Dukes County, MA Homes

• 

  

  

  /3

  $700,000 Pending

  • Land
  • 0.26 Acre
  • $2,738,654 per Acre

  2 Hope's Way Unit 31, Oak Bluffs, MA 02557

  ESTEEMED BUILDER READY to BREAK GROUND! Purchase this exceptional lot in Lagoon Ridge and start designing and building your dream 3BR + home today! Execute a BUILDING CONTRACT or choose your own builder... Call for details and schedule a tour! Welcome to Oak Bluffs’ newest and most sought-after neighborhood, where you can construct your 3-bedroom home on a lofty setting, 95 feet above Lagoon

  Marilyn Moses Ocean Park Realty Inc

  2 Hope's Way Unit 31, Oak Bluffs, MA 02557
• 

  

  

  /17

  $48,000 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 2,675 Sq Ft
  • House for Rent

  9 Thaxter Lane Ed310, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Enjoy the pool with this Stunning custom designed and professionally decorated Tri Level contemporary home with open floor plan. Once inside you will be captivated by the dramatic open spaces, soaring ceiling and walls of glass. Located in a high end neighborhood within

  Karen Overtoom Karen M. Overtoom R.E.

  9 Thaxter Lane Ed310, Edgartown, MA 02539
• 

  

  

  /18

  $3,350,000 Sold Jun 05, 2025

  25 Simpson's Ln, Edgartown, MA 02539

  • 6 Beds
  • 6 Baths
  • 3,156 Sq Ft
  • Built 1900

  Last Sold Summary

  • 4% Below List Price
  • $1,061/SF
  • 138 Days On Market

  Last Listing Agent Greg Hartel Hartel Realty

  25 Simpson's Ln, Edgartown, MA 02539
• 

  

  

  /35

  Est $2,779,375 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 2,728 Sq Ft

  89 Main St, Vineyard Haven, MA 02568

  89 Main St, Vineyard Haven, MA 02568
• 

  

  

  /9

  $1,395,000

  • 0.5 Baths
  • 1,283 Sq Ft

  4 Lagoon Pond Rd, Vineyard Haven, MA 02568

  Located at the five corners, this rare commercial property presents an opportunity to set your future business venture up for success. This prime location captures the attention of every single vehicle disembarking the Vineyard Haven Ferry! There are 2.5 parking spots included. Please note that the bike shop business is not for sale. This offering is solely for the real estate. The sellers

  Jarrett Hurwitz Keller Williams Realty

  4 Lagoon Pond Rd, Vineyard Haven, MA 02568
• 

  

  /8

  $18,000 total monthly price

  • 3 Beds
  • 2.5 Baths
  • House for Rent

  71 Bartmus Luce Road Wt154, West Tisbury, MA 02575

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard Views available. It is a short

  Karen Overtoom Karen M. Overtoom R.E.

  71 Bartmus Luce Road Wt154, West Tisbury, MA 02575
• 

  

  /43

  $1,675,000 Sold Apr 04, 2025

  7 N Bog Rd, Edgartown, MA 02539

  • 3 Beds
  • 3 Baths
  • 2,094 Sq Ft
  • Built 1994

  Last Sold Summary

  • 27% Below List Price
  • $800/SF
  • 276 Days On Market

  Last Listing Agent Robin Perschel Feiner Real Estate

  7 N Bog Rd, Edgartown, MA 02539
• 

  

  /48

  Est $1,518,324 Not Listed For Sale

  • 6 Beds
  • 5.5 Baths
  • 2,417 Sq Ft

  152 Main St, Vineyard Haven, MA 02568

  152 Main St, Vineyard Haven, MA 02568
• 

  

  /29

  $10,950,000

  • 4 Beds
  • 3.5 Baths
  • 2,050 Sq Ft

  16 Shotnaigher Ln, Chilmark, MA 02535

  New to market this completely renovated water view home is located in a private enclave of upscale homes fronting on Squibnocket Pond in Chilmark. There are 360 degree views from this 3.6 acre hilltop site offering views of the pond, Atlantic Ocean and north to Menemsha Pond and the Vineyard Sound. Sunrise and Sunset! This home, completely renovated in 2022 features a state of the art gourmet

  Rebecca V Conroy Conroy & Company R.E., Inc.

  16 Shotnaigher Ln, Chilmark, MA 02535
• 

  

  /23

  $36,000 total monthly price

  • 3 Beds
  • 3 Baths
  • 2,556 Sq Ft
  • House for Rent

  74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Less than 5 miles from the center of town, the property is a 3 bedroom uniquely-designed guest house which provides the space needed for a large family or visiting guests. Most of the living/entertaining space is on the second floor. The kitchen has granite countertops,

  Karen Overtoom Karen M. Overtoom R.E.

  74 Turkeyland Cove Rd Ed306, Edgartown, MA 02539
• 

  /2

  $880,000 Sold Oct 17, 2025

  5 Johns Way, Oak Bluffs, MA 02557

  • 3 Beds
  • 2 Baths
  • 1,365 Sq Ft
  • Built 1987

  Last Sold Summary

  • $645/SF
  • 0 Days On Market

  Current Estimated Value $1,036,850

  Last Listing Agent LINK Email Cache LINK

  5 Johns Way, Oak Bluffs, MA 02557
• 

  

  /36

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,780 Sq Ft

  52 Marthas Rd, Edgartown, MA 02539

  52 Marthas Rd, Edgartown, MA 02539
• 

  

  /26

  $1,445,000

  • 4 Beds
  • 2.5 Baths
  • 1,738 Sq Ft

  22 Oklahoma Ave, Vineyard Haven, MA 02568

  3 BEDROOM HOUSE + 1 BEDROOM APARTMENT! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This move-in ready property features a 3 BR, 1.5 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset your mortgage. The main house features a stunning solarium or sunroom, a cheerful

  Idalyn Macchia Gilstad Wallace & Co. Sotheby's

  22 Oklahoma Ave, Vineyard Haven, MA 02568
• 

  

  /28

  $29,300 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 1,871 Sq Ft
  • House for Rent

  76 Mattakesett Way Ed313, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,325. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This upside-down house was built in 2007. Sit out on the upper deck to panoramic ocean views or grill your favorite seafood while taking in the view. Watch the sun set to a new and beautiful aurora each night on either of the decks or while lazing on the porch swing.The

  Karen Overtoom Karen M. Overtoom R.E.

  76 Mattakesett Way Ed313, Edgartown, MA 02539
• 

  /2

  $1,100,000 Sold Jun 17, 2025

  17 Front St, Oak Bluffs, MA 02557

  • 2 Beds
  • 2 Baths
  • 2,912 Sq Ft
  • Built 1989

  Last Sold Summary

  • $378/SF
  • 0 Days On Market

  Current Estimated Value $1,202,757

  Last Listing Agent LINK Email Cache LINK

  17 Front St, Oak Bluffs, MA 02557
• 

  

  /31

  Est $1,455,662 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,999 Sq Ft

  48 Puritan Dr, Vineyard Haven, MA 02568

  48 Puritan Dr, Vineyard Haven, MA 02568
• 

  

  /36

  $2,900,000

  • 4 Beds
  • 5 Baths
  • 5,165 Sq Ft

  63 Bayes Hill Rd, Oak Bluffs, MA 02557

  Tucked away in a serene setting, this beautifully designed custom home offers the ultimate in privacy, comfort, and luxury living. The first floor features a spacious open-concept design, seamlessly blending the dining room, kitchen, wet bar, and living area-perfect for entertaining or relaxing with the family. Home chefs will fall in love with the gourmet kitchen complete with custom cabinetry,

  Casandra Hyland Sandpiper Realty, Inc.

  63 Bayes Hill Rd, Oak Bluffs, MA 02557
• 

  

  /10

  $11,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  15 Price's Way Ed322, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is an inviting and affordable home with air-conditioning. As you see from the pictures the sun is welcomed through many sliders and windows. Inside the furnishings are simple but well chosen. There is a splitter in the living area that cools the downstairs. The

  Karen Overtoom Karen M. Overtoom R.E.

  15 Price's Way Ed322, Edgartown, MA 02539
• 

  /2

  $1,100,000 Sold Oct 29, 2025

  11 Quammox Rd, Edgartown, MA 02539

  • 2 Beds
  • 1 Bath
  • 685 Sq Ft
  • Built 1940

  Last Sold Summary

  • $1,606/SF
  • 0 Days On Market

  Current Estimated Value $1,238,351

  Last Listing Agent LINK Email Cache LINK

  11 Quammox Rd, Edgartown, MA 02539
• 

  

  /14

  Est $1,455,134 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,717 Sq Ft

  13 Saddle Club Rd, Edgartown, MA 02539

  13 Saddle Club Rd, Edgartown, MA 02539
• 

  

  /12

  $899,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft

  8 Hitchings Cir, Oak Bluffs, MA 02557

  Nestled in a quiet Oak Bluffs neighborhood, less than a mile from the harbor, beaches, shops, and restaurants, this Cape-style home offers the perfect balance of convenience and tranquility. The interior features an open kitchen and living room, plenty of space for guests, and a full unfinished basement. The two bedroom Title V septic system has passed inspection. Outside, the property features a

  Peyton Wallace Studio Realty

  8 Hitchings Cir, Oak Bluffs, MA 02557
• 

  

  /25

  $80,000 total monthly price

  • 4 Beds
  • 4.5 Baths
  • 3,800 Sq Ft
  • House for Rent

  7 Mill Hill Farms Rd Ed315, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $20,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Gorgeous new 4 bedroom 4 bath home. Top of the line finishes and appliances. Gourmet kitchen, screened in porch with fireplace and TV. Pool with swim up bar, hot tub and grilling area. This is a cream of the crop Katama house is a short distance to downtown Edgartown and

  Karen Overtoom Karen M. Overtoom R.E.

  7 Mill Hill Farms Rd Ed315, Edgartown, MA 02539
• 

  

  /27

  $1,560,000 Sold Jan 15, 2026

  36 Ferro Way, Tisbury, MA 02568

  • 5 Beds
  • 3.5 Baths
  • 4,032 Sq Ft
  • Built 2020

  Last Sold Summary

  • 4% Below List Price
  • $387/SF
  • 33 Days On Market

  Last Listing Agent Hope O'Brien Compass Massachusetts, LLC

  36 Ferro Way, Tisbury, MA 02568
• 

  

  /20

  Est $1,768,098 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,240 Sq Ft

  11 Pine Tree Ln, Vineyard Haven, MA 02568

  11 Pine Tree Ln, Vineyard Haven, MA 02568
• 

  

  /78

  $7,950,000

  • 6 Beds
  • 6.5 Baths
  • 6,927 Sq Ft

  6 Janes Cove Rd, Edgartown, MA 02539

  Waterfront on Edgartown Great Pond with delightful water views, this newly-renovated Coastal Colonial is set on a very private 9.2 acre lot on Janes Cove. You know you are somewhere very special the moment you enter through the gates. As you travel along the cobblestone lined driveway flanked by lush lawns, the gorgeous home rises before you. Stunning the day it was originally completed, it has

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  6 Janes Cove Rd, Edgartown, MA 02539
• 

  

  /28

  $38,000 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft
  • House for Rent

  17 Otis Bassett Rd, West Tisbury, MA 02575

  THIS IS A WEEKLY RENTAL NOT MONTHLY. AUGUST WEEKLY IS $9,500. SEE OUR WEB SITE FOR WEEKLY PRICING!!!!!Are you looking for the perfect back yard Oasis? Well here it is!! Surrounding a large pool you will be able to relax on the expansive deck areas that include plenty of space for gathering. Inside is an amazing kitchen with every amenity you could want. Coffee lovers will appreciate a regular

  Karen Overtoom Karen M. Overtoom R.E.

  17 Otis Bassett Rd, West Tisbury, MA 02575
• 

  /2

  $1,390,000 Sold Jul 22, 2025

  57 Colonial Dr, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,299 Sq Ft
  • Built 1984

  Last Sold Summary

  • $1,070/SF
  • 0 Days On Market

  Current Estimated Value $1,125,215

  Last Listing Agent LINK Email Cache LINK

  57 Colonial Dr, Vineyard Haven, MA 02568
• 

  

  /27

  Est $957,203 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,116 Sq Ft

  84 Pine Tree Rd, Vineyard Haven, MA 02568

  84 Pine Tree Rd, Vineyard Haven, MA 02568
• 

  

  /30

  $840,000

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

  12 Beach Plum Path, East Falmouth, MA 02536

  Built in 2021, this home offers a layout that works for how people actually live today. The open main level connects the leathered granite kitchen with upgraded appliances to the dining and living areas, anchored by a gas fireplace that makes the space feel warm and inviting. The first-floor primary suite features a walk-in closet and full bath. The second level includes two bedrooms plus a third

  Pamela Heylin Berkshire Hathaway HomeServices Robert Paul Properties

  12 Beach Plum Path, East Falmouth, MA 02536
• 

  

  /36

  $56,800 total monthly price

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

  2 Nonamessett Rd, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING.Newly renovated architect designed home with every amenity. Cook's gourmet kitchen, open plan living/dining room, second living room, lots of outdoor patio and deck space, Set in a private 7 acre property with wildflower meadow. Relax around the beautiful in ground pool

  Karen Overtoom Karen M. Overtoom R.E.

  2 Nonamessett Rd, Edgartown, MA 02539
• 

  

  /30

  $1,050,000 Sold Oct 06, 2025

  4 Quail Run Unit 2, Oak Bluffs, MA 02557

  • 2 Beds
  • 1.5 Baths
  • 1,323 Sq Ft
  • Built 1972

  Last Sold Summary

  • 11% Below List Price
  • $794/SF
  • 62 Days On Market

  Current Estimated Value $970,344

  Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  4 Quail Run Unit 2, Oak Bluffs, MA 02557
• 

  

  /17

  Est $1,695,911 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  55 Pinehurst Rd, Edgartown, MA 02539

  55 Pinehurst Rd, Edgartown, MA 02539
• 

  

  /13

  $6,750,000

  • Land
  • 2.11 Acres
  • $3,199,052 per Acre

  5 Atlantic Dr Unit 5.2, Edgartown, MA 02539

  Located in one of Katama’s most coveted neighborhoods, this 2.11-acre parcel offers stunning ocean views and a direct path to South Beach. Surrounded by high-end homes and just minutes from Edgartown Village, it’s an ideal setting for a custom-built retreat with room for a four bedroom residence with pool and views over the dunes. A rare opportunity to own in this prestigious coastal enclave.

  Deb Levin Studio Realty

  5 Atlantic Dr Unit 5.2, Edgartown, MA 02539
• 

  

  /21

  $14,000 total monthly price

  • 4 Beds
  • 2 Baths
  • 1,505 Sq Ft
  • House for Rent

  175 Meetinghouse Way Ed321, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This updated contemporary is located in Katama area and a short bike ride to South Beach. There are 4 bedrooms, 1 down and 3 up, and a beautiful kitchen/dining which opens to a large living room. The house has a nice deck on the front and owners have added a deck off the

  Karen Overtoom Karen M. Overtoom R.E.

  175 Meetinghouse Way Ed321, Edgartown, MA 02539
• 

  

  /48

  $5,250,000 Sold Jul 02, 2025

  14 Katama Farm Rd N, Edgartown, MA 02539

  • 3 Beds
  • 4.5 Baths
  • 2,869 Sq Ft
  • Built 1988

  Last Sold Summary

  • 5% Below List Price
  • $1,830/SF
  • 54 Days On Market

  Last Listing Agent Courtney Marek Sandpiper Realty Inc

  14 Katama Farm Rd N, Edgartown, MA 02539
• 

  

  /47

  Est $2,491,900 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 3,627 Sq Ft

  24 Peacegate Way, Vineyard Haven, MA 02568

  24 Peacegate Way, Vineyard Haven, MA 02568
• 

  

  /9

  $4,995,000 Pending

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

  64 Crowell Ln, Tisbury, MA 02568

  Welcome to your Vineyard Dream in the heart of West Chop! Built by Novo Builds, a renowned construction company that is recognized for their innovative designs and high-quality craftsmanship. Novo Builds is set to enhance the landscape of this iconic island with their latest development.This stunning new build offers the perfect blend of modern luxury and coastal charm, making it an ideal

  Joe & Nicole Holland Vineyard Dream Realty LLC

  64 Crowell Ln, Tisbury, MA 02568
• 

  

  /32

  $100,000 total monthly price

  • 5 Beds
  • 4 Baths
  • 4,500 Sq Ft
  • House for Rent

  60 Witchwood Lane Ed317, Edgartown, MA 02539

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $25,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gorgeous waterfront home is well equipped with gourmet kitchen, stone fireplace, numerous sitting areas, and multiple decks each with water views over the Edgartown Harbor. Both the main and upper level have beautiful master suites and also washers & dryers. Easy

  Karen Overtoom Karen M. Overtoom R.E.

  60 Witchwood Lane Ed317, Edgartown, MA 02539
• 

  /2

  $1,555,000 Sold Apr 14, 2025

  7 Clark Dr, Edgartown, MA 02539

  • Land
  • 0.36 Acre
  • $4,349,650 per Acre

  Last Sold Summary

  • 0 Days On Market

  Current Estimated Value $2,974,501

  Last Listing Agent LINK Email Cache LINK

  7 Clark Dr, Edgartown, MA 02539
• 

  

  /16

  Est $1,252,041 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  31 Music St, Vineyard Haven, MA 02568

  31 Music St, Vineyard Haven, MA 02568

Showing Results 241 - 280, Page 7 of 18