Dukes County, MA Homes

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  /36

  $2,900,000 Pending

  • 4 Beds
  • 5 Baths
  • 5,165 Sq Ft

  63 Bayes Hill Rd, Oak Bluffs, MA 02557

  Tucked away in a serene setting, this beautifully designed custom home offers the ultimate in privacy, comfort, and luxury living. The first floor features a spacious open-concept design, seamlessly blending the dining room, kitchen, wet bar, and living area-perfect for entertaining or relaxing with the family. Home chefs will fall in love with the gourmet kitchen complete with custom cabinetry,

  Casandra Hyland Sandpiper Realty, Inc.

  63 Bayes Hill Rd, Oak Bluffs, MA 02557
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  /19

  $17,600 total monthly price

  • 4 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • House for Rent

  50 Carls Way, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Looking for that perfect setting with a water view? This is the one!!This cute cape is privately set with a water view and direct water access to Town Pond. You can dock your canoes and kyacks here and access Tisbury Great Pond and then right out to the beach. There are

  Karen Overtoom Karen M. Overtoom R.E.

  50 Carls Way, West Tisbury, MA 02575
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  /23

  $1,800,000 Sold Aug 26, 2025

  12 Martha's Park Rd, Oak Bluffs, MA 02557

  • 4 Beds
  • 1.5 Baths
  • 1,351 Sq Ft
  • Built 1910

  Last Sold Summary

  • 1% Below List Price
  • $1,332/SF
  • 0 Days On Market

  Current Estimated Value $1,721,205

  Last Listing Agent Michele Moore Island Real Estate

  12 Martha's Park Rd, Oak Bluffs, MA 02557
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  /21

  Est $1,460,973 Not Listed For Sale

  23 Anthiers Way, Edgartown, MA 02539

  • 4 Beds
  • 3 Baths
  • 2,066 Sq Ft
  • Built 1950

  23 Anthiers Way, Edgartown, MA 02539

  Last Sold Summary

  • 15% Above List Price
  • $617/SF
  • 66 Days On Market

  Last Sold Price $1,275,000

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's International Realty
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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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  /17

  $17,600 total monthly price

  • 4 Beds
  • 4 Baths
  • 2,676 Sq Ft
  • House for Rent

  40 Summer Cir, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and living room surrounded by windows and decks with an outdoor table and extra seating. An "upside down" house with the living

  Karen Overtoom Karen M. Overtoom R.E.

  40 Summer Cir, West Tisbury, MA 02575
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  /12

  $860,000 Sold Feb 09, 2026

  8 Hitchings Cir, Oak Bluffs, MA 02557

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1985

  Last Sold Summary

  • 6% Below List Price
  • $698/SF
  • 22 Days On Market

  Last Listing Agent Peyton Wallace Studio Realty

  8 Hitchings Cir, Oak Bluffs, MA 02557
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  /32

  Est $2,388,235 Not Listed For Sale

  232 Lagoon Pond Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 4 Baths
  • 2,276 Sq Ft
  • Built 1970

  232 Lagoon Pond Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 8% Below List Price
  • $1,142/SF
  • 220 Days On Market

  Last Sold Price $2,600,000

  Last Listing Agent Keith McLaughlin Grade A Realty
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  /4

  $809,000

  • Land
  • 0.39 Acre
  • $2,074,359 per Acre

  7 Highland Ave, Vineyard Haven, MA 02568

  Rare opportunity in East Chop. Buildable lot in a beautiful, wooded area, walking distance to town, beach, and ferries. Secluded yet accessible.

  Shera Toledo eXp Realty, LLC

  7 Highland Ave, Vineyard Haven, MA 02568
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  /21

  $8,000 total monthly price

  • 1 Bed
  • 1 Bath
  • 936 Sq Ft
  • House for Rent

  10 James Pond Way, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a

  Karen Overtoom Karen M. Overtoom R.E.

  10 James Pond Way, West Tisbury, MA 02575
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  /32

  $1,675,000 Sold Dec 08, 2025

  78 Whalers Walk, Edgartown, MA 02539

  • 3 Beds
  • 2.5 Baths
  • 1,914 Sq Ft
  • Built 1999

  Last Sold Summary

  • 7% Below List Price
  • $875/SF
  • 100 Days On Market

  Current Estimated Value $1,704,386

  Last Listing Agent Dawn Bellante Sandpiper Realty Inc

  78 Whalers Walk, Edgartown, MA 02539
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  /23

  Not Listed For Sale

  51 Blueberry Ridge Ln, Chilmark, MA 02535

  • 6 Beds
  • 3.5 Baths
  • 2,229 Sq Ft
  • Built 1989

  51 Blueberry Ridge Ln, Chilmark, MA 02535

  Last Sold Summary

  • $1,032/SF
  • 11 Days On Market

  Last Sold Price $2,300,000

  Last Listing Agent Rebecca V Conroy Conroy & Company R.E., Inc.
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  /78

  $7,950,000

  • 6 Beds
  • 6.5 Baths
  • 6,927 Sq Ft

  6 Janes Cove Rd, Edgartown, MA 02539

  Waterfront on Edgartown Great Pond with delightful water views, this newly-renovated Coastal Colonial is set on a very private 9.2 acre lot on Janes Cove. You know you are somewhere very special the moment you enter through the gates. As you travel along the cobblestone lined driveway flanked by lush lawns, the gorgeous home rises before you. Stunning the day it was originally completed, it has

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  6 Janes Cove Rd, Edgartown, MA 02539
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  /20

  $12,000 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,068 Sq Ft
  • House for Rent

  76 Ben Chase Rd Wt136, West Tisbury, MA 02575

  Experience a wonderful glimpse of country living in the peaceful, quiet setting of Serene Pond Cottage! This charming Martha's Vineyard retreat features a cozy interior with ample natural light, a private deck where you can take your breakfast and coffee, and a tree-lined backyard to enjoy on lazy summer days. Comfortable three bedroom single story home with one brand new renovated full bath with

  Karen Overtoom Karen M. Overtoom R.E.

  76 Ben Chase Rd Wt136, West Tisbury, MA 02575
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  /39

  $4,762,500 Sold May 14, 2025

  69 Division Rd, Edgartown, MA 02539

  • 6 Beds
  • 5.5 Baths
  • 5,103 Sq Ft
  • Built 2024

  Last Sold Summary

  • 18% Below List Price
  • $933/SF
  • 411 Days On Market

  Current Estimated Value $4,877,977

  Last Listing Agent Jennifer DaSilva Compass | Point B

  69 Division Rd, Edgartown, MA 02539
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  /36

  Est $1,621,771 Not Listed For Sale

  323 Lamberts Cove Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 1,144 Sq Ft
  • Built 1900

  323 Lamberts Cove Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 4% Below List Price
  • $1,473/SF
  • 331 Days On Market

  Last Sold Price $1,685,000

  Last Listing Agent Diana Gilmore Island Real Estate
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  /21

  $895,000 Pending

  • 3 Beds
  • 1 Bath
  • 931 Sq Ft

  22 Montgomery Square, Oak Bluffs, MA 02557

  Located in the heart of Wesleyan Grove within the historic Martha's Vineyard Camp Meeting Association, this enchanting year-round Victorian cottage captures the timeless charm and vibrant spirit of Oak Bluffs living. Just steps from lively Circuit Avenue, picturesque Oak Bluffs Harbor, and sandy beaches, the location offers the very best of in-town convenience and coastal beauty. This delightful

  Marilyn Moses Ocean Park Realty, Inc.

  22 Montgomery Square, Oak Bluffs, MA 02557
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  /19

  $30,000 total monthly price

  • 5 Beds
  • 4 Baths
  • 3,600 Sq Ft
  • House for Rent

  37 Sachem Cir, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself

  Karen Overtoom Karen M. Overtoom R.E.

  37 Sachem Cir, West Tisbury, MA 02575
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  /31

  $1,685,000 Sold Oct 09, 2025

  126 Border Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 3 Baths
  • 2,251 Sq Ft
  • Built 1979

  Last Sold Summary

  • 16% Below List Price
  • $749/SF
  • 337 Days On Market

  Current Estimated Value $1,681,084

  Last Listing Agent Natalie Conroy Conroy & Company R.E., Inc.

  126 Border Rd, Vineyard Haven, MA 02568
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  /44

  Est $1,657,025 Not Listed For Sale

  30 Hillside Path, Vineyard Haven, MA 02568

  • 3 Beds
  • 4 Baths
  • 3,114 Sq Ft
  • Built 1999

  30 Hillside Path, Vineyard Haven, MA 02568

  Last Sold Summary

  • 6% Above List Price
  • $501/SF
  • 39 Days On Market

  Last Sold Price $1,560,000

  Last Listing Agent Stephanie Roache Donnelly + Co
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  /13

  $6,750,000

  • Land
  • 2.11 Acres
  • $3,199,052 per Acre

  5 Atlantic Dr Unit 5.2, Edgartown, MA 02539

  Located in one of Katama’s most coveted neighborhoods, this 2.11-acre parcel offers stunning ocean views and a direct path to South Beach. Surrounded by high-end homes and just minutes from Edgartown Village, it’s an ideal setting for a custom-built retreat with room for a four bedroom residence with pool and views over the dunes. A rare opportunity to own in this prestigious coastal enclave.

  Deb Levin Studio Realty

  5 Atlantic Dr Unit 5.2, Edgartown, MA 02539
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  /29

  $10,900 total monthly price

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft
  • House for Rent

  58 Forest Rd Wt140, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,725.. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming rustic home is set within Seven Gates Farm in West Tisbury. Walk down your own path to a beautiful private association beach. There are shared tennis courts and miles of walking trails.

  Karen Overtoom Karen M. Overtoom R.E.

  58 Forest Rd Wt140, West Tisbury, MA 02575
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  /2

  $825,000 Sold Dec 03, 2025

  69 Summit Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1998

  Last Sold Summary

  • $661/SF
  • 1 Day On Market

  Current Estimated Value $862,879

  Last Listing Agent Susie Wallo Compass

  69 Summit Ave, Vineyard Haven, MA 02568
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  /31

  Est $2,490,884 Not Listed For Sale

  106 Panhandle Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 3.5 Baths
  • 3,310 Sq Ft
  • Built 1991

  106 Panhandle Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 1% Below List Price
  • $763/SF
  • 80 Days On Market

  Last Sold Price $2,525,000

  Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.
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  /21

  $1,445,000

  • 4 Beds
  • 2.5 Baths
  • 1,738 Sq Ft

  22 Oklahoma Ave, Vineyard Haven, MA 02568

  3 BEDROOM HOUSE + 1 BEDROOM APARTMENT! A rare opportunity in a convenient Vineyard Haven neighborhood. This move-in ready property features a 3 BR, 1.5 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset your mortgage. The main house features a stunning sun-room, a cheerful efficient kitchen, and a

  Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

  22 Oklahoma Ave, Vineyard Haven, MA 02568
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  /13

  $15,000 total monthly price

  • 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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  /40

  $650,000 Sold Sep 10, 2025

  25 Oak Ave, Oak Bluffs, MA 02557

  • 2 Beds
  • 0.5 Baths
  • 759 Sq Ft
  • Built 1900

  Last Sold Summary

  • 4% Below List Price
  • $856/SF
  • 251 Days On Market

  Current Estimated Value $822,365

  Last Listing Agent Alisan Lohan-Conway Alisan Lohan-Conway Properties

  25 Oak Ave, Oak Bluffs, MA 02557
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  /37

  Est $2,196,165 Not Listed For Sale

  24 Pulpit Ln, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 2,097 Sq Ft
  • Built 2001

  24 Pulpit Ln, Edgartown, MA 02539

  Last Sold Summary

  • 10% Above List Price
  • $953/SF
  • 5 Days On Market

  Last Sold Price $1,998,500

  Last Listing Agent Susie Wallo Compass
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  /69

  $4,175,000

  • 6 Beds
  • 3.5 Baths
  • 3,397 Sq Ft

  19 Kitts Field Cir, Edgartown, MA 02539

  Old World Vineyard Charm Meets Modern Katama Living. Welcome to this beautifully crafted Katama family compound, a private, thoughtfully designed estate offering timeless elegance and exceptional amenities. Nestled near Edgartown Village, this stunning property includes a four-bedroom main residence with three levels of living space, a charming two-bedroom guest house, pool house, pool, spa,

  Michele Casavant Vineyard Village Realty

  19 Kitts Field Cir, Edgartown, MA 02539
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  /22

  $20,000 total monthly price

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

  709 Old County Rd Wt134, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY. The weekly price in August is $5,000. per week. See website for additional weekly pricing. Mill Pond House is a completely restored 1890s farmhouse on the old Mill Pond in historic West Tisbury. Remodeled by the present owner, an interior designer, it is beautifully appointed with antiques and charming accessories. An old pine floor and columns add to the

  Karen Overtoom Karen M. Overtoom R.E.

  709 Old County Rd Wt134, West Tisbury, MA 02575
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  /40

  $1,600,000 Sold Jan 06, 2026

  44 Tiffany Dr, Oak Bluffs, MA 02557

  • 4 Beds
  • 4 Baths
  • 3,927 Sq Ft
  • Built 1987

  Last Sold Summary

  • 24% Below List Price
  • $407/SF
  • 115 Days On Market

  Current Estimated Value $1,612,340

  Last Listing Agent Sheila Morse Island Real Estate

  44 Tiffany Dr, Oak Bluffs, MA 02557
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  Est $4,829,110 Not Listed For Sale

  62 S Water St, Edgartown, MA 02539

  • 4 Beds
  • 3.5 Baths
  • 2,807 Sq Ft
  • Built 1825

  62 S Water St, Edgartown, MA 02539

  Last Sold Summary

  • 7% Above List Price
  • $1,603/SF
  • 187 Days On Market

  Last Sold Price $4,500,000

  Last Listing Agent Gerrett Conover Landvest MV
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  /8

  $475,000

  • Land
  • 0.52 Acre
  • $913,462 per Acre

  36 Boylston Dr Unit 1.329, Edgartown, MA 02539

  Buildable lot in an established Edgartown neighborhood. Approvals are in hand for the construction of a single-family residential structure not to exceed 3 bedrooms and not to exceed 1,850 square feet of heated living area (screened porches, patios, etc are not included in this square footage). Note that this property cannot be used as a seasonal home or short-term rental. Septic plan has been

  Mark Jenkins Wallace & Co. Sotheby's

  36 Boylston Dr Unit 1.329, Edgartown, MA 02539
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  /9

  $19,000 total monthly price

  • 6 Beds
  • 2.5 Baths
  • 2,155 Sq Ft
  • House for Rent

  17 Umbagog Ave Wt109, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three story home is located in a very desirable area off of Lambert's Cove Road, Makonikey, with access to a private association beach and walking trails. There are four plus bedrooms and bright and open living spaces that lead out to a deck and a screened-in porch.

  Karen Overtoom Karen M. Overtoom R.E.

  17 Umbagog Ave Wt109, West Tisbury, MA 02575
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  /18

  $1,000,000 Sold Dec 12, 2025

  1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557

  • 2 Beds
  • 2.5 Baths
  • 1 Sq Ft
  • Built 2001

  Last Sold Summary

  • 9% Below List Price
  • $1,000,000/SF
  • 13 Days On Market

  Current Estimated Value $1,169,962

  Last Listing Agent Lisa Lucier Anchor Realty of MV

  1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557
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  Est $3,767,884 Not Listed For Sale

  6 Beach Plum Way, Aquinnah, MA 02535

  • 7 Beds
  • 5.5 Baths
  • 4,875 Sq Ft
  • Built 1996

  6 Beach Plum Way, Aquinnah, MA 02535

  Last Sold Summary

  • 1% Above List Price
  • $764/SF
  • 21 Days On Market

  Last Sold Price $3,725,000

  Last Listing Agent Meg Bodnar Tea Lane Associates
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  /36

  $3,350,000

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

  4 Nomans Watch Rd, Aquinnah, MA 02535

  Perched on 2.7 acres in one of Aquinnah’s most breathtaking settings, this beautifully sited coastal retreat offers sweeping views over the Atlantic and Noman’s Land from its elevated position. Designed to embrace the light and scenery, the main level features an open living/dining/kitchen area wrapped in walls of windows—an airy, sun-soaked space where ocean views take center stage. The

  Jennifer O'hanlon Compass LLC

  4 Nomans Watch Rd, Aquinnah, MA 02535
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  /2

  $10,000 total monthly price

  • 6 Beds
  • 3.5 Baths
  • 2,100 Sq Ft
  • House for Rent

  15 Crowell Lane Wt119, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!Seven Gates Farm. This property has three ponds, overlooks rolling meadows and is very charming. Located in Seven Gates Farm association, the property affords access to association tennis and two miles of private beach as well as miles of walking trails. Bookings for tennis are available at the office for a slight fee.There is a $25 trash charge per

  Karen Overtoom Karen M. Overtoom R.E.

  15 Crowell Lane Wt119, West Tisbury, MA 02575
• 

  /2

  $965,000 Sold Sep 04, 2025

  62 Jernegan Ave, Edgartown, MA 02539

  • 3 Beds
  • 1 Bath
  • 1,886 Sq Ft
  • Built 1998

  Last Sold Summary

  • $512/SF
  • 0 Days On Market

  Current Estimated Value $1,044,362

  Last Listing Agent LINK Email Cache LINK

  62 Jernegan Ave, Edgartown, MA 02539
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  Est $3,197,761 Not Listed For Sale

  5 Katama Dr, Edgartown, MA 02539

  • 3 Beds
  • 3.5 Baths
  • 2,527 Sq Ft
  • Built 1990

  5 Katama Dr, Edgartown, MA 02539

  Last Sold Summary

  • 28% Above List Price
  • $989/SF
  • 98 Days On Market

  Last Sold Price $2,500,000

  Last Listing Agent Emma Kennedy Sandpiper Realty

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