Dukes County, MA Homes

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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 -- This home is ideal for those who love to host lively gatherings! Set at the end of a quiet cul-de-sac, this spacious Colonial offers over 3,200 sq ft designed for comfortable living and easy entertaining. The home features four bedrooms and 2.5 baths, including a primary suite with walk-in closets and private bath. The main living area flows from a living room with fireplace

  Lesley Heidt Sandpiper Realty Inc

  7 Upper Meadow Ln, Oak Bluffs, MA 02557
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  $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
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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 $1,633,982

  Last Listing Agent Lisa Da Silva Compass | Point B

  10 Red Pony Rd, West Tisbury, MA 02568
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  Est $2,262,916 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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  $1,200,000 Pending

  • 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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  $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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  $2,401,000 Sold Jan 06, 2026

  46 Bold Meadow Rd, Edgartown, MA 02539

  • 4 Beds
  • 3.5 Baths
  • 2,372 Sq Ft
  • Built 1992

  Last Sold Summary

  • $1,012/SF
  • 14 Days On Market

  Last Listing Agent Julianna Flanders Flanders Real Estate

  46 Bold Meadow Rd, Edgartown, MA 02539
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  Est $5,112,315 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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  $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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  $10,000 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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  $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 $2,460,464

  Last Listing Agent LINK Email Cache LINK

  24 Smiths Way, Edgartown, MA 02539
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  Est $3,889,960 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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  $1,099,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,306 Sq Ft

  113 Leonard Cir, Vineyard Haven, MA 02568

  This charming four-bedroom Cape features an updated, open-concept design seamlessly connecting the living, kitchen, and dining areas. The first floor includes a bright, well-lit bedroom and an updated shared bathroom. Upstairs, the three additional bedrooms boast soaring cathedral ceilings that maximize natural light, creating a bright and cheerful atmosphere. A shared bath with a shower and

  Alyson Parker Karen M. Overtoom R.E.

  113 Leonard Cir, Vineyard Haven, MA 02568
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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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  $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 $626,416

  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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  $1,495,000

  • 4 Beds
  • 4 Baths
  • 2,304 Sq Ft

  33 Alyssa Ln, Vineyard Haven, MA 02568

  Country Living so close to Town! Lovely 4 Bedroom 2,304sq ft. Colonial Cape perched on a rise on Alyssa Lane off West Spring Street. Open Kitchen with handcrafted side cabinets and Island with stool seating. Dining, sitting, entertainment area with sliders open to a generous front to back side deck. Living room with propane fired wood stove and half bath also on the first floor. Interior stairs

  Stephanie Burke Portfolio Properties

  33 Alyssa Ln, Vineyard Haven, MA 02568
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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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  $1,750,000 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 $1,659,585

  Last Listing Agent Stephanie Roache Donnelly + Co.

  97 Snake Hollow, Vineyard Haven, MA 02568
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  Est $3,507,531 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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  $3,495,000

  • Land
  • 11.49 Acres
  • $304,178 per Acre

  0 Pocha Rd, Edgartown, MA 02539

  CHAPPAQUIDDICK -Dynamic views of Poucha Pond, barrier dunes, and the waters of the Atlantic are enjoyed from this 11+ acre building lot. The close to 1⁄2 mile of private pond frontage provides easy access for swimming, kayaking, paddle boarding and everything in between. Sheltered amongst 200 acres of conservation land, enjoy and explore the wonders of the natural habitat right in your backyard.

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  0 Pocha Rd, Edgartown, MA 02539
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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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  $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 $1,201,608 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,901 Sq Ft

  19 Renear St, Vineyard Haven, MA 02568

  19 Renear St, Vineyard Haven, MA 02568
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  $1,830,000

  • 4 Beds
  • 4 Baths
  • 1,600 Sq Ft

  12 & 14 Maple Ave, Oak Bluffs, MA 02557

  Two Historic Oak Bluffs Cottages - Prime Location - Deeded Separately Perched atop a gentle hill, surrounded by lush, established gardens in one of the island's most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history--just a short distance to the harbor, downtown, and the beloved Winston's takeout. Built at a time when automobiles

  Leslie Floyd Portfolio Properties

  12 & 14 Maple Ave, Oak Bluffs, MA 02557
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  $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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  $1,200,000 Sold Jan 22, 2026

  58 Marthas Rd Unit 70, Edgartown, MA 02539

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

  Last Sold Summary

  • 8% Below List Price
  • 179 Days On Market

  Last Listing Agent Katie Donahue Sandpiper Realty

  58 Marthas Rd Unit 70, Edgartown, MA 02539
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  Est $1,901,794 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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  $1,100,000

  • Land
  • 1 Acre
  • $1,100,000 per Acre

  25 Coffins Field Rd, Edgartown, MA 02539

  Per the BOH, this property can accommodate a 3 bedroom home and with appropriate permitting may allow for an additional/separate structure such as a garage or studioProperty is not serviced by a well or septic system. Buyer is responsible for obtaining permits and installation.Association Dues $650.00

  Casandra Hyland Sandpiper Realty, Inc.

  25 Coffins Field 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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  $1,226,500 Sold Oct 16, 2025

  9 Grovedale Rd, Oak Bluffs, MA 02557

  • 3 Beds
  • 2 Baths
  • 1,637 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Above List Price
  • $749/SF
  • 6 Days On Market

  Current Estimated Value $1,224,371

  Last Listing Agent Bonnie Pierce Wallace & Co. Sotheby's International Realty

  9 Grovedale Rd, Oak Bluffs, MA 02557
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  Est $2,259,026 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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  $999,000

  • 2 Beds
  • 1 Bath
  • 1,232 Sq Ft

  28 Barling Ave, Vineyard Haven, MA 02568

  Oak Bluffs: Home Sweet HomeSituated on over a quarter acre of beautifully landscaped, level grounds with colorful perennial plantings and mature trees, this sun-filled ranch offers a perfect blend of comfort and charm. The open kitchen, dining, and living areas feature cathedral ceilings, classic vertical knotty pine walls, and a cozy brick fireplace. Enjoy a convenient first-floor bedroom

  Michael Schweikert Ocean Park Realty Inc

  28 Barling Ave, Vineyard Haven, MA 02568
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  $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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  $1,000,000 Sold Oct 21, 2025

  32 Pine St, Edgartown, MA 02539

  • 3 Beds
  • 1 Bath
  • 979 Sq Ft
  • Built 1940

  Last Sold Summary

  • $1,021/SF
  • 0 Days On Market

  Current Estimated Value $1,081,945

  Last Listing Agent LINK Email Cache LINK

  32 Pine St, Edgartown, MA 02539
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  Est $2,264,844 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,008 Sq Ft

  1 Old Squaw Cir, Edgartown, MA 02539

  1 Old Squaw Cir, Edgartown, MA 02539
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  $12,500,000

  • Land
  • 38 Acres
  • $328,947 per Acre

  2 Old Farms Trail Unit 1, Edgartown, MA 02539

  Thirty-eight (38 acres) of available land in Edgartown! This is a truly extraordinary and increasingly rare opportunity to own thirty-eight (38) acres of contiguous land in Edgartown. Come create a landmark estate or private compound in one of Edgartown’s most sought-after locations. Perfectly positioned between the charm of Edgartown Historic Village and the sweeping sands of South Beach and

  Michele Casavant Vineyard Village Realty

  2 Old Farms Trail Unit 1, Edgartown, MA 02539
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  $112,000 total monthly price

  • 6 Beds
  • 9 Baths
  • 5,732 Sq Ft
  • House for Rent

  31 Lamberts Cove Road Vh434, Tisbury, MA 02568

  Karen Overtoom Karen M. Overtoom R.E.

  31 Lamberts Cove Road Vh434, Tisbury, MA 02568
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  $1,160,000 Sold Jan 05, 2026

  208 Irenes Way, Tisbury, MA 02568

  • 4 Beds
  • 3 Baths
  • 2,961 Sq Ft
  • Built 2005

  Last Sold Summary

  • 24% Below List Price
  • $392/SF
  • 168 Days On Market

  Last Listing Agent Emma Kiley Bryant Landmarks at TODAY Real Estate

  208 Irenes Way, Tisbury, MA 02568
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  Est $1,920,577 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,668 Sq Ft

  3 Duncan Close, Edgartown, MA 02539

  3 Duncan Close, Edgartown, MA 02539

Showing Results 321 - 360, Page 9 of 18