Chilmark Real Estate

Types of homes in Chilmark include ranch style homes, charming cottages, traditional farmhouses, vacation homes, and old family homesteads. Real estate in Chilmark offers access to fishing, beaches, and miles of trails. Chilmark's coastline is very dramatic, ranging from the sloping sandy beaches of the south shore to the rocky coast of the north shore.

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18 Spruce Gate Road Chilmark MA 02535

Chilmark, MA18 Spruce Gate Road

Price$20,500,000

Est. Mortgage: $/month

MLS Number 40560

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 3.5
  • Acreage 6.2

Occupying a serene & dramatic peninsula far from the public eye, Squibnocket Farm embodies a Martha’s Vineyard lifestyle in a community that emphasizes environmental sensitivity & discreet privacy. Enjoy 500 acres of forever-deeded conservation land & private access to 2+ miles of vast dune-protected sandy beaches. Life on this quiet corner of the island is accurately described as quaint & boundless. Beyond the gates exists an enclave of 11 well designed & rarely available residential estates coveted for their uniqueness & complemented by unparalleled natural beauty. A rare opportunity to purchase a 6.2 acre ridge top home directly abutting 18 acres of conservation land w/ views of Squibnocket Pond & Atlantic Ocean perfectly framing the endless theater of passing Swans, Ospreys, Pheasants & other fauna harmoniously thriving by the community’s low-density approach on Martha's Vineyard only Pesticide-free zone. The home’s recently renovated exteriors feature cedar shakes, mahogany trim, crown moldings, copper gutters & discreetly placed solar panels on the roofs south side providing a near zero approach to external power supply. Enjoy the mahogany deck & screened in porch with fireplace. Feel the warmth of highly crafted cedar woodwork throughout the interiors. Enjoy a large dining room, living room w/ fireplace, chef’s kitchen, stone counters, custom cabinets, walk-in pantry, high end appliances, cathedral ceilings, open living space, beautiful exposed beams, cherry floors & brick fireplace. First level master suite set on the home’s southern end. Mahogany outdoor shower accessible thru the master bath. The North end has 4 additional bedrooms, 2-car garage & 2nd outdoor shower. The Home is fully wired for sound, including smart home features that control central heat & AC. Internet is robustly distributed w/enterprise grade Ubiquiti products, providing low latency & reliable throughput suitable for high quality data or video transmission. Thoughtfully designed gardens highlight ancient stone walls, flower beds, meadows & lawn overlooking water surrounding the estate. Pastures planted by The Allen Farm of Chilmark are home to sheep & lambs + barn w/ lofts, 19 solar panels, electricity, internet & year-round no freeze water supply. Mobile cedar chicken coop houses award winning French Bresse chickens that produce 2 dozen eggs/wk & meat known as the best tasting chicken in the world. This remarkable property has it all & must be seen to fully experience.

Listed by Grace Hagerty Real Estate Inc

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$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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8 Snail Road Chilmark MA 02535

Chilmark, MA8 Snail Road

Price$17,590,000

Est. Mortgage: $/month

MLS Number 40676

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 6
  • Acreage 4

Experience the ultimate luxury lifestyle at this exquisite Martha's Vineyard estate. Nestled in a private and serene location, this magnificent property offers stunning views of the Atlantic Ocean and Chilmark Pond. Chilmark House, designed by Seattle-based architect Rick Sundberg and constructed by master builder Andrew Flake, merges contemporary amenities with Vineyard themes to create a truly unique living experience. Walking up to the front door you will see an enormous boulder that sits just inches away from the home. The massive stone was deposited on the property from a receding glacier long ago. As you enter the home, you will be greeted by tall ceilings, oak flooring, and natural light. From here, your eye will immediately be drawn to the walls of glass and ocean views. The modern kitchen is a chef's dream, featuring cherry cabinets, granite countertops, and appliances from Sub Zero, Miele, Wolf, and Scotsman. The family room off the kitchen boasts a custom fireplace and is ideal for casual gatherings. Adjacent to the kitchen and deck is a wonderful screened porch with high ceilings and ample room for dining and relaxing. The primary suite is a retreat in itself, featuring access to a private study with fireplace, two luxurious baths, deck and heated floors throughout. The second wing of the house includes three large guest bedrooms, two baths and a dressing room. The heated infinity pool is awe inspiring; a centerpiece of the home with elegant terrace and ocean views. Other outdoor features include the large kitchen garden, fruit trees and half-basketball court. A detached 3-bay garage and additional parking rounds out the main house. Set apart from the main house is the two-bedroom cottage, offering guests a private spot of their own. Chilmark House includes private south shore beach rights, accessible by boat from Chilmark Pond. This one-of-a-kind property, where the Obamas have vacationed, is the ultimate in luxury living. For a truly seamless transaction, all furniture, artwork and gym equipment is available for purchase. Please inquire for more details.

Listed by Compass | The O'Hanlon Group

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$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2 Squibnocket Road Chilmark MA 02535

Chilmark, MA2 Squibnocket Road

Price$12,995,000

Est. Mortgage: $/month

MLS Number 40660

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 5.5
  • Acreage 4.5

OCEAN VIEW OASIS IN CHILMARK. This Squibnocket gem is a Hutker Architect-designed family compound on 4.5 acres. With captivating water views in every direction, this home is the perfect launch pad for the ultimate up-Island lifestyle. Grab your surf or paddle board and head down the path to Squibnocket Beach for a morning surf or swim. Pack the cooler with lunch from the Chilmark Store for a day at Lucy Vincent Beach or on the boat. Pick up some local oysters and lobster rolls in Menemsha and then head home to enjoy a perfect summer sunset on the patio overlooking Menemsha Pond and the Elizabeth Islands. The home is pristine and private with many unique features that make it the perfect place from which to enjoy all that up-Island has to offer. The chef's kitchen and dining area are serene, bright, and functional. The main floor living spaces feature unparalleled Chilmark panoramas with views of South Shore beaches, Quitsa and Menemsha Ponds, and the Vineyard Sound. A stately wood-burning stone fireplace centers the living room which overlooks the expansive lap pool and stone patio area with dining space for outdoor enjoyment. The main house has 4 bedrooms and 3 1/2 baths, all with their own unique water views. The primary bedroom, on the main level, has its own fireplace, ensuite bathroom, walk-in closet, and direct access to the outdoor shower. This rare up-Island property also includes a secluded guest house with a well-appointed kitchen, two ensuite bedrooms, and a spacious living area with wood burning fireplace. A one-car garage on the property is a plus for storing all of your Island toys such as surfboards, beach gear, and the Island car. This Chilmark retreat also features deeded access to a dock for small boat pick-up and drop-off on Menemsha Pond, just across the way. Close to the Chilmark General store, Chilmark Tavern, Beetlebung Farm Stand, and the Chilmark Community Center for your convenience. However you like to spend your days, whether at the beach, by the pool, grilling with a crowd, or curled up with a good book in front of the fire, you can do it all at this one-of-a-kind Chilmark property.

Listed by Compass | Point B

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$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1 Clam Point Cove Road Chilmark MA 02535

Chilmark, MA1 Clam Point Cove Road

Price$9,950,000

Est. Mortgage: $/month

MLS Number 40699

  • Residential
  • Mls Status Active
  • Bedrooms 7
  • Bathroom 6
  • Acreage 3

Martha's Vineyard has many fine waterfront properties but only a handful of exceptional ones. The Lee Family Compound is an exceptional 3 acre waterfront property with breathtaking unobstructed pond views from an elevated secure location, 750+ ft of pond frontage, 48 ft dock with separate mooring for easy access to Menemsha Pond and Vineyard Sound and privacy without an abutter in view - all compliment the spacious 5 bedroom 5 bath comfortable well built main house and well sited 2 bedroom 1 bath contemporary guest house. The stunning views are everywhere so 14 of the 16 rooms in both houses enjoy grand pond views. Because of the elevation -- the sunsets, moonrises, and stargazing are some of the most remarkable the island has to offer. The two home compound can house 18 comfortably and is perfect for year-round family events. Come launch your canoe, kayak or paddle board from spring to fall; swim, clam or sail from private sandy beach off the point all summer long; sunbathe on your private dock or 3 decks or on the terraced lawn overhanging the cove; and enjoy seasonal holidays by a roaring fire with extended family and loved ones. This compound is proof that a picture is worth a 1,000 words.(see Video Aerial Tour)

Listed by Tea Lane Associates

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$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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94 Menemsha Inn Road Chilmark MA 02535

Chilmark, MA94 Menemsha Inn Road

Price$9,250,000

Est. Mortgage: $/month

MLS Number 40627

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 3.5
  • Acreage 5.6

This waterfront 4 bedroom 2.5 bath quality custom home and detached 1 bedroom, 1 bath guest studio are sited on 5.6 pristine acres. Enjoy spectacular water views and magnificent sunsets from almost every room as well as from the stone terrace, screened porch and the primary bedroom balcony. This is a finely crafted home with many wonderful details including salvaged heart pine floors and beautiful old beams. A large building envelope allows room for expansion should a new owner desire. Relax amidst the gardens, expansive lawn and mature trees as you take in the beauty around you or go for a leisurely stroll to Menemsha Village. A short path leads to 340 feet of private waterfront on the Vineyard Sound where one can swim peacefully in the calm waters.

Listed by Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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94 Menemsha Inn Road Chilmark MA 02535

Chilmark, MA94 Menemsha Inn Road

Price$9,250,000

Est. Mortgage: $/month

MLS Number 40668

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 4.5
  • Acreage 5.6

Walk to a private beach and enjoy the beautifully manicured gardens and landscape of this well-loved and privately situated home! Custom designed with a charming Vineyard feel and tasteful interior design. Water view from a gourmet kitchen and formal dining area. Large open living room and spacious bedrooms. Large deck with exceptional views of the North shore and Elizabeth Island's A large enclosed sun porch off the kitchen to enjoy meals and family time and is adjoined by a breakfast nook. Three (3) Bedrooms are located on the upper level. The primary bedroom is complete with a balcony to enjoy sunrises and sunsets. The 4th bedroom is on the first floor next to a full bathroom. The basement is a finished area with an additional living area. The septic system has been upgraded to allow for six bedrooms.

Listed by Flanders Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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15 Red Valley Road Chilmark MA 02535

Chilmark, MA15 Red Valley Road

Price$5,795,000

Est. Mortgage: $/month

Pending

MLS Number 40729

  • Residential
  • Mls Status Pending
  • Bedrooms 5
  • Bathroom 3
  • Acreage 3.6

Glorious views spanning over Nashaquitsa and Menemsha Pond to the Vineyard Sound and Elizabeth Islands. This sweet Vineyard home is situated up high overlooking open meadows, old stone walls with multiple views to the Atlantic Ocean. Located in beloved Blacksmith Valley and enjoyed by the same family for over sixty years -this is a rare opportunity. With 3.6 acres of open, rolling land, classic Chilmark stonewalls and beach plum bushes, this charming 5 bedroom home with an existing pool, sits on a ridge and offers views from Noman's Land to the Edgartown shoreline. The property also includes a garage for vehicle and boat storage at the edge of the property. Squibnocket Beach is around the corner as well as an opportunity to join Zack's Cliffs for Blacksmith Valley residents. The property includes deeded access to Quitsa Pond and a small dock area where kayaks and a sunfish can be stored. Boating, swimming, fishing and bird watching are right outside your door.  This is a special opportunity for a Buyer who appreciates and understands what this location has to offer.

Listed by Tea Lane Associates

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$
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$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1 Pondmark Chilmark MA 02535

Chilmark, MA1 Pondmark

Price$4,400,000

Est. Mortgage: $/month

MLS Number 40055

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 4.7

Massive Atlantic Ocean views! This 4.7-acre lot with 120-degree views of the Atlantic Ocean over Keith Farm offers the ideal opportunity to create a stunning property with a main house, guesthouse and swimming pool. The current home is ready to make way for the new owner's vision. The property is just one mile to the entrance of Lucy Vincent Beach and half a mile to Beetlebung Corner. It is a mile and a half to Menemsha. The property is criss-crossed with ancient lichen-covered stone walls and has a feeling of having stepped back in time.

Listed by Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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300 North Road Chilmark MA 02535

Chilmark, MA300 North Road

Price$3,200,000

Est. Mortgage: $/month

MLS Number 40645

  • Residential
  • Mls Status Active
  • Bedrooms 2
  • Bathroom 3
  • Acreage 4.38

Sited on over four acres and nestled in a peaceful setting of ancient stone walls, mature plantings and trees, open meadows and large glacial boulders. The architectural design creates an entry courtyard edged with gardens and a covered porch. Single floor living, cathedral ceilings, plastered walls, and lasting quality construction. The house is designed to feel light and airy taking in the privacy of the land from the open living/dining area that leads out onto an expansive deck and onto rolling lawn and gardens. The finished lower-level walkout basement with bathroom offers up a myriad of possibilities. A separate detached garage provides extra storage along with the accompanying detached workspace and gardening room.

Listed by Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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23 Black Point Road Chilmark MA 02535

Chilmark, MA23 Black Point Road

Price$3,200,000

Est. Mortgage: $/month

Pending

MLS Number 40664

  • Residential
  • Mls Status Pending
  • Bedrooms 2
  • Bathroom 2
  • Acreage 3.88

This South Mountain built home within walking distance to Black Point Beach is a sandy beach lover’s dream. With two bedrooms and two bathrooms on just over 3.8 acres, a new owner will have room to expand. The lot size allows for a main house and guest house with a special permit (and a five year wait) and the five bedroom septic provides easy expansion. This little gem has an open floor plan, exposed beams, hardwood floors and a stone edged fireplace centering the living room. There is an abundance of south facing light on this private and generous sized lot in Chilmark. Property includes a Black Point Beach key valued at $425,000.

Listed by Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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50 South Road Chilmark MA 02535

Chilmark, MA50 South Road

Price$2,395,000

Est. Mortgage: $/month

Active With Contract

MLS Number 40343

  • Residential
  • Bedrooms 5
  • Bathroom 3
  • Acreage 6.4

Authentic and lovely Vineyard homestead on over 6 acres with hedgerow borders and stone walls, this is a special and storied piece of island history. The sweeping views over farm fields are stunning, filling the windows with light and the beauty of this natural rural landscape as it has been for hundreds of years. The 1700s post and beam home was originally a "high double house" and became a three-quarter house with an ell in the 1800s. It retains some original features like wainscoting and ancient wide plank floors. The sturdy barn, which was moved to the property in the early 1900s, is ready for it's next chapter as a work barn again, rec space, studio or entertaining spot. This antique Chilmark home awaits its rejuvenation. The property can support an additional house. Property is being sold AS IS.

Listed by Tea Lane Associates

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$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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276 South Road Chilmark MA 02535

Chilmark, MA276 South Road

Price$2,180,000

Est. Mortgage: $/month

MLS Number 40452

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 2
  • Acreage 1

Come put your finishing touches on this great 4 Bedroom cape! Located on the very popular south side of South Road in Chilmark. Enjoy your morning coffee gazing over stone walls and a quiet pasture. Or relax in the delightful four season sun room. Walking distance to a private pond where you can take your boat across to the favorable South Shore beach. A must see!

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Based on information submitted to LINKMV as of June 3, 2023 . All data is obtained from various sources and has not been, and will not be, verified by broker or LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.