Dukes, MA Homes

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  /50

  $3,250,000

  • 4 Beds
  • 3 Baths
  • 2,758 Sq Ft

  382 Lighthouse Rd, Aquinnah, MA 02535

  Spacious contemporary set high off Lighthouse Road with unobstructed, amazing water views of the Vineyard Sound and Elizabeth Islands. Open concept design with soaring ceilings and modern architecture. A retreat for all seasons this house is fully insulated, heated and has central air. A center island in the kitchen ensures the cook of the family does not miss out on the amazing sunsets. Ground

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

  382 Lighthouse Rd, Aquinnah, MA 02535
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  Explore Aquinnah

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  /8

  $3,300 per month

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft
  • House for Rent

  849 State Rd Unit 1, Aquinnah, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Charming three bedroom cottage set on a hill overlooking a tranquil meadow just 1 & 1/2 miles to Aquinnah Cliffs. Enjoy access to both Philbin and Lobsterville beaches. There is a front and back porch with rocking chairs to take in the landscape and enjoy the breeze. This sunny property is easily accessible as well as peaceful and relaxing. Owner is

  Karen Overtoom Karen M. Overtoom R.E.

  849 State Rd Unit 1, Aquinnah, MA 02535
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  /8

  $175,000 Sold Jul 17, 2025

  • Land
  • 1.60 Acres
  • $109,375 per Acre

  • 14 Days On Market

  00 Oxcart Rd, Aquinnah, MA 02535

  Do you love to fish? Beach Lot! Amazing, private, beach on the North Shore. This is a private associate beach and not a buildable parcel. 1/16th ownership. $5,000 membership fee is due at closing

  Sheila Morse Island Real Estate

  00 Oxcart Rd, Aquinnah, MA 02535
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  /58

  Est $7,053,885 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,945 Sq Ft

  394 Lighthouse Rd, Aquinnah, MA 02535

  394 Lighthouse Rd, Aquinnah, MA 02535
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  /26

  $3,500,000

  • 4 Beds
  • 3 Baths
  • 2,686 Sq Ft

  4 Nomans Watch Rd, Aquinnah, MA 02535

  You’ll always feel like you’re on vacation at this four-bedroom, two and one half bath home sited perfectly on 2.4 acres to capture sweeping vistas of the Atlantic Ocean and Noman's Island. Built in 2006, this home features an open living room, dining room and stainless steel kitchen flooded with light from the wall of windows providing wide views to the Atlantic. Enjoy dining on the wrap around

  Russell Maloney Russell Maloney Real Estate

  4 Nomans Watch Rd, Aquinnah, MA 02535
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  /4

  $6,000 per month

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft
  • House for Rent

  836 State Rd, Aquinnah, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Windy Knoll is a 3BR, 2Bath home located in Aquinnah on a secluded lot off State Road with 160 degree views of the Atlantic Ocean. Approximately 1 mile to Philbin Beach similar distance to Moshup Beach and Lobsterville beach. Take the bike ferry over to Menemsha and enjoy sunset on the beach. Outdoor shower with multiple shower heads to wash off the

  Karen Overtoom Karen M. Overtoom R.E.

  836 State Rd, Aquinnah, MA 02535
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  /34

  $4,000,000 Sold Jun 13, 2025

  • 4,000 Sq Ft
  • $1000/SF
  • 238 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 2004

  515 State Rd, Aquinnah, MA 02535

  Set atop a hill overlooking Menemsha, Quitsa and Squibnocket Pond sits this stunning home. A masterful combination of up-island elegance, fine craftsmanship and expert design sets this contemporary apart from other high end homes. Being sold completely turn key, this house was built with the finest of materials and finishes and with entertaining in mind. Large living room with magnificent

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

  515 State Rd, Aquinnah, MA 02535
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  /30

  Est $1,840,649 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,046 Sq Ft

  8 Harpoon Hollow, Aquinnah, MA 02535

  8 Harpoon Hollow, Aquinnah, 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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  /11

  $20,000 per month

  • 4 Beds
  • 4.5 Baths
  • 2,306 Sq Ft
  • House for Rent

  3 E Pasture Ln, Aquinnah, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Breathtaking water views from this contemporary home located on Menemsha Pond and recently renovated with new kitchen and baths. This four bedroom retreat offers the perfect place to come during the summer months or even enjoy during the shoulder season while sitting by the fire with a warm cup of your favorite hot beverage. PLEASE TAKE NOTE!!!!!THIS IS

  Karen Overtoom Karen M. Overtoom R.E.

  3 E Pasture Ln, Aquinnah, MA 02535
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  /39

  $2,750,000 Sold Jun 10, 2025

  • 1,008 Sq Ft
  • $2728/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1953

  25 Oxcart Rd, Aquinnah, MA 02535

  Vineyard Sound waterfront! This is what summer on the Vineyard is all about. Contemporary beach house set in the dunes on 4.6 acres amongst beach plum bushes and windswept beach grass. Open concept interior with a wall of windows facing the Vineyard Sound and Elizabeth Islands. Two guest rooms on the main level and a top floor primary bedroom with deck for star gazing and glorious sunsets. A

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

  25 Oxcart Rd, Aquinnah, MA 02535
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  /41

  Est $2,042,201 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,803 Sq Ft

  7 Tar Barrel Rd, Aquinnah, MA 02535

  7 Tar Barrel Rd, Aquinnah, MA 02535
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  /40

  $3,295,000 Pending

  • 7 Beds
  • 4 Baths
  • 2,992 Sq Ft

  7 Attaquin Way, Aquinnah, MA 02535

  This unique hilltop property is located at the end of a private drive, surrounded by the natural beauty of Aquinnah. It consists of two separate contemporary "Acorn houses," creating airy, light-filled environments and offers views over the expansive, meadow-like lawn that extends toward the ocean. From this vantage point, you can enjoy breathtaking views of the Atlantic Ocean, the Elizabeth

  Heidi Vanderhoop Tea Lane Associates

  7 Attaquin Way, Aquinnah, MA 02535
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  /15

  $5,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,300 Sq Ft
  • House for Rent

  6 Briar Path, Aquinnah, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY. PRICES ARE WEEKLY NOT MONTHLY. Down a private country road, this bright and breezy post and beam home sits on a 3-acre rolling wooded parcel. With southern views of the Atlantic Ocean, it's just a short drive or bike to Philbin and Lobsterville beaches and Gay Head cliffs. This very Vineyard house offers three levels of living space, chef's kitchen, spacious

  Karen Overtoom Karen M. Overtoom R.E.

  6 Briar Path, Aquinnah, MA 02535
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  /11

  $749,000 Sold Apr 14, 2025

  • 240 Sq Ft
  • $3121/SF
  • 0 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1980

  488 Lighthouse Rd, Aquinnah, MA 02535

  This is truly a once-in-a-lifetime opportunity…Step back in time, and away from any stress, into this magical beach shack in the dunes in Aquinnah with deeded walking path to Dog Fish Bar beach. As you follow a boardwalk toward the Sound, hidden away in the coastal brush, you’ll find this sweet little retreat with one cheery open room including kitchen, built-in bed and storage, and a

  Meg Bodnar Tea Lane Associates

  488 Lighthouse Rd, Aquinnah, MA 02535
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  /36

  Est $2,726,553 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft

  4 Sandcastle Ln, Aquinnah, MA 02535

  4 Sandcastle Ln, Aquinnah, MA 02535
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  /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
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  /13

  $15,000 per month

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  19 Lighthouse Road Aq605, Aquinnah, MA 02535

  This family-friendly, three-bedroom retreat on Lighthouse Road in Aquinnah offers all the comforts of home with stunning water views of the Vineyard Sound and the Elizabeth Islands. It is beautifully decorated and nicely furnished. The home features stylish post-and-beam architecture. The main level features cathedral ceilings, wrap-around picture windows and skylights. The main level opens out

  Karen Overtoom Karen M. Overtoom R.E.

  19 Lighthouse Road Aq605, Aquinnah, MA 02535
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  /56

  $3,725,000 Sold Nov 22, 2024

  • 4,875 Sq Ft
  • $764/SF
  • 21 Days On Market

  • 7 Beds
  • 6 Baths
  • Built 1996

  6 Beach Plum Way, Aquinnah, MA 02535

  Waterview compound with an updated, coastal move-in ready main house and a newer oversized guesthouse sited on 4 acres in the heart of Aquinnah. This exceptional property offers a rare package of two houses with a total of 7 bedrooms and 5.5 bathrooms, several decks on all levels for outdoor living and enjoying sunset skies above the meadow-like lawn, large yard with vegetable garden, mature

  Meg Bodnar Tea Lane Associates

  6 Beach Plum Way, Aquinnah, MA 02535
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  /26

  Est $2,389,636 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  437 State Rd, Aquinnah, MA 02535

  437 State Rd, Aquinnah, MA 02535
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  /10

  $350,000

  • Land
  • 0.00 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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  /26

  $18,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • House for Rent

  40 Lighthouse Rd, Aquinnah, MA 02535

  Great water view property in Aquinnah - this immaculate contemporary has that unique combination of a beautifully designed and constructed, year-round home, AND an outstanding view of the Sound and Elizabeth Islands. Not only is the water view property packed with many custom details, but the home's layout is perfect for relaxed living - with a fantastic kitchen open to the dining and living

  Karen Overtoom Karen M. Overtoom R.E.

  40 Lighthouse Rd, Aquinnah, MA 02535
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  /22

  $4,575,000 Sold Nov 19, 2024

  • 2,905 Sq Ft
  • $1575/SF
  • 0 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2001

  1 Skippers View Ln, Aquinnah, MA 02535

  Architect designed post & beam water view home with deeded private beach in Aquinnah. Walk to private beach on Dog Fish Bar for swimming, fishing and beachcombing. Top of the line house with roof deck offering stunning water views, starlit nights and sunsets. Crafted of beautiful mahogany wood, upscale materials and open concept living.

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

  1 Skippers View Ln, Aquinnah, MA 02535
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  /38

  Est $2,777,264 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,719 Sq Ft

  1 Mariners View Ln, Aquinnah, MA 02535

  1 Mariners View Ln, Aquinnah, MA 02535
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  /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
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  /12

  $13,200 per month

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • House for Rent

  8 Lobsterville Rd, Aquinnah, MA 02535

  Uniquely designed, 3-bedroom, 2 full bath contemporary home, divided between three floors and set upon an acre of lush grounds with waterviews overlooking Vineyard Sound and the Elizabeth Islands. Privacy enhanced with large tracts of conservation land nearby and walking distance to Lobsterville Beach.

  Karen Overtoom Karen M. Overtoom R.E.

  8 Lobsterville Rd, Aquinnah, MA 02535
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  /30

  $1,790,000 Sold Oct 18, 2024

  • 1,547 Sq Ft
  • $1157/SF
  • 78 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1969

  446 Lighthouse Rd, Aquinnah, MA 02535

  Located off Lighthouse Road, this sweet seasonal home is a perfect choice for those looking for a true Aquinnah summer experience. Situated amid characteristic Martha's Vineyard oak woodlands, the home features four bedrooms, an open and bright kitchen/living/dining area, and a primary suite on the main level. Three full size sliding glass doors on the northern side of the house provide beautiful

  Heidi Vanderhoop Tea Lane Associates

  446 Lighthouse Rd, Aquinnah, MA 02535
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  /33

  Est $3,617,342 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,288 Sq Ft

  3 Oxcart Rd, Aquinnah, MA 02535

  3 Oxcart Rd, Aquinnah, MA 02535
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  /41

  $1,850,000

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

  1 Harpoon Hollow, Aquinnah, MA 02535

  Custom built Red Oak Post and Beam country home, in the style of an Old English cottage mansion. The many unique and attractive features are sure to delight the most discerning buyer. A brick walk bordered by a lovely boxwood hedge leads to two separate entrances into the home. Throughout, this intriguing, creatively designed home, you will notice the high quality and attention to detail.

  Elaine Vanderhoop Beachcombers of MV

  1 Harpoon Hollow, Aquinnah, MA 02535
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  /23

  $3,175,000 Sold Oct 16, 2024

  • 1,790 Sq Ft
  • $1774/SF
  • 386 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  2 Old Field Rd, Aquinnah, MA 02535

  Located on a rise above Moshup Trail and facing active open ocean lies this manicured 5.64-acre property. Set among ancient, sculptural oaks, gorgeous lush green fields and woods, is an unusually charming 3-bedroom / 1.5-bath home. It features high ceilings, tranquil screened porch, respectful second-floor ocean views, and tons of light from great expanses of glass that bring the outside in. Add

  Gerrett Conover Landvest MV

  2 Old Field Rd, Aquinnah, MA 02535
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  /3

  Not Listed For Sale

  lot 6-2 Moshup Trail, Aquinnah, MA 02535

  lot 6-2 Moshup Trail, Aquinnah, MA 02535
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  /20

  $949,900

  • Land
  • 0.00 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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  /79

  $1,750,000 Sold Oct 10, 2024

  • 3,093 Sq Ft
  • $566/SF
  • 190 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1856

  76 State Rd, Aquinnah, MA 02535

  Sunny and bright describes this sweet home settled off of State Road in Chilmark. Well located near Menemsha Pond, the Chilmark Store and the Chilmark Community Center, this is a great home for summer or year-round living. The original house was built in 1856 and has been added onto creating a south facing kitchen and living space with wrap around windows and tons of natural light. Off the living

  Jill Napior Tea Lane Associates

  76 State Rd, Aquinnah, MA 02535
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  /7

  Not Listed For Sale

  0 Old Field Rd, Aquinnah, MA 02535

  0 Old Field Rd, Aquinnah, MA 02535
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  /8

  $1,695,000

  • Land
  • 0.00 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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  /8

  $929,000 Sold Aug 09, 2024

  • Land
  • 2.76 Acres
  • $336,594 per Acre

  • 4 Days On Market

  7 E Pasture Way, Aquinnah, MA 02535

  In a coveted part of Aquinnah just a few hundred yards from Menemsha Pond, this south facing building site is the perfect canvas for your new custom home. The property is partially cleared to allow you to envision your future home and see the potential for large meadows/pasture as most of the brush is clearable. The private site is ideal for solar and located in an area of high value homes close

  Jim Feiner Feiner Real Estate

  7 E Pasture Way, Aquinnah, MA 02535
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  /3

  Not Listed For Sale

  00 Moshup Trail Unit Lot 6-1, Aquinnah, MA 02535

  00 Moshup Trail Unit Lot 6-1, Aquinnah, MA 02535
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  /24

  $1,275,000

  • Land
  • 2.20 Acres
  • $579,545 per Acre

  0 Old Rd S Unit 58 43410, Aquinnah, MA 02535

  Oceanview parcel ready to build the home you've been dreaming of. Sited on gently sloping, extremely private 2.2 Acres, bordered on 3 sides by ancient stone walls. Second story Atlantic ocean views and the sound of the waves and breezes may be enjoyed all Summer. All systems in place: Title V, 4 BR septic, well with tested potable water and power is installed. Enjoy the unique views and amazing

  Elaine Vanderhoop Beachcombers of MV

  0 Old Rd S Unit 58 43410, Aquinnah, MA 02535
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  /4

  Est $1,481,667 Not Listed For Sale

  759 State Rd, Aquinnah, MA 02535

  759 State Rd, Aquinnah, MA 02535
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  /47

  $2,500,000

  • 3 Beds
  • 3 Baths
  • 1,784 Sq Ft

  12 Lobsterville Rd, Aquinnah, MA 02535

  12 Lobsterville Rd in Aquinnah is a uniquely designed contemporary home set on 2.6 acres of lush grounds with large tracts of conservation land nearby. Open concept living, dining, kitchen on the second floor with unobstructed ocean views of Vineyard Sound. Spacious deck for sunset viewing and grassy lawn for sundown games. Walking distance to Lobsterville Beach and a short bike ride to the

  Tina Palmer Conroy & Company R.E., Inc.

  12 Lobsterville Rd, Aquinnah, MA 02535

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