Dukes County, MA Homes

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  /25

  $3,200,000

  • Land
  • 19.3 Acres
  • $165,803 per Acre

  32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575

  A Rare Offering in West Tisbury — Over 19 Acres of OpportunityAn exceptional opportunity to own just over 19 acres in the heart of rural West Tisbury. This expansive parcel offers tremendous flexibility, with potential for multiple dwellings or subdivision into a thoughtfully designed niche development. Ideally situated near all island towns, the property is also just minutes from the

  Jill Napior Tea Lane Associates

  32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
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  /22

  $1,000,000 Sold Jul 31, 2025

  130 Wing Rd, Oak Bluffs, MA 02557

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1960

  Last Sold Summary

  • 10% Below List Price
  • $1,302/SF
  • 96 Days On Market

  Current Estimated Value $995,317

  Last Listing Agent Lynn Buder Sandpiper Realty Inc

  130 Wing Rd, Oak Bluffs, MA 02557
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  /34

  Est $2,401,696 Not Listed For Sale

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

  338 Bigelow Rd, Vineyard Haven, MA 02568

  338 Bigelow Rd, Vineyard Haven, MA 02568
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  /33

  $925,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 987 Sq Ft

  1 Cottage Park, Oak Bluffs, MA 02557

  The Star Spangled Manor, a beautifully restored gem nestled in the heart of Oak Bluffs within the historic Martha's Vineyard Camp Meeting Association. Located on a pedestrian street, you'll be mere steps away from the shops and restaurants of Circuit Ave., Ocean Park, and the Oak Bluffs beaches. This cherished three-bedroom, three-bathroom cottage seamlessly blends vintage charm with modern

  Diana Gilmore Island Real Estate

  1 Cottage Park, Oak Bluffs, MA 02557
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  /33

  $2,637,500 Sold Dec 12, 2025

  36 Tashmoo Ave, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 2,770 Sq Ft
  • Built 1888

  Last Sold Summary

  • 20% Below List Price
  • $952/SF
  • 355 Days On Market

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

  36 Tashmoo Ave, Vineyard Haven, MA 02568
• 

  

  /29

  Est $4,135,370 Not Listed For Sale

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

  26 Morse St, Edgartown, MA 02539

  26 Morse St, Edgartown, MA 02539
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  /35

  $1,150,000

  • 3 Beds
  • 2 Baths
  • 1,328 Sq Ft

  96 Dunham Ave, Vineyard Haven, MA 02568

  This attractive colonial style home is located in a terrific neighborhood. Just a short distance to the center of town with nearly 1/2 acre of rolling treed land. The features include a cathedral ceiling over the kitchen and dining room. A large fireplace highlights the living room. From upstairs you can look over the balcony to the dining area and kitchen below. The first floor bedroom with has

  Peter Cronig Cronigs Real Estate

  96 Dunham Ave, Vineyard Haven, MA 02568
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  /20

  $1,150,000 Sold Jun 13, 2025

  46 Old Coach Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,374 Sq Ft
  • Built 1981

  Last Sold Summary

  • 10% Below List Price
  • $837/SF
  • 43 Days On Market

  Current Estimated Value $1,221,384

  Last Listing Agent Lisa Gilberto C McManus Realty Group

  46 Old Coach Rd, Vineyard Haven, MA 02568
• 

  

  /8

  Not Listed For Sale

  • 2 Beds

  16 Forever Wild Way, Edgartown, MA 02539

  16 Forever Wild Way, Edgartown, MA 02539
• 

  

  /21

  $2,725,000

  • Land
  • 7.6 Acres
  • $358,553 per Acre

  34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535

  This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience —

  Peyton Wallace Studio Realty

  34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
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  /28

  $1,260,000 Sold Nov 03, 2025

  11 Flamingo Dr, Edgartown, MA 02539

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft
  • Built 2002

  Last Sold Summary

  • 16% Below List Price
  • $692/SF
  • 182 Days On Market

  Current Estimated Value $1,283,253

  Last Listing Agent Skip Dostal, Jr Martha's Vineyard Real Estate

  11 Flamingo Dr, Edgartown, MA 02539
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  /12

  Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 2,892 Sq Ft

  9 Dunes Rd, Edgartown, MA 02539

  9 Dunes Rd, Edgartown, MA 02539
• 

  

  /20

  $640,000

  • 1 Bed
  • 1 Bath
  • 354 Sq Ft

  2 Lincoln Ave, Oak Bluffs, MA 02568

  Nestled in the heart of the historic Martha’s Vineyard Camp Meeting Association, this beautifully updated suite cottage offers the rare opportunity for year-round living in Oak Bluffs’ campground community. Fully renovated in 2023, including kitchen, bath, floors and winterization, the home seamlessly blends classic Vineyard charm with modern comfort — featuring upgraded systems and finishes that

  Stacy Ickes Donnelly + Co

  2 Lincoln Ave, Oak Bluffs, MA 02568
• 

  

  /17

  $929,000 Sold Aug 18, 2025

  299 Franklin St, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,286 Sq Ft
  • Built 1950

  Last Sold Summary

  • $722/SF
  • 6 Days On Market

  Current Estimated Value $959,559

  Last Listing Agent Lisa Lucier Anchor Realty of MV

  299 Franklin St, Vineyard Haven, MA 02568
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  /18

  Est $1,084,684 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1 Sq Ft

  10 Canterbury Ln, Vineyard Haven, MA 02568

  10 Canterbury Ln, Vineyard Haven, MA 02568
• 

  

  /14

  $685,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 782 Sq Ft

  10 Siloam Ave, Oak Bluffs, MA 02557

  The cottage has been maintained throughout the years, with a new roof in 2015, at which time it was insulated. The original Campground charm has been preserved thoughtfully. New mahogany boards are on front porch and a new paint job on the exterior of the cottage was done last year. The kitchen cabinets have been crafted by a master wood worker and there is a new kitchen floor and appliances.

  Elise LeBovit Gay Head Realty

  10 Siloam Ave, Oak Bluffs, MA 02557
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  /2

  $900,000 Sold Sep 17, 2025

  45 Quenames Rd Unit 30-02, Chilmark, MA 02535

  • Land
  • 3.05 Acres
  • $295,082 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 83 Days On Market

  Last Listing Agent Candy DaRosa Feiner Real Estate

  45 Quenames Rd Unit 30-02, Chilmark, MA 02535
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  /32

  Est $1,295,089 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,118 Sq Ft

  58 Hagerty Dr, Vineyard Haven, MA 02568

  58 Hagerty Dr, Vineyard Haven, MA 02568
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  /35

  $1,870,000 Pending

  • 5 Beds
  • 3 Baths
  • 2,432 Sq Ft

  32 Flamingo Dr, Edgartown, MA 02539

  This well-maintained country farmhouse is centrally located and is situated on just over one acre of land. A circular driveway welcomes you to the home with plenty of parking. There is a garden storage shed, irrigation system, playground, fire pit with outdoor seating, and wraparound covered porch. The rear entry door from the kitchen leads to the outdoor shower and spacious sunny deck. The first

  Skip Dostal Martha's Vineyard R.E.

  32 Flamingo Dr, Edgartown, MA 02539
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  /17

  $1,300,000 Sold Mar 03, 2025

  22 Briarwood Ln, Vineyard Haven, MA 02568

  • 2 Beds
  • 2 Baths
  • 1,241 Sq Ft
  • Built 2018

  Last Sold Summary

  • 4% Below List Price
  • $1,048/SF
  • 4 Days On Market

  Current Estimated Value $1,187,266

  Last Listing Agent Carol Shore Donnelly + Co

  22 Briarwood Ln, Vineyard Haven, MA 02568
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  /35

  Est $3,445,406 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,407 Sq Ft

  5 Hillman Dr, Edgartown, MA 02539

  5 Hillman Dr, Edgartown, MA 02539
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  /8

  $3,495,000

  • Land
  • 11.39 Acres
  • $306,848 per Acre

  0 Pocha Road Extension Unit 1.1,1.2 43325, 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

  Katie Donahue Sandpiper Realty

  0 Pocha Road Extension Unit 1.1,1.2 43325, Edgartown, MA 02539
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  /22

  $1,299,000 Sold Jun 25, 2025

  2 Boylston Dr, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1984

  Last Sold Summary

  • 13% Below List Price
  • $859/SF
  • 77 Days On Market

  Current Estimated Value $1,297,350

  Last Listing Agent Martha Smith C McManus Realty Group

  2 Boylston Dr, Edgartown, MA 02539
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  /42

  Est $4,196,204 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,467 Sq Ft

  8 Jennifer Way, Edgartown, MA 02539

  8 Jennifer Way, Edgartown, MA 02539
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  /15

  $1,495,000

  • Land
  • 3.01 Acres
  • $496,678 per Acre

  11 Beach Pebble Rd Unit 48.3, West Tisbury, MA 02568

  Over 3 acres in the West Tisbury section of Makonikey. This buildable lot is a short distance from the Lower Makonikey Association beach. The prime home site on this property was recently cleared to reveal beautifully contoured land with several ancient white oak trees. The property is situated in an area of several multimillion-dollar homes and will accommodate a house, a guesthouse, and a

  Cassie Courtney Wallace & Co. Sotheby's

  11 Beach Pebble Rd Unit 48.3, West Tisbury, MA 02568
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  /28

  $1,320,000 Sold Aug 29, 2025

  10 Eagles Nest, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • Built 1987

  Last Sold Summary

  • 5% Below List Price
  • $910/SF
  • 6 Days On Market

  Current Estimated Value $1,293,614

  Last Listing Agent Jennifer B. DaSilva Compass

  10 Eagles Nest, Edgartown, MA 02539
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  /35

  Est $2,049,197 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,995 Sq Ft

  159 Charles Neck Way, Vineyard Haven, MA 02568

  159 Charles Neck Way, Vineyard Haven, MA 02568
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  /6

  $4,800,000

  • 4 Beds
  • 4.5 Baths
  • 3,816 Sq Ft

  7 Marthas Rd, Edgartown, MA 02539

  Welcome to this coastal chic farmhouse set in the heart of Katama, a few blocks from the Field Club, close to SOUTH BEACH and close to Edgartown Village. To be built is a four bedroom en-suite home with a heated saltwater POOL. This home sits upon a flat, beautiful parcel of land with mature trees. The facade of the home offers an inviting covered porch with free standing columns, a granite entry

  Michele Casavant Vineyard Village Realty

  7 Marthas Rd, Edgartown, MA 02539
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  /2

  $60,000 Sold Jul 01, 2025

  0 North Rd Unit 40 43533, Aquinnah, MA 02535

  • Land
  • 0 Acre

  Last Sold Summary

  Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

  0 North Rd Unit 40 43533, Aquinnah, MA 02535
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  /18

  Est $1,171,874 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,038 Sq Ft

  5 Windsor Dr, Edgartown, MA 02539

  5 Windsor Dr, Edgartown, MA 02539
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  /63

  $2,999,000

  • 8 Beds
  • 7.5 Baths
  • 3,770 Sq Ft

  72 Chappaquiddick Ave, Edgartown, MA 02539

  WELCOME to this turn-key CHAPPY COMPOUND! This property offers it ALL, with its Six (6) Bedroom, Five (5) bath Primary Home, Two (2) bedroom, Two (2) bath GUEST HOUSE, expansive POOL HOUSE with a bath, kitchenette, large lounge area topped with a cathedral ceiling, a WORKOUT & GAME BARN, a POOL, a VOLLEY BALL COURT and a TENNIS and PICKLEBALL COURT that has recently been resurfaced with the

  Michele Casavant Vineyard Village Realty

  72 Chappaquiddick Ave, Edgartown, MA 02539
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  /37

  $2,100,000 Sold Aug 27, 2025

  42 Daggett Ave, Vineyard Haven, MA 02568

  • 3 Beds
  • 3.5 Baths
  • 3,310 Sq Ft
  • Built 2009

  Last Sold Summary

  • 4% Below List Price
  • $634/SF
  • 60 Days On Market

  Current Estimated Value $2,256,709

  Last Listing Agent Rene Jackson Island Real Estate

  42 Daggett Ave, Vineyard Haven, MA 02568
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  /41

  Est $1,992,398 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,803 Sq Ft

  7 Tar Barrel Rd, Aquinnah, MA 02535

  7 Tar Barrel Rd, Aquinnah, MA 02535
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  /50

  $1,900,000

  • 4 Beds
  • 3 Baths
  • 2,056 Sq Ft

  20 Brook Hollow Rd, Vineyard Haven, MA 02568

  This spacious custom designed home is well sited to offer maximum privacy in the lush area of Long View. A short bike ride to Lambert's Cove beach, it's also about a 20-minute walk down a quiet private road. The home lays out well for family and extended guests with a roomy living room boasting vaulted ceilings and large windows. The house is designed to have an intimate relationship with the

  Jim Feiner Feiner Real Estate

  20 Brook Hollow Rd, Vineyard Haven, MA 02568
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  /2

  $3,772,500 Sold May 29, 2025

  3 Tennis Ln, Chilmark, MA 02535

  • 4 Beds
  • 4.5 Baths
  • 3,234 Sq Ft
  • Built 1999

  Last Sold Summary

  • 3% Below List Price
  • $1,167/SF
  • 0 Days On Market

  Last Listing Agent Candy DaRosa Feiner Real Estate

  3 Tennis Ln, Chilmark, MA 02535
• 

  

  /22

  Est $1,125,796 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,025 Sq Ft

  10 Saddle Club Rd, Edgartown, MA 02539

  10 Saddle Club Rd, Edgartown, MA 02539
• 

  

  /20

  $1,300,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,566 Sq Ft

  344 Greenwood Ave, Vineyard Haven, MA 02568

  This move-in ready four-bedroom, being offered fully furnished, delivers effortless living, simply bring your swimsuit and settle in. Featuring an open and inviting layout, the living space seamlessly extends to the large deck and heated pool, perfect for relaxing or entertaining. Conveniently located just one mile from the shops and restaurants of downtown Vineyard Haven and less than two miles

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  344 Greenwood Ave, Vineyard Haven, MA 02568
• 

  

  /9

  $1,500,000 Sold Oct 20, 2025

  49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535

  • Land
  • 3.9 Acres
  • $384,615 per Acre

  Last Sold Summary

  Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

  49 Cobbs Hill Rd Unit 24.3, Chilmark, MA 02535
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  /32

  Est $1,153,337 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,429 Sq Ft

  10 Elm St, Vineyard Haven, MA 02568

  10 Elm St, Vineyard Haven, MA 02568
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  /5

  $1,100,000

  • Land
  • 1 Acre
  • $1,102,204 per Acre

  25 Coffins Field Rd Unit 18, Edgartown, MA 02539

  One acre lot situated in a peaceful, centrally located neighborhood. The parcel will support 3-bedrooms and offers privacy by abutting conservation land, convenience to town and beaches and access to bike paths, public gym, veterinarian, shopping, airport and restaurants.

  Casandra Hyland Sandpiper Realty

  25 Coffins Field Rd Unit 18, Edgartown, MA 02539

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