19,872

Dukes County, MA Homes

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  • /21

    $869,000

    • 1 Bed
    • 1 Bath
    • 797 Sq Ft

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

    In the heart of Downtown Oak Bluffs Restless Winds Unit #5 comes with an amazing roof top deck shared with only one other condo (unit #4). You're in the middle of it all with this great location, yet you have easy access to a private and peaceful deck overlooking the town of Oak Bluffs and the surrounding waters. This incredible space takes you to another level of relaxation and a birds eye view

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 544-0253

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
  • /29

    $64,000 Per Month

    • 4 Beds
    • 7 Baths
    • 3,600 Sq Ft
    • House for Rent

    385 Barnes Rd Ob534, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in

    Karen Overtoom Karen M. Overtoom R.E.

    385 Barnes Rd Ob534, Oak Bluffs, MA 02557
  • /27

    $1,070,000

    Sold Apr 17, 2026

    70 Carol Ln, Oak Bluffs, MA 02557

    • 2 Beds
    • 2.5 Baths
    • 1,500 Sq Ft
    • Built 1971

    Last Sold Summary

    • 14% Below List Price
    • $713/SF
    • 463 Days On Market

    Current Estimated Value $1,131,267

    Last Listing Agent Lisa Lucier Anchor Realty of Martha's Vineyard

    70 Carol Ln, Oak Bluffs, MA 02557
    • /3

      Est $1,558,471

      Not Listed For Sale

      18 Towanticut Ave, Oak Bluffs, MA 02557

      • 4 Beds
      • 2.5 Baths
      • 2,329 Sq Ft
      • Built 1989
      18 Towanticut Ave, Oak Bluffs, MA 02557

      Last Sold Summary

      • 4% Above List Price
      • $644/SF
      • 13 Days On Market
      • Last Sold Price $1,500,000
      • Apr 29, 2024

      Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.

  • /31

    $1,699,999

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    43 N Slope Ln, Chilmark, MA 02535

    Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha's Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring

    Agent Photo

    Barbara O'Hara

    North Star Real Estate, LLC

    (508) 850-0854

    43 N Slope Ln, Chilmark, MA 02535
  • /12

    $15,000 Per Month

    • 5 Beds
    • 6.5 Baths
    • 4,137 Sq Ft
    • House for Rent

    41 Naushon Rd Wt116, Aquinnah, MA 02575

    Stunning water views from this expansive beachfront estate in Makonikey off Lambert's Cove Rd. Enjoy the large living area with comfortable couches, floor to ceiling windows and french doors for seamless indoor to outdoor living and dining. There is a fully equipped kitchen. Some folks will enjoy the treadmill and elliptical while watching boats pass by or even play squash in the indoor squash

    Karen Overtoom Karen M. Overtoom R.E.

    41 Naushon Rd Wt116, Aquinnah, MA 02575
  • /42

    $1,300,000

    Sold Feb 13, 2026

    169 Clover Hill Dr, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,809 Sq Ft
    • Built 1977

    Last Sold Summary

    • 4% Below List Price
    • $719/SF
    • 9 Days On Market

    Current Estimated Value $1,321,749

    Last Listing Agent Stephanie Roache Donnelly + Co

    169 Clover Hill Dr, Vineyard Haven, MA 02568
    • /41

      Not Listed For Sale

      3A Magnolia Way, Edgartown, MA 02539

      • 4 Beds
      • 5 Baths
      • 2,150 Sq Ft
      • Built 2007
      3A Magnolia Way, Edgartown, MA 02539

      Last Sold Summary

      • $953/SF
      • 268 Days On Market
      • Last Sold Price $2,050,000
      • Mar 24, 2023

      Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

  • /6

    $1,125,000

    • Land
    • 10,018 Sq Ft
    • $4,891,304 per Acre

    15 Chapman La, Edgartown, MA 02539

    Opportunity Abounds - This conforming parcel offers a great opportunity to build with close proximity to Edgartown Village! This adjoining lot offers ability to connect to Town Water and Sewer creating the perfect setting for your custom dream home or next investment. Located just moments from shops, restaurants, parks, and everyday conveniences, this is a chance to enjoy all the benefits of

    Agent Photo

    Wendy Harman

    Compass

    (508) 625-9227

    15 Chapman La, Edgartown, MA 02539
  • /12

    $5,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,200 Sq Ft
    • House for Rent

    2 Fishermans Knot Rd Ed309 Unit 1, Edgartown, MA 02539

    THIS PROPERTY IS A WEEKLY VACATION RENTAL PROPERTY. The home’s timeless interior offers a sitting room with a wood-burning fireplace, a hallway opening to a large, bright, modern kitchen featuring a Viking range and large dining table. Ample counter space and a wall of built-ins are the perfect complement to family and friends that enjoy cooking together. A gas grill and outdoor seating are only

    Karen Overtoom Karen M. Overtoom R.E.

    2 Fishermans Knot Rd Ed309 Unit 1, Edgartown, MA 02539
  • /46

    $3,120,000

    Sold Sep 16, 2025

    140 Pond Rd, Vineyard Haven, MA 02568

    • 4 Beds
    • 3 Baths
    • 3,669 Sq Ft
    • Built 1993

    Last Sold Summary

    • 10% Below List Price
    • $850/SF
    • 84 Days On Market

    Current Estimated Value $3,739,883

    Last Listing Agent Jon Hartzband Martha's Vineyard Island-Wide Realty

    140 Pond Rd, Vineyard Haven, MA 02568
    • /16

      Not Listed For Sale

      38 N Water St Unit R-2, Edgartown, MA 02539

      • 2 Beds
      • 2 Baths
      • 795 Sq Ft
      • Built 1890
      38 N Water St Unit R-2, Edgartown, MA 02539

      Last Sold Summary

      • $315/SF
      • 8 Days On Market
      • Last Sold Price $250,500
      • Feb 03, 2015

      Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

  • /24

    $899,000

    • 2 Beds
    • 1 Bath
    • 990 Sq Ft

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

    In the heart of Downtown Oak Bluffs- Restless Winds Condominium Unit #4 comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a ships feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest bedroom, a tiled bathroom

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 546-9282

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
  • /33

    $22,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    2 Strikers Way Ch211, Chilmark, MA 02535

    SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable drip coffee maker with glass carafe. There is a coffee grinder provided in the

    Karen Overtoom Karen M. Overtoom R.E.

    2 Strikers Way Ch211, Chilmark, MA 02535
  • /3

    $105,000

    Sold Sep 05, 2025

    00 Eliot Ave Unit 17, Chilmark, MA 02535

    • Land
    • 30,492 Sq Ft
    • $150,000 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 29 Days On Market

    Last Listing Agent Julianna Flanders Flanders Real Estate

    00 Eliot Ave Unit 17, Chilmark, MA 02535
    • /2

      Est $2,575,443

      Not Listed For Sale

      28 Woodhaven Dr, Edgartown, MA 02539

      • 3 Beds
      • Built 2013
      28 Woodhaven Dr, Edgartown, MA 02539

      Last Sold Summary

      • 12% Above List Price
      • $662/SF
      • 6,292 Days On Market
      • Last Sold Price $2,300,000
      • Oct 13, 2021

      Last Listing Agent Stephanie Roache Donnelly + Co

  • /41

    $2,295,000

    • 4 Beds
    • 3.5 Baths
    • 3,016 Sq Ft

    3 Hidden Cove Rd, Oak Bluffs, MA 02557

    Hidden Cove Gem with Serene Pond Views And Coveted Water Access - Located in the desirable Hidden Cove enclave—a 65+ acre water-access community—this inviting contemporary home offers privacy and high-end finishes with direct access to Sengekontacket Pond and Nantucket Sound. Community amenities include a private boat dock, walking trails, pickleball and tennis, all near Oak Bluffs. The

    Agent Photo

    Wendy Harman

    Compass

    (508) 456-9911

    3 Hidden Cove Rd, Oak Bluffs, MA 02557
  • /20

    $20,000 Per Month

    • 3 Beds
    • 3 Baths
    • House for Rent

    40 Hidden Cove Rd, Oak Bluffs, MA 02557

    THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living room with views and bedrooms

    Karen Overtoom Karen M. Overtoom R.E.

    40 Hidden Cove Rd, Oak Bluffs, MA 02557
  • /2

    $10,189,494

    Sold Nov 03, 2025

    55 King Point Way, Edgartown, MA 02539

    • 4 Beds
    • 8 Baths
    • 9,900 Sq Ft
    • Built 2021

    Last Sold Summary

    • $1,029/SF
    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    55 King Point Way, Edgartown, MA 02539
    • /37

      Est $3,602,361

      Not Listed For Sale

      149 Litchfield Rd, Edgartown, MA 02539

      • 3 Beds
      • 5 Baths
      • 4,417 Sq Ft
      • Built 2011
      149 Litchfield Rd, Edgartown, MA 02539

      Last Sold Summary

      • 15% Above List Price
      • $711/SF
      • 12 Days On Market
      • Last Sold Price $3,140,000
      • Jun 17, 2024

      Last Listing Agent Peyton Wallace Compass

  • /34

    $3,350,000

    • 3 Beds
    • 4.5 Baths
    • 2,912 Sq Ft

    40 Edgewood Dr, Edgartown, MA 02539

    This is an excellent opportunity to own a beautiful crafted custom home set on over half an acre in a peaceful neighborhood just minutes from downtown Edgartown. The property offers striking curb appeal with stone walls, granite steps, professional landscaping, and ample parking, and it borders protected association land that will remain undeveloped. Inside, the home features three spacious

    Carol McManus C McManus Realty Group

    40 Edgewood Dr, Edgartown, MA 02539
  • /29

    $34,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,300 Sq Ft
    • House for Rent

    15 Loon Lane Ch203, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Modern 4 bedroom home completed in 2019, in Menemsha. Located on a quiet road with waterviews from the upstairs bedrooms also offers views of the famous Menemsha sunsets from the deck. Sustainably harvested flooring features silky smooth and buttery hard wood floors from

    Karen Overtoom Karen M. Overtoom R.E.

    15 Loon Lane Ch203, Chilmark, MA 02535
  • /30

    $1,550,000

    Sold Oct 16, 2025

    251 State Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,986 Sq Ft
    • Built 1986

    Last Sold Summary

    • 9% Below List Price
    • $780/SF
    • 114 Days On Market

    Current Estimated Value $1,608,294

    Last Listing Agent Meg Bodnar Tea Lane Associates

    251 State Rd, Vineyard Haven, MA 02568
    • /26

      Est $3,389,645

      Not Listed For Sale

      53 Pinehurst Rd, Edgartown, MA 02539

      • 4 Beds
      • 5.5 Baths
      • 3,916 Sq Ft
      • Built 2018
      53 Pinehurst Rd, Edgartown, MA 02539

      Last Sold Summary

      • 6% Below List Price
      • $916/SF
      • 50 Days On Market
      • Last Sold Price $3,589,000
      • Dec 16, 2024

      Last Listing Agent Michele Casavant Vineyard Village Realty

  • /33

    $3,150,000

    • 4 Beds
    • 3.5 Baths
    • 2,791 Sq Ft

    8 Atwood Cir, Edgartown, MA 02539

    This charming and historic home is ideally situated at the head of Atwood Circle, a private neighborhood just off Dunham Road, and only a short stroll to town. Recently renovated, the residence blends classic character with modern comfort. The main level features a spacious living room, a cozy den with fireplace, a dining area, and an updated kitchen—perfect for both everyday living and

    Gerrett Conover Landvest MV

    8 Atwood Cir, Edgartown, MA 02539
  • /26

    $50,000 Per Month

    • 4 Beds
    • 3 Baths
    • 3,237 Sq Ft
    • House for Rent

    29 Naushon Rd Wt142, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfortable single level 4 BR 3 bath home has central air and heat. Enjoy summer star-studded skies from your patio or through skylights in each bedroom.

    Karen Overtoom Karen M. Overtoom R.E.

    29 Naushon Rd Wt142, West Tisbury, MA 02575
  • /28

    $1,350,000

    Sold Nov 20, 2025

    16 Majors Cove Ln, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,965 Sq Ft
    • Built 1986

    Last Sold Summary

    • 26% Below List Price
    • $687/SF
    • 156 Days On Market

    Current Estimated Value $1,436,329

    Last Listing Agent Stephanie Roache Donnelly + Co

    16 Majors Cove Ln, Edgartown, MA 02539
    • /10

      Not Listed For Sale

      0 Bridle Path Rd, Vineyard Haven, MA 02568

      0 Bridle Path Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 17 Days On Market
      • Last Sold Price $885,000
      • Jun 29, 2023

      Last Listing Agent Diana Gilmore Island Real Estate

  • /48

    $3,950,000

    • 3 Beds
    • 4.5 Baths
    • 3,314 Sq Ft

    20 Edson Forrest Rd, West Tisbury, MA 02575

    Exquisite home befitting its stunning location on four serene acres surrounded by conservation and agricultural lands and overlooking a neighbor's private pond. This special spot is authentic up-island character at its best. A full restoration of this this three-bedroom house (with six-bedroom septic) in 2022 created a luxury home with a thoughtful layout, 2 story expansion, and exceptional

    Meg Bodnar Tea Lane Associates

    20 Edson Forrest Rd, West Tisbury, MA 02575
  • /22

    $20,000 Per Month

    • 5 Beds
    • 3 Baths
    • 3,000 Sq Ft
    • House for Rent

    55 Samoset Ave, Oak Bluffs, MA 02557

    Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Formal dining for eight. A/C, WIFI and

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    55 Samoset Ave, Oak Bluffs, MA 02557
  • /29

    $1,970,000

    Sold Jun 26, 2025

    493 Katama Rd Unit E2, Edgartown, MA 02539

    • 3 Beds
    • 2.5 Baths
    • 1,410 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Below List Price
    • $1,397/SF
    • 0 Days On Market

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

    493 Katama Rd Unit E2, Edgartown, MA 02539
    • /15

      Est $1,164,649

      Not Listed For Sale

      15 14th St N, Edgartown, MA 02539

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 2018
      15 14th St N, Edgartown, MA 02539

      Last Sold Summary

      • 19% Above List Price
      • $923/SF
      • 55 Days On Market
      • Last Sold Price $975,000
      • May 02, 2025

      Last Listing Agent Mike Sawyer Sawyer Realty Group

  • /36

    $5,325,000

    • 6 Beds
    • 4 Baths
    • 2,890 Sq Ft

    4 Canonicus Ave, Oak Bluffs, MA 02557

    Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    4 Canonicus Ave, Oak Bluffs, MA 02557
  • /20

    $16,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,638 Sq Ft
    • House for Rent

    31 S Ridge Rd Ch218, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and

    Karen Overtoom Karen M. Overtoom R.E.

    31 S Ridge Rd Ch218, Chilmark, MA 02535
  • /26

    $1,500,000

    Sold Mar 30, 2026

    68 20th St S, Edgartown, MA 02539

    • 4 Beds
    • 3 Baths
    • 1,975 Sq Ft
    • Built 1997

    Last Sold Summary

    • 6% Below List Price
    • $759/SF
    • 28 Days On Market

    Current Estimated Value $1,610,146

    Last Listing Agent Carol Shore Donnelly + Co

    68 20th St S, Edgartown, MA 02539
    • /38

      Est $1,020,600

      Not Listed For Sale

      287 County Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft
      • Built 1998
      287 County Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 20% Above List Price
      • $759/SF
      • 10 Days On Market
      • Last Sold Price $850,000
      • Dec 14, 2023

      Last Listing Agent Jill Napior Tea Lane Associates

  • /23

    $3,100,000

    • 1 Bed
    • 1 Bath
    • 1,250 Sq Ft

    114 Meeting House Way, Edgartown, MA 02539

    3 Acre Katama Building Lot with Existing Guest House. This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, substantial residences. Located one mile from Edgartown Great Pond and 2 miles from both South Beach

    Rose Ryley Wallace & Co. Sotheby's International Realty

    114 Meeting House Way, Edgartown, MA 02539
  • /21

    $9,500 Per Month

    • 4 Beds
    • 2 Baths
    • 1,579 Sq Ft
    • House for Rent

    155 Skiff Ave, Vineyard Haven, MA 02568

    **SUMMER RENTAL ONLY** PRICE IS WEEKLY** Enjoy the serenity of a four bedroom, two full bathroom peaceful oasis complete with private in-ground pool. Close to lively dining and boutiques of downtown Vineyard Haven. Unwind at neighborhood beaches; Eastville, Owen Park, Tashmoo beaches all just a few minutes drive from your vacation retreat.This lovely home spread over 1600ft of living area

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    155 Skiff Ave, Vineyard Haven, MA 02568
  • /2

    $3,300,000

    Sold Dec 09, 2025

    1 Muskoday Way, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 2,194 Sq Ft
    • Built 1972

    Last Sold Summary

    • $1,504/SF
    • 0 Days On Market

    Current Estimated Value $2,777,258

    Last Listing Agent LINK Email Cache LINK

    1 Muskoday Way, Edgartown, MA 02539
    • /26

      Est $1,529,549

      Not Listed For Sale

      19 Quantapog Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 3 Baths
      • 1,822 Sq Ft
      • Built 1988
      19 Quantapog Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 11% Above List Price
      • $757/SF
      • 177 Days On Market
      • Last Sold Price $1,380,000
      • Jan 23, 2014

      Last Listing Agent Leslie C. Floyd Portfolio Properties

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