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Homes for Sale near Martha's Vineyard Regional High School

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  • 111 Charles Neck Way, Vineyard Haven, MA 02568
    111 Charles Neck Way, Vineyard Haven, MA 02568
    111 Charles Neck Way, Vineyard Haven, MA 02568
    /21

    $1,599,000

    • 3 Beds
    • 2 Baths
    • 1,562 Sq Ft

    111 Charles Neck Way, Vineyard Haven, MA 02568

    Tucked away on 1.6 wooded acres in West Tisbury, this classic Cape-style home offers both privacy and convenience, with easy access to the charm of Up-Island and the amenities of Down-Island. Located on a paved road near Long Point Beach, it also includes coveted access to Lambert’s Cove Beach.The bright, open interior features a living and dining area with a wood-burning fireplace, a kitchen

    Emma Kennedy Sandpiper Realty

    111 Charles Neck Way, Vineyard Haven, MA 02568
  • 00 Old Field Rd, Aquinnah, MA 02535
    00 Old Field Rd, Aquinnah, MA 02535
    00 Old Field Rd, Aquinnah, MA 02535
    /13

    $1,150,000

    • Land
    • 2.02 Acres
    • $569,307 per Acre

    00 Old Field Rd, Aquinnah, MA 02535

    The nearby roar of the Atlantic can be heard from this pristine two-acre building opportunity in Aquinnah, ideally located at the end of Old Field Road with easy access from Moshup Trail. A storybook walking path through woods and fields over an easement bordering a majestic beetlebung grove and over a bubbling stream, leads directly to the entrance of cherished Philbin Beach. A thoughtfully

    Katherine Donahue Sandpiper Realty Inc

    00 Old Field Rd, Aquinnah, MA 02535
  • 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

    $2,450,000

    • 6 Beds
    • 4.5 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

    $2,450,000

    • 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
  • 15 Tamarack Ln, Oak Bluffs, MA 02557
    15 Tamarack Ln, Oak Bluffs, MA 02557
    15 Tamarack Ln, Oak Bluffs, MA 02557
    /43

    $4,999,000

    • 6 Beds
    • 5.5 Baths
    • 3,214 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

    Michael Schweikert Ocean Park Realty, Inc.

    15 Tamarack Ln, Oak Bluffs, MA 02557
  • 46 Kennebec Ave, Oak Bluffs, MA 02557
    46 Kennebec Ave, Oak Bluffs, MA 02557
    46 Kennebec Ave, Oak Bluffs, MA 02557
    /34

    $1,495,000

    • 4 Beds
    • 1.5 Baths
    • 1,305 Sq Ft

    46 Kennebec Ave, Oak Bluffs, MA 02557

    Enjoy the convenience of being just steps away from the Public Beach, Steamship Authority, Oak Bluffs Harbor, a supermarket, and a variety of charming restaurants and shops that contribute to Oak Bluffs' allure as a premier summer destination on Martha's Vineyard. This delightful three-season cottage has been carefully modernized over the years, offering a rare investment opportunity. Located

    Michael Schweikert Ocean Park Realty, Inc.

    46 Kennebec Ave, Oak Bluffs, MA 02557
  • 124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
    124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
    124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
    /8

    $799,000

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft

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

    Bright first-floor, three-bedroom, two bath condo in the popular Vineyard Haven Causeway Harborview association. Easy access to downtown shops, restaurants, harbor, ferry, and beaches. Building amenities include a shared pool, convenient storage, and on-site laundry facilities. The perfect blend of convenience and comfort for year-round living or as your ideal summer retreat.

    Emma Kennedy Sandpiper Realty Inc

    124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
  • 300 North Rd, Chilmark, MA 02535
    300 North Rd, Chilmark, MA 02535
    300 North Rd, Chilmark, MA 02535
    /36

    $2,995,000

    • 4 Beds
    • 3.5 Baths
    • 2,515 Sq Ft

    300 North Rd, Chilmark, MA 02535

    Winding tree lined driveway off North Rd brings you to this commanding, custom designed residence built by a top tier island builder. This home is set on over 4 private acres of rolling meadows and big sky views. Main living space is all on one level which includes primary bedroom with en-suite bath, large living area with fireplace, bright sunroom or second living room, custom kitchen and

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

    300 North Rd, Chilmark, MA 02535
  • 174 Middle Rd, Chilmark, MA 02535
    174 Middle Rd, Chilmark, MA 02535
    174 Middle Rd, Chilmark, MA 02535
    /40

    $1,895,000

    • 4 Beds
    • 3.5 Baths
    • 2,061 Sq Ft

    174 Middle Rd, Chilmark, MA 02535

    Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

    Sheila Morse Island Real Estate

    174 Middle Rd, Chilmark, MA 02535
  • 63 Saddle Club Rd, Edgartown, MA 02539
    63 Saddle Club Rd, Edgartown, MA 02539
    63 Saddle Club Rd, Edgartown, MA 02539
    /30

    $1,699,000

    • 4 Beds
    • 2.5 Baths
    • 2,291 Sq Ft

    63 Saddle Club Rd, Edgartown, MA 02539

    Welcoming and Picturesque from outside to inside! Thru the door, into the entryway you immediately sense comfort and well-being in this beautifully cared for 4-bedroom home. Open floor plan stars a chef’s kitchen outfitted with premium luxury appliances, granite counters, and loads of cabinets along with a dining area perfect for family and friend gatherings. Family room, along with a

    Martha Smith C McManus Realty Group

    63 Saddle Club Rd, Edgartown, MA 02539
  • 44 Tiffany Dr, Oak Bluffs, MA 02557
    44 Tiffany Dr, Oak Bluffs, MA 02557
    44 Tiffany Dr, Oak Bluffs, MA 02557
    /40

    $1,600,000

    • 4 Beds
    • 4 Baths
    • 3,927 Sq Ft

    44 Tiffany Dr, Oak Bluffs, MA 02557

    Nestled within the desirable Lagoon Estates development and set on a beautifully wooded 1.38-acre lot abutting Land Bank property, this expansive and sun-filled home offers versatile living space and a flexible floor plan. The main house features generously sized rooms enhanced by large windows that flood the interior with natural light. The kitchen boasts white cabinetry, a wall-mounted

    Sheila Morse Island Real Estate

    44 Tiffany Dr, Oak Bluffs, MA 02557
  • 53 Stoney Hill Rd, Vineyard Haven, MA 02568
    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    /39

    $3,299,000

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

    53 Stoney Hill Rd, Vineyard Haven, MA 02568

    This custom-built residence is nestled in one of Martha’s Vineyard’s most coveted up-island towns. At the heart of the home lies a professionally designed chef’s kitchen, featuring bespoke cabinetry, honed Carrara marble countertops, Wolf stove and wall oven, Sub-Zero refrigerator, Miele dishwasher, Kohler farmhouse sink, and Rohl satin nickel gooseneck faucet. A custom bar is appointed with

    Jennifer B. DaSilva Compass

    53 Stoney Hill Rd, 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
  • 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
    /66

    $6,495,000

    • 7 Beds
    • 5.5 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
  • 2 Farmers Rd, Edgartown, MA 02539
    2 Farmers Rd, Edgartown, MA 02539
    2 Farmers Rd, Edgartown, MA 02539
    /27

    $1,900,000

    • 4 Beds
    • 4 Baths
    • 2,202 Sq Ft

    2 Farmers Rd, Edgartown, MA 02539

    This house and guesthouse combination are situated in a very special location. Located equidistant between town and South Beach. The neighboring properties are quite impressive. Across the lane is over 28 acres of Edgartown Conservation Commission land. The property currently has two dwellings, a three bedroom main house and a one bedroom guesthouse. A separate toolshed has an additional finished

    Neal Stiller Cronigs Real Estate

    2 Farmers Rd, Edgartown, MA 02539
  • 0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    /4

    $675,000

    • Land
    • 0.23 Acre
    • $2,941,176 per Acre

    0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568

    Oak Bluffs Buildable Lot – Prime LocationThis flat 3-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to

    Andrew McElhinney Compass LLC

    0-B California Ave Unit Part lot 79, Oak Bluffs, MA 02568
  • 0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
    /4

    $625,000

    • Land
    • 0.34 Acre
    • $1,815,277 per Acre

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

    Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

    Andrew McElhinney Compass LLC

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
  • 16 South Rd, Chilmark, MA 02535
    16 South Rd, Chilmark, MA 02535
    16 South Rd, Chilmark, MA 02535
    /36

    $2,500,000

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

    16 South Rd, Chilmark, MA 02535

    Where Vineyard history meets pastoral beauty.Classic, lovingly restored 1800’s Chilmark farmhouse with multiple outbuildings, which includes a large barn with second floor loft, a run-in barn with two horse stalls, both overlook an expansive, pastoral fenced pasture for horses to run or field games to be played. This historic farmhouse home offers four bedrooms, three baths and has been

    Michele Casavant Vineyard Village Realty

    16 South Rd, Chilmark, MA 02535
  • 44 Iron Hill Rd Unit 1.7, Oak Bluffs, MA 02557
    44 Iron Hill Rd Unit 1.7, Oak Bluffs, MA 02557
    44 Iron Hill Rd Unit 1.7, Oak Bluffs, MA 02557
    /8

    $1,250,000

    • Land
    • 1.62 Acres
    • $771,605 per Acre

    44 Iron Hill Rd Unit 1.7, Oak Bluffs, MA 02557

    Drive past bucolic horse pastures and Duartes Pond to a sweet neighborhood near the Alpaca Farm. This property at the end of a cul-de-sac on Iron Hill Road is filled with possibilities. This 1.6-acre lot has 60,000 sq ft+ and can therefore accommodate up to 6 bedrooms with the 10,000 sq ft per bedroom rule. There is a current home on the property is in need of renovations or start fresh and build

    Cheri Mason Landvest MV

    44 Iron Hill Rd Unit 1.7, Oak Bluffs, MA 02557
  • 0 Moshup Trail Unit 32500206, Aquinnah, MA 02535
    0 Moshup Trail Unit 32500206, Aquinnah, MA 02535
    0 Moshup Trail Unit 32500206, Aquinnah, MA 02535
    /10

    $350,000

    • Land
    • 0 Acre

    0 Moshup Trail Unit 32500206, Aquinnah, MA 02535

    Enjoy coveted access to one of Martha's Vineyard's most stunning sandy beaches, located just off Moshup Trail in Aquinnah. This secluded beach is shared with only seven other members, ensuring a peaceful and private coastal experience. Located near Aquinnah's iconic ''Painted House,'' the property includes use of a private gated parking area and a picturesque stretch of shoreline perfect for

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    0 Moshup Trail Unit 32500206, Aquinnah, MA 02535
  • 0 Moshup Trail Unit 27 & 146 43498, Aquinnah, MA 02535
    0 Moshup Trail Unit 27 & 146 43498, Aquinnah, MA 02535
    0 Moshup Trail Unit 27 & 146 43498, Aquinnah, MA 02535
    /10

    $350,000

    • Land
    • 1.26 Acres
    • $277,778 per Acre

    0 Moshup Trail Unit 27 & 146 43498, Aquinnah, MA 02535

    Enjoy coveted access to one of Martha's Vineyard’s most stunning sandy beaches, located just off Moshup Trail in Aquinnah. This secluded beach is shared with only seven other members, ensuring a peaceful and private coastal experience. Located near Aquinnah’s iconic “Painted House,” the property includes use of a private gated parking area and a picturesque stretch of shoreline perfect for

    Alyssa Halisky Wallace & Co. Sotheby's

    0 Moshup Trail Unit 27 & 146 43498, Aquinnah, MA 02535
  • 17 John Wesley Ave, Vineyard Haven, MA 02568
    17 John Wesley Ave, Vineyard Haven, MA 02568
    17 John Wesley Ave, Vineyard Haven, MA 02568
    /46

    $1,795,000

    • 3 Beds
    • 2.5 Baths
    • 1,406 Sq Ft

    17 John Wesley Ave, Vineyard Haven, MA 02568

    Welcome to this year-round East Chop Victorian Gingerbread home, close to Oak Bluffs Harbor, Jetty Beach, and downtown. The amazing wrap-around porch is perfectly designed for spending lazy summers with friends and family. Many a party has been hosted on this generous porch, made more enticing by an open-plan first floor with a large kitchen, living room, and dining area. The first floor

    kyle Neyer Tea Lane Associates

    17 John Wesley Ave, 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
  • 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
  • 21 Clay Pit Rd, Edgartown, MA 02539
    21 Clay Pit Rd, Edgartown, MA 02539
    21 Clay Pit Rd, Edgartown, MA 02539
    /20

    $850,000

    • 2 Beds
    • 1 Bath
    • 834 Sq Ft

    21 Clay Pit Rd, Edgartown, MA 02539

    EDGARTOWN COTTAGE ON A COUNTRY LANE - Nestled on a spacious .56-acre lot in the Lily Pond District, this charming 2-bedroom, 1-bath cottage offers a rare opportunity to create your own Island haven. Renovate or build to suit just a short distance from all that Edgartown village has to offer — shops, restaurants, harbor, and beaches — you’ll enjoy both privacy and convenience in one of the

    Leslie C. Floyd Portfolio Real Estate, Inc.

    21 Clay Pit Rd, 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
    • 8.5 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
  • 61 Butlers Cove Rd, Edgartown, MA 02539
    61 Butlers Cove Rd, Edgartown, MA 02539
    61 Butlers Cove Rd, Edgartown, MA 02539
    /29

    $33,000,000

    • 9 Beds
    • 11 Baths
    • 7,190 Sq Ft

    61 Butlers Cove Rd, Edgartown, MA 02539

    Beach Farm is a breathtaking 18.6 acre waterfront estate on Martha’s Vineyard featuring unrivaled privacy, serenity, awe-inspiring views, private beaches, water sports and a rare walking path to the pristine beaches of the south shore. This truly one-of-a-kind estate borders Edgartown Great Pond, the famed South Shore, and is part of the storied Herring Creek Farm, an exclusive 200+ acre enclave

    Brian Dougherty Corcoran Property Advisors

    61 Butlers Cove Rd, Edgartown, MA 02539
  • 4 Hye Ln, Edgartown, MA 02539
    4 Hye Ln, Edgartown, MA 02539
    4 Hye Ln, Edgartown, MA 02539
    /41

    $1,850,000

    • 4 Beds
    • 3 Baths
    • 2,068 Sq Ft

    4 Hye Ln, Edgartown, MA 02539

    Pristine and superbly maintained, this two bedroom home and two bedroom guest house has tremendous upside potential and a substantial rental history. This property is tied to town sewer and will allow for up to 7 bedrooms. Two additional bedrooms in the main house are possible within the existing footprint with appropriate town approvals.There is an additional 668 sq. ft.of finished space in the

    Lynn Buder Sandpiper Realty Inc

    4 Hye Ln, Edgartown, MA 02539
  • 0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568
    0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568
    0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568
    /4

    $425,000

    • Land
    • 0.23 Acre
    • $1,845,419 per Acre

    0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568

    Lovely untouched piece of land waiting for you to create your own special island retreat. Property, being sold "AS IS", is nestled on a quiet dead end road off of DeBettencourt Place in Oak Bluffs. Conveniently located within walking distance to downtown OB, OB Ferry, beaches, parks, arts district and more... Included on the "Sea View Bluffs Subdivision Plan of Land" and recorded with Dukes

    Rosemary Byrd Ocean Park Realty Inc

    0 Heather Ln Unit 11 43465, Oak Bluffs, MA 02568
  • 124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
    124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
    124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
    /21

    $650,000

    • 2 Beds
    • 1 Bath
    • 725 Sq Ft

    124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568

    Outstanding year-round, two-bedroom condo on the ground level with dedicated parking, and close to the ferry, shops, and restaurants on Main Street, Vineyard Haven. The common grounds feature colorful landscaping, picnic tables, grills, and a swimming pool with a distant peek at the Lagoon. This unit has been delightfully renovated, featuring new hardwood floors, an updated bathroom, updated

    Stephanie Roache Donnelly + Co.

    124 Skiff Ave Unit A-11, 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
  • 28 Marthas Rd, Edgartown, MA 02539
    28 Marthas Rd, Edgartown, MA 02539
    28 Marthas Rd, Edgartown, MA 02539
    /31

    $2,750,000

    • 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
  • 14 Trapps Pond Rd, Edgartown, MA 02539
    14 Trapps Pond Rd, Edgartown, MA 02539
    14 Trapps Pond Rd, Edgartown, MA 02539
    /7

    $10,850,000

    • 7 Beds
    • 8 Baths
    • 12,051 Sq Ft

    14 Trapps Pond Rd, Edgartown, MA 02539

    Located on nearly 2-acres in the exclusive and newly created Trapps Pond Preserve, is this grand luxuriously appointed home. This is one of four homes being built and will be the first to be completed. Every room in the house is on a scale not often afforded in a Vineyard home, with 10 ft coffered ceilings and open/flowing floor plan. There is an abundance of light streaming in from the oversized

    Gerrett Conover Landvest MV

    14 Trapps Pond Rd, Edgartown, MA 02539
  • 122 Old Farm Rd, Chilmark, MA 02535
    122 Old Farm Rd, Chilmark, MA 02535
    122 Old Farm Rd, Chilmark, MA 02535
    /36

    $4,950,000

    • 5 Beds
    • 4 Baths
    • 3,413 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 historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

    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

    $4,950,000

    • 5 Beds
    • 4.5 Baths
    • 3,413 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 historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
  • 11 Bernard Way, Edgartown, MA 02539
    11 Bernard Way, Edgartown, MA 02539
    11 Bernard Way, Edgartown, MA 02539
    /11

    $4,250,000

    • 5 Beds
    • 5.5 Baths
    • 2,205 Sq Ft

    11 Bernard Way, Edgartown, MA 02539

    To be built by a luxury home builder! Located at the end of a quiet cul de sac, just half a mile to the top of Main Street, this Coastal Contemporary-styled home can be completed by July of 2026. Please review the digital renderings which show the vision for this high-end 5-bedroom home, swimming pool and guest house/pool house. High-end details include all ensuite bedrooms in the main house,

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    11 Bernard Way, 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

    $3,200,000

    • 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
  • 40 Scotchmans Ln, Vineyard Haven, MA 02568
    40 Scotchmans Ln, Vineyard Haven, MA 02568
    40 Scotchmans Ln, Vineyard Haven, MA 02568
    /36

    $1,495,000

    • 4 Beds
    • 2 Baths
    • 1,332 Sq Ft

    40 Scotchmans Ln, Vineyard Haven, MA 02568

    A home with history, built in the early 1800s this dwelling was originally built on a local farm and moved to its present location in the 1920's. The structure sits nestled amongst mature plantings and out buildings facing the Mill Brook. The studio and covered patio offer opportunities to entertain, relax and reflect. This 3.76 parcel was created from a larger parcel by the owner (see attached

    Jim Osmundsen Donnelly + Co.

    40 Scotchmans Ln, Vineyard Haven, MA 02568
  • 23 Pinehurst Rd, Edgartown, MA 02539
    23 Pinehurst Rd, Edgartown, MA 02539
    23 Pinehurst Rd, Edgartown, MA 02539
    /31

    $4,900,000

    • 5 Beds
    • 5.5 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
  • 7 Marthas Rd, Edgartown, MA 02539
    7 Marthas Rd, Edgartown, MA 02539
    7 Marthas Rd, Edgartown, MA 02539
    /8

    $4,800,000

    • 4 Beds
    • 4.5 Baths
    • 3,816 Sq Ft

    7 Marthas Rd, Edgartown, MA 02539

    Welcome to this coastal chic farmhouse set in the heart of Katama, a few blocks from the Field Club, close to SOUTH BEACH and close to Edgartown Village. To be built is a four bedroom en-suite home with a heated saltwater POOL. This home sits upon a flat, beautiful parcel of land with mature trees. The facade of the home offers an inviting covered porch with free standing columns, a granite

    Michele Casavant Vineyard Village Realty

    7 Marthas Rd, Edgartown, MA 02539

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