Oak Bluffs, MA Homes for Sale

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  /38

  $4,195,000

  • 3 Beds
  • 4 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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  /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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  /36

  $3,250,000

  • 4 Beds
  • 4 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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  /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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  /36

  $5,450,000

  • 5 Beds
  • 4 Baths
  • 2,913 Sq Ft

  122 Old Farm Rd, Chilmark, MA 02535

  An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The original section of this 3000 sq ft home dates from the late 1700s and is on Chilmark's register of historic homes, but it has been expanded with new additions to create a thoroughly modern

  Mark Jenkins Wallace & Co. Sotheby's

  122 Old Farm Rd, Chilmark, MA 02535
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  /42

  $4,600,000

  • 3 Beds
  • 6 Baths
  • 3,171 Sq Ft

  15 Old Farm Rd, Chilmark, MA 02535

  CHILMARK BLISS- 15 Old Farm Rd, sits on over 3 beautiful acres, blends refined architecture with serene natural beauty. Reimagined in 2020 by Peter Breese and crafted by Doug Best, this timeless retreat offers open-concept living, anchored by a stunning kitchen, large pantry, screen porch, and a stone fireplace, with seamless indoor-outdoor flow. The main level includes a sunny primary suite

  Tina Miller Compass

  15 Old Farm Rd, Chilmark, MA 02535
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  /34

  $5,450,000

  • 5 Beds
  • 4.5 Baths
  • 2,913 Sq Ft

  124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535

  An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The original section of this 3000 sq ft home dates from the late 1700s and is on Chilmark's register of historic homes, but it has been expanded with new additions to create a thoroughly modern

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
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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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  /46

  $6,750,000

  • 3 Beds
  • 3 Baths
  • 3,432 Sq Ft

  44 Cencelle St, Chilmark, MA 02535

  This private 21-acre Chilmark estate with ocean views, tucked away in the rolling hills and farmlands of Chilmark, offers sweeping ocean views to the south and a rare sense of seclusion and serenity. At the heart of the property is a striking modern style home, thoughtfully designed to bring the outdoors in. Expansive walls of glass flood the interior with natural light and frame panoramic views

  Meg Bodnar Tea Lane Associates

  44 Cencelle St, Chilmark, MA 02535
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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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  /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
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  /46

  $3,500,000

  • 4 Beds
  • 3 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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  /7

  $650,000

  • Land
  • 0.20 Acre
  • $3,250,000 per Acre

  00 Hancock Beach Lot Unit 73, Chilmark, MA 02535

  Spectacular Hancock beach lot on the Atlantic Ocean. Ownership of this lot allows you access to one of the world's most beautiful beaches, plenty of parking and away from the crowds. It is a most enjoyable spot to spend a relaxing day on the Vineyard, sunbathing, fishing, kayaking, canoeing, etc. as you also gain access to Chilmark Pond. Any property on the Vineyard would be greatly enhanced by

  Deb Hancock Hancock Real Estate

  00 Hancock Beach Lot Unit 73, Chilmark, 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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  /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
  • 2 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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  /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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  /36

  $2,500,000

  • 4 Beds
  • 3 Baths
  • 2,350 Sq Ft

  16 South Rd, Chilmark, MA 02535

  Where Vineyard history meets pastoral beauty.Classic, lovingly restored 1800’s Chilmark farmhouse with multiple outbuildings, which includes a large barn with second floor loft, a run-in barn with two horse stalls, both overlook an expansive, pastoral fenced pasture for horses to run or field games to be played. This historic farmhouse home offers four bedrooms, three baths and has been

  Michele Casavant Vineyard Village Realty

  16 South Rd, Chilmark, MA 02535
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  /25

  $1,295,000

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft

  140 Longview Rd, Vineyard Haven, MA 02568

  Nestled in the hills of Longview, less than 1 mile from beautiful Lambert's Cove Beach, this 3-bedroom retreat is a cozy year-round home or an airy summer getaway - whatever your needs might be. The vaulted ceilings throughout the home allow it to live much larger than its square footage - and the expansive front deck stretches the living space all through the spring, summer and even fall

  Candy DaRosa Feiner Real Estate

  140 Longview Rd, Vineyard Haven, MA 02568
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  /26

  $1,597,500

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  190 Longview Rd, Vineyard Haven, MA 02568

  Ask listing office. This property is in West Tisbury, 02575 NOT Tisbury 02568

  Kathleen Kendrick Kathleen Kendrick

  190 Longview Rd, Vineyard Haven, MA 02568
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  /36

  $1,495,000

  • 4 Beds
  • 2 Baths
  • 1,332 Sq Ft

  40 Scotchmans Ln, Vineyard Haven, MA 02568

  A home with history, built in the early 1800s this dwelling was originally built on a local farm and moved to its present location in the 1920's. The structure sits nestled amongst mature plantings and out buildings facing the Mill Brook. The studio and covered patio offer opportunities to entertain, relax and reflect. This 3.76 parcel was created from a larger parcel by the owner (see attached

  Jim Osmundsen Donnelly + Co.

  40 Scotchmans Ln, Vineyard Haven, MA 02568
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  /45

  $1,795,000

  • 7 Beds
  • 5 Baths
  • 3,213 Sq Ft

  51 Skiffs Ln, Vineyard Haven, MA 02568

  Roomy, 5 bedroom, 3.5 bath home warmed by walls of knotty pine and sited on a 3-acre parcel with nicely cleared areas around the house bringing in the sunlight and enticing you outside for games, gardening and relaxation on the expansive deck. There is a wood-burning brick fireplace in the living room to gather around on chilly nights - and a full, dry basement great for kids games on rainy days

  Candy DaRosa Feiner Real Estate

  51 Skiffs Ln, Vineyard Haven, MA 02568
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  /49

  $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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  /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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  /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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  /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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  /37

  $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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  /28

  $1,695,000

  • 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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  /59

  $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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  /41

  $2,950,000

  • 4 Beds
  • 3 Baths
  • 2,424 Sq Ft

  19 Old Woods Rd, Chilmark, MA 02535

  Tucked away in the heart of Chilmark, this nearly 3-acre property blends rustic Vineyard charm with unique creative potential. Chilmark was a very special place for the former owner, American artist Thomas Hart Benton, who summered on the Island for 50 years. Professor and Art Historian, Erika Doss, said “the years he spent in Chilmark honed the artistic style and subjects that led to his

  Cheri Mason Landvest MV

  19 Old Woods Rd, Chilmark, MA 02535
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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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  /35

  $2,850,000

  • 4 Beds
  • 3 Baths
  • 2,967 Sq Ft

  11 By the Woods, Chilmark, MA 02535

  Dreamlike Chilmark retreat on 4.5+/- acres overlooking the Chilmark Pond & Atlantic Ocean beyond. Uniquely designed with European and medieval history in mind. The House has 3 bedrooms, 3 bathrooms, an atrium dining area, a two-story library, a kitchen, and a pantry/wet bar. Charming garden and plantings surround the home.A must-see to appreciate all the special touches throughout the Main House,

  Julianna Flanders Flanders Real Estate

  11 By the Woods, Chilmark, MA 02535
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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
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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
• 

  

  /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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