Dukes County, MA Homes

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  /17

  $725,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  181 Circuit Ave, Oak Bluffs, MA 02557

  Location, location, location!! This chic, turnkey cottage has been completely renovated! Park your car, drop your bags and walk to everything - beaches, shops, restaurants, parks and the ferry! Enjoy the front deck, backyard patio or saunter across to Veira Park. Perfect family getaway or a great investment property with strong rental income history! Enjoy this adorable home all year around!

  Jennifer B. DaSilva Compass

  181 Circuit Ave, Oak Bluffs, MA 02557
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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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  /30

  $830,000 Sold Mar 24, 2026

  12 Beach Plum Path, East Falmouth, MA 02536

  • 3 Beds
  • 2.5 Baths
  • 2,679 Sq Ft
  • Built 2021

  Last Sold Summary

  • 1% Below List Price
  • $310/SF
  • 101 Days On Market

  Last Listing Agent Pamela Heylin Berkshire Hathaway HomeServices Robert Paul Properties

  12 Beach Plum Path, East Falmouth, MA 02536
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  /34

  Est $4,565,089 Not Listed For Sale

  25 Down Harbor Rd, Edgartown, MA 02539

  • 4 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • Built 1972

  25 Down Harbor Rd, Edgartown, MA 02539

  Last Sold Summary

  • 17% Below List Price
  • $3,183/SF
  • 107 Days On Market

  Last Sold Price $5,500,000

  Last Listing Agent Wendy Harman Compass
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  /7

  $400,000 Pending

  • Land
  • 0.2 Acre
  • $2,000,000 per Acre

  99 Cygnet Way Unit 103, Chilmark, MA 02535

  Escape the crowds at Lucy Vincent and Squibnocket and take advantage of this very rare opportunity to own a private, 17 member, Atlantic Ocean beach lot at Thumb Cove (abuts Hancock Beach). Included in the sale of this property is a deeded .2 acres of sandy beach, a deeded parking spot at Chilmark Pond and the right to launch boats from a dock in the pond. Sail, kayak, row, swim(!) or motor

  Russell Maloney Russell Maloney Real Estate

  99 Cygnet Way Unit 103, Chilmark, MA 02535
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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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  /2

  $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 $1,590,391

  Last Listing Agent Lisa Da Silva Compass | Point B

  10 Red Pony Rd, West Tisbury, MA 02568
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  /42

  Est $3,431,545 Not Listed For Sale

  16 Mill St, Edgartown, MA 02539

  • 4 Beds
  • 4 Baths
  • 2,090 Sq Ft
  • Built 1908

  16 Mill St, Edgartown, MA 02539

  Last Sold Summary

  • 7% Above List Price
  • $1,531/SF
  • 120 Days On Market

  Last Sold Price $3,200,000

  Last Listing Agent Wendy Harman Compass | Point B
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  /3

  $857,000

  • Land
  • 0.39 Acre
  • $2,209,902 per Acre

  24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568

  OAK BLUFFS - A Rare Opportunity to purchase an Eight (8) Bedroom lot. This already cleared, oversized lot, 16,895sq.ft., (more than 1/3 acre) comes with an Approved Eight (8) Bedroom Septic Design, ready to build. Exceptional potential for a spacious custom home, family compound, or a rental property. Utilities are available by the lot, which significantly reduces development costs and time.

  Alisan Lohan-Conway Alisan Lohan-Conway Properties

  24 Towanticut Ave Unit 188, Oak Bluffs, MA 02568
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  /39

  $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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  /28

  $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

  Current Estimated Value $2,264,342

  Last Listing Agent Julianna Flanders Flanders Real Estate

  46 Bold Meadow Rd, Edgartown, MA 02539
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  /30

  Est $1,301,244 Not Listed For Sale

  19 Renear St, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 1,901 Sq Ft
  • Built 1985

  19 Renear St, Vineyard Haven, MA 02568

  Last Sold Summary

  • 16% Above List Price
  • $592/SF
  • 109 Days On Market

  Last Sold Price $1,125,000

  Last Listing Agent Michael Schweikert Ocean Park Realty, Inc.
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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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  /34

  $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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  /2

  $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 $2,420,211

  Last Listing Agent LINK Email Cache LINK

  24 Smiths Way, Edgartown, MA 02539
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  Est $1,848,571 Not Listed For Sale

  2 Fishermans Knot Rd, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • Built 1986

  2 Fishermans Knot Rd, Edgartown, MA 02539

  Last Sold Summary

  • 16% Above List Price
  • $727/SF
  • 0 Days On Market

  Last Sold Price $1,600,000

  Last Listing Agent Candy DaRosa Feiner Real Estate
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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 Properties

  9 N Neck 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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  /10

  $4,895,000 Sold Feb 13, 2026

  64 Crowell Ln, Tisbury, MA 02568

  • 5 Beds
  • 6.5 Baths
  • 4,216 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $1,161/SF
  • 307 Days On Market

  Current Estimated Value $2,576,333

  Last Listing Agent Joe & Nicole Holland Vineyard Dream Realty LLC

  64 Crowell Ln, Tisbury, MA 02568
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  /29

  Est $2,197,012 Not Listed For Sale

  22 Kitts Field Cir, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,552 Sq Ft
  • Built 1986

  22 Kitts Field Cir, Edgartown, MA 02539

  Last Sold Summary

  • 5% Above List Price
  • $1,353/SF
  • 11 Days On Market

  Last Sold Price $2,100,000

  Last Listing Agent Wendy Harman Compass
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  /41

  $1,800,000

  • 4 Beds
  • 3 Baths
  • 1 Sq Ft

  18 Wood Duck Way, Edgartown, MA 02539

  Turnkey modern home with 4 bedrooms and 3 full baths, filled with natural light from large windows and soaring ceilings. The first floor offers three bedrooms and a full bath with double sinks, while warm oak and maple floors are accented by cherry stairs and custom built-ins.The open-concept second level features a spacious kitchen, living, and dining area, along with a private primary en suite

  Janna O'Loughlin Portfolio Properties

  18 Wood Duck Way, Edgartown, MA 02539
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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

  $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 $635,734

  Last Listing Agent LINK Email Cache LINK

  84 12th St S, Edgartown, MA 02539
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  /40

  Est $2,192,934 Not Listed For Sale

  1 Old Squaw Cir, Edgartown, MA 02539

  • 4 Beds
  • 2.5 Baths
  • 2,008 Sq Ft
  • Built 1996

  1 Old Squaw Cir, Edgartown, MA 02539

  Last Sold Summary

  • 3% Above List Price
  • $1,058/SF
  • 52 Days On Market

  Last Sold Price $2,125,000

  Last Listing Agent Grace Bishop Compass
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  /28

  $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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  /9

  $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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  /31

  $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 $1,640,149

  Last Listing Agent Stephanie Roache Donnelly + Co.

  97 Snake Hollow, Vineyard Haven, MA 02568
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  Est $4,921,178 Not Listed For Sale

  5 Armstrong Ln, Edgartown, MA 02539

  • 3 Beds
  • 3.5 Baths
  • 4,084 Sq Ft
  • Built 2005

  5 Armstrong Ln, Edgartown, MA 02539

  Last Sold Summary

  • 6% Above List Price
  • $1,139/SF
  • 572 Days On Market

  Last Sold Price $4,650,000

  Last Listing Agent Thomas Leclair Landvest MV
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  /5

  $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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  /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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  /2

  $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 $1,872,748 Not Listed For Sale

  3 Duncan Close, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,668 Sq Ft
  • Built 1979

  3 Duncan Close, Edgartown, MA 02539

  Last Sold Summary

  • 1% Above List Price
  • $1,115/SF
  • 353 Days On Market

  Last Sold Price $1,860,000

  Last Listing Agent Wendy Harman Compass | Point B
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  /23

  $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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  /35

  $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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  /5

  $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 $2,274,925 Not Listed For Sale

  338 Bigelow Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 1,783 Sq Ft
  • Built 1978

  338 Bigelow Rd, Vineyard Haven, MA 02568

  Last Sold Summary

  • 1% Above List Price
  • $1,262/SF
  • 68 Days On Market

  Last Sold Price $2,250,000

  Last Listing Agent Emily Flake Viewpoints; Bobbi Flake Reed, Inc.
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  /12

  $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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  /30

  $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 $1,214,456

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

  9 Grovedale Rd, Oak Bluffs, MA 02557
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  /29

  Est $4,079,201 Not Listed For Sale

  26 Morse St, Edgartown, MA 02539

  • 4 Beds
  • 2.5 Baths
  • 2,408 Sq Ft
  • Built 2016

  26 Morse St, Edgartown, MA 02539

  Last Sold Summary

  • 7% Above List Price
  • $1,578/SF
  • 86 Days On Market

  Last Sold Price $3,800,000

  Last Listing Agent Stephanie Burke Portfolio Properties
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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

Showing Results 321 - 360, Page 9 of 18