Dukes County, MA Homes

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  $14,500,000

  • 4 Beds
  • 4.5 Baths
  • 3,705 Sq Ft

  64 Squibnocket Farm Rd, Chilmark, MA 02535

  Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within

  Thomas Wallace Wallace & Co. Sotheby's

  64 Squibnocket Farm Rd, Chilmark, MA 02535
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  $19,000 total monthly price

  • 6 Beds
  • 6.5 Baths
  • 6,950 Sq Ft
  • House for Rent

  40 Sweet William Way, West Tisbury, MA 02575

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the

  Karen Overtoom Karen M. Overtoom R.E.

  40 Sweet William Way, West Tisbury, MA 02575
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  $1,350,000 Sold Aug 15, 2025

  35 Vineyard Avenue Extension, Oak Bluffs, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,864 Sq Ft
  • Built 1970

  Last Sold Summary

  • 7% Below List Price
  • $724/SF
  • 12 Days On Market

  Last Listing Agent Lesley Heidt Sandpiper Realty Inc

  35 Vineyard Avenue Extension, Oak Bluffs, MA 02568
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  Est $2,311,723 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,436 Sq Ft

  377 State Rd, Vineyard Haven, MA 02568

  377 State Rd, Vineyard Haven, MA 02568
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  $1,350,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,959 Sq Ft

  48 Edgartown - West Tisbury Rd, Edgartown, MA 02539

  This rare multi-family residence offers a unique investment opportunity or the perfect island retreat. Whether you're looking to generate rental income, host guests, or settle into island life, this 3-bedroom, 3-bathroom property checks all the boxes. With numerous bonus spaces, off-street parking, a cozy backyard, and expansion potential (pending town approval), this is a truly exceptional

  Mavis Francis eXp Realty

  48 Edgartown - West Tisbury Rd, Edgartown, MA 02539
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  $18,840 total monthly price

  • 3 Beds
  • 2.5 Baths
  • House for Rent

  21 William St Vh430, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,710. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely elegant home with wonderful art and furnishings. Once you step in the front door you will fall in love with this lovely home. Each room is a delight. Large nicely appointed kitchen with easy access to a beautiful dining room. A formal living room is next to a less

  Karen Overtoom Karen M. Overtoom R.E.

  21 William St Vh430, Tisbury, MA 02568
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  $776,500 Sold Mar 05, 2025

  32 Clark Ave, Vineyard Haven, MA 02568

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1968

  Last Sold Summary

  • 7% Below List Price
  • $1,011/SF
  • 17 Days On Market

  Current Estimated Value $784,709

  Last Listing Agent Diana Gilmore Island Real Estate

  32 Clark Ave, Vineyard Haven, MA 02568
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  /36

  Est $3,865,688 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 3,902 Sq Ft

  94 Marthas Rd, Edgartown, MA 02539

  94 Marthas Rd, Edgartown, MA 02539
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  /13

  $1,150,000

  • Land
  • 2.02 Acres
  • $569,307 per Acre

  00 Old Field Rd, Aquinnah, MA 02535

  The nearby roar of the Atlantic can be heard from this pristine two-acre building opportunity in Aquinnah, ideally located at the end of Old Field Road with easy access from Moshup Trail. A storybook walking path through woods and fields over an easement bordering a majestic beetlebung grove and over a bubbling stream, leads directly to the entrance of cherished Philbin Beach. A thoughtfully

  Katherine Donahue Sandpiper Realty Inc

  00 Old Field Rd, Aquinnah, MA 02535
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  $32,000 total monthly price

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

  37 Mempremagog Ave Vh410, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in

  Karen Overtoom Karen M. Overtoom R.E.

  37 Mempremagog Ave Vh410, Tisbury, MA 02568
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  $700,500 Sold May 07, 2025

  72 Windsor Dr Unit 99.71, Edgartown, MA 02539

  • Land
  • 0.55 Acre
  • $1,273,636 per Acre

  Last Sold Summary

  • 3% Above List Price
  • 0 Days On Market

  Last Listing Agent Jim Joyce Carroll & Vincent R.E.

  72 Windsor Dr Unit 99.71, Edgartown, MA 02539
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  /5

  Est $2,512,811 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,657 Sq Ft

  21 Old Oklahoma Rd, Vineyard Haven, MA 02568

  21 Old Oklahoma Rd, Vineyard Haven, MA 02568
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  $1,700,000

  • Land
  • 0.96 Acre
  • $1,770,833 per Acre

  108 Bay View, Edgartown, MA 02539

  Enchanting 2-bed waterfront cottage in Edgartown's coveted Chappaquiddick neighborhood, Martha's Vineyard. Exuding coastal charm, it features old boat masts as columns, decor from washed-up treasures, and a historic silo from Sweetened Water Farm, rebuilt as a unique bedroom wing. The silo hosts a cozy bedroom on the first level and a second bedroom on the upper level, offering breathtaking

  Derick Freitas Amaral & Associates RE

  108 Bay View, Edgartown, MA 02539
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  /18

  $10,000 total monthly price

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft
  • House for Rent

  100 Franklin Terrace Vh411, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming 3 bedroom home offers open living, dining and kitchen space that open to a screened-in porch and patio. You are located in a peaceful setting yet with-in walking distance to Lake Tashmoo, town beaches, and the Vineyard Haven Village for dining, shopping and

  Karen Overtoom Karen M. Overtoom R.E.

  100 Franklin Terrace Vh411, Tisbury, MA 02568
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  $1,067,000 Sold Sep 26, 2025

  112 W Spring St, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 1,503 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $710/SF
  • 95 Days On Market

  Last Listing Agent Katherine Donahue Sandpiper Realty Inc

  112 W Spring St, Vineyard Haven, MA 02568
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  /20

  Est $1,569,993 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,532 Sq Ft

  39 Prices Way, Edgartown, MA 02539

  39 Prices Way, Edgartown, MA 02539
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  $1,669,000 Pending

  • 3 Beds
  • 4 Baths
  • 2,308 Sq Ft

  453 Lighthouse Rd, Aquinnah, MA 02535

  HUGE PRICE CUT! Aquinnah Retreat, set on a private 1.1-acre lot! This beautiful single-family home was lovingly built & cared for by one family, offering peaceful surroundings & beautiful ocean views, now, move-in ready for new owners to relax & put their own personal touch to. The wrap-around deck provides a stunning viewpoint to take in the coastal air & setting. Inside, the kitchen & dining

  Chelsea Brennan Lamacchia Realty

  453 Lighthouse Rd, Aquinnah, MA 02535
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  $10,800 total monthly price

  • 2 Beds
  • 4 Baths
  • 1,800 Sq Ft
  • House for Rent

  256 Sandpiper Lane Vh417, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This well appointed condo will make you feel comfortable and at home the moment you walk in. Swimming, kayaking, tennis, walking trails, and shopping are all at your finger tips. Mink Meadows Golf Course is just a stroll down the street as well. Enjoy all the Island has

  Karen Overtoom Karen M. Overtoom R.E.

  256 Sandpiper Lane Vh417, Tisbury, MA 02568
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  $1,525,000 Sold Oct 07, 2025

  15 Jernegan Pond Rd, Edgartown, MA 02539

  • 2 Beds
  • 2 Baths
  • 2,042 Sq Ft
  • Built 1945

  Last Sold Summary

  • 23% Below List Price
  • $747/SF
  • 233 Days On Market

  Last Listing Agent Lesley Heidt Sandpiper Realty Inc

  15 Jernegan Pond Rd, Edgartown, MA 02539
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  /14

  Est $2,771,008 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,926 Sq Ft

  30 Pond Ln, Vineyard Haven, MA 02568

  30 Pond Ln, Vineyard Haven, MA 02568
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  $2,375,000

  • 6 Beds
  • 4.5 Baths
  • 2,970 Sq Ft

  128 W Spring St, Vineyard Haven, MA 02568

  A Rare Compound Opportunity in the Heart of Vineyard Haven - 128 & 136 Spring Street - Two adjacent properties being sold together create a flexible compound just moments from downtown Vineyard Haven. The 4-bedroom, 2-1/2 bath main house also includes a separate, 1-bedroom in-law/nanny apartment with a full bath. The guest house has 1 bedroom and 1 bath, with a 4-bedroom septic system allowing

  David Dickinson Compass

  128 W Spring St, Vineyard Haven, MA 02568
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  /15

  $7,500 total monthly price

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  83 Ashtons Way, Vineyard Haven, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $1,875. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This two bedroom cottage is set in a private setting in the woods, just a short distance to downtown Vineyard Haven. Sleeps four comfortably, open living space, deck and outside shower. If rented with the main house, access to private association beach and golf would be

  Karen Overtoom Karen M. Overtoom R.E.

  83 Ashtons Way, Vineyard Haven, MA 02568
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  $1,662,000 Sold Apr 16, 2025

  395 Edgartown - West Tisbury Rd, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,794 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Below List Price
  • $926/SF
  • 0 Days On Market

  Current Estimated Value $1,680,058

  Last Listing Agent Janna O'Loughlin Portfolio Real Estate, Inc.

  395 Edgartown - West Tisbury Rd, Edgartown, MA 02539
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  Est $1,179,160 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft

  16 Rock Pond Rd, Vineyard Haven, MA 02568

  16 Rock Pond Rd, Vineyard Haven, MA 02568
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  /7

  $795,000 Pending

  • Land
  • 2.52 Acres
  • $315,476 per Acre

  0 W End Rd, Gosnold, MA 02713

  Vacant, buildable, water-view lot comprised of 2.52 ± wooded acres with subdivision potential and views of Martha’s Vineyard and Vineyard Sound. Buyer should do their own due-diligence on subdivision. Located on Cuttyhunk Island, part of the Elizabeth Islands off the southern coast of Massachusetts is located between Buzzards Bay and Vineyard Sound. At just 550± acres Cuttyhunk Island offers a

  Slater Anderson LandVest, Inc.

  0 W End Rd, Gosnold, MA 02713
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  $50,700 total monthly price

  • 4 Beds
  • 3 Baths
  • 2,346 Sq Ft
  • House for Rent

  6 Trails End Ch241, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,675. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set atop a hill you will find this wonderful 4 bedroom home with distant views and a wonderful lap pool. Enjoy your days on the large deck or take a swim in the pool. This great vacation home is tastefully decorated and is located on one level with plenty of space for

  Karen Overtoom Karen M. Overtoom R.E.

  6 Trails End Ch241, Chilmark, MA 02535
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  $1,865,000 Sold Dec 04, 2025

  71 Netock Ave, Oak Bluffs, MA 02557

  • 4 Beds
  • 5 Baths
  • 2,820 Sq Ft
  • Built 1982

  Last Sold Summary

  • 7% Below List Price
  • $661/SF
  • 11 Days On Market

  Last Listing Agent Ellen Valentgas Sotheby's International Realty

  71 Netock Ave, Oak Bluffs, MA 02557
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  Est $1,938,772 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1 Sq Ft

  179 Main St, Vineyard Haven, MA 02568

  179 Main St, Vineyard Haven, MA 02568
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  /14

  $835,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  51 Lantern Ln, Vineyard Haven, MA 02568

  Find your sweet spot in this charming starter home, ideally located on a quiet street yet within an effortless walk of everything. Forget the car and get your steps in! You're a short jaunt to essentials like Cronig's Market and Shirley's Hardware, AND local favorites including The Maker, Black Dog Cafe, Island Fresh Pizza, Pie Chicks, and Island Adventures Mini Golf. Also within walking distance

  Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

  51 Lantern Ln, Vineyard Haven, MA 02568
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  $25,000 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 2,334 Sq Ft
  • House for Rent

  100 Connie's Way Vh401, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,250. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

  Karen Overtoom Karen M. Overtoom R.E.

  100 Connie's Way Vh401, Tisbury, MA 02568
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  $1,125,000 Sold Oct 28, 2025

  140 Longview Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 1.5 Baths
  • 1,432 Sq Ft
  • Built 1964

  Last Sold Summary

  • 13% Below List Price
  • $786/SF
  • 97 Days On Market

  Last Listing Agent Candy DaRosa Feiner Real Estate

  140 Longview Rd, Vineyard Haven, MA 02568
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  Est $2,127,593 Not Listed For Sale

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

  31 Pulpit Ln, Edgartown, MA 02539

  31 Pulpit Ln, Edgartown, MA 02539
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  /15

  $625,000

  • 2 Beds
  • 1 Bath
  • 704 Sq Ft

  124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568

  MOVE RIGHT IN! This sunny end unit is being offered furnished! Spacious living area opens to an eat-in kitchen with a new Bosch dishwasher. Bedroom number one has a queen bed. Bedroom two has two single beds. Conveniently located within close proximity to Main Street shops, the ferry and bus terminal, and the scenic bike path that extends across the island. At the bottom of the hill you will find

  Rene Jackson Island Real Estate

  124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
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  $13,200 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • House for Rent

  224 N Rd Ch248, Chilmark, MA 02535

  THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room.

  Karen Overtoom Karen M. Overtoom R.E.

  224 N Rd Ch248, Chilmark, MA 02535
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  $2,380,000 Sold Jan 21, 2025

  41 Bold Meadow Rd, Edgartown, MA 02539

  • 4 Beds
  • 3 Baths
  • 2,770 Sq Ft
  • Built 2012

  Last Sold Summary

  • 7% Below List Price
  • $859/SF
  • 94 Days On Market

  Current Estimated Value $2,452,280

  Last Listing Agent Emma Kennedy Sandpiper Realty Inc

  41 Bold Meadow Rd, Edgartown, MA 02539
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  Est $3,136,932 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 3,440 Sq Ft

  8 Coffins Field Rd, Edgartown, MA 02539

  8 Coffins Field Rd, Edgartown, MA 02539
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  $1,193,000

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  50 Lantern Ln, Vineyard Haven, MA 02568

  *NOTE: The seller is offering a $25,000 credit towards the required septic upgrade. Nestled in a quiet enclave on Lantern Lane, this charming 3-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and island charm. Located just moments from the heart of Vineyard Haven, you'll enjoy easy access to shops, restaurants, and the ferry. The interior of the home features a bright and

  Madelyn Silvia Wallace & Co. Sotheby's International Realty

  50 Lantern Ln, Vineyard Haven, MA 02568
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  $12,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • House for Rent

  223 Sandpiper Lane Vh405, Tisbury, MA 02568

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three bedroom two bath condo is just a short walk to association tennis, pool and the beach. Comfortable easy summer living with outdoor shower, spacious deck, and central AC for those really hot August days!Amenities include Direct TV DVD set up. There is an open

  Karen Overtoom Karen M. Overtoom R.E.

  223 Sandpiper Lane Vh405, Tisbury, MA 02568
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  $2,075,000 Sold Sep 29, 2025

  24 Dark Woods Rd, Edgartown, MA 02539

  • 3 Beds
  • 3.5 Baths
  • 2,638 Sq Ft
  • Built 1998

  Last Sold Summary

  • 23% Below List Price
  • $787/SF
  • 372 Days On Market

  Last Listing Agent Stephanie Burke Portfolio Real Estate, Inc.

  24 Dark Woods Rd, Edgartown, MA 02539
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  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,092 Sq Ft

  670 State Rd, Vineyard Haven, MA 02568

  670 State Rd, Vineyard Haven, MA 02568

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