Dukes County, MA Homes

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  /23

  $3,100,000

  • 1 Bed
  • 1 Bath
  • 1,250 Sq Ft

  114 Meeting House Way, Edgartown, MA 02539

  3 Acre Katama Building Lot with Existing Guest House. This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, substantial residences. Located one mile from Edgartown Great Pond and 2 miles from both South Beach

  Rose Ryley Wallace & Co. Sotheby's International Realty

  114 Meeting House Way, Edgartown, MA 02539
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  /12

  $5,500 total monthly price

  • 3 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • House for Rent

  2 Fishermans Knot Rd Ed309 Unit 1, Edgartown, MA 02539

  THIS PROPERTY IS A WEEKLY VACATION RENTAL PROPERTY. The home’s timeless interior offers a sitting room with a wood-burning fireplace, a hallway opening to a large, bright, modern kitchen featuring a Viking range and large dining table. Ample counter space and a wall of built-ins are the perfect complement to family and friends that enjoy cooking together. A gas grill and outdoor seating are only

  Karen Overtoom Karen M. Overtoom R.E.

  2 Fishermans Knot Rd Ed309 Unit 1, Edgartown, MA 02539
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  $3,300,000 Sold Sep 18, 2025

  28 Crocker Dr, Edgartown, MA 02539

  • 4 Beds
  • 6 Baths
  • 3,793 Sq Ft
  • Built 1960

  Last Sold Summary

  • 11% Below List Price
  • $870/SF
  • 139 Days On Market

  Current Estimated Value $3,448,308

  Last Listing Agent Jennifer O'hanlon Compass

  28 Crocker Dr, Edgartown, MA 02539
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  /13

  Est $1,200,225 Not Listed For Sale

  33 Menahan St, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft
  • Built 1993

  33 Menahan St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 1% Above List Price
  • $830/SF
  • 48 Days On Market

  Last Sold Price $1,185,000

  Last Listing Agent Katherine Donahue Sandpiper Realty Inc
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  /42

  $2,395,000

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

  21 & 25 Fulling Mill Rd, Chilmark, MA 02535

  Jessie Holtham Wallace & Co. Sotheby's International Realty

  21 & 25 Fulling Mill Rd, Chilmark, MA 02535
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  /8

  $17,500 total monthly price

  • 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 relaxing

  Karen Overtoom Karen M. Overtoom R.E.

  550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568
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  /3

  $435,000 Sold Jul 23, 2025

  0 Blackpoint Key Unit 14-13 43139, Chilmark, MA 02535

  • Land
  • 0.3 Acre
  • $1,457,775 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 96 Days On Market

  Last Listing Agent Jill Napior Tea Lane Associates

  0 Blackpoint Key Unit 14-13 43139, Chilmark, MA 02535
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  /14

  Est $971,572 Not Listed For Sale

  51 Manchester Ave, Vineyard Haven, MA 02568

  • 2 Beds
  • 1 Bath
  • 1,024 Sq Ft
  • Built 1978

  51 Manchester Ave, Vineyard Haven, MA 02568

  Last Sold Summary

  • 2% Above List Price
  • $933/SF
  • 22 Days On Market

  Last Sold Price $955,000

  Last Listing Agent Roy Cutrer LAER Realty Partners
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  /29

  $2,600,000

  • 3 Beds
  • 1 Bath
  • 1,336 Sq Ft

  23 Circuit Avenue Extension, Oak Bluffs, MA 02557

  Rare Opportunity with Endless Possibilities – Unmatched Harbor & Vineyard Sound Views.Location, Location, Location! A truly rare offering in the heart of Oak Bluffs, where properties like this seldom become available. Positioned directly across from the iconic Oak Bluffs Harbor, this property boasts unobstructed harbor views and sweeping vistas of Vineyard Sound—a setting that captures the

  Rene Ben David Ocean Park Realty Inc

  23 Circuit Avenue Extension, Oak Bluffs, MA 02557
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  /10

  $8,500 total monthly price

  • 3 Beds
  • 2 Baths
  • House for Rent

  29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

  Karen Overtoom Karen M. Overtoom R.E.

  29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
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  /18

  $4,200,000 Sold Jan 15, 2026

  1 Wilsons Ln, Edgartown, MA 02539

  • 4 Beds
  • 3.5 Baths
  • 3,715 Sq Ft
  • Built 2025

  Last Sold Summary

  • $1,131/SF
  • 68 Days On Market

  Current Estimated Value $3,376,181

  Last Listing Agent Michele Casavant Vineyard Village Realty

  1 Wilsons Ln, Edgartown, MA 02539
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  /30

  Est $2,327,720 Not Listed For Sale

  10 Crow Hollow Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 2,555 Sq Ft
  • Built 1983

  10 Crow Hollow Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 6% Above List Price
  • $861/SF
  • 197 Days On Market

  Last Sold Price $2,200,000

  Last Listing Agent Julianna Flanders Flanders Real Estate
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  /42

  $2,495,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,530 Sq Ft

  61 Causeway Rd, Vineyard Haven, MA 02568

  Welcome to this fabulous property, within close proximity to the ferry, downtown shops, restaurants, galleries, Owen Park Beach, and the MV Playhouse. This beautifully designed home has been lovingly maintained and offers the ideal balance of Vineyard charm and modern convenience. Designed across multi-levels of living spaces, the home provides a flexible layout that works beautifully for

  Stephanie Roache Donnelly + Co.

  61 Causeway Rd, Vineyard Haven, MA 02568
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  /8

  $11,800 total monthly price

  • 4 Beds
  • 4 Baths
  • 2,612 Sq Ft
  • House for Rent

  46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

  Karen Overtoom Karen M. Overtoom R.E.

  46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
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  $1,470,000 Sold Mar 24, 2026

  654 Lighthouse Rd, Aquinnah, MA 02535

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1972

  Last Sold Summary

  • 22% Below List Price
  • $919/SF
  • 195 Days On Market

  Current Estimated Value $2,186,920

  Last Listing Agent Heidi Vanderhoop Tea Lane Associates

  654 Lighthouse Rd, Aquinnah, MA 02535
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  /2

  Est $2,455,030 Not Listed For Sale

  230 Pond Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 4 Baths
  • 3,527 Sq Ft
  • Built 1999

  230 Pond Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 8% Above List Price
  • $646/SF
  • 100 Days On Market

  Last Sold Price $2,280,000

  Last Listing Agent Rose Ryley Sandpiper Realty Inc
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  /42

  $2,575,000

  • 4 Beds
  • 2.5 Baths
  • 1,910 Sq Ft

  76 Washque Ave, Edgartown, MA 02539

  This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick's most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird's-eye views capture the natural beauty that surrounds you. Thoughtfully renovated, the home blends

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  76 Washque Ave, Edgartown, MA 02539
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  /8

  $6,000 total monthly price

  • 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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  $1,500,000 Sold Sep 03, 2025

  37 Knoll Dr, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1972

  Last Sold Summary

  • 15% Below List Price
  • $1,218/SF
  • 158 Days On Market

  Current Estimated Value $1,595,760

  Last Listing Agent Josseph Barkett Compass

  37 Knoll Dr, Edgartown, MA 02539
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  /4

  Est $2,859,238 Not Listed For Sale

  188 Pond Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 2,789 Sq Ft
  • Built 1996

  188 Pond Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 9% Below List Price
  • $1,124/SF

  Last Sold Price $3,135,000

  Last Listing Agent Rose Ryley Wallace & Co. Sotheby's
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  /61

  $2,250,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,250 Sq Ft

  28 Pine Tree Ln, Vineyard Haven, MA 02568

  Enjoy beach-close living—just 0.2 miles to the shore—in sought-after West Chop. This welcoming 5BR/3.5BA colonial blends classic Vineyard character with New Roof '26, modern comforts, including central air, an updated kitchen, and three fireplaces. Approximately 3,152± sq ft (expanded from 2,632± with a 520± sq ft finished space over the garage) offers flexible, easy flow to a large fenced

  Wendy Harman Compass | Point B

  28 Pine Tree Ln, Vineyard Haven, MA 02568
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  /8

  $13,600 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,967 Sq Ft
  • Condo for Rent

  1 Meetinghouse Village Way Unit 1 ED335, Edgartown, MA 02539

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Enjoy this well appointed and immaculately clean two bedroom condo located just steps from the association pool and a short drive to South Beach with its gorgeous white sands. An open living room, kitchen and dining room with walk-out access to the deck and back yard offer plenty of gathering spaces to enjoy your company over meals, snacks and games

  Karen Overtoom Karen M. Overtoom R.E.

  1 Meetinghouse Village Way Unit 1 ED335, Edgartown, MA 02539
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  /2

  $1,700,000 Sold Oct 20, 2025

  37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

  • 5 Beds
  • 3 Baths
  • 1,803 Sq Ft
  • Built 1982

  Last Sold Summary

  • $943/SF
  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK

  37 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
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  /34

  Est $2,339,682 Not Listed For Sale

  248 Pond Rd, Vineyard Haven, MA 02568

  • 5 Beds
  • 3.5 Baths
  • 1 Sq Ft
  • Built 1998

  248 Pond Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 2% Above List Price
  • $2,300,000/SF
  • 174 Days On Market

  Last Sold Price $2,300,000

  Last Listing Agent Brenda Galligan Karen M. Overtoom R E
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  /28

  $2,295,000

  • 4 Beds
  • 3.5 Baths
  • 2,690 Sq Ft

  151 Tashmoo Ave, Vineyard Haven, MA 02568

  The Colonial Style home with wrap around porch is beautifully maintained and nicely sited on almost a half acre. The first floor is thoughtfully designed and offers an open floor plan that includes an ample mudroom with half bath and is just off the side porch that takes you into the well equipped kitchen with a center island, stainless appliances, custom cabinetry and dining room with sliders to

  Brenda Galligan Karen M. Overtoom R.E.

  151 Tashmoo Ave, Vineyard Haven, MA 02568
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  /4

  $6,000 total monthly price

  • 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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  $1,800,000 Sold Oct 15, 2025

  82 Skiff Ave, Tisbury, MA 02568

  • 3 Beds
  • 3.5 Baths
  • 1,913 Sq Ft
  • Built 2020

  Last Sold Summary

  • 10% Below List Price
  • $941/SF
  • 128 Days On Market

  Current Estimated Value $1,663,874

  Last Listing Agent Lenny Altieri Premier Properties

  82 Skiff Ave, Tisbury, MA 02568
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  /25

  Est $2,022,018 Not Listed For Sale

  131 Shubael Weeks Path, Vineyard Haven, MA 02568

  • 5 Beds
  • 3 Baths
  • 3,636 Sq Ft
  • Built 1985

  131 Shubael Weeks Path, Vineyard Haven, MA 02568

  Last Sold Summary

  • 1% Above List Price
  • $550/SF
  • 0 Days On Market

  Last Sold Price $2,000,000

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's
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  $2,700,000

  • 4 Beds
  • 4.5 Baths
  • 2,750 Sq Ft

  6 Laura's Way, Edgartown, MA 02568

  Welcome to the opportunity to own a brand-new, GORGEOUS, custom-built home in Edgartown, set on a one-acre plot with a detached 900 sq ft accessory dwelling. The main residence opens to an inviting two-story foyer, leading to an expansive, living room featuring a wall of glass sliders. The gourmet kitchen is a chef’s dream, boasting Bosch appliances, a large quartz-topped island with seating for

  Michele Casavant Vineyard Village Realty

  6 Laura's Way, Edgartown, MA 02568
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  /8

  $16,000 total monthly price

  • 7 Beds
  • 3.5 Baths
  • 4,000 Sq Ft
  • House for Rent

  5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite.

  Karen Overtoom Karen M. Overtoom R.E.

  5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
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  /5

  $1,200,000 Sold Jan 22, 2026

  58 Marthas Rd, Edgartown, MA 02539

  • Land
  • 0.5 Acre
  • $2,400,000 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 182 Days On Market

  Last Listing Agent Katherine Donahue Sandpiper Realty Inc

  58 Marthas Rd, Edgartown, MA 02539
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  /2

  Est $1,714,607 Not Listed For Sale

  26 Old Coach Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 2,102 Sq Ft
  • Built 1998

  26 Old Coach Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 3% Above List Price
  • $795/SF
  • 26 Days On Market

  Last Sold Price $1,671,100

  Last Listing Agent Dawn Bellante Sandpiper Realty Inc
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  /31

  $2,395,000

  • 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

  25 Fulling Mill Rd, Chilmark, MA 02535
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  /8

  $3,300 total monthly price

  • 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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  $2,700,000 Sold Dec 19, 2025

  43 Cottage St, Edgartown, MA 02539

  • 2 Beds
  • 2 Baths
  • 1,112 Sq Ft
  • Built 1945

  Last Sold Summary

  • 16% Below List Price
  • $2,428/SF
  • 7 Days On Market

  Current Estimated Value $2,942,751

  Last Listing Agent Michele Casavant Vineyard Village Realty

  43 Cottage St, Edgartown, MA 02539
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  Est $1,826,904 Not Listed For Sale

  38 Edgewood Dr, Edgartown, MA 02539

  • 3 Beds
  • 2.5 Baths
  • 2,576 Sq Ft
  • Built 1987

  38 Edgewood Dr, Edgartown, MA 02539

  Last Sold Summary

  • 7% Above List Price
  • $660/SF
  • 48 Days On Market

  Last Sold Price $1,700,000

  Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty
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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 & 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 stainless

  Leslie Graham Anchor Realty of Martha's Vineyard

  55 Old House Way, West Tisbury, MA 02575
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  /26

  $7,000 total monthly price

  • 7 Beds
  • 1.5 Baths
  • 2,900 Sq Ft
  • House for Rent

  39 N Neck Rd, Edgartown, MA 02539

  Historic Quaint Waterfront Cottage with spectacular 180 degree views of Edgartown Harbor, Oak Bluffs, Cape Cod and Cape Poge, Over 200 feet of secluded, completely private beach, The back yard abuts the fairways and club house of the ''Royal Ancient Chappaquiddick Links'' Private Golf Course. (You must pay dues to play golf), Great outdoor shower. You can see the fireworks (in 5 locations at

  Charles Petitti Coldwell Banker Realty - Newton

  39 N Neck Rd, Edgartown, MA 02539
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  /7

  $650,000 Sold Aug 14, 2025

  00 Hancock Beach Lot Unit 73, Chilmark, MA 02535

  • Land
  • 0.2 Acre
  • $3,250,000 per Acre

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Deb Hancock Hancock Real Estate

  00 Hancock Beach Lot Unit 73, Chilmark, MA 02535
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  /41

  Est $2,564,989 Not Listed For Sale

  53 Peases Point Way N, Edgartown, MA 02539

  • 4 Beds
  • 2 Baths
  • 1,704 Sq Ft
  • Built 1928

  53 Peases Point Way N, Edgartown, MA 02539

  Last Sold Summary

  • 3% Above List Price
  • $1,467/SF
  • 0 Days On Market

  Last Sold Price $2,500,000

  Last Listing Agent Jennifer O'hanlon Compass LLC

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