Dukes County MA Homes for Sale

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  $4,495,000

  • 4 Beds
  • 5 Baths
  • 2,792 Sq Ft

  118 William St, Vineyard Haven, MA 02568

  The Captain George Harding Home sits gracefully on the westerly side of iconic William Street overlooking Vineyard Haven village with distant views of the harbor. This immaculate and re-imagined Gothic Revival offers both timeless elegance and modern luxury. Completed in 2024, the comprehensive down-to-the-studs renovation includes all new systems like central air and dehumidification. Every

  Alexis Holden Tea Lane Associates

  118 William St, Vineyard Haven, MA 02568
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  /42

  $9,900,000

  • 8 Beds
  • 9 Baths
  • 8,560 Sq Ft

  150 E Chop Dr, Oak Bluffs, MA 02557

  Big Bluff. The crown jewel of East Chop. Timeless elegance and unmatched craftsmanship on the shores of Martha’s Vineyard. Renowned architect M. Hutker and preeminent builder J.G.Early teamed up to create this magnificent waterfront estate. 8,500 Sq. ft. of pure luxury. Open-concept living with large picture windows, a chef’s kitchen with island, high-end appliances, wet bar, and sunlit breakfast

  Moira Lown Coldwell Banker Realty - Wellesley

  150 E Chop Dr, Oak Bluffs, MA 02557
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  $1,460,000

  • 4 Beds
  • 3 Baths
  • 2,961 Sq Ft

  208 Irenes Way, Tisbury, MA 02568

  Welcome to this 4 bedroom 3 bathroom 2,961 square foot home! Enjoy the open, first floor layout, finished walk out basement, beautiful hardwood flooring and a quality kitchen with new granite countertops. Just off of the kitchen there is a convenient first floor bedroom, bathroom and laundry room, as well as a lovely bonus space currently enjoyed as a sunroom with a sliding door to the large

  Emma Bryant Landmarks at TODAY Real Estate

  208 Irenes Way, Tisbury, MA 02568
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  $9,995,000

  • 4 Beds
  • 7 Baths
  • 5,458 Sq Ft

  43 Peases Point Way S, Edgartown, MA 02539

  Refined, timeless, and unparalleled, 43 Peases Point Way South effortlessly blends warmth, elegance, and sophistication to create a truly distinctive living experience in one of Edgartown’s most coveted locations. Designed by celebrated architect Patrick Ahearn, this exceptional residence is just a short stroll from historic Main Street. From the gated arbor entry and tranquil courtyard to the

  Katie Donahue Sandpiper Realty

  43 Peases Point Way S, Edgartown, MA 02539
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  /47

  $2,500,000

  • 3 Beds
  • 3 Baths
  • 1,784 Sq Ft

  12 Lobsterville Rd, Aquinnah, MA 02535

  12 Lobsterville Rd in Aquinnah is a uniquely designed contemporary home set on 2.6 acres of lush grounds with large tracts of conservation land nearby. Open concept living, dining, kitchen on the second floor with unobstructed ocean views of Vineyard Sound. Spacious deck for sunset viewing and grassy lawn for sundown games. Walking distance to Lobsterville Beach and a short bike ride to the

  Tina Palmer Conroy & Company R.E., Inc.

  12 Lobsterville Rd, Aquinnah, MA 02535
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  $6,490,000

  • 6 Beds
  • 8 Baths
  • 5,660 Sq Ft

  60 Meetinghouse Rd, Chilmark, MA 02535

  This spectacular and bright modern american farmhouse is perfectly sited to capture the varied scenic beauty that surrounds the farm. Built in 2021 with great attention to detail and materials, this home was created around gatherings and community with ample space for the extended family. The land has been lovingly curated into a place which can grow, generate and support those who want to have

  Jim Feiner Feiner Real Estate

  60 Meetinghouse Rd, Chilmark, MA 02535
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  /26

  $1,985,000

  • Land
  • 3.58 Acres
  • $554,469 per Acre

  4 Cedar Ln Unit 2.2, Chilmark, MA 02535

  Premier Build-Ready Lot with Private Beach AccessGet to know Stonewall Association, one of Chilmark’s most sought-after enclaves on the South Shore. This sunny, build-ready parcel offers a rare opportunity to own land with deeded private access to Stonewall Beach—a beloved destination for swimming, surfing, excellent fishing and summer memories. Set on beautifully contoured land with southern

  Jill Napior Tea Lane Associates

  4 Cedar Ln Unit 2.2, Chilmark, MA 02535
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  /12

  $1,325,000

  • Land
  • 4.12 Acres
  • $321,602 per Acre

  25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568

  This beautiful wooded 4.12 acre parcel of land is peaceful, serene and ready to build. The well is installed, boundaries staked, perc test approved for a five-bedroom home and a septic plan designed. This is an opportunity to realize your vision and build a home that reflects your lifestyle. The large, flat building envelope offers many siting possibilities and, should you choose, the property

  Abby Rabinovitz Tea Lane Associates

  25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568
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  $3,995,000

  • 5 Beds
  • 3 Baths
  • 2,791 Sq Ft

  20 James Pond Way, Vineyard Haven, MA 02568

  Nestled on a serene 4.5-acre parcel of land off Lambert's Cove Road, this exquisite property offers unparalleled privacy, views and direct access to James Pond and beyond to the Land Bank's Lambert's Cove Beach property. In addition to the custom heated Gunite pool, the expansive yard provides space for many outdoor activities while relishing the tranquility of the location. The residence

  Sheila Morse Island Real Estate

  20 James Pond Way, Vineyard Haven, MA 02568
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  /21

  $1,795,000

  • 3 Beds
  • 4 Baths
  • 2,312 Sq Ft

  7 Candlemaker Cir, Edgartown, MA 02539

  3 bedroom 2.5 bath main house consisting of 2 separate living spaces. First unit has 1st floor with livingroom, kitchen and bathroom. The second floor has an additional livingroom with two bedrooms. The second unit has 1st floor living area with kitchenette and bathroom, bedroom is in basement with walkout egress. 2 Car Garage has a permitted finished living space above with livingroom, full

  Roy Cutrer Jr Laer Realty Partners

  7 Candlemaker Cir, Edgartown, MA 02539
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  /3

  $1,795,000

  • 3 Beds
  • 3.5 Baths
  • 2,311 Sq Ft

  7 Candle Maker Cir, Edgartown, MA 02539

  3 bedroom 2.5 bath main house consisting of 2 separate living spaces. First unit has 1st floor with livingroom, kitchen and bathroom. The second floor has an additional livingroom with two bedrooms. The second unit has 1st floor living area with kitchenette and bathroom, bedroom is in basement with walkout egress. 2 Car Garage has a permitted finished living space above with livingroom, full

  Roy Cutrer LAER Realty Partners

  7 Candle Maker Cir, Edgartown, MA 02539
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  $6,795,000

  • 3 Beds
  • 3 Baths
  • 2,589 Sq Ft

  57 Hines Point Rd, Vineyard Haven, MA 02568

  Lily Hill - a rare Hines Point offering that includes a waterfront home with exquisite views, a deep water mooring and dock, and 130 feet of private fine-sand beach. Poised on a knoll on the western shore of the Lagoon, Lily Hill evokes a more peaceful time with sweeping views of the sky and water. Enjoy a swim at your private beach morning, noon or night. Watch the play of light across the water

  Elissa Lash Tea Lane Associates

  57 Hines Point Rd, Vineyard Haven, MA 02568
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  $4,600,000

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

  370 Lighthouse Rd, Aquinnah, MA 02535

  Stunning waterview living with an active view that will never disappoint. Wake up every morning to breathtaking 180 degree water views in this beautifully appointed 4-bedroom, 3-bath coastal retreat. Perfectly situated to capture sunrise to sunset vistas, this home offers a blend of summer vibes with year-round living amenities. Step inside to find an open-concept living space filled with natural

  Jill Napior Tea Lane Associates

  370 Lighthouse Rd, Aquinnah, MA 02535
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  /21

  $949,900

  • Land
  • 3.80 Acres
  • $249,974 per Acre

  0 Jeffers Way Unit 165 43370, Aquinnah, MA 02535

  This lovely parcel in Aquinnah offers a rare opportunity to own a pristine 3.8 acre parcel on Martha's Vineyard. This elevated, hilly lot is bordered by Classic New England stone walls and surrounded by mature trees, providing both privacy and a serene natural setting. The property is prepared for development, featuring an installed well, a 3-bedroom septic, electric and a completed

  Brenda Galligan Karen M. Overtoom R.E.

  0 Jeffers Way Unit 165 43370, Aquinnah, MA 02535
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  $1,950,000

  • 4 Beds
  • 2 Baths
  • 1,750 Sq Ft

  16 Schoolhouse Rd, Edgartown, MA 02539

  Vacation Getaway in Edgartown Estates - This sunny and welcoming contemporary home could be yours this summer! With an open layout, vaulted ceilings, and lots of windows and glass doors, the home feels bright and airy. Step outside to a spacious wrap-around deck--great for relaxing or entertaining. Inside, the living, dining, and kitchen areas flow nicely and are just the right size for

  Lesley Heidt Sandpiper Realty Inc

  16 Schoolhouse Rd, Edgartown, MA 02539
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  /35

  $13,000,000

  • 5 Beds
  • 5 Baths
  • 3,758 Sq Ft

  6 Wakeman Rd, Chilmark, MA 02535

  A 1930s-built home that has been remarkably updated to retain its historic charm while incorporating sophisticated and modern amenities. The house overlooks the Chilmark Great Pond and the Atlantic Ocean beyond. The Main House includes 3 bedrooms, 3 beautifully renovated bathrooms, a walk-in closet, a Pantry, a Library/Media room, a full basement, Outdoor showers, and a screened-in porch. The

  Julianna Flanders Flanders Real Estate

  6 Wakeman Rd, Chilmark, MA 02535
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  $3,600,000

  • 3 Beds
  • 3 Baths
  • 4,382 Sq Ft

  88 & 90 Quenames Rd, Chilmark, MA 02535

  Make your own Chilmark dream come true!12.6 +/- acres of prime land allows you to create your own familycompound or Island Farm. Enjoy the peacefulness of the Chilmarkwith room to expand. Two separate buildable lots provides you uniqueoptions. The Main house has three bedrooms, three bathrooms, twostudies, multiple living spaces and a large three-car garage

  Julianna Flanders Flanders Real Estate

  88 & 90 Quenames Rd, Chilmark, MA 02535
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  /6

  $2,950,000

  • Land
  • 2.36 Acres
  • $1,250,000 per Acre

  18 Allen Farm Rd Unit 20-2, Chilmark, MA 02535

  This private and serene 2.36 acre property is located one mile from Lucy Vincent Beach. There is a large building envelope located between the eighty and one hundred foot contour with exciting architectural options. The land has open woodlands, a small pasture and a fenced garden area. A charming cottage on the property is offered fully furnished and has everything you need to enjoy your stays

  Patty Kendall Kendall & Kendall

  18 Allen Farm Rd Unit 20-2, Chilmark, MA 02535
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  /17

  $1,900,000

  • Land
  • 3.30 Acres
  • $575,758 per Acre

  32 Stonewall Rd Unit 2.1, Chilmark, MA 02535

  South shore beachy living in Stonewall Association with private parking and access to a lovely swim and surf beach in a beloved area of Chilmark. There are second floor water views over Squibnocket Point and the Atlantic Ocean. This lot is fully engineered and ready to be built on! Single-family dwelling, plus a detached bedroom and accessory buildings, permitted according to the Chilmark

  Jill Napior Tea Lane Associates

  32 Stonewall Rd Unit 2.1, Chilmark, MA 02535
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  $5,295,000

  • 7 Beds
  • 5 Baths
  • 5,320 Sq Ft

  8 Fresh Pond Rd, Oak Bluffs, MA 02557

  The Ultimate Oak Bluffs Compound: A rare opportunity to own a stunning seven-bedroom estate, thoughtfully designed for both luxurious living and exceptional rental potential. This expansive property features a newly built pool, lush landscaping, and direct access to Fresh Pond—ideal for kayaking, paddleboarding, and swimming. Perfect for entertaining, the home showcases a dramatic great room, an

  Jarrett Hurwitz Keller Williams Realty

  8 Fresh Pond Rd, Oak Bluffs, MA 02557
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  /4

  $1,695,000

  • Land
  • 6 Acres
  • $273,829 per Acre

  19A Locust Ln Unit part of lot 175.1, Aquinnah, MA 02535

  This private 6.19 acres parcel has been approved for sub-division and not yet recorded. Potential to add acreage. Proposed lot lines and designated building envelope. Lovely rolling topography with mature trees. Septic & Well not installed

  Brenda Galligan Karen M. Overtoom R.E.

  19A Locust Ln Unit part of lot 175.1, Aquinnah, MA 02535
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  $1,550,000 Open Sat 3:15PM - 5PM

  • 3 Beds
  • 2 Baths
  • 2,311 Sq Ft

  61 Dodgers Hill Rd, Edgartown, MA 02539

  Located in the sought-after Dodgers Hole neighborhood, this beautifully renovated home blends modern style with coastal ease. Sunlight fills the main living area, where cathedral ceilings and hardwood floors create a bright and welcoming space. The kitchen has been completely redone with fresh finishes and thoughtful design, and the brand-new baths add to the turnkey appeal. The finished lower

  Ellen Valentgas Sotheby's International Realty

  61 Dodgers Hill Rd, Edgartown, MA 02539
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  $1,550,000 Open Sat 3:15PM - 5PM

  • 3 Beds
  • 2 Baths
  • 2,311 Sq Ft

  61 Dodgers Hole Rd, Edgartown, MA 02539

  Located in the sought-after Dodgers Hole neighborhood, this beautifully renovated home blends modern style with coastal ease. Sunlight fills the main living area, where cathedral ceilings and hardwood floors create a bright and welcoming space.The kitchen has been completely redone with fresh finishes and thoughtful design, and the brand-new baths add to the turnkey appeal. The finished lower

  Ellen Valentgas Sotheby's International Realty

  61 Dodgers Hole Rd, Edgartown, MA 02539
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  $4,250,000

  • 4 Beds
  • 3 Baths
  • 3,159 Sq Ft

  3 Down Harbor Rd, Edgartown, MA 02539

  Exceptional Opportunity in Down Harbor.Here’s a rare chance to own a property in Edgartown’s exclusive Down Harbor community. Known for its serene setting and prime access to Katama Bay, this neighborhood offers more than just scenic beauty— Ownership includes deeded rights to a pristine, sandy association beach, along with coveted mooring and dock privileges on Katama Bay — a benefit

  Susan Wallo Compass | The O'Hanlon Group

  3 Down Harbor Rd, Edgartown, MA 02539
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  $6,000,000

  • 5 Beds
  • 7 Baths
  • 5,104 Sq Ft

  10 Puwal Ln, Edgartown, MA 02539

  KATAMA COMPOUND WITH POOL - TURNKEY & READY FOR USE THIS SUMMER! In an enclave of luxury homes in Katama, this 2021-built 5 bedroom, 5 bathroom property with three half-baths is being delivered turnkey with fine furnishings and most artwork. The home has everything the modern buyer wants, including two primary bedroom suites (one upstairs, one downstairs), all bedrooms with ensuite bathrooms, two

  Mark Jenkins Wallace & Co. Sotheby's

  10 Puwal Ln, Edgartown, MA 02539
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  /3

  $925,000

  • 2 Beds

  90 17th St N, Edgartown, MA 02539

  90 Seventeenth Street NorthEdgartown, MassachusettsFOR SALEHere is a chance for you to own a water view property in Edgartown. Property is located just off the Boulevard on a quiet dead end lane. This property has been in the same family for decades and is now offered for sale. It is a blank canvas for you to create your dream home. Interior has been gutted and is ready for your renovation. The

  Theodore Saulnier TAS Real Estate, LLC

  90 17th St N, Edgartown, MA 02539
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  $4,350,000

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

  131 State Rd, Chilmark, MA 02535

  Magical waterfront Quitsa pond cottage with private dock. This home has the most spectacular views including sunsets and an intimate relationship with the charming and timeless waterfront at Quitsa Pond. Designed with the setting in mind this sublime piece of architecture has wonderful spaces, fantastic detail and so much packed into a smaller home. Landscape design by Edwina von Gal accentuates

  Jim Feiner Feiner Real Estate

  131 State Rd, Chilmark, MA 02535
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  $2,050,000

  • 4 Beds
  • 2.5 Baths
  • 2,855 Sq Ft

  5 Bayes Hill Cir, Vineyard Haven, MA 02568

  On a quiet cul-de-sac in the Bayes Hill neighborhood is this spacious traditional Colonial-style home adorned with charm. As you enter the home from the idyllic covered porch, you are welcomed into the foyer. The home is filled with intimate spaces while offering the opportunity for larger parties to gather. The living room has built-in shelving that flank the gas fireplace and it is connected to

  Michele Moore Island Real Estate

  5 Bayes Hill Cir, Vineyard Haven, MA 02568
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  /7

  $1,900,000

  • Land
  • 2.06 Acres
  • $922,330 per Acre

  34 Paddock Rd, Oak Bluffs, MA 02568

  The Preserve - A terrific opportunity to build in this beautiful and prestigious neighborhood in Oak Bluffs. The Preserve has matured into an enclave of significant residences and offers excellent privacy, with convenience to downtown, harbor and beaches. The orientation of this parcel is prime with southern exposure for backyard pool and patio, and it is abutting dedicated open space on two

  Lesley Heidt Sandpiper Realty Inc

  34 Paddock Rd, Oak Bluffs, MA 02568
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  $7,975,000

  • 4 Beds
  • 5 Baths
  • 3,777 Sq Ft

  25 Osprey Ln, Chilmark, MA 02535

  Spectacular views from one of the most sought after private enclaves on Chilmark's South Shore. This lovely home was built to take advantage of this magical location. Just steps to the shared dock on the shores of Upper Chilmark Pond and minutes to the extraordinary deeded Atlantic Beach front. The homeowners worked with world renowned architects, Crissman & Solomon, along with revolutionary

  Deb Hancock Hancock Real Estate

  25 Osprey Ln, Chilmark, MA 02535
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  /8

  $3,495,000

  • Land
  • 11 Acres
  • $306,848 per Acre

  0 Pocha Road Extension Unit 1.1,1.2 43325, Edgartown, MA 02539

  CHAPPAQUIDDICK - Dynamic views of Poucha Pond, barrier dunes, and the waters of the Atlantic are enjoyed from this 11+ acre building lot. The close to mile of private pond frontage provides easy access for swimming, kayaking, paddle boarding, and everything in between. Sheltered amongst 200 acres of conservation land, enjoy and explore the wonders of the natural habitat right in your backyard.

  Katie Donahue Sandpiper Realty

  0 Pocha Road Extension Unit 1.1,1.2 43325, Edgartown, MA 02539
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  $1,695,000 Open Sat 10AM - 12PM

  • 4 Beds
  • 1.5 Baths
  • 1,592 Sq Ft

  5 Scottys Ln, Vineyard Haven, MA 02568

  Attention Developers and Island Lovers! Take note of this rare opportunity in a prime West Tisbury Location with a new price! This mid-century home with excellent bones fronts on Seth's Pond, a beloved locale perfect for swimming, paddle-boarding, and kayaking. 5 Scotty's Lane has an existing 4-bedroom main house with the first floor and lower walk-out level equaling 2,704 of finished space. This

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

  5 Scottys Ln, Vineyard Haven, MA 02568
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  /35

  $2,495,000

  • 4 Beds
  • 3 Baths
  • 2,968 Sq Ft

  9 Beetlebung Grove Way, Chilmark, MA 02535

  Beautifully sited on 3.4 acres, this distinctive Chilmark home offers a rare blend of privacy, comfort, and expansive living space, ideal for entertaining, both inside and outside. From the welcoming foyer, step into the dramatic vaulted living room, where wood-paneled ceilings, a gas fireplace, and abundant natural light from skylights and picture windows create a warm and inviting atmosphere.

  Stephanie Roache Donnelly + Co.

  9 Beetlebung Grove Way, Chilmark, MA 02535
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  $1,750,000

  • 5 Beds
  • 2 Baths
  • 1,440 Sq Ft

  393 Lighthouse Rd, Aquinnah, MA 02535

  Ranch style home & Guest camp situated on 1+/- acre lot. The Main House offers distant views of Lobersterville beach and the Vineyard Sound beyond. Located in the desirable Lighthouse Road area, which offers walkable/close-by beach access and quiet roads. The view can be enjoyed from the Kitchen/Living/Dining as well as the wrap-around deck. Enjoy the open concept main living area, two bedrooms,

  Julianna Flanders Flanders Real Estate

  393 Lighthouse Rd, Aquinnah, MA 02535
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  $1,925,000

  • 3 Beds
  • 3 Baths
  • 1,728 Sq Ft

  212 Charles Neck Way, Vineyard Haven, MA 02568

  This beautifully renovated contemporary South Shore retreat, located in a tranquil setting, features three bedrooms, two and one-half bathrooms, central air, all new appliances, in ground pool and mature perennial gardens galore! Sitting on 1.5 acres, this location provides easy access to Long Point Beach and the Red Pony Farm equestrian center and, includes access to the coveted Lamberts Cove

  Perry Patterson MV Luxury Homes

  212 Charles Neck Way, Vineyard Haven, MA 02568
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  $1,795,000

  • 3 Beds
  • 2.5 Baths
  • 2,236 Sq Ft

  71 6th St N, Edgartown, MA 02539

  Classic three-bedroom farmhouse offers the perfect blend of island charm and laid-back comfort. Located within walking distance to scenic Sengekontacket Pond, it’s an ideal retreat for nature lovers, kayakers, or anyone looking to enjoy the Vineyard lifestyle. The home features a welcoming front porch and back deck—perfect spaces to relax, dine, or entertain outdoors. Inside, you'll find a warm

  Erin Leighton Compass

  71 6th St N, Edgartown, MA 02539
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  /23

  $1,164,000

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft

  96 Manchester Ave, Oak Bluffs, MA 02557

  Nestled in a quiet neighborhood less than two miles from the heart of Circuit Avenue, this contemporary cape-style home is ready to welcome you. A charming farmer's porch invites you into a spacious living area with cathedral ceilings and an open-concept design that seamlessly connects the kitchen, dining, and living spaces—perfect for gathering with family and friends.The main level features

  Michele Moore Island Real Estate

  96 Manchester Ave, Oak Bluffs, MA 02557
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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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  /37

  $3,400,000

  • 5 Beds
  • 2 Baths
  • 3,133 Sq Ft

  19 Old Woods Rd, Chilmark, MA 02535

  Nestled in the heart of Chilmark, this 12.5-acre property offers two charming dwellings, each with 3 bedrooms, set in a landscape of privacy and timeless Vineyard character. Built in 1950 and 1963 for American artist, Thomas Hart Benton, the homes were lovingly created as a compound for friends and family to return to year after year. Tucked down a quiet driveway, the two share a special legacy

  Cheri Mason Landvest MV

  19 Old Woods Rd, Chilmark, MA 02535
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  /11

  $1,250,000

  • Land
  • 6 Acres
  • $219,298 per Acre

  14 Ridge Rd Unit 94, Aquinnah, MA 02535

  Idyllic gently rolling parcel of mixed hardwoods, meadow and stone walls awaits your vision. A large level building envelope has been cleared. A house and an ADU are permitted by right and a barn(subject to town approval) will fit nicely on this secluded parcel with room for a horse to graze and access nearby Land Bank and Sheriffs Meadow conservation land .It is walking distance to Menemsha

  Jim Wallen Feiner Real Estate

  14 Ridge Rd Unit 94, Aquinnah, MA 02535

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