Dukes, MA Homes

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  /40

  $2,495,000 Pending

  • 5 Beds
  • 5 Baths
  • 3,213 Sq Ft

  174 Tashmoo Ave, Vineyard Haven, MA 02568

  Welcome to your dream home! The perfect blend of comfort and luxury awaits you in this custom-designed 5-bedroom, 4.5-bathroom residence. Over 3200 square feet of spacious living, upscale furnishings, finished basement with entertainment bar, and all the right touches to make every day feel like a retreat. Conveniently located under a half mile from downtown Vineyard Haven, where you will find

  

  Lisa Lucier

  Anchor Realty of Martha's Vineyard

  (508) 901-2347

  174 Tashmoo Ave, Vineyard Haven, MA 02568
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  /8

  $17,500 per month

  • 8 Beds
  • 4.5 Baths
  • 3,876 Sq Ft
  • House for Rent

  550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!!!!!! Classic vineyard cottage with large open indoor and outdoor spaces to choose from while you and your family create memories to last a lifetime. Enjoy creating appetizers or three course meals in the newly renovated kitchen, bask in the light filled sun room or one of several covered porches while you take in the smell of fresh ocean air and

  Karen Overtoom Karen M. Overtoom R.E.

  550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568
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  /2

  $1,595,000 Sold Jul 01, 2025

  • 1,176 Sq Ft
  • $1356/SF

  • 2 Beds
  • 2 Baths
  • Built 1998

  10 Red Pony Rd, West Tisbury, MA 02568

  Pastoral and perfect. Room to grow or just move in.

  Lisa Da silva Compass | Point B

  10 Red Pony Rd, West Tisbury, MA 02568
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  /25

  Est $2,093,611 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,636 Sq Ft

  131 Shubael Weeks Path, Vineyard Haven, MA 02568

  131 Shubael Weeks Path, Vineyard Haven, MA 02568
• 

  

  

  /20

  $929,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,286 Sq Ft

  299 Franklin St, Vineyard Haven, MA 02568

  Walkable to downtown Vineyard Haven, offering shops, dining, and waterfront access. Close to everything, yet tucked away on a peaceful corner lot is this classic 3-bedroom, 1.5-bathroom ranch home. The possibilities abound on a spacious .27-acre level yard where you can add more bedrooms and an ADU. The extra long detached 2-car garage with high ceilings is a great spot to store your vehicles

  

  Lisa Lucier

  Anchor Realty of Martha's Vineyard

  (508) 876-3522

  299 Franklin St, Vineyard Haven, MA 02568
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  /8

  $6,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • House for Rent

  33 Kennebago Ave Vh414, Tisbury, MA 02568

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This beautiful home has lots of open space for cooking, yard activities or just plain relaxing. Private association beach overlooking the Elizabethan Islands. Plan a sunset picnic on the beach or plan in the morning to see the rays of sun break on the water.

  Karen Overtoom Karen M. Overtoom R.E.

  33 Kennebago Ave Vh414, Tisbury, MA 02568
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  /32

  $3,925,000 Sold Jul 01, 2025

  • 5,603 Sq Ft
  • $701/SF
  • 238 Days On Market

  • 6 Beds
  • 7 Baths
  • Built 1995

  140 Merry Farm Rd, Vineyard Haven, MA 02568

  Site of the original Rainbow Farm, this 8.05-acre parcel is one of the most beautiful pieces of land in West Tisbury. The warm and convivial 5,000 sq ft home with its 4 bedrooms looks out onto a setting that is as if from a bygone era, the vast fields stretching into the distance. The spring-fed pond is a centerpiece of the pastoral view. The home itself has many surprising and charming design

  Mark Jenkins Wallace & Co. Sotheby's

  140 Merry Farm Rd, Vineyard Haven, MA 02568
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  /45

  Est $1,772,609 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,576 Sq Ft

  38 Edgewood Dr, Edgartown, MA 02539

  38 Edgewood Dr, Edgartown, MA 02539
• 

  

  /22

  $1,250,000

  • 2 Beds
  • 1 Bath
  • 742 Sq Ft

  47 Winemack St, Oak Bluffs, MA 02557

  Oak Bluffs -East Chop-Close to the ocean. Two cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a

  

  Lisa Lucier

  Anchor Realty of MV

  (508) 403-9601

  47 Winemack St, Oak Bluffs, MA 02557
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  /12

  $15,000 per month

  • 5 Beds
  • 6.5 Baths
  • 4,137 Sq Ft
  • House for Rent

  41 Naushon Rd Wt116, Aquinnah, MA 02575

  Stunning water views from this expansive beachfront estate in Makonikey off Lambert's Cove Rd. Enjoy the large living area with comfortable couches, floor to ceiling windows and french doors for seamless indoor to outdoor living and dining. There is a fully equipped kitchen. Some folks will enjoy the treadmill and elliptical while watching boats pass by or even play squash in the indoor squash

  Karen Overtoom Karen M. Overtoom R.E.

  41 Naushon Rd Wt116, Aquinnah, MA 02575
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  /31

  $1,325,000 Sold Jun 30, 2025

  • 2,292 Sq Ft
  • $578/SF
  • 10 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1992

  191 Spring Hill Rd, Vineyard Haven, MA 02568

  This pristine cape-style home is located in the heart of Vineyard Haven. This home features five bedrooms, four bathrooms, a beautifully landscaped yard, and an energy-efficient solar panel system installed by South Mountain Company. The functional and efficient floor plan with an open kitchen, living, and dining concept, makes entertaining family and guests seamless, with easy access to the

  Madelyn Silvia Wallace & Co. Sotheby's

  191 Spring Hill Rd, Vineyard Haven, MA 02568
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  /2

  Est $1,376,724 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,400 Sq Ft

  45 Pine Tree Ln, Vineyard Haven, MA 02568

  45 Pine Tree Ln, Vineyard Haven, MA 02568
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  /28

  $1,950,000

  • 4 Beds
  • 2.5 Baths
  • 3,268 Sq Ft

  7 Upper Meadow Ln, Oak Bluffs, MA 02557

  Tucked at the end of a quiet cul-de-sac in the desirable Meadow View Farms neighborhood, this spacious Colonial offers over 3,200 square feet of comfortable and inviting living space. This home is ideal for those who love to host lively gatherings while providing comfortable accommodations for all. Inside, you'll find four well-sized bedrooms and two and a half baths, including a generous primary

  Lesley Heidt Sandpiper Realty Inc

  7 Upper Meadow Ln, Oak Bluffs, MA 02557
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  /8

  $18,500 per month

  • 4 Beds
  • 3.5 Baths
  • 1,714 Sq Ft
  • House for Rent

  4 Windy Way Wt143, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! The 3.3 acre private setting is most picturesque with its positioning in private Upper Makonikey , the long circular driveway , its grassy lawn, and rolling landscape fields . Only a short distance away is over 3,000 feet of PRIVATE sandy association Beaches , directly below , with two nearby parking lot access-ways . Nestled onto this promontory is a

  Karen Overtoom Karen M. Overtoom R.E.

  4 Windy Way Wt143, West Tisbury, MA 02575
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  /34

  $1,050,000 Sold Jun 30, 2025

  • 1,606 Sq Ft
  • $654/SF
  • 45 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1977

  160 Bernard Cir, Vineyard Haven, MA 02568

  Charming, four bedroom home with impressive rental history, new roof and septic in 2021/2022. Being offered turn-key, fully furnished with coastal decor, ready to move in and enjoy. Soaring cathedral ceilings highlight the open floor plan of the main living area on the second floor. Granite counters, stainless steel appliances and a center island in the kitchen leads to the dining area with

  Dawn Bellante-Holand Sandpiper Realty

  160 Bernard Cir, Vineyard Haven, MA 02568
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  /36

  Est $2,321,551 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,436 Sq Ft

  377 State Rd, Vineyard Haven, MA 02568

  377 State Rd, Vineyard Haven, MA 02568
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  /32

  $1,750,000

  • 5 Beds
  • 4 Baths
  • 2,436 Sq Ft

  128 W Spring St, Vineyard Haven, MA 02568

  128 Spring Street—just moments from the Tisbury School and downtown Vineyard Haven. Built in 2013 and sited on an ample 1/4-acre lot, the house features four bedrooms and two-and-a-half bathrooms, along with a separate first floor one-bedroom in-law apartment complete with a full bath—ideal for extended family, guests, or added rental flexibility. The central location offers convenience to

  David Dickinson Compass | Point B

  128 W Spring St, Vineyard Haven, MA 02568
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  /8

  $4,800 per month

  • 3 Beds
  • 3 Baths
  • 3,279 Sq Ft
  • House for Rent

  165 Christiantown Rd, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

  Karen Overtoom Karen M. Overtoom R.E.

  165 Christiantown Rd, West Tisbury, MA 02575
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  /29

  $1,100,000 Sold Jun 27, 2025

  • 1,976 Sq Ft
  • $557/SF
  • 9 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1985

  10 Kims Way, Oak Bluffs, MA 02557

  Located under a mile from downtown Oak Bluffs, this well-maintained 4-bedroom home includes a 3-bedroom main house and a 1-bedroom basement apartment. Recent upgrades include a new roof, Title V septic system, electric service, and town water connection. The first floor features a spacious living/dining area, kitchen, half bath, and a cozy den. Upstairs are 3 bedrooms and a full bath. The

  Michael Schweikert Ocean Park Realty Inc

  10 Kims Way, Oak Bluffs, MA 02557
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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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  /47

  $2,675,000

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

  128 & 136 Spring St, Vineyard Haven, MA 02568

  A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street—two adjacent properties being sold together to create a unique, flexible compound just moments from the Tisbury School and downtown Vineyard Haven. With a spacious main residence and a separate guest house, this rare combination presents a compelling opportunity for multigenerational living, seasonal enjoyment,

  David Dickinson Compass | Point B

  128 & 136 Spring St, Vineyard Haven, MA 02568
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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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  /32

  $1,100,000 Sold Jun 27, 2025

  • 1,976 Sq Ft
  • $557/SF
  • 156 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1985

  10 Kims Way, Oak Bluffs, MA 02568

  Located under a mile from downtown Oak Bluffs, this well-maintained 4-bedroom home includes a 3-bedroom main house and a 1-bedroom basement apartment. Recent upgrades include a new roof, Title V septic system, electric service, and town water connection. The first floor features a spacious living/dining area, kitchen, half bath, and a cozy den. Upstairs are 3 bedrooms and a full bath. The

  Michael Schweikert Ocean Park Realty, Inc.

  10 Kims Way, Oak Bluffs, 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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  /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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  /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
• 

  

  /22

  $1,299,000 Sold Jun 25, 2025

  • 1,512 Sq Ft
  • $859/SF
  • 77 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  2 Boylston Dr, Edgartown, MA 02539

  Edgartown: MOVE IN READY! Stylish 3-bedroom 2 bath home with inviting and charming floor plan integrates comfort and function. Cathedral ceilings with skylight and 2 sets of sliders providing natural light and a bright open floor plan.Updated kitchen with breakfast bar and dining area. 1st Floor bedroom. Full bathroom and spacious living room perfect for gatherings and relaxing. There is

  Martha Smith C McManus Realty Group

  2 Boylston Dr, Edgartown, MA 02539
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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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  /30

  $1,850,000

  • 4 Beds
  • 3 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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  /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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  /29

  $1,925,000 Sold Jun 24, 2025

  • 2,378 Sq Ft
  • $810/SF
  • 0 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1928

  21 William St, Vineyard Haven, MA 02568

  Nestled at the quiet end of William Street, just moments from the lively charm of downtown Vineyard Haven, this delightful 3-bedroom home offers the perfect blend of comfort and convenience. The spacious primary suite is thoughtfully located on the main level, providing both privacy and ease of living. Inside, an open and airy floor plan combines timeless character with modern touches—ideal for

  Laura Finney Wallace & Co. Sotheby's

  21 William St, Vineyard Haven, MA 02568
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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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  /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 the island’s most sought-after locations, this exceptional property offers refined coastal living with access to the famed Lambert’s Cove Beach yet a short drive to VH.Thoughtfully designed, it features 3 spacious bedrooms each with an en suite bath, providing comfort and privacy for all. Primary suite is a true retreat with a brand new luxurious bathroom. At the heart of the

  Jennifer B. DaSilva Compass

  53 Stoney Hill Rd, Vineyard Haven, MA 02568
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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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  /7

  $600,000 Sold Jun 23, 2025

  • Land
  • 0.50 Acre
  • $1,200,000 per Acre

  • 4 Days On Market

  27 7th St N Unit 198, Edgartown, MA 02539

  This .5-acre lot is located in a favorable Edgartown neighborhood with proximity to the bike path, public transportation, and close to town. The property has been staked and perc tested, and will support 2 bedrooms with a standard Title V septic system or 3 bedrooms with an advanced treatment system. Information should be verified by the Edgartown Board of Health Department. Embrace the unique

  Stephanie Roache Donnelly + Co

  27 7th St N Unit 198, Edgartown, MA 02539
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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
• 

  

  /40

  $1,925,000

  • 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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  /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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  /6

  $600,000 Sold Jun 23, 2025

  • Land
  • 0.50 Acre
  • $1,200,000 per Acre

  • 4 Days On Market

  27 7th St N, Edgartown, MA 02539

  This .5-acre lot is located in a very favorable Edgartown neighborhood with proximity to the bike path, public transportation, and close to town. The property has been staked and perc tested, and will support 2 bedrooms with a standard Title V septic system or 3 bedrooms with an advanced treatment system. Information should be verified by the Edgartown Board of Health Department. Embrace the

  Stephanie Roache Donnelly + Co.

  27 7th St N, Edgartown, MA 02539
• 

  

  /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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