Dukes County, MA Homes

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  /23

  $1,099,000

  • 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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  /39

  $1,650,000 Sold Jan 07, 2025

  3 Danls Way, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 2,146 Sq Ft
  • Built 1982

  Last Sold Summary

  • 28% Below List Price
  • $769/SF
  • 202 Days On Market

  Current Estimated Value $1,815,727

  Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  3 Danls Way, Vineyard Haven, MA 02568
• 

  

  

  /40

  Est $2,290,495 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
• 

  

  

  /35

  $1,095,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,046 Sq Ft

  9 Sampson Ave, Edgartown, MA 02539

  INVESTORS, EMPLOYERS, FAMILIES! This is the best single family home value on Martha’s Vineyard at $535 per square foot, plus a 1280 square foot, oversize, two-car garage all on a 20,000 square foot lot! You'll love this convenient Edgartown home, centrally located on the tranquil island of Chappaquiddick. This low-maintenance, 3 bedroom, 2 bathroom, 2,046 square foot home, situated on almost a

  Lynn Buder Sandpiper Realty

  9 Sampson Ave, Edgartown, MA 02539
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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

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

  9 Grovedale Rd, Oak Bluffs, MA 02557
• 

  

  /37

  Est $1,960,769 Not Listed For Sale

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

  3 Duncan Close, Edgartown, MA 02539

  3 Duncan Close, Edgartown, MA 02539
• 

  

  /12

  $1,495,000

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

  33 Alyssa Ln, Vineyard Haven, MA 02568

  Country Living so close to Town! Lovely 3/4 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 Real Estate, Inc.

  33 Alyssa Ln, Vineyard Haven, MA 02568
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  /2

  $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

  Last Listing Agent LINK Email Cache LINK

  32 Pine St, Edgartown, MA 02539
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  /34

  Est $2,404,950 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
• 

  

  /20

  $749,900

  • Land
  • 1 Acre
  • $749,900 per Acre

  0 W End Rd Unit 1B, Gosnold, MA 02713

  A rare opportunity to build your Island dream retreat on an elevated 1 acre lot with water-views on picturesque Cuttyhunk Island! This buildable lot offers sweeping views and the perfect quiet setting to design your coastal getaway or inherit house plans already drawn up for the perfect fit. Enjoy the serenity of Island living surrounded by natural beauty, gentle sea breezes and panoramic vistas.

  Amanda Defazio William Raveis Real Estate & Home Services

  0 W End Rd Unit 1B, Gosnold, MA 02713
• 

  

  /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 $1,014,081

  Last Listing Agent Lynn Buder Sandpiper Realty Inc

  130 Wing Rd, Oak Bluffs, MA 02557
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  /29

  Est $4,175,061 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
• 

  

  /54

  $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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  /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
• 

  

  /8

  Not Listed For Sale

  • 2 Beds

  16 Forever Wild Way, Edgartown, MA 02539

  16 Forever Wild Way, Edgartown, MA 02539
• 

  

  /17

  $1,995,000

  • 2 Beds
  • 1 Bath
  • 802 Sq Ft

  47 E Chop Dr Unit 3, Oak Bluffs, MA 02568

  East Chop Water Front Luxury Condominiums -- This 2BR, waterfront condominium, the ''Highlands'', features outstanding water views of the harbor, the sound and the Cape beyond and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 2nd floor unit includes new kitchen with Bosch appliances, living and dining areas and a

  Perry Patterson MV Luxury Homes, LLC

  47 E Chop Dr Unit 3, Oak Bluffs, 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 $1,233,069

  Last Listing Agent Lisa Gilberto C McManus Realty Group

  46 Old Coach Rd, Vineyard Haven, MA 02568
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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
• 

  

  /30

  $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

  Alan Schweikert Ocean Park Realty Inc

  28 Barling Ave, Vineyard Haven, MA 02568
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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

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

  11 Flamingo Dr, Edgartown, MA 02539
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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
• 

  

  /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
• 

  

  /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 $953,949

  Last Listing Agent Lisa Lucier Anchor Realty of MV

  299 Franklin St, Vineyard Haven, MA 02568
• 

  

  /32

  Est $1,395,117 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
• 

  

  /27

  $19,900,000

  • 5 Beds
  • 7 Baths
  • 6,577 Sq Ft

  33 Boldwater Rd, Edgartown, MA 02539

  Exquisite Waterfront Retreat - A rare opportunity to purchase a meticulously crafted 5,600 square-foot stone main house and 900 square-foot stone guesthouse with pool in a naturalized wooded setting. This extraordinary compound redefines the conventions of traditional Vineyard architecture in the most charming and sophisticated of ways. The house was sited to offer views of Edgartown Great Pond

  Deb Hancock Hancock Real Estate

  33 Boldwater Rd, Edgartown, MA 02539
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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
• 

  

  /35

  Est $3,260,623 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
• 

  

  /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
• 

  

  /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 $1,161,794

  Last Listing Agent Carol Shore Donnelly + Co

  22 Briarwood Ln, Vineyard Haven, MA 02568
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  /42

  Est $4,016,153 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
• 

  

  /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
• 

  

  /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 $1,315,556

  Last Listing Agent Martha Smith C McManus Realty Group

  2 Boylston Dr, Edgartown, MA 02539
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  /35

  Est $2,069,424 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
• 

  

  /11

  $495,000

  • Land
  • 0.23 Acre
  • $2,152,174 per Acre

  0 Barnes Rd Unit 32400334, Oak Bluffs, MA 02557

  Located in the heart of Oak Bluffs, this land offering abuts a protected Town park and is within close proximity to the various public access points to the sandy shoreline of Lagoon Pond. With engineering in place for a 1 bedroom home, embrace the unique opportunity to build your own custom residence. Whether you envision a cozy cottage, a modern retreat, or a traditional island dwelling, the

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  0 Barnes Rd Unit 32400334, Oak Bluffs, MA 02557
• 

  

  /14

  $839,000 Sold Jan 31, 2025

  9 Leslies Ln, Oak Bluffs, MA 02557

  • 3 Beds
  • 1 Bath
  • 816 Sq Ft
  • Built 1974

  Last Sold Summary

  • 1% Below List Price
  • $1,028/SF
  • 70 Days On Market

  Current Estimated Value $900,692

  Last Listing Agent Michele Moore Island Real Estate

  9 Leslies Ln, Oak Bluffs, MA 02557
• 

  

  /18

  Est $1,190,146 Not Listed For Sale

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

  5 Windsor Dr, Edgartown, MA 02539

  5 Windsor Dr, 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
• 

  

  /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 $1,288,617

  Last Listing Agent Jennifer B. DaSilva Compass

  10 Eagles Nest, Edgartown, MA 02539
• 

  

  /41

  Est $2,008,761 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

Showing Results 361 - 400, Page 10 of 18