Marthas Vineyard, MA Homes for Sale with Acreage

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  /37

  $9,995,000

  • 6 Beds
  • 7.5 Baths
  • 7,205 Sq Ft

  25 Lelands Path, Edgartown, MA 02539

  Casual Elegance On Katama Bay - Welcome to 25 Leland’s Path on Katama Bay, a stunning property that embodies the perfect blend of casual elegance and serene waterfront living on Chappquiddick. This magnificent home offers over 7,200 square feet of living space, six bedrooms, all with en suite baths, and a three-room Owner's Suite with sweeping water views and a private second-floor deck. The

  

  Wendy Harman

  Compass

  (508) 625-9706

  25 Lelands Path, Edgartown, MA 02539
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  /42

  $3,695,000

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

  37 Road To the Plains, Edgartown, MA 02539

  Exceptional Opportunity to Create Your Signature Vineyard Compound. Behind a charming white picket fence with blooming hydrangeas, this beautifully renovated Edgartown property blends island charm with new construction. Renovated in 2024 by top-tier builders, the nearly new home offers immediate comfort and timeless style, with potential for expansion into a luxury compound. On a private

  

  Wendy Harman

  Compass

  (508) 274-5363

  37 Road To the Plains, Edgartown, MA 02539
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  /23

  $8,995,000

  • 11 Beds
  • 8.5 Baths
  • 6,289 Sq Ft

  1 Louis Field Rd, Edgartown, MA 02539

  SWEETENED WATER FARM ESTATE. Located just one mile from the heart of historic Edgartown Village, this compound in Sweetened Water Farm presents a rare opportunity to become the next steward of this extraordinary Martha’s Vineyard estate. Privately sited on 4.6 acres of exquisitely cultivated gardens, this remarkable property has been featured in several publications celebrating the island’s most

  

  Wendy Harman

  Compass

  (508) 715-8610

  1 Louis Field Rd, Edgartown, MA 02539
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  /41

  $9,495,000

  • 4 Beds
  • 6 Baths
  • 4,605 Sq Ft

  29 Slough Cove Rd, Edgartown, MA 02539

  LUXURIOUS COUNTRY ESTATE IN KATAMA. Sited at the end of a long private drive, amid a bucolic 1.5-acre meadow setting with stone retaining walls and lush perennial gardens, this elegant country estate, designed by noted architect Patrick Ahearn, offers the epitome of luxurious living in Katama. The home’s timeless and charming character is highlighted by thoughtful, top-notch architectural details

  

  Wendy Harman

  Compass

  (508) 691-8146

  29 Slough Cove Rd, Edgartown, MA 02539
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  /47

  $5,450,000

  • 4 Beds
  • 5.5 Baths
  • 3,300 Sq Ft

  8 Paddock Rd, Oak Bluffs, MA 02557

  Refined Vineyard Living in The Preserve - Set gracefully on a knoll with sweeping views of a tranquil pond and surrounding grasslands, this beautiful residence offers a masterful blend of traditional coastal architecture and modern luxury. Located in the prestigious enclave of The Preserve, this sprawling home is designed for effortless elegance, privacy, and indoor-outdoor living.At the heart of

  Lesley Heidt Sandpiper Realty Inc

  8 Paddock Rd, Oak Bluffs, MA 02557
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  /38

  $4,195,000

  • 3 Beds
  • 3.5 Baths
  • 3,426 Sq Ft

  96 Hammett Ln, Chilmark, MA 02535

  This beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher soapstone counters and a butlers pantry with extra cupboards, shelving and a wine

  Brenda Galligan Karen M. Overtoom R.E.

  96 Hammett Ln, Chilmark, MA 02535
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  /44

  $6,395,000

  • 6 Beds
  • 5.5 Baths
  • 7,000 Sq Ft

  400 Barnes Rd, Vineyard Haven, MA 02568

  Experience the quiet elegance of this rare Asian-inspired contemporary estate set on 2.42 acres in a prime Oak Bluffs location. Tucked behind a long private drive and surrounded by 234 acres of Southern Woodlands conservation land offering biking and hiking, this expansive property offers unparalleled privacy just minutes from Featherstone Center for the Arts, Farm Neck Golf Club and the island’s

  Jennifer DaSilva Compass | Point B

  400 Barnes Rd, Vineyard Haven, MA 02568
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  /41

  $3,600,000

  • 3 Beds
  • 4 Baths
  • 2,500 Sq Ft

  27 Clambelly Rd, Chilmark, MA 02535

  A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media

  Julianna Flanders Flanders Real Estate

  27 Clambelly Rd, Chilmark, MA 02535
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  /59

  $6,495,000

  • 6 Beds
  • 5.5 Baths
  • 3,998 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

  Alan Schweikert Ocean Park Realty Inc

  15 Tamarack Ln, Oak Bluffs, MA 02557
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  /39

  $3,299,000

  • 3 Beds
  • 3.5 Baths
  • 3,082 Sq Ft

  53 Stoney Hill Rd, Vineyard Haven, MA 02568

  Nestled in one of the island’s most sought-after locations, this exceptional property offers refined coastal living with access to the famed Lambert’s Cove Beach yet a short drive to VH.Thoughtfully designed, it features 3 spacious bedrooms each with an en suite bath, providing comfort and privacy for all. Primary suite is a true retreat with a brand new luxurious bathroom. At the heart of the

  Jennifer B. DaSilva Compass

  53 Stoney Hill Rd, Vineyard Haven, MA 02568
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  /29

  $4,500,000

  • 5 Beds
  • 6 Baths
  • 5,598 Sq Ft

  71 Stoney Hill Rd, Vineyard Haven, MA 02568

  A combination of luxury, comfort, and natural beauty, this expansive custom, 6,000+ square foot, five bedroom, post and beam home is sited on more than seven acres of land, surrounded by more than 200 acres of Land Bank property. From the moment you step inside, you'll be captivated by the attention to detail and the high-end finishes throughout. The open concept layout allows for seamless flow

  Sheila Morse Island Real Estate

  71 Stoney Hill Rd, Vineyard Haven, MA 02568
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  /114

  $6,900,000

  • 7 Beds
  • 5.5 Baths
  • 4,730 Sq Ft

  180 Pilot Hill Farm Rd, Vineyard Haven, MA 02568

  A storybook sanctuary in Pilot Hill. For the first time in 37 years, one of the rarest and most beautiful properties within Pilot Hill Farm is being offered for sale.Set on nearly eight acres, this unique estate includes a thoughtfully renovated antique farmhouse and several distinctive outbuildings: a pool, guest house, an art studio, and a carriage house with room for three cars, plus a

  Alexis Holden Tea Lane Associates

  180 Pilot Hill Farm Rd, Vineyard Haven, MA 02568
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  /32

  $4,075,000

  • 4 Beds
  • 3.5 Baths
  • 2,861 Sq Ft

  39 Sengekontacket Rd, Edgartown, MA 02539

  SPECTACULAR WATERFRONT home with stunning water views from every room and completely renovated in 2014. Situated in a private location in the Sengekontacket Association, this is an exceptional property in a rare setting. In addition to the breathtaking water view of Major's Cove and of Felix Neck throughout the home, the front of the property faces serene pastoral views. This home offers four

  Jayne Isford Ocean Park Realty, Inc.

  39 Sengekontacket Rd, Edgartown, MA 02539
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  /30

  $3,900,000

  • 4 Beds
  • 2 Baths
  • 2,813 Sq Ft

  179 Tisbury Ln E, West Tisbury, MA 02575

  Seven Gates Farm: This warm and convivial home in one of the island’s most desirable communities is less than 1/10th of a mile to the private association beach. The house was designed to accentuate indoor-outdoor living; there is generous decking for morning or afternoon sun, and a screened porch which is the perfect place to enjoy shade and breeze after a day spent at one of the nearby beaches.

  Mark Jenkins Wallace & Co. Sotheby's

  179 Tisbury Ln E, West Tisbury, MA 02575
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  /76

  $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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  /25

  $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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  /44

  $3,950,000

  • 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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  /94

  $4,395,000

  • 3 Beds
  • 4.5 Baths
  • 3,314 Sq Ft

  20 Edson Forest Rd, Vineyard Haven, MA 02568

  Exquisite home befitting its stunning location on four serene acres surrounded by conservation and agricultural lands and overlooking a neighbor's private pond. This special spot is authentic up-island character at its best. This three bedroom home (with six-bedroom septic system) was fully renovated down to the studs and finished in 2022, resulting in a truly beautiful luxury home with a

  Meg Bodnar Tea Lane Associates

  20 Edson Forest Rd, Vineyard Haven, MA 02568
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  /26

  $3,500,000

  • 4 Beds
  • 2.5 Baths
  • 2,686 Sq Ft

  4 Nomans Watch Rd, Aquinnah, MA 02535

  You’ll always feel like you’re on vacation at this four-bedroom, two and one half bath home sited perfectly on 2.4 acres to capture sweeping vistas of the Atlantic Ocean and Noman's Island. Built in 2006, this home features an open living room, dining room and stainless steel kitchen flooded with light from the wall of windows providing wide views to the Atlantic. Enjoy dining on the wrap around

  Russell Maloney Russell Maloney Real Estate

  4 Nomans Watch Rd, Aquinnah, MA 02535
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  /31

  $3,950,000

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft

  29 Oxcart Rd, Aquinnah, MA 02535

  Waterfront beach house on Dogfish Bar in Aquinnah. Take in the beauty of this gem of a location with rolling dunes, waterviews and immense sunsets! This property is one of only a few homes on this stretch of private and preserved beach. This 2009 contemporary beach house offers a reverse floor plan with the entire top floor as the living area, kitchen & dining, and more windows than walls to

  Michelle Kelly Tea Lane Associates

  29 Oxcart Rd, Aquinnah, MA 02535
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  /42

  $4,150,000

  • 4 Beds
  • 3.5 Baths
  • 3,552 Sq Ft

  4 Boldwater Rd, Edgartown, MA 02539

  A private Edgartown home in the distinguished Boldwater neighborhood on Martha's Vineyard. This property is spread over 8.5 acres of pristine land and fruit trees and includes a 4 bedroom/3.5 bathroom main house and a 1 car garage. A winding drive leads from the road to the main residence which features a generous first floor plan with an open living room with a brick fireplace, dining room, and

  Thomas Wallace Wallace & Co. Sotheby's International Realty

  4 Boldwater Rd, Edgartown, MA 02539
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  /27

  $3,350,000

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft

  11 Greenhouse Ln, Chilmark, MA 02535

  11 Greenhouse Lane...an incredible opportunity to own in this sought after private enclave with deeded private south shore beach and pond access close by...this charming vintage cape enjoys views over wetlands out to the Atlantic beyond! Three bedrooms, two baths, living room with fireplace, dining area, updated kitchen, screened porch and outside shower. The owners have taken full advantage of

  Deb Hancock Hancock Real Estate

  11 Greenhouse Ln, Chilmark, MA 02535
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  /46

  $3,500,000

  • 4 Beds
  • 2.5 Baths
  • 2,383 Sq Ft

  100 Gosnolds Way, Chilmark, MA 02535

  Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound & the Elizabeth Islands. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where

  Julianna Flanders Flanders Real Estate

  100 Gosnolds Way, Chilmark, MA 02535
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  /45

  $3,000,000

  • 3 Beds
  • 3.5 Baths
  • 2,898 Sq Ft

  4 Pip'N Rd, Edgartown, MA 02539

  Chappaquiddick charm meets Edgartown elegance at this meticulously maintained property. No detail has been overlooked in this spacious custom home. The foyer entry greets you with a sizable dining room to your right which flows into an open eat in kitchen with a built in banquet, a granite kitchen island overlooking the masonry fireplace and wall of glass sliders in the living room. A wet bar

  Michele Casavant Vineyard Village Realty

  4 Pip'N Rd, Edgartown, MA 02539
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  /27

  $1,995,000

  • 3 Beds
  • 4 Baths
  • 2,526 Sq Ft

  56 Bridle Path Rd, Vineyard Haven, MA 02568

  POOL & LUSH GARDENS — Nestled on 3 acres beside 25 acres of conservation land, this 2,500+ sq. ft. home offers tranquility and convenience. The sun-filled living room with fireplace flows to the kitchen, dining area, screened porch, and sunny deck—perfect for enjoying serene views. The main floor hosts a spacious primary suite with en-suite bath; upstairs offers two large bedrooms, a full bath,

  Tina Miller Donnelly + Co.

  56 Bridle Path Rd, Vineyard Haven, MA 02568
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  /77

  $9,500,000

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

  6 Janes Cove Rd, Edgartown, MA 02539

  Waterfront on Edgartown Great Pond, 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 now been completely renovated

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  6 Janes Cove Rd, Edgartown, MA 02539
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  /25

  $2,595,000

  • Land
  • 8 Acres
  • $334,839 per Acre

  50 Iron Hill Rd Unit 31, Oak Bluffs, MA 02568

  Nestled beside the beloved Island Alpaca Farm, this rare 7.75-acre parcel offers an exceptional blend of open space, agricultural use, and development potential. Approximately 4.38 acres are protected by a conservation restriction, allowing for limited farming and equestrian activities—perfect for those seeking a pastoral lifestyle. The remaining 3.37 acres provide a prime opportunity to build

  Trish Lyman Compass | Point B

  50 Iron Hill Rd Unit 31, Oak Bluffs, MA 02568
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  /33

  $4,995,000

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

  19 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. 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 fireplace and concrete floors heated by radiant heat. French doors take

  Brenda Galligan Karen M. Overtoom R.E.

  19 Locust Ln, Aquinnah, MA 02535
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  /13

  $2,595,000

  • Land
  • 8 Acres
  • $334,839 per Acre

  50 Iron Hill Rd, Oak Bluffs, MA 02568

  This rare 7.75-acre parcel offers a unique combination of open space and development potential. Approximately 4.38 acres are protected by a conservation restriction, allowing for limited farming and equestrian use—ideal for those seeking pastoral pursuits. The remaining 3.37 acres offers the potential to build your dream home- while simply enjoying Island Life. The property features two barns

  Patricia Lyman Compass

  50 Iron Hill Rd, Oak Bluffs, MA 02568
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  /32

  $2,250,000

  • 4 Beds
  • 2.5 Baths
  • 2,522 Sq Ft

  29 Old Nursery Ln, Chilmark, MA 02535

  Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and projects. Wood working area in the basement is a plus. Enjoy the outdoors via the screened porch, large

  Julianna Flanders Flanders Real Estate

  29 Old Nursery Ln, Chilmark, MA 02535
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  /29

  $2,950,000

  • 4 Beds
  • 3 Baths
  • 2,758 Sq Ft

  382 Lighthouse Rd, Aquinnah, MA 02535

  Spacious contemporary set high off Lighthouse Road with unobstructed, amazing water views of the Vineyard Sound and Elizabeth Islands. Open concept design with soaring ceilings and modern architecture. A retreat for all seasons this house is fully insulated, heated and has central air. A center island in the kitchen ensures the cook of the family does not miss out on the amazing sunsets. Ground

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

  382 Lighthouse Rd, Aquinnah, MA 02535
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  /26

  $3,695,000

  • Land
  • 7 Acres
  • $551,493 per Acre

  32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, Chilmark, MA 02535

  Discover an exceptional opportunity with this rare combination of two abutting parcels spanning more than 6 acres in a coveted location offering water views and Atlantic Ocean private beach access. Surfers and fishermen delight in this location! The Stonewall Association is a beloved area of Chilmark in a supreme location for easy Chilmark living close to the Chilmark Store, the Chilmark

  Jill Napior Tea Lane Associates

  32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, Chilmark, MA 02535
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  /8

  $3,200,000

  • Land
  • 19 Acres
  • $165,803 per Acre

  32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575

  A Rare Offering in West Tisbury — Over 19 Acres of OpportunityAn exceptional opportunity to own just over 19 acres in the heart of rural West Tisbury. This expansive parcel offers tremendous flexibility, with potential for multiple dwellings or subdivision into a thoughtfully designed niche development. Ideally situated near all island towns, the property is also just minutes from the

  Jill Napior Tea Lane Associates

  32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
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  /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
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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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  /21

  $1,675,000

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft

  111 Charles Neck Way, Vineyard Haven, MA 02568

  Tucked away on 1.6 wooded acres in West Tisbury, this classic Cape-style home offers both privacy and convenience, with easy access to the charm of Up-Island and the amenities of Down-Island. Located on a paved road near Long Point Beach, it also includes coveted access to Lambert's Cove Beach. The bright, open interior features a living and dining area with a wood-burning fireplace, a kitchen

  Emma Kennedy Sandpiper Realty Inc

  111 Charles Neck Way, Vineyard Haven, MA 02568
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  /15

  $2,770,000

  • 3 Beds
  • 1.5 Baths
  • 1,540 Sq Ft

  5 Ocean View Farm Rd, Chilmark, MA 02535

  Designed by the famous mid century architect Andrew Geller, this contemporary home is situated at the top of the parcel with ocean views and a glimpse of Chilmark pond. There is ample open space to accommodate family and friends and overlooks the large meadow which follows the stone wall to South Road. Access to walking trails, and Lucy Vincent Beach is a short distance away.

  Natalie Conroy Conroy & Company R.E., Inc.

  5 Ocean View Farm Rd, Chilmark, MA 02535
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  /36

  $3,250,000

  • 4 Beds
  • 3.5 Baths
  • 2,515 Sq Ft

  300 North Rd, Chilmark, MA 02535

  Winding tree lined driveway off North Rd brings you to this commanding, custom designed residence built by a top tier island builder. This home is set on over 4 private acres of rolling meadows and big sky views. Main living space is all on one level which includes primary bedroom with en-suite bath, large living area with fireplace, bright sunroom or second living room, custom kitchen and

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

  300 North Rd, Chilmark, MA 02535
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  /40

  $1,899,000

  • 4 Beds
  • 3.5 Baths
  • 2,061 Sq Ft

  174 Middle Rd, Chilmark, MA 02535

  Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

  Sheila Morse Island Real Estate

  174 Middle Rd, Chilmark, MA 02535
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  /40

  $1,825,000

  • 4 Beds
  • 4 Baths
  • 3,927 Sq Ft

  44 Tiffany Dr, Oak Bluffs, MA 02557

  Nestled within the desirable Lagoon Estates development and set on a beautifully wooded 1.38-acre lot abutting Land Bank property, this expansive and sun-filled home offers versatile living space and a flexible floor plan. The main house features generously sized rooms enhanced by large windows that flood the interior with natural light. The kitchen boasts white cabinetry, a wall-mounted

  Nora Jardin Island Real Estate

  44 Tiffany Dr, Oak Bluffs, MA 02557

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