Dukes County MA Houses for Sale

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  /18

  $1,195,000

  • 3 Beds
  • 2 Baths
  • 1,469 Sq Ft

  12 Park Ave, Vineyard Haven, MA 02568

  Welcome to this delightful Cape-style home offering easy access to Vineyard Haven shopping and the Island's bike paths. Nestled on just under an acre of land, this inviting residence features three spacious bedrooms and two full bathrooms, providing ample space for year-round living or weekend getaways. Inside, you'll find a warm and welcoming open concept, perfect for both relaxing and

  Sheila Morse Island Real Estate

  12 Park Ave, Vineyard Haven, MA 02568
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  /40

  $6,395,000

  • 8 Beds
  • 7 Baths
  • 6,921 Sq Ft

  19BC Locust Ln, Aquinnah, MA 02535

  This beautifully designed and built home is privately sited on 4.02 acres overlooking a pastoral setting with amazing ocean views and bordered by stone walls. There is also an additional 2.02 acre parcel included with purchase. The spacious entry hall steps into a formal living and dining room with oversized windows that take in the amazing North Shore ocean views, tall ceilings, a field stone

  Brenda Galligan Karen M. Overtoom R.E.

  19BC Locust Ln, Aquinnah, MA 02535
• 

  

  

  /42

  $1,675,000

  • 3 Beds
  • 2 Baths
  • 2,015 Sq Ft

  48 Vineyard Avenue Extension, Oak Bluffs, MA 02568

  Bright, Open Living Steps from the Lagoon!This sun-filled 3-bedroom, 2-bath home offers easy single-level living with a spacious, open-concept layout—ideal for entertaining and everyday comfort. A welcoming sitting area flows into the living room, dining space, and modern kitchen. A separate home office/den adds flexibility to this 2,015 sq ft home. Set on a generous 11,000 sq ft corner lot,

  Susie Wallo Compass

  48 Vineyard Avenue Extension, Oak Bluffs, MA 02568
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  /108

  $4,800,000

  • 6 Beds
  • 5 Baths
  • 2,960 Sq Ft

  104 Pond View Farm Rd, Vineyard Haven, MA 02568

  An exceptional Waterfront Compound on Tisbury Great Pond. Located across the Tisbury Great Pond from the exclusive Blue Heron Farm, this remarkable waterfront property offers a rare opportunity to own a serene compound with two homes and a private permitted dock—ideal for boating to the Atlantic barrier beach, fishing, kayaking, and enjoying the peaceful beauty of the pond.Both the main house and

  Alexis Holden Tea Lane Associates

  104 Pond View Farm Rd, Vineyard Haven, MA 02568
• 

  

  

  /20

  $1,295,000

  • 4 Beds
  • 2 Baths
  • 1,306 Sq Ft

  113 Leonard Cir, Vineyard Haven, MA 02568

  Adorable four bedroom cape features an updated open concept living, kitchen and dining area with a cozy screened in porch accessed via French doors. Wood floors, high ceilings and an abundance of windows throughout the home create a unified and pleasing aesthetic as well as a sense of light and spaciousness. Also included on the first floor are a bedroom with lots of natural light and a nicely

  Alyson Parker Karen M. Overtoom R.E.

  113 Leonard Cir, Vineyard Haven, MA 02568
• 

  

  /26

  $3,390,000

  • 5 Beds
  • 4 Baths
  • 3,678 Sq Ft

  15 Crowell Rd, West Tisbury, MA 02575

  Hickory Hollow is one of the most enchanting parcels of land in Seven Gates Farm. You enter the property and feel as if you have stepped back in time. The cozy antique farmhouse is the centerpiece of the 6.8-acre property which includes rolling lawns, lichen-covered stone walls and boulders, numerous specimen trees, and no fewer than 3 ponds. In addition to the main house there are 3 additional

  Mark Jenkins Wallace & Co. Sotheby's

  15 Crowell Rd, West Tisbury, MA 02575
• 

  

  /25

  $3,390,000

  • 3 Beds
  • 2.5 Baths
  • 1,514 Sq Ft

  15 Crowell Ln, Tisbury, MA 02568

  Hickory Hollow is one of the most enchanting parcels of land in Seven Gates Farm. You enter the property and feel as if you have stepped back in time. The cozy antique farmhouse is the centerpiece of the 6.8-acre property which includes rolling lawns, lichen-covered stone walls and boulders, numerous specimen trees, and no fewer than 3 ponds. In addition to the main house there are 3 additional

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  15 Crowell Ln, Tisbury, MA 02568
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  /123

  $5,975,000

  • 5 Beds
  • 4 Baths
  • 4,050 Sq Ft

  78 Hammett Rd, Chilmark, MA 02535

  Wonderful elevated Chilmark north shore 3.8 acre secure waterfront property with dramatic year round sunset water views to the Gay Head Lighthouse and Elizabeth Islands. The Vineyard Sound expanse enjoys peaceful sailing, fishing and other boating activity to enhance the ocean splendor. The 5 bedroom 3 1/2 bath 4,050 sq ft home is literally in move-in condition. Architect designed and built by

  Robert Kenney Tea Lane Associates

  78 Hammett Rd, Chilmark, MA 02535
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  /23

  $1,790,000

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  11 Beach Rd, Oak Bluffs, MA 02557

  Oak Bluffs: Waterfront Property at Vineyard Haven Outer Harbor**This is an exceptional opportunity to acquire a stunning white sandy beach property on Vineyard Haven Harbor. This charming Island cottage boasts breathtaking panoramic views of the harbor and sound, showcasing magnificent sunsets each evening over the West Chop Peninsula. You can enjoy the lively boating scene, with yachts from

  Alan Schweikert Ocean Park Realty Inc

  11 Beach Rd, Oak Bluffs, MA 02557
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  /30

  $829,000

  • 3 Beds
  • 1 Bath
  • 907 Sq Ft

  17 Siloam Ave, Oak Bluffs, MA 02557

  Welcome to 17 Siloam Avenue, a delightful cottage nestled in the historic Martha’s Vineyard Camp Meeting Association, offering spectacular sunset views of Sunset Lake and the distant harbor from its inviting porches. The current owners have cherished this home year-round for 13 years, and it’s easy to see why. This spacious residence features an open living and dining area that seamlessly flows

  Marilyn Moses Ocean Park Realty Inc

  17 Siloam Ave, Oak Bluffs, MA 02557
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  /29

  $2,275,000

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft

  9 Moshup Trail, Aquinnah, MA 02535

  Spectacular property in Aquinnah, featuring a newly installed and town-approved 6-bedroom septic system, ready to support your vision for expansion and renovation.Located on 4.7 acres filled with rolling meadows and stone walls, this property boasts a truly remarkable barn that was transported from Maine, and rebuilt on the Island. The grandfathered-in barn spans approximately 61' by 45' with

  Patrick McCarthy Grace Hagerty Real Estate Inc

  9 Moshup Trail, Aquinnah, MA 02535
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  /16

  $1,195,000

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

  50 Lantern Ln, Vineyard Haven, MA 02568

  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 welcoming layout with an open living and dining area, hardwood floors, and a private

  Madelyn Silvia Wallace & Co. Sotheby's International Realty

  50 Lantern Ln, Vineyard Haven, MA 02568
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  /45

  $19,500,000

  • 7 Beds
  • 6 Baths
  • 3,344 Sq Ft

  104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535

  This beautiful 2-parcel compound totals 9.5-acre of land and 600 feet of private Vineyard Sound beach. There is a renovated 4-bedroom beach cottage on one of the parcels which includes all modern amenities and offers spectacular views from almost every room. The second parcel has an older 3-bedroom home located high on a ridge. Both parcels offer wonderful walking paths to the sandy beach below.

  Thomas Leclair Landvest MV

  104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535
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  /23

  $1,135,000

  • 3 Beds
  • 3 Baths
  • 1,503 Sq Ft

  112 W Spring St, Vineyard Haven, MA 02568

  This delightful three-bedroom Cape is ideally situated just under a mile from Main Street and the harbor, offering easy access to Tisbury Center. The inviting open floor plan blends comfort and functionality, with multiple seating areas ideal for relaxing or entertaining. A finished basement adds over 600 square feet of living space, complete with a half bath—making it ideal for a home office,

  Katie Donahue Sandpiper Realty

  112 W Spring St, Vineyard Haven, MA 02568
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  /32

  $999,000

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft

  400 Edgartown-Vineyard Haven Rd, Edgartown, MA 02539

  Close to downtown Edgartown, yet far enough away to be in a residential location with a nice yard, this home is a must-see! This is a ranch style home with two bedrooms and two bathrooms, plus an office. Open concept for the living, dining and kitchen area with a slider to the back deck. With a few updates and finishing touches, this could transform into your perfect family home. It is being sold

  Kelly Mercier Match Point Properties

  400 Edgartown-Vineyard Haven Rd, Edgartown, MA 02539
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  /23

  $6,000,000

  • 3 Beds
  • 2 Baths
  • 2,710 Sq Ft

  35 S Bowl Rd, Chilmark, MA 02535

  This exceptionally elegant and tranquil home in Seven Gates Farm combines contemporary architectural design with timeless high-end features for Vineyard casual, nature-inspired living. Extraordinary and rare, this move-in ready three-bedroom home with six-bedroom septic system sits on an oversized 5.3-acre parcel in Chilmark. This thoughtful layout has an easy flow, soothing tones with cypress

  Meg Bodnar Tea Lane Associates

  35 S Bowl Rd, Chilmark, MA 02535
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  /39

  $1,795,000

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

  453 Lighthouse Rd, Aquinnah, MA 02535

  Aquinnah Retreat set on a private 1.1-acre lot! This beautiful single-family home was lovingly built and cared for by one family, offering peaceful surroundings and ocean views. Now move-in ready, it's the perfect place for new owners to relax and make it their own. The wrap-around deck provides a scenic spot to enjoy the coastal air. Inside, the kitchen and dining area are filled with natural

  We Close Deals Team Lamacchia Realty, Inc.

  453 Lighthouse Rd, Aquinnah, MA 02535
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  /39

  $3,649,000

  • 5 Beds
  • 4.5 Baths
  • 4,218 Sq Ft

  7 Whistling Swan Cir, Edgartown, MA 02539

  Located in the sought-after Island Grove neighborhood, this Edgartown home is near Morning Glory Farm, Downtown, and South Beach. Designed for entertaining, the first floor features a custom kitchen, dining and living rooms, den, screened porch, half bath, and a seamless flow to outdoor living and a new heated pool. A spacious first-floor primary suite includes a walk-in closet and full bath.

  Jarrett Hurwitz Keller Williams Realty

  7 Whistling Swan Cir, Edgartown, MA 02539
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  /52

  $12,500,000

  • 5 Beds
  • 4 Baths
  • 3,700 Sq Ft

  18 Spruce Gate Rd, Chilmark, MA 02535

  Welcome to an extraordinary ocean view coastal sanctuary set within the exclusive gates of Squibnocket Farm—a 450+ acre private community with access to over 2 miles of oceanfront, 1.5 miles of pond frontage, and 300+ acres of conservation land. Set on a peaceful, pastoral landscape abutting 17 acres of preserved land, this stately home was designed and built by Soikkeli & Company, one of the

  Alyssa Halisky Wallace & Co. Sotheby's

  18 Spruce Gate Rd, Chilmark, MA 02535
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  /51

  $7,950,000

  • 4 Beds
  • 5 Baths
  • 3,490 Sq Ft

  308 South Rd, Chilmark, MA 02535

  Commanding Pondfront Retreat with Private Dock and South Shore Views. This exceptional Chilmark residence offers a rare blend of privacy, elegance, and modern comfort. Originally built by Tom Tate and renovated in 2018, it exudes contemporary sophistication while embracing its natural surroundings. A private dock on Chilmark Pond provides direct water access and stunning South Shore sunsets.

  Rose Ryley Sandpiper Realty Inc

  308 South Rd, Chilmark, MA 02535
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  /22

  $1,449,000

  • 3 Beds
  • 1.5 Baths
  • 1,404 Sq Ft

  32 MacHipscat Trail, Vineyard Haven, MA 02568

  This Cape Style home privately sited on 1.89 acres at the end of a cul-de-sac abutting conservation land with many walking trails. Nice features include spacious living spaces that include a well equipped kitchen with custom cherry cabinets, dining room, living room with fireplace, wood stove and french doors that lead you out to a private patio and backyard. Second floor offers two guest

  Brenda Galligan Karen M. Overtoom R.E.

  32 MacHipscat Trail, Vineyard Haven, MA 02568
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  /51

  $4,950,000

  • 5 Beds
  • 4 Baths
  • 4,044 Sq Ft

  49 Gosnold's Way, Chilmark, MA 02535

  Perched high on the north shore with sweeping views of the Vineyard Sound, this expansive and private property is surrounded by Menemsha Hills conservation land and trails and offers broad water views, even from ground floor of house. The house is large and well maintained with an upside down floor plan allowing for high ceilings and bright spaces in the open plan kitchen/dining/living room, as

  Meg Bodnar Tea Lane Associates

  49 Gosnold's Way, Chilmark, MA 02535
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  /29

  $1,725,000

  • 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!

  Heidi Vanderhoop Tea Lane Associates

  654 Lighthouse Rd, Aquinnah, MA 02535
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  /42

  $2,500,000

  • 4 Beds
  • 3.5 Baths
  • 1 Sq Ft

  10 Wood Duck Way, Oak Bluffs, MA 02557

  Perched on a hill, this waterfront house encompasses three levels of living. Thoughtfully designed and well cared for, this home provides calming water views and direct access to Wiggy's freshwater Pond from almost every room. The main level boasts a kitchen fitted with high-end appliances and opens to the dining room, deck, and airy living room with exposed beams, a gas fireplace, and large

  Marcia Sullivan Garvey Donnelly + Co.

  10 Wood Duck Way, Oak Bluffs, MA 02557
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  /37

  $2,725,000 Open Fri 11AM - 1PM

  • 5 Beds
  • 4.5 Baths
  • 4,982 Sq Ft

  79 David Ave, Vineyard Haven, MA 02568

  BEAUTIFUL CUSTOM-BUILT RETREAT- LAMBERT'S COVE This impressive property offers the perfect blend of privacy and convenient access to downtown and the picturesque James Pond Reserve at Lambert's Cove Beach. Step inside to discover over 4,900 sq ft of recently renovated living space. The home boasts 5 bedrooms and 4.5 bathrooms, including a stunning chef's kitchen that will ignite your culinary

  Tina Miller Compass

  79 David Ave, Vineyard Haven, MA 02568
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  /33

  $2,395,000

  • 3 Beds
  • 3 Baths
  • 1,862 Sq Ft

  6 Church St, Aquinnah, MA 02535

  This beautifully renovated contemporary home is perched on a hillside, offering views of the Atlantic Ocean. Upon entering the home has a light and airy atmosphere with cathedral ceilings and a wall of windows connecting you with the outdoors. The main level consists of an open-concept kitchen, living, and dining area with soaring ceilings and sliding glass doors that overlook the treetops of

  Heidi Vanderhoop Tea Lane Associates

  6 Church St, Aquinnah, MA 02535
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  /13

  $2,650,000

  • 4 Beds
  • 3 Baths
  • 2,299 Sq Ft

  26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575

  Discover the rare opportunity to build your dream home in one of the island’s most sought-after locations off Lamberts Cove Road. This parcel offers year-round waterfront living with the ultimate blend of privacy, beach access, and design potential, without the usual coastal erosion concerns. Approved architectural plans by Moskow Linn Architects are in place for a four-bedroom main residence, a

  Jill Napior Tea Lane Associates

  26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575
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  /30

  $1,695,000

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

  251 State Rd, Vineyard Haven, MA 02568

  This private and pastoral year-round home with fine craftsmanship and loads of character is a classic up-island refuge, yet in a location that is central on the island and convenient to town. Abutting Land Bank property, the charming home features an open living and dining room with wide plank floors and beams flowing into the kitchen, all surrounding a central brick fireplace. An expansive

  Meg Bodnar Tea Lane Associates

  251 State Rd, Vineyard Haven, MA 02568
• 

  

  /37

  $1,349,000

  • 4 Beds
  • 2 Baths
  • 2,059 Sq Ft

  4 Rock Pond Rd, Vineyard Haven, MA 02568

  4 Bedroom ++ home, has room for your family and your in-home business. This is the home that has it all. An abundance of light, space and potential. A large Atrium off the living room invites in the light and warmth of outside, creating an oasis of possibilities-The expansive open living-kitchen-dining area has space for all to gather, the wood stove and kitchen bringing warmth and sunlight into

  Kerry Quinlan-Potter Breakwater MV

  4 Rock Pond Rd, Vineyard Haven, MA 02568
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  /42

  $7,450,000

  • 5 Beds
  • 3 Baths
  • 2,269 Sq Ft

  34 Edys Island Way, Chilmark, MA 02535

  Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by anIsland legacy family, this property is unique among Island estates for its combination of privacy yet convenience and seclusion yet expansive views. To the

  Jill Napior Tea Lane Associates

  34 Edys Island Way, Chilmark, MA 02535
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  /19

  $2,295,000

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

  71 Netock Ave, Oak Bluffs, MA 02557

  On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated 4-bed home w/separate, office or studio space, ensconced in professionally landscaped grounds. Blending modern comfort w/timeless island charm, house features wide plank white oak floors, beautiful ceiling height & natural light, open-concept living-dining space w/new kitchen, 1st-floor primary bedroom w/ensuite bath,

  Ellen Valentgas Sotheby's International Realty

  71 Netock Ave, Oak Bluffs, MA 02557
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  /30

  $2,195,000

  • 4 Beds
  • 2.5 Baths
  • 1,825 Sq Ft

  4 Dempster Park, Oak Bluffs, MA 02568

  This handsome, meticulously maintained 4-bedroom gambrel roof house, nestled in one of the prime locations of East Chop, has had substantial renovations and upgrades over the years since 2017. First floor includes large living room with dining area and Rumford wood burning fireplace that opens out to a front porch and deck running the length of the house and which wraps around to the rear patio.

  Perry Patterson MV Luxury Homes LLC

  4 Dempster Park, Oak Bluffs, MA 02568
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  /58

  $5,999,000

  • 4 Beds
  • 3.5 Baths
  • 2,995 Sq Ft

  135 The Blvd, Edgartown, MA 02539

  Exceptional Waterfront Living ~ Stunning, active views of Sengekontacket Pond and Nantucket Sound set the tone for this spectacular coastal retreat. Thoughtfully designed to showcase its breathtaking surroundings, the main house captures sweeping vistas from nearly every room. With over 300 feet of frontage, you'll enjoy immediate access to the water for swimming, paddleboarding, kayaking, and a

  Stephanie Roache Donnelly + Co.

  135 The Blvd, Edgartown, MA 02539
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  /39

  $1,195,000

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

  9 Sampson Ave, Edgartown, MA 02539

  A home for all seasons and multiple purposes --- If you choose to have a comfortable, kick-your-shoes-off, not-fussy, beach home on the tranquil non-commercial island of Chappaquiddick, then this is your destination. The fabulous, pristine, seemingly endless miles of shoreline at East Beach, just over Dike Bridge, is only 1.3 miles distant. The gorgeous beaches at Wasque Point, where you also

  Lynn Buder Sandpiper Realty Inc

  9 Sampson Ave, Edgartown, MA 02539
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  /39

  $2,650,000

  • 4 Beds
  • 6 Baths
  • 2,694 Sq Ft

  16 Mockingbird Dr, Edgartown, MA 02539

  Experience the ultimate Vineyard getaway in this custom Colonial that perfectly balances sophistication with Island charm. This thoughtfully designed property features soaring 9-foot ceilings, authentic Heart Pine flooring, and a show-stopping gourmet kitchen complete with professional-grade Viking appliances, handcrafted soapstone countertops, and a statement Carrara marble island. The spacious

  Emma Kennedy Sandpiper Realty Inc

  16 Mockingbird Dr, Edgartown, MA 02539
• 

  

  /37

  $4,850,000

  • 5 Beds
  • 3 Baths
  • 3,440 Sq Ft

  146 Quansoo Rd, Chilmark, MA 02535

  Nestled along the beautiful and tranquil shoreline of Tisbury Great Pond and surrounded by a stunning natural environment of water, sand and sky, this is an unparallelled beach house experience on the south shore of Chilmark. The five-bedroom home consists of a three-bedroom main house connected by walkways to a two-bedroom guest wing with studio space above, all with spectacular water views

  Meg Bodnar Tea Lane Associates

  146 Quansoo Rd, Chilmark, MA 02535
• 

  

  /27

  $2,700,000

  • 4 Beds
  • 3 Baths
  • 2,001 Sq Ft

  2 Orchard Ln, Edgartown, MA 02539

  Welcome to this 4 bedroom home, with a pool, perched on the neighborhood hilltop. This tri-level cape offers an eat in kitchen featuring granite countertops, a Viking gas range, a double basin sink, a built in banquette and views of the front covered porch and hardscaped rear yard. The primary level presents with a living room, a separate bar area offering a wine refrigerator/dishwasher, a full

  Michele Casavant Vineyard Village Realty

  2 Orchard Ln, Edgartown, MA 02539
• 

  

  /28

  $1,650,000

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

  16 Majors Cove Ln, Edgartown, MA 02539

  Nestled in the prestigious Majors Cove community, this lovingly maintained home offers the perfect blend of comfort, style, and Vineyard charm. Enjoy access to exceptional amenities, including tennis courts, a boat launch ideal for kayaking to State Beach, and proximity to the bike path for easy access to Edgartown, Oak Bluffs, and Vineyard Haven. Set on a pleasantly landscaped lot, this inviting

  Stephanie Roache Donnelly + Co.

  16 Majors Cove Ln, Edgartown, MA 02539
• 

  

  /27

  $1,695,000

  • 3 Beds
  • 3 Baths
  • 1,740 Sq Ft

  27 Chapde Ln, Tisbury, MA 02568

  CLASSIC STYLE MEETS TIMELESS CHARM. Located at the end of a lightly traveled lane and surrounded by stunning gardens and stone retaining walls, this meticulously maintained home provides a modern and spacious environment for comfortable island living. Upon entry, the home welcomes you with an open and bright layout, featuring sleek finishes and an abundance of natural light. The gourmet kitchen

  Wendy Harman Compass | Point B

  27 Chapde Ln, Tisbury, MA 02568
• 

  

  /41

  $1,795,000

  • 2 Beds
  • 3 Baths
  • 1,737 Sq Ft

  150 Cove Rd Unit 10, Vineyard Haven, MA 02568

  The Premiere Townhouse at Tashmoo Wood. Elegantly renovated, this sun-filled end unit is fresh and modern with finish details. From the moment you step onto the expanded wrap-around deck, you will begin to see the fine craftsmanship of the property. Walk through the front entry and you will gain further appreciation for the meticulous attention to detail. Expansive windows fill the living area

  Michele Moore Island Real Estate

  150 Cove Rd Unit 10, Vineyard Haven, MA 02568

Showing Results 121 - 160, Page 4 of 7