Martha's Vineyard, MA Homes for Sale

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  $3,250,000

  • 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
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  /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
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  /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
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  /39

  $3,299,000

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

  53 Stoney Hill Rd, Vineyard Haven, MA 02568

  Nestled in one of Martha’s Vineyard’s most sought-after locations, this custom home combines timeless elegance with modern luxury and exclusive access to Lambert’s Cove Beach. At its heart is a chef’s kitchen with custom cabinetry, honed Carrera countertops, handmade subway tile backsplash, Wolf stove and wall oven, Sub Zero refrigerator, Miele dishwasher, Kohler farmhouse sink, Rohl gooseneck

  Jennifer B. DaSilva Compass

  53 Stoney Hill Rd, Vineyard Haven, MA 02568
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  /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
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  /40

  $1,825,000

  • 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

  Nora Jardin Island Real Estate

  44 Tiffany Dr, Oak Bluffs, MA 02557
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  /66

  $6,900,000

  • 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
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  /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
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  /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
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  /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
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  /8

  $1,350,000

  • Land
  • 1.62 Acres
  • $833,333 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
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  /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
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  $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
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  /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
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  /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
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  /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
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  $1,895,000

  • 3 Beds
  • 4 Baths
  • 2,558 Sq Ft

  35 Tower Ridge Rd, Oak Bluffs, MA 02557

  Thoughtfully designed post-and-beam home that blends character with modern comfort and flexible living in Tower Ridge. The open-concept main floor features spacious gathering areas, while the finished basement offers a quiet retreat for work, relaxation, or play. The outdoor living space is just as inviting, with an oversized deck overlooking mature plantings and a generous side yard--perfect for

  Katherine Donahue Sandpiper Realty Inc

  35 Tower Ridge Rd, Oak Bluffs, MA 02557
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  /20

  $910,000

  • 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
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  $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
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  /35

  $1,690,000

  • 3 Beds
  • 4 Baths
  • 3,027 Sq Ft

  110 Clover Hill Dr, Vineyard Haven, MA 02568

  Perfect Location just minutes from Downtown and the ferry terminal this updated year round home offers flexible living with three bedrooms four bathrooms plus additional interior/exterior living areas to enjoy. It has a private lower level apartment large fenced in yard and a detached garage for boat/car storage. Many renovations have been completed. Seven new mini-splits (7), bathrooms

  Janna O'Loughlin Portfolio Real Estate, Inc.

  110 Clover Hill Dr, Vineyard Haven, MA 02568
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  /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
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  $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
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  /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
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  $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
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  $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
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  $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
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  $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
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  /18

  $835,000

  • 1 Bed
  • 1 Bath
  • 960 Sq Ft

  1 Onondaga Ave, Oak Bluffs, MA 02557

  Charming Single Story Cottage on a Beautiful Oak Bluffs Lot - Perfect for Your Vineyard Retreat! Discover the timeless appeal of this cozy 1-bedroom, 1-bath home nestled on a spacious 0.31-acre lot in the heart of Oak Bluffs. Built in 2000 and lovingly owned by the same family since its inception, this property offers a fantastic opportunity for both comfortable living and future expansion.

  Leslie Floyd Portfolio Real Estate Inc.

  1 Onondaga Ave, Oak Bluffs, MA 02557
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  /11

  $4,250,000

  • 5 Beds
  • 5.5 Baths
  • 4,200 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

  11 Bernard Way, Edgartown, MA 02539
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  $3,200,000 Open Sat 10AM - 12PM

  • 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
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  $1,850,000

  • 3 Beds
  • 3.5 Baths
  • 2,986 Sq Ft

  1 Harpoon Hollow, Aquinnah, MA 02535

  Beautiful, solidly custom built home featuring red oak Post and Beam work throughout. The many unique and attractive features are sure to delight the most discerning buyer. Abuts 5.9 acres of forever protected Landbank property extending the 2 private acres of this property for extraordinary privacy. A brick walk bordered by a lovely boxwood hedge leads to two separate entrances into the home.

  Elaine Vanderhoop Beachcombers of MV

  1 Harpoon Hollow, Aquinnah, MA 02535
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  /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
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  $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
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  $2,495,000

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

  21 Woodlawn Ave, Vineyard Haven, MA 02568

  Experience the perfect blend of coastal charm and modern sophistication in this beautifully designed Vineyard Haven home. Ideally situated in-town, this 4-bedroom, 3-bath home offers a comfortable, easy flowing layout, complemented by gleaming hardwood floors and a warm, inviting atmosphere. Located just a short stroll from the ferry, vibrant shops, restaurants and the Vineyard Haven Yacht Club,

  Beth Welch Viewpoints

  21 Woodlawn Ave, Vineyard Haven, MA 02568
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  /46

  $6,750,000

  • 3 Beds
  • 3 Baths
  • 3,432 Sq Ft

  44 Cencelle St, Chilmark, MA 02535

  This private 21-acre Chilmark estate with ocean views, tucked away in the rolling hills and farmlands of Chilmark, offers sweeping ocean views to the south and a rare sense of seclusion and serenity. At the heart of the property is a striking modern style home, thoughtfully designed to bring the outdoors in. Expansive walls of glass flood the interior with natural light and frame panoramic views

  Meg Bodnar Tea Lane Associates

  44 Cencelle St, Chilmark, MA 02535
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  /20

  $895,000

  • Land
  • 0 Acre

  0 Jeffers Way Unit 73387831, Aquinnah, MA 02535

  This lovely parcel in Aquinnah offers a rare opportunity to own a pristine 3.8 acre parcel on Martha's Vineyard. This elevated, hilly lot is bordered by Classic New England stone walls and surrounded by mature trees, providing both privacy and a serene natural setting. The property is prepared for development, featuring an installed well, a 3-bedroom septic, electric and a completed archeological

  Brenda Galligan Karen M. Overtoom R.E.

  0 Jeffers Way Unit 73387831, Aquinnah, MA 02535
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  /8

  $1,695,000

  • Land
  • 0 Acre

  19A Locust Ln, Aquinnah, MA 02535

  This private 6.19 acres parcel has been approved for sub-division and not yet recorded. Potential to add acreage. Proposed lot lines and designated building envelope. Lovely rolling topography with mature trees. Septic & Well not installed

  Brenda Galligan Karen M. Overtoom R.E.

  19A Locust Ln, Aquinnah, MA 02535
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  /23

  $1,090,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  54 Towanticut Ave, Oak Bluffs, MA 02568

  Living is Easy in this 3-bedroom 2 bath air-conditioned Ranch located 1 mile from the Center of Oak Bluffs. Features include a spacious living room with a wood-burning fireplace and lovely built-ins, an updated kitchen with granite countertops and stainless-steel appliances. The dining area has sliders leading to a spacious deck and outdoor shower overlooking the yard space with plenty of room

  JoJo Lambert Island Home Realty Inc.

  54 Towanticut Ave, Oak Bluffs, MA 02568
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  /62

  $1,895,000

  • 3 Beds
  • 2 Baths
  • 2,462 Sq Ft

  129 Beach Rd, Tisbury, MA 02568

  Unique, waterfront property with amazing, 180 degree views of the lagoon from one side of the property, and the Vineyard Haven Harbor on the north side of the property. Zoned both residential and commercial, rarely does such a unique property become available. Elevated above Beach Road and the lagoon, there are 2 structures on the property. The first, sited on the lagoon with private access, is

  Michele Moore Island Real Estate

  129 Beach Rd, Tisbury, MA 02568
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  /39

  $1,369,000

  • 2 Beds
  • 3 Baths
  • 1,632 Sq Ft

  35 Stevens Ave, Oak Bluffs, MA 02557

  Nestled in a quiet Oak Bluffs neighborhood, this colonial-style home and its surrounding area gives the feel of being up-Island. The well-kept home was built in 2008 and is move-in ready. Located 1 mile to Circuit Avenue, and less than a mile to both the Oak Bluffs School and the Oak Bluffs Library, the property is also conveniently close to a bus stop and the bike path. Its many features include

  Paul Thoutsis Dockside Real Estate

  35 Stevens Ave, Oak Bluffs, MA 02557

Showing Results 121 - 160, Page 4 of 9