Chilmark Homes from $1M-$3M

Scroll down to find current homes from $1M-$3M for sale in Martha's Vineyard, MA's town of Chilmark. Look through a variety of listings to find your new home. Register with us to save your favorite properties, and you can get email updates when new listings match your search criteria.

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5 Tree Frog Lane, Chilmark, MA

Price$1,250,000

Est. Mortgage: $/month

MLS Number 32822

  • Residential
  • Square Feet 1944
  • Bedrooms 4
  • Bathroom 2
  • Acreage 4

Post-and-beam home set on 4 gorgeous acres in Chilmark with undulating land, fruit trees, a pond, and lichen-covered stone walls. The interior is warm and inviting - a real country home complete with fireplace. Two outbuildings offer opportunities to create a studio or workshop. Lucy Vincent Beach and Menemsha are equidistant, each being 3 miles away. The seasonal Menemsha shuttle leaves from a spot on Tabor House Road just 100 yards away. A guesthouse is permitted after 5 years.

Listed by Wallace & Co. Sotheby's

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Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

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Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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7 Clambelly Road, Chilmark, MA

Price$1,250,000

Est. Mortgage: $/month

MLS Number 32609

  • Residential
  • Square Feet 1876
  • Bedrooms 4
  • Bathroom 3
  • Acreage 3.5

This charming Chilmark cottage offers unexpected water views of the Vineyard Sound. Private and tranquil, the two bedroom, two bath main house and separate two bedroom guest suite, and garage is nestled in the woods off of Tea Lane on Chilmark's North Shore. The main house features an open concept living space comprised of a great room, open kitchen, and dining area with high ceilings, wide planked hardwood floors, an impressive stone fireplace and a wall of windows looking out onto a surprisingly broad view of the Sound. The main house has two bedrooms, both facing the water, and two bathrooms, designed with a sweetly rustic post and beam style that fits so well in the natural beauty of the Chilmark woods. The property has a spacious two car garage with a guest suite above which offers two bedrooms, a bathroom, and study space. The property has a six bedroom septic in place that has passed Title V offering the possibility for expansion. The Seller has scheduled tree maintenance this fall to broaden the view. Currently, the house is a three season home, but the Seller has an estimate for installing insulation and heat while maintaining the charm and look of the interior, roughly $50,000. This is a wonderful investment opportunity for a Chilmark Buyer looking for a special view at a great price.

Listed by Tea Lane Associates

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Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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 Valley Lane, Chilmark, MA

Price$2,600,000

Est. Mortgage: $/month

MLS Number 32252

  • Residential
  • Square Feet 4976
  • Bedrooms 6
  • Bathroom 5
  • Acreage 3

End-of-the-road privacy off Old Farm Rd in Chilmark. As you enter through an attractively designed entrance to this property, you'll discover a contemporary farmhouse enveloped in a landscape with vibrant, mature perennials and lush lawns with a wooded backdrop and conservation land beyond. Enter into a dramatic, over-sized living-dining area with beach stone fireplace. Walking through to the left, Patrick Ahearn has designed a gorgeous master bedroom and bath that opens through French doors to both a screened porch and open deck. Circle through the other way to a connecting first floor study/TV room. To the right of the living area is a sensational gourmet kitchen loaded with amenities. Three bedroom/bath suites are located on the second floor. A 2-room detached bedroom is located over a 2-car garage. This is a comfortable year-round house, and one that will accommodate family and friends for many summers filled with great memories. Don't miss the video, see link below!

Listed by Wallace & Co. Sotheby's

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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34 Bijahs Way, Chilmark, MA

Price$1,100,000

Est. Mortgage: $/month

MLS Number 32139

  • Residential
  • Square Feet 2293
  • Bedrooms 4
  • Bathroom 2
  • Acreage 4.2

Well designed for low maintenance this 4 bedroom home located off Tea Lane in Chilmark has plenty to offer. With over 4 acres and access from 2 different roads a guest house could be added with it's own entrance for total privacy. The open kitchen living floor plan with sliders to a large 25 ft deck offers great entertaining space. Built in bookcases and window seat adds to the charm of the room and tie in nicely with the hardwood floors. The renovated kitchen with lots of counter space and large pantry provides ample room to create. There are 2 floors of outside decks overlooking the garden area and the walkout basement adds additional living space. Spacious entryway leads to first floor master bedroom and 2 additional bedrooms that share a bath. This home is in excellent condition and ready for summer enjoyment. Seasonal water views from the living room.

Listed by Carroll & Vincent R.E.

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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100 South Road, Chilmark, MA

Price$1,450,000

Est. Mortgage: $/month

MLS Number 31585

  • Residential
  • Square Feet 2877
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1

Classic features blend seamlessly with modern sensibilities in this expanded Cape Cod-style home. With double the square footage of the original and updated for the 21st-century lifestyle (including a first-floor master suite), this home is perfect for year-round living or as an all-seasons Vineyard retreat. The property adjoins acres of untouched woods, providing ample privacy, while remaining easily accessible throughout the year on a town-maintained paved road. First floor consists of formal living room with fireplace, separate dining room, master suite with large sitting room and private screened-in sunroom, laundry room, additional bedroom and bath, kitchen, 650 sq. ft. mahogany deck for outdoor entertaining, and sun-filled, 530 sq. ft. great room with 14' ceiling, exposed antique beams and radiant floor heating for the ultimate in winter comfort. Second floor contains two large bedrooms with cozy dormer alcoves, and full bath. Oversized two-car garage with built-in work bench. 1500 sq. ft. basement provides lots of storage space, additional refrigerator and freezer, and second laundry room. The many updates and improvements include new well, architectural-shingle roof, cedar-siding shingles, HVAC, Title V septic system, top-quality insulation, upgraded electrical and plumbing, and energy-efficient Marvin windows and French doors throughout. This home is turn key. Fully furnished with just a few exceptions!

Listed by Up Island Realty

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Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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 Old Farm Road, Chilmark, MA

Price$1,195,000

Est. Mortgage: $/month

MLS Number 32030

  • Residential
  • Square Feet 800
  • Bedrooms 2
  • Bathroom 1
  • Acreage 3.2

This year round house provides the perfect balance of modern and minimal, style and simplicity, compact design and interior spaces that make a big impact. Set on just over three acres in Chilmark, this house is sited on a cleared, gentle rise and is surrounded by towering pine and oak trees that provide a serene and private setting. Built in 2003, this architect owned home features two distinct living spaces joined by a large mahogany deck, perfect for outdoor dining. The primary space contains the kitchen, dining area, one bedroom, one full and one half bath and a covered porch. The secondary space features an open living barn design with a wood burning, double sided, fireplace that can be enjoyed both in and outdoors. This space is currently configured for living and dining and has ample room for sleeping quarters and a half bath. Features and architectural elements present in both structures include radiant heating, two full walkout basements, whole house generator, Marvin windows and doors, wide pine plank flooring, concrete foundation with fieldstone veneer, mahogany decking, outdoor shower and a new cedar shake roof. Community tennis court within walking distance. Lot size can accommodate multiple structures with an additional 2,700 square feet of living space. Owner in residence, please no drive-bys.

Listed by Russell Maloney Real Estate

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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7 Black Point Road, Chilmark, MA

Price$2,100,000

Est. Mortgage: $/month

MLS Number 31969

  • Residential
  • Square Feet 2120
  • Bedrooms 4
  • Bathroom 2
  • Acreage 5.9

Come see this charming architect designed retreat with main house & two connecting guest wings, set on 5.5 pristine acres plus 17,424 SF deeded Atlantic Ocean Beach lot valued at $303,000 included with sale for a total acreage of 5.9 acres (SEE Comments/directions). Impeccably maintained the property is designed for relaxing and enjoying the unpretentious beauty of Black Point and the beach. The great room with banks of sliding doors beacons you the deck & patio. Ocean breezes & the sound of the surf gently wake you in the morning & help you drift off to sleep. The evening sky will make an Astronomer out of you. Main house features the great room, dining area, kitchen, laundry, pantry, master, full bath & outdoor shower. 1st guest wing has 2 BR'S, full bath with outdoor shower. Built in 2007 the 2nd guest wing has living area, BR, bath and outdoor shower. With town permitting you can add a guest house & pool. While you feel miles away you are still less than 10 minutes to Alley's store.

Listed by Laer Realty Partners

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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27 Hewing Field, Chilmark, MA

Price$1,550,000

Est. Mortgage: $/month

MLS Number 31822

  • Residential
  • Square Feet 4652
  • Bedrooms 10
  • Bathroom 6
  • Acreage 4.5

This is a compound for someone with a dream. Whether to connect family and friends in comfort the year round, to host workshops, to garden, to conduct a professional practice or pursue creative endeavors - there's ample room to do it all here. With the treasure of Chilmark beaches to enjoy, it's just a scenic 5-minute drive from Alley's. Tucked away on a hilltop meadow bordered by conservation land, an extensive trail network beckons just steps from the decks leading down to the mossy banks of the Tiasquam. Besides the space and versatility here, the main house has extra insulation in the interior walls for an added sense of quiet, a 2015 Buderus 7-zone heating system, three stairways to the second floor, additional attic and basement rooms, an attached 2-car garage and a generator. There's great privacy between the dwellings and a general sense of sanctuary and expansiveness on these bright acres. PLEASE NOTE: As of 11/17/17, this price reflects a temporary reduction. If a Buyer is able to close before 1/31/18, the price will apply. Otherwise the property will be taken off the market and reintroduced in Spring 2018.

Listed by Tashmoo Realty

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Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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 Boston Hill Road, Chilmark, MA

Price$2,850,000

Est. Mortgage: $/month

MLS Number 31742

  • Residential
  • Square Feet 2500
  • Bedrooms 4
  • Bathroom 3
  • Acreage 3.5

This 3.5 acre home with beautiful grounds, waterviews of Menemsha pond, Vineyard sound and Squibnocket point has a light filled interior rising above the in-ground pool. The center of the home with soaring cathedral ceilings has a unique open staircase rising to the second floor Master bedroom en-suite with study and private sunning deck. Creative designed open living, kitchen and dining areas overlook the pool from every room. 6 bedroom septic for 2 additional bedrooms or guest house.

Listed by Conroy & Company R.E., Inc.

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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24 Bassett Place Road, Chilmark, MA

Price$2,100,000

Est. Mortgage: $/month

MLS Number 31720

  • Residential
  • Square Feet 1473
  • Bedrooms 4
  • Bathroom 1
  • Acreage 15.8

Chilmark Pond front cottage with Atlantic Ocean views and private beach lot. YOU CAN'T BE CLOSER TO CHILMARK POND. Unique waterfront summer house with outstanding ocean and pond views on Chilmark Pond. Very private. Nature preserve setting on 15 acres surrounded by marsh lands, heron and osprey.Nothing between you, the pond and ocean. Big deck for dining and relaxation. Shared dock on the pond. Private ownership in Atlantic Ocean beach short boat ride away.

Listed by Conroy & Company R.E., Inc.

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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 Rockrose Path, Chilmark, MA

Price$1,755,000

Est. Mortgage: $/month

MLS Number 30666

  • Residential
  • Square Feet 1973
  • Bedrooms 4
  • Bathroom 2
  • Acreage 1.6

This is a ranch style summer cottage set high on Rockrose Path (off King's Highway) with wide views of Chilmark Pond and the Atlantic Ocean beyond. A private Atlantic Ocean beach lot, Thumb Cove, is included with the sale of this home. Master suite with full bath, three additional bedrooms, and second full bath, cathedral ceilings, sleep loft, large wraparound mahogany decking provides plenty of seating area for taking in ocean views and starlit skies. This home has an outdoor shower, wood burning stove, insulation, whole house fan, and basement storage. Easy expansion possibilities for larger kitchen and additional master suite with terrific views possible. Furnishings, motor boat and Sunfish available separately.

Listed by Russell Maloney Real Estate

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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4 Peases Point Way, Chilmark, MA

Price$1,050,000

Est. Mortgage: $/month

MLS Number 30444

  • Residential
  • Square Feet 1652
  • Bedrooms 3
  • Bathroom 2
  • Acreage 3.2

Located down an idyllic country lane, this beautiful 3 bedroom home offers an inviting open floor plan with cathedral beamed ceilings perfect for entering summer family and friends. Renovated in 2004, updates include a new kitchen with granite counters and new appliances, updated bathrooms, new roof and new outside shower. This charming space flows gracefully out to a spacious sun room leading out to a large back deck. The private, first floor master en-suite includes a large inviting window seat perfect for morning coffee. Two second floor bedrooms and a small loft complete the picture. Located just minutes to Menemsha for an early morning swim or idyllic sunset lobster dinner. Check out the 3D Tour - https://livetour.istaging.com/590cc123becd360054078dae?ui=true

Listed by Kelleher R.E.

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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3 Catherines Way, Chilmark, MA

Price$1,050,000

Est. Mortgage: $/month

MLS Number 30329

  • Residential
  • Square Feet 2000
  • Bedrooms 4
  • Bathroom 2
  • Acreage 1.8

A lovely traditional farmhouse with great history located just a short distance from Chilmark Center. This well maintained home boasts beautiful perennial gardens, and well manicured landscapes. A spacious interior provides the first floor with 2 separate large living areas, a large formal dining room and a renovated granite counter top kitchen. This house is full of character and charm and also offers an additional outbuilding that can be used as an oversized shed, studio or transformed into an endearing summer bunkhouse for overflow guests. A spacious deck space off the back of the house is great for entertaining or can serve as a quiet reading spot to enjoy the blooming gardens that surround this home. Only a short distance to the Chilmark store, Chilmark Chocolates and approximately a mile and half from Squibnocket and Lucy Vincent beaches.

Listed by Flanders Real Estate

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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11 Howell Lane, Chilmark, MA

Price$2,850,000

Est. Mortgage: $/month

MLS Number 29242

  • Residential
  • Square Feet 4000
  • Bedrooms 4
  • Bathroom 3
  • Acreage 4.68

Nestled down Flanders Lane, this spacious, post-and-beam custom built contemporary home has an open and airy interior. This 4.68 acre property is the ideal retreat. Featuring four bedrooms, three and a half bathrooms (each with heated towel racks) and lovingly maintained landscapes. The Gourmet kitchen has top of the line appliances, 8 burner gas stove, built in booths as well as a formal dining area. Relax in the sauna, or read a book by the large brick fireplace in the living room. The outdoor space is perfect for entertaining company on the stone patio with views of the rolling backyard. A beautifully constructed outdoor shower and fully fenced expansive garden with raised beds also adorn this property. An Expansive attached garage (With radiant heated floors!), workshop, and so many other details embellish this home. All of this, plus only a short distance to swim, clam or kayak at your own private access on Menemsha Pond. With 200' of deeded frontage on Menemhsa pond and area for boat storage on the shore. This home is in immaculate condition with impeccable craftsmanship and is turnkey for you and your family. Ask about the permit for a pool!

Listed by Flanders Real Estate

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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 Lake Road, Chilmark, MA

Price$3,000,000

Est. Mortgage: $/month

MLS Number 25297

  • Residential
  • Square Feet 1927
  • Bedrooms 5
  • Bathroom 2
  • Acreage 2.7

Endless Atlantic Ocean views, Squibnocket Pond, rolling hillsides, dramatic vistas, centuries old stone walls, gravel roads... these are just some of the features of this extraordinary property new to market for the first time in nearly fifty five years. This architect designed modern Cape Cod home with five bedrooms and two and one half baths on nearly three acres can be your summer place. Swim, kayak, row or clam in Nashaquitsa Pond, surf at Squibnocket or relax and enjoy the unspoiled, crowd free beach at Zacks in Aquinnah (with membership).

Listed by Russell Maloney Real Estate

{$agent->Name}

Sandpiper Realty, Inc.
60 Winter Street
P.O. Box 2248
Edgartown MA, 02539
Office: 508.627.3737

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Jul 13, 2017
* 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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