Chilmark, MA homes for sale & real estate

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16 South Rd, Chilmark, MA 02535
16 South Rd, Chilmark, MA 02535
16 South Rd, Chilmark, MA 02535
ABOUT THIS HOME
Chilmark, MA Homes for Sale
Restored antique Chilmark farmhouse with multiple outbuildings which includes a large barn with 2nd floor loft, a run-in barn with 2 horse stalls, both overlooking an expansive, fenced pasture for horses to run or field games to be played. This farmhouse home offers 4 bedrooms, 3 baths and has been updated to include modern bathrooms and an upscale kitchen, while remaining respectful to the charm and integrity of the antique home. The inviting spaces offer a masonry wood burning fireplace in the dining/living area, a 2nd lounge area off of the front foyer, and a period stairway leading to the second floor. The location is as stellar as its setting. It is blocks from the historic West Tisbur

$2,500,000

4 beds3 baths2,350 sq ft

16 South Rd, Chilmark, MA 02535

1.6 acre lot • Garage • Car-dependent

15 Old Farm Rd, Chilmark, MA 02535
15 Old Farm Rd, Chilmark, MA 02535
15 Old Farm Rd, Chilmark, MA 02535
ABOUT THIS HOME
Chilmark, MA Homes for Sale
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 with a private deck and an en-suite bath. Plus, a formal foyer and a cozy library/media room. A second-floor bedroom and a separate third suite with its fireplace and patio offer privacy and charm. The lower level features a bright bonus room, ideal for a gym, media room, or guests. The curated landsca

$4,825,000

3 beds5 baths3,171 sq ft

15 Old Farm Rd, Chilmark, MA 02535

3.2 acre lot • Car-dependent

124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
ABOUT THIS HOME
Chilmark, MA Homes for Sale
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 residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to detail, and very good taste. In addition to the beautifully renovated home there is a very large enclosed garden, pickleball court, and a wind turbine that produces large amounts of energy. SHOWI

$5,450,000

5 beds4.5 baths2,913 sq ft

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

13.7 acre lot • $283 HOA • Car-dependent

9 Beetlebung Grove Way, Chilmark, MA 02535
9 Beetlebung Grove Way, Chilmark, MA 02535
9 Beetlebung Grove Way, Chilmark, MA 02535
ABOUT THIS HOME
Chilmark, MA Homes for Sale
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. Adjacent to the living area, the dining room and well-appointed kitchen flow effortlessly into a fabulous screened porch. The primary suite is on the main level, featuring a large walk-in closet, a full bath, and a striking double-sided stone gas fireplace connecting the bedroom to an adjoining sitti

$2,495,000

4 beds3 baths2,968 sq ft

9 Beetlebung Grove Way, Chilmark, MA 02535

3.4 acre lot • $83 HOA • Garage

308 South Rd, Chilmark, MA 02535
308 South Rd, Chilmark, MA 02535
308 South Rd, Chilmark, MA 02535
ABOUT THIS HOME
Chilmark, MA Homes for Sale
Commanding Pondfront Retreat with Private Dock and South Shore Views. This exceptional Chilmark residence offers a rare blend of privacy, elegance, and modern comfort. Originally built by Tom Tate and renovated in 2018, it exudes contemporary sophistication while embracing its natural surroundings. A private dock on Chilmark Pond provides direct water access and stunning South Shore sunsets. Follow a beautifully manicured path--an iconic Vineyard feature--to your dock and cross the pond to your private beach lot. Surrounded by over 7 acres of abutting conservation land, the setting is peaceful and secluded. Meticulously designed gardens enhance the home's timeless charm. The expansive first

$7,950,000

4 beds4 baths3,490 sq ft

308 South Rd, Chilmark, MA 02535

3.4 acre lot • Car-dependent

Property at 25 Fulling Mill Rd, Chilmark, MA 02535, 4 beds, 3 baths

$2,450,000

4 beds3 baths1,918 sq ft

25 Fulling Mill Rd, Chilmark, MA 02535

Property at 345 North Rd, Chilmark, MA 02535, 5 beds, 5 baths

$1,625,000

5 beds5 baths2,316 sq ft

345 North Rd, Chilmark, MA 02535

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NEW 35 HRS AGO

53 Stoney Hill Rd, West Tisbury, MA 02575
53 Stoney Hill Rd, West Tisbury, MA 02575
53 Stoney Hill Rd, West Tisbury, MA 02575
ABOUT THIS HOME
Chilmark, MA Homes for Sale
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 home is a chef’s kitchen with stainless steel appliances, generous counter space and custom cabinetry. A butler’s pantry offers additional prep/storage space, making entertaining effortless. The home boasts 3 fireplaces that bring warmth and charm to the living room, screened

$3,299,000

3 beds3.5 baths3,082 sq ft

53 Stoney Hill Rd, West Tisbury, MA 02575

2.86 acre lot • 3 garage spots • Car-dependent

COMING SOON

420 Lamberts Cove Rd, West Tisbury, MA 02575
420 Lamberts Cove Rd, West Tisbury, MA 02575
420 Lamberts Cove Rd, West Tisbury, MA 02575
ABOUT THIS HOME
Chilmark, MA Homes for Sale
Charming West Tisbury Estate with Waterfront on Seth's Pond. This stunning property offers the perfect blend of vintage charm and modern convenience, set against the tranquil backdrop of Seth's Pond. Featuring a main house, guest house, boathouse, and barn/workshop, this property provides a rare opportunity for both relaxation and recreation. The main house, a well maintained farmhouse dating back to 1900, has been thoughtfully updated over the years while preserving its timeless appeal. The kitchen has been fully renovated to include modern finishes, creating a perfect balance of old-world character and contemporary style. From the primary bedroom's private deck, enjoy sweeping water views

$4,495,000

5 beds3 baths4,125 sq ft

420 Lamberts Cove Rd, West Tisbury, MA 02575

3.9 acre lot

40 Scotchmans Ln, West Tisbury, MA 02575
40 Scotchmans Ln, West Tisbury, MA 02575
40 Scotchmans Ln, West Tisbury, MA 02575
ABOUT THIS HOME
Chilmark, MA Homes for Sale
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 approved WT Planning Board survey). The proposed survey/subdivision plan has a driveway easement area, a buyer, will acknowledge and agree to the driveway easement location upon completion of a sale. Note: The 2025 taxes for this smaller parcel have not been assessed due to the fact it is currently p

$1,495,000

4 beds2 baths1,332 sq ft

40 Scotchmans Ln, West Tisbury, MA 02575

Car-dependent

234 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
234 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
234 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
ABOUT THIS HOME
Chilmark, MA Homes for Sale
LONG POINT BEACH RETREAT. Privately set on a spacious 1.4-acre parcel in the highly coveted Long Point area of West Tisbury, this beautifully renovated beach house offers the ultimate Vineyard escape. Move-in ready and being sold fully turnkey, it combines style, comfort, and convenience in an unbeatable location. The sun-filled living room and dining area with French doors to the wrap-around deck are perfect for alfresco dining and entertaining. A bright, modern kitchen with an induction stove will delight any home chef. The main floor offers two comfortable bedrooms and a full bath. The entire second floor is dedicated to the spacious primary suite, complete with a cathedral ceiling, skyl

$1,895,000

3 beds2.5 baths1,918 sq ft

234 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

1.4 acre lot • $29 HOA

20 James Pond Way, West Tisbury, MA 02575
20 James Pond Way, West Tisbury, MA 02575
20 James Pond Way, West Tisbury, MA 02575
ABOUT THIS HOME
Chilmark, MA Homes for Sale
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 features a spacious living room with a cathedral ceiling, air conditioning, and a cozy fireplace, seamlessly opening onto a patio that presents serene views of the pond. A screened porch offers an inviting space to enjoy the outdoors. The large, sunlit kitchen boasts an informal eating area, ideal for casu

$3,995,000

5 beds3 baths2,701 sq ft

20 James Pond Way, West Tisbury, MA 02575

4.51 acre lot • 2 garage spots • Pool

212 Charles Neck Way, West Tisbury, MA 02575
212 Charles Neck Way, West Tisbury, MA 02575
212 Charles Neck Way, West Tisbury, MA 02575
ABOUT THIS HOME
Chilmark, MA Homes for Sale
This beautifully renovated South Shore retreat, located in a tranquil setting, features 3 bedrooms, 2 1/2 bathrooms, central air, all new Bosch 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 Beach. The first floor welcomes you with its sun-filled cathedral ceiling open layout. The living room area is flanked by walls of windows to bring the outside in, opens to the outside decks, and boasts a 6' wall mounted fireplace with large screen TV above. The kitchen area with all new Bosch appliances opens to a center

$1,925,000

3 beds2.5 baths1,728 sq ft

212 Charles Neck Way, West Tisbury, MA 02575

1.5 acre lot • Car-dependent

Property at 15 Crowell Ln, West Tisbury, MA 02575, 3 beds, 2.5 baths

$3,390,000

3 beds2.5 baths1,514 sq ft

15 Crowell Ln, West Tisbury, MA 02575

Property at 453 Lighthouse Rd, Aquinnah, MA 02535, 3 beds, 3 baths

$1,795,000

3 beds3 baths2,308 sq ft

453 Lighthouse Rd, Aquinnah, MA 02535

Property at 32 Machipscat Trl, West Tisbury, MA 02575, 3 beds, 1.5 baths

$1,499,000

3 beds1.5 baths1,404 sq ft

32 Machipscat Trl, West Tisbury, MA 02575

Property at 176 Middle Point Rd, West Tisbury, MA 02575, 5 beds, 3 baths

$3,450,000

5 beds3 baths2,713 sq ft

176 Middle Point Rd, West Tisbury, MA 02575

Property at 19 S Vine Ln, West Tisbury, MA 02575, 3 beds, 2 baths

$1,500,000

3 beds2 baths1,982 sq ft

19 S Vine Ln, West Tisbury, MA 02575

Property at 35 Woody Bottom Rd, West Tisbury, MA 02575, 5 beds, 3.5 baths

$2,495,000

5 beds3.5 baths2,685 sq ft

35 Woody Bottom Rd, West Tisbury, MA 02575

Property at 85 Reservoir Road North, West Tisbury, MA 02575, 5 beds, 6 baths

$8,995,000

5 beds6 baths3,762 sq ft

85 Reservoir Road North, West Tisbury, MA 02575

Property at 19 Locust Ln, Aquinnah, MA 02535, 6 beds, 34.5 baths

$7,775,000

6 beds34.5 baths5,982 sq ft

19 Locust Ln, Aquinnah, MA 02535

Property at 0 Moshup Trl, Aquinnah, MA 02535

$350,000

— beds— baths— sq ft

0 Moshup Trl, Aquinnah, MA 02535

Property at 0 Jeffers, Aquinnah, MA 02535

$949,900

— beds— baths— sq ft

0 Jeffers, Aquinnah, MA 02535

Property at 22 Bramble Path, West Tisbury, MA 02575

$799,000

— beds— baths— sq ft

22 Bramble Path, West Tisbury, MA 02575

Property at 25 N North Vine Ln, West Tisbury, MA 02575

$975,000

— beds— baths— sq ft

25 N North Vine Ln, West Tisbury, MA 02575

Average home prices near Chilmark, MA

Cities

Mattapoisett homes for sale
$849,450
New Bedford homes for sale
$499,999
Westport homes for sale
$799,900
Mashpee homes for sale
$699,000
Dartmouth homes for sale
$921,400
Edgartown homes for sale
$5,075,000
Oak Bluffs homes for sale
$2,022,500
East Falmouth homes for sale
$1,285,000
North Falmouth homes for sale
$1,050,000
Falmouth homes for sale
$869,000
Popponesset homes for sale
$927,000
Woods Hole homes for sale
$2,285,000
New Seabury homes for sale
$906,950
Vineyard Haven homes for sale
$2,172,500
Fairhaven homes for sale
$606,950

Neighborhoods
Zip Codes

Martha's Vineyard homes for sale
$2,450,000

Chilmark, MA real estate trends

$12.36M

Sale price

$1.91K

Sale $/sq ft

Over list price

1.1%

Days on market

Down payment

—

Total homes sold

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