Dukes County, MA Homes

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  $6,700,000

  • 8 Beds
  • 9.5 Baths
  • 6,229 Sq Ft

  26 Curtis Ln, Edgartown, MA 02539

  Exceptional 8 bedroom home with attached artist/fitness barn studios. Each bedroom includes a en-suite bathroom.The kitchen/dining area includes: 3 refrigerators and 6 freezer drawers, a 5-burner gas stove and oven, dishwasher and microwave. Finished basement (1,000 square feet). Basement includes: 3 washer/dryer units. Outdoor deck with table, chairs and an outdoor grill.

  Thomas Melone Thomas Melone

  26 Curtis Ln, Edgartown, MA 02539
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  /25

  $13,600 total monthly price

  • 2 Beds
  • 2 Baths
  • 792 Sq Ft
  • House for Rent

  64 Bartimus Luce Road Wt125, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!!!!Idyllic location right above a sandy private beach on the North Shore. This beach cottage affords views of the Sound and the Elizabeth Islands with a front row seat on unrivaled sunsets. It is rustic and cozy with a large screened porch overlooking the view. Have a getaway like in days of yore when life was simple and the beach at your doorstep.Take

  Karen Overtoom Karen M. Overtoom R.E.

  64 Bartimus Luce Road Wt125, West Tisbury, MA 02575
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  $1,125,000 Sold Jan 21, 2025

  13 Flamingo Dr, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1994

  Last Sold Summary

  • 4% Below List Price
  • $744/SF
  • 32 Days On Market

  Current Estimated Value $1,212,920

  Last Listing Agent Katherine Donahue Sandpiper Realty Inc

  13 Flamingo Dr, Edgartown, MA 02539
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  Est $1,571,787 Not Listed For Sale

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

  323 Lamberts Cove Rd, Vineyard Haven, MA 02568

  323 Lamberts Cove Rd, Vineyard Haven, MA 02568
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  $1,250,000

  • 3 Beds
  • 3 Baths
  • 1,628 Sq Ft

  261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

  Welcome to this meticulously maintained 2+ bedroom, 3 bathroom end unit condo in Tashmoo Woods, built in 1998. The updated kitchen with granite countertops and high-end appliances opens to a dining room with a private deck overlooking lush woods. The first floor includes a den and a renovated bathroom. Upstairs, both bedrooms have ensuite bathrooms. Upgrades include propane heat, central air, a

  Jennifer O'hanlon Compass

  261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
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  /18

  $10,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,439 Sq Ft
  • House for Rent

  24 Nat's Farm Lane Wt113, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Charming three bedroom home located in a private neighborhood close to bike path, walking trails and public tennis courts. Just a short drive to Lambert's Cove Beach, West Tisbury Village and down island restaurants and shops.Amenities include High definition TV, wifi

  Karen Overtoom Karen M. Overtoom R.E.

  24 Nat's Farm Lane Wt113, 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

  Last Listing Agent Lisa Lucier Anchor Realty of MV

  1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557
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  Est $1,667,732 Not Listed For Sale

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

  30 Hillside Path, Vineyard Haven, MA 02568

  30 Hillside Path, Vineyard Haven, MA 02568
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  /39

  $2,950,000

  • 3 Beds
  • 3.5 Baths
  • 2,268 Sq Ft

  23 Thaxter Ln, Edgartown, MA 02539

  OPEN AND AIRY COASTAL RETREAT WITH EASY ACCESS TO SOUTH BEACH and EDGARTOWN VILLAGE. Welcome to this tri-level contemporary home in the heart of KATAMA. This home offers the perfect blend of spacious indoor-outdoor living with three levels of outdoor decking nestled amongst mature vegetation and a quick stroll to South Beach. The home features vaulted ceilings, two first floor bedroom en-suites,

  Michele Casavant Vineyard Village Realty

  23 Thaxter Ln, Edgartown, MA 02539
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  $46,000 total monthly price

  • 6 Beds
  • 4.5 Baths
  • 3,800 Sq Ft
  • House for Rent

  99 Pond Road Wt104, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!! Beautiful bright sunny home with open concept living. Main floor features a gourmet kitchen with stainless appliances, breakfast bar and formal dining table to seat 10. Large glass sliders open up to expansive views of the deck, pool and pasture beyond. Also on the main level is a separate living area with large screen TV, powder room, and den with twin

  Karen Overtoom Karen M. Overtoom R.E.

  99 Pond Road Wt104, West Tisbury, MA 02575
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  /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 $1,038,384

  Last Listing Agent LINK Email Cache LINK

  62 Jernegan Ave, Edgartown, MA 02539
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  Est $2,043,138 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  119 Herring Creek Rd, Edgartown, MA 02539

  119 Herring Creek Rd, Edgartown, MA 02539
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  /12

  $2,950,000

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft

  9 N Neck Rd, Edgartown, MA 02539

  COMMANDING WATER VIEWS ON CHAPPAQUIDDICK - This beloved fishing cottage rests high above one of the premier fishing areas on the island of Chappaquiddick. Set apart from the hustle and bustle of downtown, but within easy reach of all Edgartown offers, the pristine views over the wilds of Cape Pogue and the outer harbor bring peace and serenity for all who visit. Fishing, clamming, swimming,

  Leslie C. Floyd Portfolio Real Estate, Inc.

  9 N Neck Rd, Edgartown, MA 02539
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  $12,000 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • House for Rent

  267 Great Plains Road Wt117, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Large spacious home with open concept living and dining area. This house has gorgeous hardwood floors throughout, separate media room, and loads of natural sunlight. It also features an exceptionally large master bedroom with en-suite bath, and private deck. There is

  Karen Overtoom Karen M. Overtoom R.E.

  267 Great Plains Road Wt117, West Tisbury, MA 02575
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  $1,595,000 Sold Jul 01, 2025

  10 Red Pony Rd, West Tisbury, MA 02568

  • 2 Beds
  • 1.5 Baths
  • 1,176 Sq Ft
  • Built 1998

  Last Sold Summary

  • $1,356/SF

  Current Estimated Value $1,626,116

  Last Listing Agent Lisa Da Silva Compass | Point B

  10 Red Pony Rd, West Tisbury, MA 02568
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  Est $2,344,422 Not Listed For Sale

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

  24 Pulpit Ln, Edgartown, MA 02539

  24 Pulpit Ln, Edgartown, MA 02539
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  $1,799,000

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

  7 Upper Meadow Ln, Oak Bluffs, MA 02557

  Meadowview Farms - Tucked at the end of a quiet cul-de-sac, this spacious Colonial offers more than 3,200 square feet of comfortable living space. This home is ideal for those who love to host lively gatherings while providing ample accommodations. Inside, you'll find four well-sized bedrooms and two and a half baths, including a generous primary suite with double walk-in closets and a private

  Lesley Heidt Sandpiper Realty Inc

  7 Upper Meadow Ln, Oak Bluffs, MA 02557
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  $14,500 total monthly price

  • 5 Beds
  • 5.5 Baths
  • 3,392 Sq Ft
  • House for Rent

  76 School House Lane Wt101, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!! An elegant, whimsical house full of color, quality and artistic touches. The grounds are sumptuous, nature at its apotheosis. There is gentle movement in the landscape with flowering trees and shrubs everywhere replete with a babbling brook flowing into a pond bordering the garden behind the house. The stonework is finely crafted with balanced proportions

  Karen Overtoom Karen M. Overtoom R.E.

  76 School House Lane Wt101, West Tisbury, MA 02575
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  $3,280,000 Sold Dec 30, 2024

  0 Chappaquiddick Rd, Edgartown, MA 02539

  • Land
  • 35.94 Acres
  • $91,263 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK

  0 Chappaquiddick Rd, Edgartown, MA 02539
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  Est $5,188,237 Not Listed For Sale

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

  62 S Water St, Edgartown, MA 02539

  62 S Water St, Edgartown, MA 02539
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  /29

  $1,200,000

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  34 Pine Ln, Vineyard Haven, MA 02568

  One level living! This ranch-style home has a great layout and some sweet, unexpected features. The living spaces are opened up to each other allowing the wall of sliders in the living room to flood the rooms with light - and these sliders give access out to the deck with serene views of the woodlands beyond; where Stoney Hill Path bounds the entire south side of the property. The primary suite

  Candy DaRosa Feiner Real Estate

  34 Pine Ln, Vineyard Haven, MA 02568
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  /22

  $3,000 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 2,703 Sq Ft
  • House for Rent

  41 Oak Lane Wt147, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Inside the front entrance is a large open living room with a comfortable L-shaped couch facing the floor to ceiling windows which look out onto the spacious tree lined back yard and a wall mounted flat screen television. Off the open concept living/dining room is a large

  Karen Overtoom Karen M. Overtoom R.E.

  41 Oak Lane Wt147, West Tisbury, MA 02575
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  $2,375,000 Sold Jul 01, 2025

  24 Smiths Way, Edgartown, MA 02539

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft
  • Built 1964

  Last Sold Summary

  • $970/SF
  • 0 Days On Market

  Current Estimated Value $2,472,147

  Last Listing Agent LINK Email Cache LINK

  24 Smiths Way, Edgartown, MA 02539
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  Est $3,790,555 Not Listed For Sale

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

  6 Beach Plum Way, Aquinnah, MA 02535

  6 Beach Plum Way, Aquinnah, MA 02535
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  $2,850,000

  • Land
  • 1.52 Acres
  • $1,875,000 per Acre

  39 Slough Cove Rd, Edgartown, MA 02539

  NEWLY LISTED | Build Your Katama Dream ✨Set in one of Martha's Vineyard's most sought-after locations, this newly created 1.5-acre parcel offers a rare opportunity to build your custom island retreat in the heart of Katama.Perfectly positioned near the pristine shores of South Beach, the level and conforming R60 lot provides endless potential for a main residence and an outdoor oasis

  Francine Agnoli The Agency Martha's Vineyard

  39 Slough Cove Rd, Edgartown, MA 02539
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  $10,800 total monthly price

  • 4 Beds
  • 2 Baths
  • 702 Sq Ft
  • House for Rent

  141 N Rd Ch202, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a

  Karen Overtoom Karen M. Overtoom R.E.

  141 N Rd Ch202, Chilmark, MA 02535
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  $600,000 Sold Jul 23, 2025

  84 12th St S, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 1978

  Last Sold Summary

  • $383/SF
  • 0 Days On Market

  Current Estimated Value $626,316

  Last Listing Agent LINK Email Cache LINK

  84 12th St S, Edgartown, MA 02539
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  Est $3,162,855 Not Listed For Sale

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

  5 Katama Dr, Edgartown, MA 02539

  5 Katama Dr, Edgartown, MA 02539
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  /13

  $1,495,000

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft

  47 E Chop Dr Unit 2, Oak Bluffs, MA 02568

  East Chop Water Front Luxury Condominium -- This 1-bedroom, waterfront condominium, ''Cottage City'', features outstanding water views of the harbor and sound beyond, a cozy propane fireplace and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 1st-floor unit includes new kitchen with Bosch appliances, living room with

  Perry Patterson MV Luxury Homes, LLC

  47 E Chop Dr Unit 2, Oak Bluffs, MA 02568
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  /21

  $13,000 total monthly price

  • 4 Beds
  • 3 Baths
  • 2,500 Sq Ft
  • House for Rent

  14 Pulpit Rock Rd, Oak Bluffs, MA 02557

  PRICES ARE WEEKLY NOT MONTHLY. Located in Waterview Farms, this four bedroom home features a private beach on Sengekontacket Pond, private dock access to Land Bank boat launch and several walking trails. Just minutes to Farm Neck Golf Course, beaches and town.

  Karen Overtoom Karen M. Overtoom R.E.

  14 Pulpit Rock Rd, Oak Bluffs, MA 02557
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  $1,750,000 Sold Jun 06, 2025

  97 Snake Hollow, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft
  • Built 1981

  Last Sold Summary

  • 11% Below List Price
  • $946/SF
  • 226 Days On Market

  Current Estimated Value $1,680,423

  Last Listing Agent Stephanie Roache Donnelly + Co.

  97 Snake Hollow, Vineyard Haven, MA 02568
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  Est $3,625,815 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,090 Sq Ft

  16 Mill St, Edgartown, MA 02539

  16 Mill St, Edgartown, MA 02539
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  $1,350,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,959 Sq Ft

  48 W Tisbury Rd, Edgartown, MA 02539

  This rare multi-family residence offers a unique investment opportunity or the perfect island retreat. Whether you're looking to generate rental income, host guests, or settle into island life, this 3 bedrooms, 3 bathrooms property checks all the boxes. With lots of bonus spaces, off-street parking, a cozy backyard, and expansion potential (pending town approval) this is a truly exceptional find.

  Mavis Francis eXp Realty

  48 W Tisbury Rd, Edgartown, MA 02539
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  $18,000 total monthly price

  • 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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  $1,150,000 Sold Jan 15, 2025

  1 Rock Pond Rd, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,818 Sq Ft
  • Built 1999

  Last Sold Summary

  • $633/SF
  • 0 Days On Market

  Current Estimated Value $1,178,762

  Last Listing Agent LINK Email Cache LINK

  1 Rock Pond Rd, Vineyard Haven, MA 02568
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  Est $1,895,168 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,200 Sq Ft

  2 Fishermans Knot Rd, Edgartown, MA 02539

  2 Fishermans Knot Rd, Edgartown, MA 02539
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  $1,090,000

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

  54 Towanticut Ave, Oak Bluffs, MA 02568

  Living is Easy in this 3-bedroom 2 bath air-conditioned Ranch located 1 mile from the Center of Oak Bluffs. Features include a spacious living room with a wood-burning fireplace, an updated kitchen with granite countertops and stainless-steel appliances. The dining area has sliders leading to a spacious deck and outdoor shower overlooking the yard space with plenty of room for gardens, pets or

  JoJo Lambert Island Home Realty Inc.

  54 Towanticut Ave, Oak Bluffs, MA 02568
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  /8

  $7,900 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 2,107 Sq Ft
  • House for Rent

  2 Paddock Cir, Chilmark, MA 02535

  Karen Overtoom Karen M. Overtoom R.E.

  2 Paddock Cir, Chilmark, MA 02535
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  $700,000 Sold Jun 30, 2025

  8 Baylies Way Unit 15.5, Edgartown, MA 02539

  • Land
  • 1.03 Acres
  • $679,612 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 0 Days On Market

  Last Listing Agent Wendy Harman Compass | Point B

  8 Baylies Way Unit 15.5, Edgartown, MA 02539
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  Est $2,117,156 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,552 Sq Ft

  22 Kitts Field Cir, Edgartown, MA 02539

  22 Kitts Field Cir, Edgartown, MA 02539

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