Gosnold, MA Homes for Sale

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  /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
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  /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
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  /45

  $19,500,000

  • 7 Beds
  • 6 Baths
  • 3,344 Sq Ft

  104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535

  This beautiful 2-parcel compound totals 9.5-acre of land and 600 feet of private Vineyard Sound beach. There is a renovated 4-bedroom beach cottage on one of the parcels which includes all modern amenities and offers spectacular views from almost every room. The second parcel has an older 3-bedroom home located high on a ridge. Both parcels offer wonderful walking paths to the sandy beach below.

  Thomas Leclair Landvest MV

  104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535
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  /23

  $6,000,000

  • 3 Beds
  • 2 Baths
  • 2,710 Sq Ft

  35 S Bowl Rd, Chilmark, MA 02535

  This exceptionally elegant and tranquil home in Seven Gates Farm combines contemporary architectural design with timeless high-end features for Vineyard casual, nature-inspired living. Extraordinary and rare, this move-in ready three-bedroom home with six-bedroom septic system sits on an oversized 5.3-acre parcel in Chilmark. This thoughtful layout has an easy flow, soothing tones with cypress

  Meg Bodnar Tea Lane Associates

  35 S Bowl Rd, Chilmark, MA 02535
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  /39

  $1,669,000

  • 3 Beds
  • 4 Baths
  • 2,308 Sq Ft

  453 Lighthouse Rd, Aquinnah, MA 02535

  Aquinnah Retreat set on a private 1.1-acre lot! This beautiful single-family home was lovingly built and cared for by one family, offering peaceful surroundings and ocean views. Now move-in ready, it's the perfect place for new owners to relax and make it their own. The wrap-around deck provides a scenic spot to enjoy the coastal air. Inside, the kitchen and dining area are filled with natural

  We Close Deals Team Lamacchia Realty, Inc.

  453 Lighthouse Rd, Aquinnah, MA 02535
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  /41

  $1,299,999

  • 4 Beds
  • 4.5 Baths
  • 3,586 Sq Ft

  16 Wadsworth Ln, South Dartmouth, MA 02748

  WELCOME TO 16 WADSWORTH LN, where privacy, elegance, and coastal charm meet. Set high on 1.76 acres abutting conservation land with nearby access to the Slocum River, this custom-built estate offers over 3,500 sq ft of thoughtfully designed living space. The sunken living room with fireplace and rich maple and Brazilian cherry wood accents sets the tone for timeless comfort. The chef’s kitchen

  David Castro Coldwell Banker Realty - Easton

  16 Wadsworth Ln, South Dartmouth, MA 02748
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  /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
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  /29

  $1,725,000

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft

  654 Lighthouse Rd, Aquinnah, MA 02535

  Waterview beach house in Aquinnah. Just a short deeded walking path to the calm and sandy shores of the North Shore. The traditional layout features the kitchen, living room, dining room, and a full bath on the first floor. The living room offers water views, a cozy fireplace, and multiple sliding doors leading out to the wrap-around porch. Upstairs, the views are even more stunning!

  Heidi Vanderhoop Tea Lane Associates

  654 Lighthouse Rd, Aquinnah, MA 02535
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  /36

  $2,250,000

  • 3 Beds
  • 4 Baths
  • 4,894 Sq Ft

  22 Hetty Green St, Dartmouth, MA 02748

  Striking single-family contemporary colonial in the highly desirable gated community of Round Hill. A grand foyer with soaring cathedral ceilings welcomes you upon entering this meticulous residence. Spacious eat-in kitchen opens to the family room with slider to the deck, overlooking the nearly one acre lot and Trent Jones inspired golf course beyond. The first-floor primary suite features a

  Liza Danforth Milbury and Company

  22 Hetty Green St, Dartmouth, MA 02748
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  /13

  $2,650,000

  • 4 Beds
  • 3 Baths
  • 2,299 Sq Ft

  26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575

  Discover the rare opportunity to build your dream home in one of the island’s most sought-after locations off Lamberts Cove Road. This parcel offers year-round waterfront living with the ultimate blend of privacy, beach access, and design potential, without the usual coastal erosion concerns. Approved architectural plans by Moskow Linn Architects are in place for a four-bedroom main residence, a

  Jill Napior Tea Lane Associates

  26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575
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  /30

  $1,695,000

  • 3 Beds
  • 2 Baths
  • 1,986 Sq Ft

  251 State Rd, Vineyard Haven, MA 02568

  This private and pastoral year-round home with fine craftsmanship and loads of character is a classic up-island refuge, yet in a location that is central on the island and convenient to town. Abutting Land Bank property, the charming home features an open living and dining room with wide plank floors and beams flowing into the kitchen, all surrounding a central brick fireplace. An expansive

  Meg Bodnar Tea Lane Associates

  251 State Rd, Vineyard Haven, MA 02568
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  /42

  $7,450,000

  • 5 Beds
  • 3 Baths
  • 2,269 Sq Ft

  34 Edys Island Way, Chilmark, MA 02535

  Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by anIsland legacy family, this property is unique among Island estates for its combination of privacy yet convenience and seclusion yet expansive views. To the

  Jill Napior Tea Lane Associates

  34 Edys Island Way, Chilmark, MA 02535
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  /15

  $14,995,000

  • 7 Beds
  • 11 Baths
  • 8,765 Sq Ft

  1 Mattarest Ln, South Dartmouth, MA 02748

  This sensational oceanfront estate is located in the coveted, gated beachfront community of Nonquitt. The 7+ bed Main House boasts breathtaking water views through expansive walls of glass, while the guest and pool houses are seamlessly integrated to create a one-of-a-kind coastal retreat. Light-filled living and dining spaces are designed for effortless indoor-outdoor living and entertaining,

  Maggie Gold Seelig MGS Group Real Estate LTD

  1 Mattarest Ln, South Dartmouth, MA 02748
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  /41

  $1,200,000

  • 3 Beds
  • 3.5 Baths
  • 3,100 Sq Ft

  61 Pardon Hill Rd, South Dartmouth, MA 02748

  Nestled in the heart of South Dartmouth, where rolling hills meet timeworn stone walls and the ocean whispers nearby, awaits a truly exceptional New England estate. Offering a rare sense of privacy and connection to the land, this unique property presents a remarkable lifestyle opportunity. The centerpiece is a custom-built Lindel Cedar Home, a post-and-beam masterpiece that seamlessly integrates

  Bernadette Kelly Bernadette Kelly Group

  61 Pardon Hill Rd, South Dartmouth, MA 02748
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  /37

  $4,850,000

  • 5 Beds
  • 3 Baths
  • 3,440 Sq Ft

  146 Quansoo Rd, Chilmark, MA 02535

  Nestled along the beautiful and tranquil shoreline of Tisbury Great Pond and surrounded by a stunning natural environment of water, sand and sky, this is an unparallelled beach house experience on the south shore of Chilmark. The five-bedroom home consists of a three-bedroom main house connected by walkways to a two-bedroom guest wing with studio space above, all with spectacular water views

  Meg Bodnar Tea Lane Associates

  146 Quansoo Rd, Chilmark, MA 02535
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  /16

  $1,325,000

  • Land
  • 4.40 Acres
  • $301,136 per Acre

  37 Bijah's Way, Chilmark, MA 02535

  This quiet and lovely four-and-a-half-acre lot in Chilmark is set on a gentle rise, bounded on one side by an old stone wall. The land features graceful trees and a distant water view is possible from a second floor. The lot has been staked, including a proposed home site at the highest elevation. There are so many outstanding possibilities for a future Buyer to build their dream home on this

  Elissa Lash Tea Lane Associates

  37 Bijah's Way, Chilmark, MA 02535
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  /60

  $14,000,000

  • 6 Beds
  • 7 Baths
  • 6,967 Sq Ft

  8 Snail Rd, Chilmark, MA 02535

  This exceptional Martha's Vineyard estate promises unmatched privacy and breathtaking views of the Atlantic Ocean and Chilmark Pond. Masterfully designed by acclaimed architect Rick Sundberg and built by renowned island builder Andrew Flake, this three-parcel property seamlessly blends modern sophistication with the timeless charm of the Vineyard. Upon entering, you are greeted by soaring

  Alyssa Halisky Wallace & Co. Sotheby's

  8 Snail Rd, Chilmark, MA 02535
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  /48

  $1,875,000

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  3 Fulling Mill Rd, Chilmark, MA 02535

  Tucked away in a prime location just off Middle Road is this bright modern home offering the perfect blend of comfort and style. The main level features a large bedroom or first-floor office and a full bath, while the upper floor boasts two additional bedrooms and a beautifully appointed bathroom with a steam shower and double vanity. The open concept living and dining areas flow effortlessly

  Jill Napior Tea Lane Associates

  3 Fulling Mill Rd, Chilmark, MA 02535
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  /31

  $2,450,000

  • 4 Beds
  • 3 Baths
  • 1,918 Sq Ft

  25 Fulling Mill Rd, Chilmark, MA 02535

  Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to

  Thomas Wallace Wallace & Co. Sotheby's International Realty

  25 Fulling Mill Rd, Chilmark, MA 02535
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  /94

  $4,395,000

  • 3 Beds
  • 5 Baths
  • 3,314 Sq Ft

  20 Edson Forest Rd, Vineyard Haven, MA 02568

  Exquisite home befitting its stunning location on four serene acres surrounded by conservation and agricultural lands and overlooking a neighbor's private pond. This special spot is authentic up-island character at its best. This three bedroom home (with six-bedroom septic system) was fully renovated down to the studs and finished in 2022, resulting in a truly beautiful luxury home with a

  Meg Bodnar Tea Lane Associates

  20 Edson Forest Rd, Vineyard Haven, MA 02568
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  /44

  $8,995,000

  • 5 Beds
  • 7 Baths
  • 3,762 Sq Ft

  85 Reservoir Rd, Vineyard Haven, MA 02568

  Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  85 Reservoir Rd, Vineyard Haven, MA 02568
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  /42

  $2,399,000

  • 4 Beds
  • 4.5 Baths
  • 4,572 Sq Ft

  180 Rock O'Dundee Rd, Dartmouth, MA 02748

  South Dartmouth-This Extraordinary Williamsburg-inspired cape is nestled on 3 acres of an enchanting home site, framed by a picturesque spring fed pond. A peaceful retreat, accessed through a private community, this property is surrounded by natural beauty & tranquility, yet within minutes to Round Hill Beach and Padanaram Village. This Iconic home was designed w/symmetry & balance in mind,

  Fatima Simas Anne Whiting Real Estate

  180 Rock O'Dundee Rd, Dartmouth, MA 02748
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  /27

  $2,380,000

  • 3 Beds
  • 4.5 Baths
  • 4,299 Sq Ft

  533 Woods Hole Rd Unit B102, Falmouth, MA 2543

  Walk to Woods Hole Village - New Construction Luxury Townhome with Views of Vineyard Sound. Welcome home to Lighthouse Station at Woods Hole, a 55+ community perched on 5.3 acres overlooking Little Harbor & Vineyard Sound. Enjoy a true residential feel in this spacious, 2550 SF + 1748 SF finished basement unit. With 3 ensuite bedrooms, a home office, 2 separate living areas and double laundry

  Mark Bogosian Waterside Real Estate LLC

  533 Woods Hole Rd Unit B102, Falmouth, MA 2543
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  /2

  $439,000

  • Land
  • 1.88 Acres
  • $233,511 per Acre

  Lot 1 Rafael Rd, Dartmouth, MA 02748

  Welcome to South Dartmouth's newest premier subdivision "Bakerville Vineyards". ONLY TWO REMAINING LOTS!!!! The road is being paved within two weeks. It is a little over one mile to Padanaram Village and will consist of seven lots that are all approximately 2 acres each in size. Very close to Demarest Lloyd State Park and Round Hill Beach. The subdivision will be one road with a cul-de-sac

  Jeffrey Hathaway Seaport Realty

  Lot 1 Rafael Rd, Dartmouth, MA 02748
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  /59

  $2,550,000

  • 4 Beds
  • 3 Baths
  • 2,983 Sq Ft

  157 Ben Chase Rd, West Tisbury, MA 02575

  You will find this outstanding property at the end of a quiet country lane in West Tisbury nestled alongside hundreds of acres of conservation land and walking trails that extend all the way to Lamberts Cove Road. The setting is magical - 4 acres of rolling lawns with specimen trees and ponds. There are multiple structures to allow you to customize this compound to your personal needs. The main

  Madelyn Silvia Wallace & Co. Sotheby's

  157 Ben Chase Rd, West Tisbury, MA 02575
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  /23

  $1,625,000

  • 5 Beds
  • 5 Baths
  • 2,316 Sq Ft

  345 North Rd, Chilmark, MA 02535

  Abutting hundreds of acres of conservation land and walking trails leading to the second-highest point on Martha's Vineyard with views of the Elizabeth Islands, this classically-styled house with detached guest quarters offers 5 total bedrooms and 4 full baths plus an outdoor shower. The primary bedroom suite is a generous size and has its own small deck that overlooks the charming front yard.

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  345 North Rd, Chilmark, MA 02535
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  /7

  $2,500,000

  • Land
  • 1.40 Acres
  • $1,785,714 per Acre

  2 Other House Rd, Chilmark, MA 02535

  Rare opportunity to build on Chilmark's south shore. This 1.4 acre parcel should allow for new construction of 3,100 square feet and 24 feet in height, by right, with building department approval. Views to the Atlantic Ocean and Chilmark Pond can be seen from the second floor. This parcel comes with a dock on the pond which provides access to a beautiful barrier beach on the Atlantic. Well in

  Russell Maloney Russell Maloney Real Estate

  2 Other House Rd, Chilmark, MA 02535
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  /31

  $3,950,000

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft

  29 Oxcart Rd, Aquinnah, MA 02535

  Waterfront beach house on Dogfish Bar in Aquinnah. Take in the beauty of this gem of a location with rolling dunes, waterviews and immense sunsets! This property is one of only a few homes on this stretch of private and preserved beach. This 2009 contemporary beach house offers a reverse floor plan with the entire top floor as the living area, kitchen & dining, and more windows than walls to

  Michelle Kelly Tea Lane Associates

  29 Oxcart Rd, Aquinnah, MA 02535
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  /42

  $3,950,000

  • 5 Beds
  • 7 Baths
  • 7,561 Sq Ft

  1069 Horseneck Rd, Westport, MA 02790

  A mint condition 5 bedroom home on 16+ acres in sought after South Westport on a private road. This 7,500 sq. ft. residence was created in the 1980s with large spacious rooms over steel framing designed to withstand nor’easters and hurricanes. The 1st floor hosts a large, versatile airy living room with fireplace, dining room with a fireplace, den/entertainment center, a fully equipped eat-in

  Freeman 'Mike' Hill Coldwell Banker Realty - Marion

  1069 Horseneck Rd, Westport, MA 02790
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  /13

  $975,000

  • Land
  • 3.73 Acres
  • $261,394 per Acre

  25 N Vine Ln Unit 70.3, West Tisbury, MA 02568

  Exceptional opportunity in West Tisbury! This 3.73-acre parcel offers peace and privacy on a quiet dead-end road, moments from Sepiessa, Tiah’s Cove, and Long Point beaches. With potential for up to 10+ bedrooms (1 per 10,000 SF), the property is a blank canvas for your dream Vineyard compound—main house, guest house, barn, garage, and more with proper permits. Pool/pool house possible by special

  Janna O'Loughlin Portfolio Real Estate, Inc.

  25 N Vine Ln Unit 70.3, West Tisbury, MA 02568
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  /14

  $975,000

  • Land
  • 3.83 Acres
  • $254,569 per Acre

  25 N Vine Ln, West Tisbury, MA 02568

  Exceptional opportunity in West Tisbury! This 3.73-acre parcel offers peace and privacy on a quiet dead-end road, moments from Sepiessa, Tiah's Cove, and Long Point beaches. With potential for up to 16 bedrooms (1 per 10,000 SF), the property is a blank canvas for your dream Vineyard compound--main house, guest house, barn, garage, and more with proper permits. Pool/pool house possible by special

  Janna O'Loughlin Portfolio Properties

  25 N Vine Ln, West Tisbury, MA 02568
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  /33

  $349,000

  • Land
  • 0.27 Acre
  • $1,292,593 per Acre

  238-242 E Beach Rd, Westport, MA 02790

  2 private Waterfront Lots by the ocean side by side on East Beach. Best place for morning sunrises and awesome views of Buzzards Bay, the Elizabeth Islands and Cuttyhunk. Sale includes a 2003 Breckenridge Park Model that sleeps 12 ! Electric on site. Includes a Shed. Close to Gooseberry Island's public boat ramp and walking path loop, also across from the walking trail on Horseneck Beach. Here is

  Michael Amaral Amaral & Associates RE

  238-242 E Beach Rd, Westport, MA 02790
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  /8

  $1,425,000

  • Land
  • 3.01 Acres
  • $473,422 per Acre

  38 Fire Tower Rd, West Tisbury, MA 02568

  The Tower Hill land, once known as the Dancing Hills, is considered by many a sacred Island space. Standing on the ridge top, you're at one of the highest points on Martha's Vineyard. This 3.01 acre parcel looks out over the trees of Red Farm and the dramatic blue expanse of Vineyard Sound. It's easy to understand why this property is so special. There's a generous designated building envelope of

  Elissa Lash Tea Lane Associates

  38 Fire Tower Rd, West Tisbury, MA 02568
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  /26

  $1,345,000

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft

  9 Galway Rd, Vineyard Haven, MA 02568

  Tucked away off Old County Road in West Tisbury, this 3 bedroom 1 bath cape home has been owned by the same family for years. Sitting on 1.6 acres in a quiet area that is centrally located on the Island for easy access to up or down Island towns. Short walk to bike path and state forest. West Tisbury residents have access to the lovely Lambert's Cove Beach, with purchased sticker. Included on

  Julianna Flanders Flanders Real Estate

  9 Galway Rd, Vineyard Haven, MA 02568
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  /15

  $1,895,000

  • Land
  • 3.01 Acres
  • $629,568 per Acre

  11 Beach Pebble Rd Unit 48.3, West Tisbury, MA 02568

  Over 3 acres in the West Tisbury section of Makonikey. This buildable lot is a short distance from the Lower Makonikey Association beach. The prime home site on this property was recently cleared to reveal beautifully contoured land with several ancient white oak trees. The property is situated in an area of several multimillion-dollar homes and will accommodate a house, a guesthouse, and a

  Cassie Courtney Wallace & Co. Sotheby's

  11 Beach Pebble Rd Unit 48.3, West Tisbury, MA 02568
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  /9

  $1,895,000

  • Land
  • 3.01 Acres
  • $629,568 per Acre

  11 Beach Pebble Rd, West Tisbury, MA 02568

  Over 3 acres in the West Tisbury section of Makonikey. This buildable lot is a short distance from the Lower Makonikey Association beach. The prime home site on this property was recently cleared to reveal beautifully contoured land with several ancient white oak trees. The property is situated in an area of several multimillion-dollar homes and will accommodate a house, a guesthouse, and a

  Cassie Bradley Wallace & Co. Sotheby's International Realty

  11 Beach Pebble Rd, West Tisbury, MA 02568
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  /65

  $2,690,000

  • 6 Beds
  • 4 Baths
  • 2,618 Sq Ft

  55 Old House Way, West Tisbury, MA 02575

  Lambert’s Cove/West Tisbury- custom-built contemporary farmhouse style . 4 bedrooms & 3 bathrooms in main house & 2 bedrooms & 1 bath guest cottage on 3 acres in a private neighborhood. Enter Main house from the covered porch -matching custom arch doors lead you to either the mudroom/laundry room-kitchen entry, or the living room. The kitchen has Mexican tiled floor & granite counters with

  Leslie Graham Anchor Realty of Martha's Vineyard

  55 Old House Way, West Tisbury, MA 02575
• 

  /2

  $995,000

  • Land
  • 3.05 Acres
  • $326,230 per Acre

  00 Quenames Rd, Chilmark, MA 02535

  Handsome, large level parcel of land in Chilmark! Bounds are in, lot lines are flagged and brush cut, as well as a bit of the lot interior so that you can appreciate the size and orientation of the parcel. 6-Bedroom septic design has been approved and well will be installed soon. Quenames Road is off South Road, a short hop to West Tisbury village center with Alley's General Store, the Town's

  Candy DaRosa Feiner Real Estate

  00 Quenames Rd, Chilmark, MA 02535
• 

  /2

  $799,000

  • Land
  • 0.92 Acre
  • $868,478 per Acre

  22 Bramble Path, West Tisbury, MA 02568

  Flat building lot centrally located in West Tisbury. It is the Buyer's responsibility to conduct a perc test and install utilities, well and septic.

  Michele Casavant Vineyard Village Realty

  22 Bramble Path, West Tisbury, MA 02568
• 

  

  /13

  $1,325,000 New Construction

  • 2 Beds
  • 2.5 Baths
  • 1,466 Sq Ft

  533 Woods Hole Rd Unit E202, Falmouth, MA 2543

  Walk to Woods Hole Village - Construction Pricing! Luxury Townhome within walking distance to Woods Hole Village - Ready Late 2025. Welcome home to Lighthouse Station at Woods Hole, a 55+ community perched on 5.3 acres overlooking Little Harbor & Vineyard Sound. Enjoy this lovely, 1466+ SF 2 bedroom/2.5 bath one-level unit on the 2nd story overlooking a quiet, wooded neighborhood. This unit

  Mark Bogosian Waterside Real Estate LLC

  533 Woods Hole Rd Unit E202, Falmouth, MA 2543

Showing Results 41 - 80, Page 2 of 3