, Oak Bluffs, MA 02557
    150 E Chop Dr, Oak Bluffs, MA 02557
    150 E Chop Dr, Oak Bluffs, MA 02557
    /41

    $9,900,000

    • 8 Beds
    • 9 Baths
    • 8,560 Sq Ft

    150 E Chop Dr, Oak Bluffs, MA 02557

    Big Bluff. The crown jewel of East Chop. Timeless elegance and unmatched craftsmanship on the shores of Martha’s Vineyard. Renowned architect M. Hutker and preeminent builder J.G.Early teamed up to create this magnificent waterfront estate. 8,500 Sq. ft. of pure luxury. Open-concept living with large picture windows, a chef’s kitchen with island, high-end appliances, wet bar, and sunlit breakfast

    Moira Lown Coldwell Banker Realty - Wellesley

    150 E Chop Dr, Oak Bluffs, MA 02557
  • 60 Meetinghouse Rd, Chilmark, MA 02535
    60 Meetinghouse Rd, Chilmark, MA 02535
    60 Meetinghouse Rd, Chilmark, MA 02535
    /49

    $6,490,000

    • 6 Beds
    • 8 Baths
    • 5,660 Sq Ft

    60 Meetinghouse Rd, Chilmark, MA 02535

    This spectacular and bright modern american farmhouse is perfectly sited to capture the varied scenic beauty that surrounds the farm. Built in 2021 with great attention to detail and materials, this home was created around gatherings and community with ample space for the extended family. The land has been lovingly curated into a place which can grow, generate and support those who want to have

    Jim Feiner Feiner Real Estate

    60 Meetinghouse Rd, Chilmark, MA 02535
  • 6 Wakeman Rd, Chilmark, MA 02535
    6 Wakeman Rd, Chilmark, MA 02535
    6 Wakeman Rd, Chilmark, MA 02535
    /35

    $13,000,000

    • 5 Beds
    • 5 Baths
    • 3,758 Sq Ft

    6 Wakeman Rd, Chilmark, MA 02535

    A 1930s-built home that has been remarkably updated to retain its historic charm while incorporating sophisticated and modern amenities. The house overlooks the Chilmark Great Pond and the Atlantic Ocean beyond. The Main House includes 3 bedrooms, 3 beautifully renovated bathrooms, a walk-in closet, a Pantry, a Library/Media room, a full basement, Outdoor showers, and a screened-in porch. The

    Julianna Flanders Flanders Real Estate

    6 Wakeman Rd, Chilmark, MA 02535
  • 8 Fresh Pond Rd, Oak Bluffs, MA 02557
    8 Fresh Pond Rd, Oak Bluffs, MA 02557
    8 Fresh Pond Rd, Oak Bluffs, MA 02557
    /40

    $5,295,000

    • 7 Beds
    • 5 Baths
    • 5,320 Sq Ft

    8 Fresh Pond Rd, Oak Bluffs, MA 02557

    The Ultimate Oak Bluffs Compound: A rare opportunity to own a stunning seven-bedroom estate, thoughtfully designed for both luxurious living and exceptional rental potential. This expansive property features a newly built pool, lush landscaping, and direct access to Fresh Pond—ideal for kayaking, paddleboarding, and swimming. Perfect for entertaining, the home showcases a dramatic great room, an

    Jarrett Hurwitz Keller Williams Realty

    8 Fresh Pond Rd, Oak Bluffs, MA 02557
  • 10 Puwal Ln, Edgartown, MA 02539
    10 Puwal Ln, Edgartown, MA 02539
    10 Puwal Ln, Edgartown, MA 02539
    /30

    $6,000,000

    • 5 Beds
    • 7 Baths
    • 5,104 Sq Ft

    10 Puwal Ln, Edgartown, MA 02539

    KATAMA COMPOUND WITH POOL - TURNKEY & READY FOR USE THIS SUMMER! In an enclave of luxury homes in Katama, this 2021-built 5 bedroom, 5 bathroom property with three half-baths is being delivered turnkey with fine furnishings and most artwork. The home has everything the modern buyer wants, including two primary bedroom suites (one upstairs, one downstairs), all bedrooms with ensuite bathrooms, two

    Mark Jenkins Wallace & Co. Sotheby's

    10 Puwal Ln, Edgartown, MA 02539
  • 19BC Locust Ln, Aquinnah, MA 02535
    19BC Locust Ln, Aquinnah, MA 02535
    19BC Locust Ln, Aquinnah, MA 02535
    /40

    $6,395,000

    • 8 Beds
    • 7 Baths
    • 6,921 Sq Ft

    19BC Locust Ln, Aquinnah, MA 02535

    This beautifully designed and built home is privately sited on 4.02 acres overlooking a pastoral setting with amazing ocean views and bordered by stone walls. There is also an additional 2.02 acre parcel included with purchase. The spacious entry hall steps into a formal living and dining room with oversized windows that take in the amazing North Shore ocean views, tall ceilings, a field stone

    Brenda Galligan Karen M. Overtoom R.E.

    19BC Locust Ln, Aquinnah, MA 02535
  • 78 Hammett Rd, Chilmark, MA 02535
    78 Hammett Rd, Chilmark, MA 02535
    78 Hammett Rd, Chilmark, MA 02535
    /63

    $5,975,000

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

    78 Hammett Rd, Chilmark, MA 02535

    Wonderful elevated Chilmark north shore 3.8 acre secure waterfront property with dramatic year round sunset water views to the Gay Head Lighthouse and Elizabeth Islands. The Vineyard Sound expanse enjoys peaceful sailing, fishing and other boating activity to enhance the ocean splendor. The 5 bedroom 3 1/2 bath 4,050 sq ft home is literally in move-in condition. Architect designed and built by

    Robert Kenney Tea Lane Associates

    78 Hammett Rd, Chilmark, MA 02535
  • 18 Spruce Gate Rd, Chilmark, MA 02535
    18 Spruce Gate Rd, Chilmark, MA 02535
    18 Spruce Gate Rd, Chilmark, MA 02535
    /52

    $12,500,000

    • 5 Beds
    • 4 Baths
    • 3,700 Sq Ft

    18 Spruce Gate Rd, Chilmark, MA 02535

    Welcome to an extraordinary ocean view coastal sanctuary set within the exclusive gates of Squibnocket Farm—a 450+ acre private community with access to over 2 miles of oceanfront, 1.5 miles of pond frontage, and 300+ acres of conservation land. Set on a peaceful, pastoral landscape abutting 17 acres of preserved land, this stately home was designed and built by Soikkeli & Company, one of the

    Alyssa Halisky Wallace & Co. Sotheby's

    18 Spruce Gate Rd, Chilmark, MA 02535
  • 49 Gosnold's Way, Chilmark, MA 02535
    49 Gosnold's Way, Chilmark, MA 02535
    49 Gosnold's Way, Chilmark, MA 02535
    /51

    $4,950,000

    • 5 Beds
    • 4 Baths
    • 4,044 Sq Ft

    49 Gosnold's Way, Chilmark, MA 02535

    Perched high on the north shore with sweeping views of the Vineyard Sound, this expansive and private property is surrounded by Menemsha Hills conservation land and trails and offers broad water views, even from ground floor of house. The house is large and well maintained with an upside down floor plan allowing for high ceilings and bright spaces in the open plan kitchen/dining/living room, as

    Meg Bodnar Tea Lane Associates

    49 Gosnold's Way, Chilmark, MA 02535
  • 26 Curtis Ln, Edgartown, MA 02539
    26 Curtis Ln, Edgartown, MA 02539
    26 Curtis Ln, Edgartown, MA 02539
    /16

    $6,700,000

    • 8 Beds
    • 10 Baths
    • 6,229 Sq Ft

    26 Curtis Ln, Edgartown, MA 02539

    Exceptional 8 bedroom home with attached artist/fitness barn studios. Each bedroom includes a en-suite bathroom.The kitchen/dining area includes: 3 refrigerators and 6 freezer drawers, a 5-burner gas stove and oven, dishwasher and microwave. Finished basement (1,000 square feet). Basement includes: 3 washer/dryer units. Outdoor deck with table, chairs and an outdoor grill.

    Thomas Melone Thomas Melone

    26 Curtis Ln, Edgartown, MA 02539
  • 10 Tilton Way, Edgartown, MA 02539
    10 Tilton Way, Edgartown, MA 02539
    10 Tilton Way, Edgartown, MA 02539
    /38

    $6,500,000

    • 5 Beds
    • 6 Baths
    • 4,136 Sq Ft

    10 Tilton Way, Edgartown, MA 02539

    This newly built traditionally styled Greek Reival home offers a wonderful open floor plan with refreshing interior design, all presented in excellent condition. The first floor front foyer, leads to the well-appointed kitchen with high-end appliances and large island. A dining area and living room with fireplace, all with an abundance of natural light. There are French doors leading to a covered

    Gerrett Conover Landvest MV

    10 Tilton Way, Edgartown, MA 02539
  • 41 Crowell Ln, Tisbury, MA 02568
    41 Crowell Ln, Tisbury, MA 02568
    41 Crowell Ln, Tisbury, MA 02568
    /10

    $4,995,000 New Construction

    • 5 Beds
    • 5 Baths
    • 4,185 Sq Ft

    41 Crowell Ln, Tisbury, MA 02568

    Slated for summer 2025 occupancy and nestled in the picturesque landscape of West Chop, this luxurious new development by Novo Builds offers an exquisite blend of modern design and coastal charm. Known for their innovative designs and high-quality craftsmanship, Novo Builds is transforming this iconic island with their latest project, providing an ideal sanctuary for families or those who love to

    Joe & Nicole Holland Vineyard Dream Realty LLC

    41 Crowell Ln, Tisbury, MA 02568
  • 23 Pinehurst Rd, Edgartown, MA 02539
    23 Pinehurst Rd, Edgartown, MA 02539
    /2

    $5,300,000 New Construction

    • 5 Beds
    • 6 Baths
    • 5,394 Sq Ft

    23 Pinehurst Rd, Edgartown, MA 02539

    New Construction with POOL, GUEST HOUSE and PRIMARY HOME, all within close proximity to Main Street, Edgartown. This gorgeous four bedroom gambrel home offers comfort and ease of coastal luxurious living. The primary home welcomes you with a two story foyer which opens to a large great room with a gourmet kitchen, with a bar area and a central island offering seating for at least four. The

    Michele Casavant Vineyard Village Realty

    23 Pinehurst Rd, Edgartown, MA 02539
  • 128 W Spring St, Vineyard Haven, MA 02568
    128 W Spring St, Vineyard Haven, MA 02568
    128 W Spring St, Vineyard Haven, MA 02568
    /32

    $1,750,000

    • 5 Beds
    • 4 Baths
    • 2,436 Sq Ft

    128 W Spring St, Vineyard Haven, MA 02568

    128 Spring Street—just moments from the Tisbury School and downtown Vineyard Haven. Built in 2013 and sited on an ample 1/4-acre lot, the house features four bedrooms and two-and-a-half bathrooms, along with a separate first floor one-bedroom in-law apartment complete with a full bath—ideal for extended family, guests, or added rental flexibility. The central location offers convenience to

    David Dickinson Compass | Point B

    128 W Spring St, Vineyard Haven, MA 02568
  • 139 Main St, Vineyard Haven, MA 02568
    139 Main St, Vineyard Haven, MA 02568
    139 Main 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
  • 128 & 136 Spring St, Vineyard Haven, MA 02568
    128 & 136 Spring St, Vineyard Haven, MA 02568
    128 & 136 Spring St, Vineyard Haven, MA 02568
    /47

    $2,675,000

    • 6 Beds
    • 5 Baths
    • 2,970 Sq Ft

    128 & 136 Spring St, Vineyard Haven, MA 02568

    A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street—two adjacent properties being sold together to create a unique, flexible compound just moments from the Tisbury School and downtown Vineyard Haven. With a spacious main residence and a separate guest house, this rare combination presents a compelling opportunity for multigenerational living, seasonal enjoyment,

    David Dickinson Compass | Point B

    128 & 136 Spring St, Vineyard Haven, MA 02568
  • 128 W Spring St, Vineyard Haven, MA 02568
    128 W Spring St, Vineyard Haven, MA 02568
    128 W Spring St, Vineyard Haven, MA 02568
    /42

    $2,675,000

    • 6 Beds
    • 4.5 Baths
    • 2,970 Sq Ft

    128 W Spring St, Vineyard Haven, MA 02568

    A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street - Two adjacent properties being sold together create a flexible compound just moments from downtown Vineyard Haven. The 4-bedroom, 2-1/2 bath main house also includes a separate, 1-bedroom in-law/nanny apartment with a full bath. The guest house has 1 bedroom and 1 bath, with a 4-bedroom septic system allowing

    David Dickinson Compass

    128 W Spring St, Vineyard Haven, MA 02568
  • 71 Stoney Hill Rd, Vineyard Haven, MA 02568
    71 Stoney Hill Rd, Vineyard Haven, MA 02568
    71 Stoney Hill 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
  • 4 Canonicus Ave, Oak Bluffs, MA 02557
    4 Canonicus Ave, Oak Bluffs, MA 02557
    4 Canonicus Ave, Oak Bluffs, MA 02557
    /39

    $5,325,000

    • 6 Beds
    • 4 Baths
    • 2,890 Sq Ft

    4 Canonicus Ave, Oak Bluffs, MA 02557

    With a striking presence overlooking Nantucket Sound and just moments from the vibrant pulse of downtown, this distinctive compound is infused with a laid-back West Coast spirit while honoring the vintage charm of Oak Bluffs. Airy and effortlessly elegant, the four-bedroom main house has been masterfully updated, introducing refined, contemporary comforts, designed for every season. Tucked to the

    Katherine Donahue Sandpiper Realty Inc

    4 Canonicus Ave, Oak Bluffs, MA 02557
  • 23 Crowell Ln, Vineyard Haven, MA 02568
    23 Crowell Ln, Vineyard Haven, MA 02568
    23 Crowell Ln, Vineyard Haven, MA 02568
    /53

    $2,075,000

    • 5 Beds
    • 4 Baths
    • 3,273 Sq Ft

    23 Crowell Ln, Vineyard Haven, MA 02568

    WEST CHOP! Farmhouse charm and comfortable elegance define this very spacious 5 Bedroom, 3,200 s/f home that is set on just over an acre on a private wooded lot. Hear the ferry, spot the osprey, and unwind on the back deck. This is your invitation to island living!The home welcomes you with an expansive front porch that overlooks a mature landscape that is framed with a stone wall and

    Rene Jackson Island Real Estate

    23 Crowell Ln, Vineyard Haven, MA 02568
  • 11 Huckleberry Hill Ln, Edgartown, MA 02539
    11 Huckleberry Hill Ln, Edgartown, MA 02539
    11 Huckleberry Hill Ln, Edgartown, MA 02539
    /40

    $1,890,000

    • 5 Beds
    • 3 Baths
    • 2,704 Sq Ft

    11 Huckleberry Hill Ln, Edgartown, MA 02539

    Turn-Key 5-Bedroom Home with Legal Apartment Near Edgartown Village — Set back from the road and less than a mile from Main Street, this spacious and stylish Edgartown property offers an ideal blend of privacy, comfort, and investment potential. The main home features four well-proportioned bedrooms—including one conveniently located on the first floor—and an open kitchen and dining area designed

    Jennifer O'hanlon Compass

    11 Huckleberry Hill Ln, Edgartown, MA 02539
  • 5 Louis Field Rd, Edgartown, MA 02539
    5 Louis Field Rd, Edgartown, MA 02539
    5 Louis Field Rd, Edgartown, MA 02539
    /33

    $8,995,000

    • 11 Beds
    • 9 Baths
    • 9,678 Sq Ft

    5 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 an 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

    Wendy Harman Compass | Point B

    5 Louis Field Rd, Edgartown, MA 02539
  • 735 Franklin St, Vineyard Haven, MA 02568
    735 Franklin St, Vineyard Haven, MA 02568
    735 Franklin St, Vineyard Haven, MA 02568
    /41

    $3,400,000

    • 5 Beds
    • 4 Baths
    • 3,361 Sq Ft

    735 Franklin St, Vineyard Haven, MA 02568

    Welcome to this stunning 4-bedroom, 3-bathroom primary residence along with a 1-bedroom studio apartment over the one-car garage, ideally located in West Chop! Together, they include approximately 3,871 square feet of beautifully renovated living space (an additional 510 sqft of living space on the 3rd floor in the main house is not included on the town assessment). Situated on a .99-acre lot,

    Emily Flake Viewpoints

    735 Franklin St, Vineyard Haven, MA 02568
  • 50 Hidden Cove Rd, Edgartown, MA 02539
    50 Hidden Cove Rd, Edgartown, MA 02539
    50 Hidden Cove Rd, 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
  • 20 James Pond Way, Vineyard Haven, MA 02568
    20 James Pond Way, Vineyard Haven, MA 02568
    20 James Pond Way, Vineyard Haven, MA 02568
    /76

    $3,995,000

    • 5 Beds
    • 3 Baths
    • 2,791 Sq Ft

    20 James Pond Way, Vineyard Haven, MA 02568

    Nestled on a serene 4.5-acre parcel of land off Lambert's Cove Road, this exquisite property offers unparalleled privacy, views and direct access to James Pond and beyond to the Land Bank's Lambert's Cove Beach property. In addition to the custom heated Gunite pool, the expansive yard provides space for many outdoor activities while relishing the tranquility of the location. The residence

    Sheila Morse Island Real Estate

    20 James Pond Way, Vineyard Haven, MA 02568
  • 393 Lighthouse Rd, Aquinnah, MA 02535
    393 Lighthouse Rd, Aquinnah, MA 02535
    393 Lighthouse Rd, Aquinnah, MA 02535
    /34

    $1,750,000

    • 5 Beds
    • 2 Baths
    • 1,440 Sq Ft

    393 Lighthouse Rd, Aquinnah, MA 02535

    Ranch style home & Guest camp situated on 1+/- acre lot. The Main House offers distant views of Lobersterville beach and the Vineyard Sound beyond. Located in the desirable Lighthouse Road area, which offers walkable/close-by beach access and quiet roads. The view can be enjoyed from the Kitchen/Living/Dining as well as the wrap-around deck. Enjoy the open concept main living area, two bedrooms,

    Julianna Flanders Flanders Real Estate

    393 Lighthouse Rd, Aquinnah, MA 02535
  • 19 Old Woods Rd, Chilmark, MA 02535
    19 Old Woods Rd, Chilmark, MA 02535
    19 Old Woods Rd, Chilmark, MA 02535
    /37

    $3,400,000

    • 5 Beds
    • 2 Baths
    • 3,133 Sq Ft

    19 Old Woods Rd, Chilmark, MA 02535

    Nestled in the heart of Chilmark, this 12.5-acre property offers two charming dwellings, each with 3 bedrooms, set in a landscape of privacy and timeless Vineyard character. Built in 1950 and 1963 for American artist, Thomas Hart Benton, the homes were lovingly created as a compound for friends and family to return to year after year. Tucked down a quiet driveway, the two share a special legacy

    Cheri Mason Landvest MV

    19 Old Woods Rd, Chilmark, MA 02535
  • 104 Pond View Farm Rd, Vineyard Haven, MA 02568
    104 Pond View Farm Rd, Vineyard Haven, MA 02568
    104 Pond View Farm Rd, Vineyard Haven, MA 02568
    /108

    $4,800,000

    • 6 Beds
    • 5 Baths
    • 2,960 Sq Ft

    104 Pond View Farm Rd, Vineyard Haven, MA 02568

    An exceptional Waterfront Compound on Tisbury Great Pond. Located across the Tisbury Great Pond from the exclusive Blue Heron Farm, this remarkable waterfront property offers a rare opportunity to own a serene compound with two homes and a private permitted dock—ideal for boating to the Atlantic barrier beach, fishing, kayaking, and enjoying the peaceful beauty of the pond.Both the main house and

    Alexis Holden Tea Lane Associates

    104 Pond View Farm Rd, Vineyard Haven, MA 02568
  • 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

Showing Results 1 - 40, Page 1 of 2

Massachusetts Dukes County

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