Dukes, MA Homes

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  /42

  $2,675,000

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

  128 W Spring St, Vineyard Haven, MA 02568

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

  David Dickinson Compass

  128 W Spring St, Vineyard Haven, MA 02568
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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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  /47

  $1,595,500 Sold Jun 23, 2025

  • 1,822 Sq Ft
  • $876/SF
  • 73 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2003

  21 Coffins Field Rd, Edgartown, MA 02539

  EDGARTOWN SOUTH SHORE BEACH HOUSE. Imagine a countryside abode with nearby access to a pristine south shore stretch of beach and less than 6 miles to Edgartown Village and Harbor. Architect-designed as a low-key getaway, this delightful five bedroom year-round home has three full bathrooms plus a freestanding outdoor shower, decks, screened-in porch and is comfortably sited in an established well

  Helena Kirschenbaum Studio Realty

  21 Coffins Field Rd, Edgartown, MA 02539
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  /14

  Est $2,704,037 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,926 Sq Ft

  30 Pond Ln, Vineyard Haven, MA 02568

  30 Pond Ln, Vineyard Haven, MA 02568
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  /36

  $3,250,000

  • 4 Beds
  • 4 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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  /42

  $19,000 per month

  • 6 Beds
  • 6.5 Baths
  • 6,950 Sq Ft
  • House for Rent

  40 Sweet William Way, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the

  Karen Overtoom Karen M. Overtoom R.E.

  40 Sweet William Way, West Tisbury, MA 02575
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  /25

  $949,000 Sold Jun 23, 2025

  • 1,012 Sq Ft
  • $938/SF
  • 49 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1986

  345 Franklin St, Vineyard Haven, MA 02568

  Charming Cape-style home in Vineyard Haven, ideally located just minutes from Downtown and Owen Little Beach. This well-maintained property sits on a 0.26-acre lot, offering a private back deck, a spacious yard, and an outdoor shower perfect for after beach days. The home boasts 3 bedrooms and 1.5 bathrooms, with a thoughtful layout that includes a bedroom on the first floor and two on the

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  345 Franklin St, Vineyard Haven, MA 02568
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  /36

  Est $1,288,385 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft

  16 Rock Pond Rd, Vineyard Haven, MA 02568

  16 Rock Pond Rd, Vineyard Haven, MA 02568
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  /27

  $2,500,000

  • 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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  /27

  $18,840 per month

  • 3 Beds
  • 2.5 Baths
  • House for Rent

  21 William St Vh430, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,710. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely elegant home with wonderful art and furnishings. Once you step in the front door you will fall in love with this lovely home. Each room is a delight. Large nicely appointed kitchen with easy access to a beautiful dining room. A formal living room is next to a less

  Karen Overtoom Karen M. Overtoom R.E.

  21 William St Vh430, Tisbury, MA 02568
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  /56

  $1,699,000 Sold Jun 20, 2025

  • 2,954 Sq Ft
  • $575/SF
  • 314 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1900

  9 Goode St, Oak Bluffs, MA 02557

  Welcome to your dream home, located on a very quiet street in Oak Bluffs, yet just a short walk to downtown & the elementary school. This prime location offers the perfect blend of serenity and convenience. This well appointed home features 4 bedrooms and 4.5 bathrooms. Included in this is a 1-bedroom, 1-bathroom apartment attached to the home, providing a perfect space for guest accommodation.

  Grace Hagerty Grace Hagerty Real Estate Inc

  9 Goode St, Oak Bluffs, MA 02557
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  /40

  Est $1,844,798 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1 Sq Ft

  179 Main St, Vineyard Haven, MA 02568

  179 Main St, Vineyard Haven, MA 02568
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  /46

  $2,495,000

  • 5 Beds
  • 4 Baths
  • 3,873 Sq Ft

  50 Hidden Cove Rd, Edgartown, MA 02539

  Sengekontacket–Walk into a “turn-key” opportunity in the desirable Hidden Cove community, just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering an abundance of natural light that flows into the open living and entertaining spaces. The

  Sean Federowicz Landmarks at TODAY Real Estate

  50 Hidden Cove Rd, Edgartown, MA 02539
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  /25

  $10,800 per month

  • 2 Beds
  • 4 Baths
  • 1,800 Sq Ft
  • House for Rent

  256 Sandpiper Lane Vh417, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This well appointed condo will make you feel comfortable and at home the moment you walk in. Swimming, kayaking, tennis, walking trails, and shopping are all at your finger tips. Mink Meadows Golf Course is just a stroll down the street as well. Enjoy all the Island has

  Karen Overtoom Karen M. Overtoom R.E.

  256 Sandpiper Lane Vh417, Tisbury, MA 02568
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  /17

  $700,000 Sold Jun 20, 2025

  • 725 Sq Ft
  • $966/SF
  • 111 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1870

  2 Fisk Ave, Oak Bluffs, MA 02557

  Gingerbread Cottage full of character and personality! Part of Martha's Vineyard Camp Meeting Association, this Oak Bluffs seasonal antique with beautiful trim and scrollwork sits on a lovely little avenue. The cottage features charming period details, a covered front porch with rocking chairs & upper balcony. Step inside the unique front door into a cozy living room enhanced by beamed ceiling,

  Julie Walker Century 21 North East

  2 Fisk Ave, Oak Bluffs, MA 02557
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  /23

  Est $2,154,681 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,704 Sq Ft

  31 Pulpit Ln, Edgartown, MA 02539

  31 Pulpit Ln, Edgartown, MA 02539
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  /39

  $2,900,000

  • 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; Bobbi Flake Reed, Inc.

  21 Woodlawn Ave, Vineyard Haven, MA 02568
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  /18

  $10,000 per month

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft
  • House for Rent

  100 Franklin Terrace Vh411, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming 3 bedroom home offers open living, dining and kitchen space that open to a screened-in porch and patio. You are located in a peaceful setting yet with-in walking distance to Lake Tashmoo, town beaches, and the Vineyard Haven Village for dining, shopping and

  Karen Overtoom Karen M. Overtoom R.E.

  100 Franklin Terrace Vh411, Tisbury, MA 02568
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  /6

  $430,000 Sold Jun 18, 2025

  • Land
  • 1.40 Acres
  • $307,143 per Acre

  • 0 Days On Market

  0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535

  Not listed in LINK.

  LINK Email Cache LINK

  0 Quansoo Beach Lot Unit 48 43485, Chilmark, MA 02535
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  /48

  Est $2,960,910 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 3,440 Sq Ft

  8 Coffins Field Rd, Edgartown, MA 02539

  8 Coffins Field Rd, Edgartown, MA 02539
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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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  /28

  $32,000 per month

  • 4 Beds
  • 4 Baths
  • 3,200 Sq Ft
  • House for Rent

  37 Mempremagog Ave Vh410, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in

  Karen Overtoom Karen M. Overtoom R.E.

  37 Mempremagog Ave Vh410, Tisbury, MA 02568
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  /30

  $1,525,000 Sold Jun 18, 2025

  • 2,016 Sq Ft
  • $756/SF
  • 110 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1967

  54 Lake St, Vineyard Haven, MA 02568

  Welcome to this delightful 4-bedroom, 3-bathroom home, perfectly situated in a highly desirable location where convenience meets tranquility. Just a short stroll from town, restaurants, Tashmoo Landing, and tennis courts, this property offers the ideal combination of lifestyle and leisure.Step onto the covered front porch and into a warm, inviting space featuring two living rooms—one on each

  Jon Hartzband Martha's Vineyard Island-Wide Realty

  54 Lake St, Vineyard Haven, MA 02568
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  /49

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,092 Sq Ft

  670 State Rd, Vineyard Haven, MA 02568

  670 State Rd, Vineyard Haven, MA 02568
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  /35

  $2,495,000

  • 4 Beds
  • 3 Baths
  • 2,968 Sq Ft

  9 Beetlebung Grove Way, Chilmark, MA 02535

  Beautifully sited on 3.4 acres, this distinctive Chilmark home offers a rare blend of privacy, comfort, and expansive living space, ideal for entertaining, both inside and outside. From the welcoming foyer, step into the dramatic vaulted living room, where wood-paneled ceilings, a gas fireplace, and abundant natural light from skylights and picture windows create a warm and inviting atmosphere.

  Stephanie Roache Donnelly + Co.

  9 Beetlebung Grove Way, Chilmark, MA 02535
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  /15

  $7,500 per month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  83 Ashtons Way, Vineyard Haven, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $1,875. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This two bedroom cottage is set in a private setting in the woods, just a short distance to downtown Vineyard Haven. Sleeps four comfortably, open living space, deck and outside shower. If rented with the main house, access to private association beach and golf would be

  Karen Overtoom Karen M. Overtoom R.E.

  83 Ashtons Way, Vineyard Haven, MA 02568
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  /20

  $821,000 Sold Jun 17, 2025

  • Land
  • 1.40 Acres
  • $586,429 per Acre

  • 0 Days On Market

  168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568

  Large 1.4 Acre Corner lot in Vineyard Meadow Farms South side of West Tisbury Road. Private, flat, level parcel, paved dead end road with no unnecessary through traffic. Six bedrooms, a 3,000SF Main House, a 2,000SF detached/attached Secondary Building allowed per the Town. Pool allowed with standard Special permit. Centrally located to all Island Towns. Great neighborhood. Great location with

  Janna O'Loughlin Portfolio Real Estate, Inc.

  168 Charles Neck Way Unit 49, Vineyard Haven, MA 02568
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  /35

  Est $1,246,812 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,368 Sq Ft

  29 Dunham Ave, Vineyard Haven, MA 02568

  29 Dunham Ave, Vineyard Haven, MA 02568
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  /41

  $2,950,000

  • 4 Beds
  • 3 Baths
  • 2,424 Sq Ft

  19 Old Woods Rd, Chilmark, MA 02535

  Tucked away in the heart of Chilmark, this nearly 3-acre property blends rustic Vineyard charm with unique creative potential. Chilmark was a very special place for the former owner, American artist Thomas Hart Benton, who summered on the Island for 50 years. Professor and Art Historian, Erika Doss, said “the years he spent in Chilmark honed the artistic style and subjects that led to his

  Cheri Mason Landvest MV

  19 Old Woods Rd, Chilmark, MA 02535
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  /3

  $13,200 per month

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • House for Rent

  224 N Rd Ch248, Chilmark, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room.

  Karen Overtoom Karen M. Overtoom R.E.

  224 N Rd Ch248, Chilmark, MA 02535
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  /18

  $1,219,000 Sold Jun 16, 2025

  • 1,512 Sq Ft
  • $806/SF
  • 99 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1986

  108 Charles Neck Way, Vineyard Haven, MA 02568

  This charming reverse-style home is ideally located near Long Point Beach and offers a perfect blend of comfort and functionality for year-round living or seasonal getaways. The first floor features three spacious bedrooms, a full bath, and a convenient laundry room. On the second floor, you'll find soaring cathedral ceilings and an open-concept living area, complete with a cozy living room,

  Alyssa Halisky Wallace & Co. Sotheby's

  108 Charles Neck Way, Vineyard Haven, MA 02568
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  /75

  Est $4,011,141 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,362 Sq Ft

  4 Tilton Rd, Chilmark, MA 02535

  4 Tilton Rd, Chilmark, MA 02535
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  /35

  $2,850,000

  • 4 Beds
  • 3 Baths
  • 2,967 Sq Ft

  11 By the Woods, Chilmark, MA 02535

  Dreamlike Chilmark retreat on 4.5+/- acres overlooking the Chilmark Pond & Atlantic Ocean beyond. Uniquely designed with European and medieval history in mind. The House has 3 bedrooms, 3 bathrooms, an atrium dining area, a two-story library, a kitchen, and a pantry/wet bar. Charming garden and plantings surround the home.A must-see to appreciate all the special touches throughout the Main House,

  Julianna Flanders Flanders Real Estate

  11 By the Woods, Chilmark, MA 02535
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  /40

  $32,500 per month

  • 6 Beds
  • 4.5 Baths
  • 3,222 Sq Ft
  • House for Rent

  100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

  Karen Overtoom Karen M. Overtoom R.E.

  100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568
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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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  Est $5,460,636 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,740 Sq Ft

  12 Plantingfield Wood Cir, Edgartown, MA 02539

  12 Plantingfield Wood Cir, Edgartown, MA 02539
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  /29

  $2,275,000

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft

  9 Moshup Trail, Aquinnah, MA 02535

  Spectacular property in Aquinnah, featuring a newly installed and town-approved 6-bedroom septic system, ready to support your vision for expansion and renovation.Located on 4.7 acres filled with rolling meadows and stone walls, this property boasts a truly remarkable barn that was transported from Maine, and rebuilt on the Island. The grandfathered-in barn spans approximately 61' by 45' with

  Patrick McCarthy Grace Hagerty Real Estate Inc

  9 Moshup Trail, Aquinnah, MA 02535
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  /17

  $12,000 per month

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • House for Rent

  223 Sandpiper Lane Vh405, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three bedroom two bath condo is just a short walk to association tennis, pool and the beach. Comfortable easy summer living with outdoor shower, spacious deck, and central AC for those really hot August days!Amenities include Direct TV DVD set up. There is an open

  Karen Overtoom Karen M. Overtoom R.E.

  223 Sandpiper Lane Vh405, Tisbury, MA 02568
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  /20

  $1,150,000 Sold Jun 13, 2025

  • 1,374 Sq Ft
  • $837/SF
  • 43 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  46 Old Coach Rd, Vineyard Haven, MA 02568

  Charming and Spacious 3-Bedroom Cape with large Loft and Deck Welcome to your dream West Tisbury home! This comfortable and spacious 3-bedroom, 2-bath Cape boasts a thoughtfully designed floor plan perfect for comfortable living. The first-floor features two bedrooms and a full bath, ideal for use as sleeping quarters or a home office. Moving to the second floor, discover privacy with a third

  Lisa Gilberto C McManus Realty Group

  46 Old Coach Rd, Vineyard Haven, MA 02568
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  /27

  Est $1,373,100 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,228 Sq Ft

  24 Alyssa Ln, Vineyard Haven, MA 02568

  24 Alyssa Ln, Vineyard Haven, MA 02568

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