Dukes County, MA Homes

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  /23

  $4,288,000

  • 7 Beds
  • 3.5 Baths
  • 2,461 Sq Ft

  69 School St, Edgartown, MA 02539

  Located in the heart of Edgartown Village, this circa 1840 Greek Revival residence offers a rare opportunity to own a piece of island history on a coveted block. The property features a total of seven bedrooms across the main house and carriage house, making it a superb destination for family and guests. The main house features wide plank hardwood flooring and bright and sunny spaces with five

  Peyton Wallace Studio Realty

  69 School St, Edgartown, MA 02539
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  /12

  $6,180 total monthly price

  • 3 Beds
  • 3.5 Baths
  • 1,872 Sq Ft
  • House for Rent

  44 Music St Wt153, West Tisbury, MA 02575

  PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

  Karen Overtoom Karen M. Overtoom R.E.

  44 Music St Wt153, West Tisbury, MA 02575
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  /34

  $8,250,000 Sold Feb 21, 2025

  93 Edgartown Bay Rd, Edgartown, MA 02539

  • 4 Beds
  • 4.5 Baths
  • 3,596 Sq Ft
  • Built 1978

  Last Sold Summary

  • 7% Below List Price
  • $2,294/SF
  • 95 Days On Market

  Current Estimated Value $8,631,934

  Last Listing Agent Jarrett Hurwitz Keller Williams Realty

  93 Edgartown Bay Rd, Edgartown, MA 02539
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  /25

  Est $2,110,942 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,636 Sq Ft

  131 Shubael Weeks Path, Vineyard Haven, MA 02568

  131 Shubael Weeks Path, Vineyard Haven, MA 02568
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  /4

  $625,000

  • Land
  • 0.34 Acre
  • $1,815,277 per Acre

  0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

  Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

  Andrew McElhinney Compass LLC

  0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
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  /12

  $15,000 total monthly price

  • 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
• 

  

  /19

  $1,110,000 Sold May 08, 2025

  31 9th St N, Edgartown, MA 02539

  • 2 Beds
  • 1.5 Baths
  • 1,275 Sq Ft
  • Built 1972

  Last Sold Summary

  • 7% Below List Price
  • $871/SF
  • 45 Days On Market

  Current Estimated Value $1,137,743

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

  31 9th St N, Edgartown, MA 02539
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  /2

  Est $1,809,965 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,102 Sq Ft

  26 Old Coach Rd, Vineyard Haven, MA 02568

  26 Old Coach Rd, Vineyard Haven, MA 02568
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  /43

  $4,999,000

  • 6 Beds
  • 5.5 Baths
  • 3,214 Sq Ft

  15 Tamarack Ln, Oak Bluffs, MA 02557

  FARM NECK: The original 1780 Farm House was tastefully restored in 1985 to honor the land and legacy of Farm Neck. This serene 3.7 acre oasis of rolling greenery with a variety of mature trees and lots of natural privacy has an up Island feel with the down Island convenience to fine dining, shopping, ferry, airport, bike paths and includes Stockholder Membership in the popular Farm Neck Golf

  Michael Schweikert Ocean Park Realty, Inc.

  15 Tamarack Ln, Oak Bluffs, MA 02557
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  /11

  $20,000 total monthly price

  • 4 Beds
  • 4.5 Baths
  • 2,306 Sq Ft
  • House for Rent

  3 E Pasture Ln, Aquinnah, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Breathtaking water views from this contemporary home located on Menemsha Pond and recently renovated with new kitchen and baths. This four bedroom retreat offers the perfect place to come during the summer months or even enjoy during the shoulder season while sitting by the fire with a warm cup of your favorite hot beverage. PLEASE TAKE NOTE!!!!!THIS IS

  Karen Overtoom Karen M. Overtoom R.E.

  3 E Pasture Ln, Aquinnah, MA 02535
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  /29

  $1,350,000 Sold Apr 18, 2025

  87 Schoolhouse Rd, Edgartown, MA 02539

  • 2 Beds
  • 2.5 Baths
  • 1,119 Sq Ft
  • Built 1983

  Last Sold Summary

  • 16% Below List Price
  • $1,206/SF
  • 123 Days On Market

  Current Estimated Value $1,415,233

  Last Listing Agent Stephanie Roache Donnelly + Co

  87 Schoolhouse Rd, Edgartown, MA 02539
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  /45

  Est $1,801,795 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,576 Sq Ft

  38 Edgewood Dr, Edgartown, MA 02539

  38 Edgewood Dr, Edgartown, MA 02539
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  /27

  $1,630,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 4,032 Sq Ft

  36 Ferro Way, Tisbury, MA 02568

  Welcome to 36 Ferro Way in beautiful Tisbury, MA! This stunning Colonial-style home, built in 2020, is where classic charm meets modern comfort. As you step onto the inviting farmer’s porch, you can immediately feel the warmth this home exudes.Inside, spread out across 4,032 square feet of well-designed space, you'll find five spacious bedrooms and three and a half bathrooms. The main floor

  Hope O'Brien Compass LLC

  36 Ferro Way, Tisbury, MA 02568
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  /8

  $8,250 total monthly price

  • 7 Beds
  • 5 Baths
  • 3,528 Sq Ft
  • House for Rent

  227 S Gate Rd Wt120, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through open

  Karen Overtoom Karen M. Overtoom R.E.

  227 S Gate Rd Wt120, West Tisbury, MA 02575
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  /12

  $37,500,000 Sold Oct 30, 2025

  48 Witchwood Ln, Edgartown, MA 02539

  • 9 Beds
  • 9.5 Baths
  • 16,209 Sq Ft
  • Built 2000

  Last Sold Summary

  • $2,314/SF
  • 0 Days On Market

  Last Listing Agent Gerrett Conover Landvest MV

  48 Witchwood Ln, Edgartown, MA 02539
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  /41

  Est $2,666,431 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,704 Sq Ft

  53 Peases Point Way N, Edgartown, MA 02539

  53 Peases Point Way N, Edgartown, MA 02539
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  /18

  $4,200,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,715 Sq Ft

  1 Wilsons Ln, Edgartown, MA 02539

  Welcome to this NEWLY CONSTRUCTED gorgeous gambrel home with a POOL that is close to SOUTH BEACH and EDGARTOWN VILLAGE! This home sits upon a flat, beautiful parcel of land with mature trees. The facade of the home presents an inviting covered porch with free standing columns, a granite entry step, mahogany decking and shiplapped ceiling. Attention to architectural detail presents at moment one.

  Michele Casavant Vineyard Village Realty

  1 Wilsons Ln, Edgartown, MA 02539
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  /8

  $18,500 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 1,714 Sq Ft
  • House for Rent

  4 Windy Way Wt143, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! The 3.3 acre private setting is most picturesque with its positioning in private Upper Makonikey , the long circular driveway , its grassy lawn, and rolling landscape fields . Only a short distance away is over 3,000 feet of PRIVATE sandy association Beaches , directly below , with two nearby parking lot access-ways . Nestled onto this promontory is a

  Karen Overtoom Karen M. Overtoom R.E.

  4 Windy Way Wt143, West Tisbury, MA 02575
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  /31

  $1,325,000 Sold Jun 30, 2025

  191 Spring Hill Rd, Vineyard Haven, MA 02568

  • 5 Beds
  • 4 Baths
  • 2,292 Sq Ft
  • Built 1992

  Last Sold Summary

  • 5% Below List Price
  • $578/SF
  • 10 Days On Market

  Current Estimated Value $1,272,229

  Last Listing Agent Madelyn Silvia Wallace & Co. Sotheby's

  191 Spring Hill Rd, Vineyard Haven, MA 02568
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  /38

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,328 Sq Ft

  56 Pinehurst Rd, Edgartown, MA 02539

  56 Pinehurst Rd, Edgartown, MA 02539
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  /29

  $1,725,000 Under Contract

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

  654 Lighthouse Rd, Aquinnah, MA 02535

  Waterview beach house in Aquinnah. Just a short deeded walking path to the calm and sandy shores of the North Shore. The traditional layout features the kitchen, living room, dining room, and a full bath on the first floor. The living room offers water views, a cozy fireplace, and multiple sliding doors leading out to the wrap-around porch. Upstairs, the views are even more stunning! There are

  Heidi Vanderhoop Tea Lane Associates

  654 Lighthouse Rd, Aquinnah, MA 02535
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  /8

  $4,500 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • House for Rent

  33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535

  THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

  Karen Overtoom Karen M. Overtoom R.E.

  33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
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  /26

  $1,600,000 Sold Nov 07, 2025

  96 Pondview Dr, Oak Bluffs, MA 02536

  • 4 Beds
  • 2.5 Baths
  • 2,115 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $757/SF
  • 35 Days On Market

  Last Listing Agent Doug Burke Cronigs Real Estate

  96 Pondview Dr, Oak Bluffs, MA 02536
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  /79

  Not Listed For Sale

  • 6 Beds
  • 2.5 Baths
  • 2,604 Sq Ft

  260 South Rd, Chilmark, MA 02535

  260 South Rd, Chilmark, MA 02535
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  /9

  $2,450,000

  • Land
  • 5.37 Acres
  • $456,238 per Acre

  9 Maqua Way, Edgartown, MA 02539

  Chappaquiddick: Beautiful 5-acre parcel offering private frontage on Katama Bay. The generous-sized lot affords plenty of development flexibility, with the ability to capture the view from nearly any location. Located on Maqua Way, a quiet subdivision just off the paved road, the property is conveniently situated near all the Chappy favorites: beaches, trails, a community center, and Slip Away

  Katherine Donahue Sandpiper Realty Inc

  9 Maqua Way, Edgartown, MA 02539
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  /8

  $19,000 total monthly price

  • 5 Beds
  • 5 Baths
  • 3,137 Sq Ft
  • House for Rent

  19 Morse St, Edgartown, MA 02539

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated historical home in the heart of Edgartown Village, close to Fuller Street & Lighthouse Beaches. Beautifully designed interior with open gourmet kitchen and pickled hardwood floors, marble countertops, top of the line appliances and a large center island. Cozy family room with fireplace, formal living room, office/den and a full bath all

  Karen Overtoom Karen M. Overtoom R.E.

  19 Morse St, Edgartown, MA 02539
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  /25

  $949,000 Sold Jun 23, 2025

  345 Franklin St, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,012 Sq Ft
  • Built 1986

  Last Sold Summary

  • $938/SF
  • 49 Days On Market

  Current Estimated Value $941,182

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

  345 Franklin St, Vineyard Haven, MA 02568
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  /7

  Not Listed For Sale

  • 4 Beds

  53 N Neck Rd, Edgartown, MA 02539

  53 N Neck Rd, Edgartown, MA 02539
• 

  

  /15

  $2,490,000

  • Land
  • 7.2 Acres
  • $345,833 per Acre

  3 Jacobs Neck Road (North Lot 1) Unit 2, Edgartown, MA 02539

  Build your dream home on the special 7.2 acre North lot 1 private wooded property with 1/2 ownership in the beautiful 4.5 acre meadow in the grand Boldwater Association(BWA) on the glorious Edgartown Great Pond with approx. 3,000 ft of private barrier beach. BWA is 40 homesites on 450 acres with 150 acres of conservation abutting another 1,500 acres of conservation and a few large estates - all

  Robert Kenney Tea Lane Associates

  3 Jacobs Neck Road (North Lot 1) Unit 2, Edgartown, MA 02539
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  /8

  $4,800 total monthly price

  • 3 Beds
  • 3 Baths
  • 3,279 Sq Ft
  • House for Rent

  165 Christiantown Rd, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

  Karen Overtoom Karen M. Overtoom R.E.

  165 Christiantown Rd, West Tisbury, MA 02575
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  /34

  $1,050,000 Sold Jun 30, 2025

  160 Bernard Cir, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,606 Sq Ft
  • Built 1977

  Last Sold Summary

  • 12% Below List Price
  • $654/SF
  • 45 Days On Market

  Current Estimated Value $1,084,752

  Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

  160 Bernard Cir, Vineyard Haven, MA 02568
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  /14

  Est $6,153,094 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,193 Sq Ft

  100 Meetinghouse Way, Edgartown, MA 02539

  100 Meetinghouse Way, Edgartown, MA 02539
• 

  

  /5

  $1,300,000 Pending

  • Land
  • 0.5 Acre
  • $2,600,000 per Acre

  58 Marthas Rd, Edgartown, MA 02539

  Island Grove Building Lot - A highly desirable Edgartown location near Morning Glory Farm, the Village, and South Beach. The 1/2 acre parcel is conforming in nature, allowing for maximum development. With approval for 6 bedrooms with sewer tie-in, the opportunities are endless! A great opportunity to get into this terrific community. *SELLER FINANCING AVAILABLE*

  Katherine Donahue Sandpiper Realty Inc

  58 Marthas Rd, Edgartown, MA 02539
• 

  

  /15

  $5,000 total monthly price

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

  6 Briar Path, Aquinnah, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY. PRICES ARE WEEKLY NOT MONTHLY. Down a private country road, this bright and breezy post and beam home sits on a 3-acre rolling wooded parcel. With southern views of the Atlantic Ocean, it's just a short drive or bike to Philbin and Lobsterville beaches and Gay Head cliffs. This very Vineyard house offers three levels of living space, chef's kitchen, spacious

  Karen Overtoom Karen M. Overtoom R.E.

  6 Briar Path, Aquinnah, MA 02535
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  /42

  $3,695,000 Sold Nov 20, 2025

  37 Road To the Plains, Edgartown, MA 02539

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 1986

  Last Sold Summary

  • $1,478/SF
  • 40 Days On Market

  Last Listing Agent Wendy Harman Compass

  37 Road To the Plains, Edgartown, MA 02539
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  /2

  Est $1,397,387 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,400 Sq Ft

  45 Pine Tree Ln, Vineyard Haven, MA 02568

  45 Pine Tree Ln, Vineyard Haven, MA 02568
• 

  

  /39

  $5,325,000

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

  4 Canonicus Ave, Oak Bluffs, MA 02557

  With a striking presence overlooking Nantucket Sound and just moments from the vibrant pulse of downtown, this distinctive compound is infused with a laid-back West Coast spirit while honoring the vintage charm of Oak Bluffs. Airy and effortlessly elegant, the four-bedroom main house has been masterfully updated, introducing refined, contemporary comforts, designed for every season. Tucked to the

  Katherine Donahue Sandpiper Realty Inc

  4 Canonicus Ave, Oak Bluffs, MA 02557
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  /8

  $8,000 total monthly price

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

  56 Chilmark Rd, Chilmark, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and master

  Karen Overtoom Karen M. Overtoom R.E.

  56 Chilmark Rd, Chilmark, MA 02535
• 

  

  /21

  $982,000 Sold Dec 19, 2025

  25 Windy Hill Rd, Oak Bluffs, MA 02557

  • 3 Beds
  • 1 Bath
  • 980 Sq Ft
  • Built 1971

  Last Sold Summary

  • 1% Below List Price
  • $1,002/SF
  • 10 Days On Market

  Last Listing Agent Rene Jackson Island Real Estate

  25 Windy Hill Rd, Oak Bluffs, MA 02557
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  /36

  Est $1,800,714 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,122 Sq Ft

  62 Whalers Walk, Edgartown, MA 02539

  62 Whalers Walk, Edgartown, MA 02539

Showing Results 81 - 120, Page 3 of 18