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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165 State Road Chilmark MA

Price$1,100,000

Est. Mortgage: $/month

MLS Number 35624

  • Residential
  • Square Feet 900
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.2

A quintessential Chilmark cottage offering gorgeous water views of Quitsa and Menemsha Ponds, access easements to both the Pond and Atlantic, and much more! The home's renovated interior is recently refreshed, cute and charming, just right for your summer retreat. The exterior has undergone extensive upgrading, including a new roof completed in 2019. Also with an excellent rental history, this property offers a rare combination of proximity to beaches, views, and charming indoor/outdoor living spaces. An outstanding waterview offering - welcome to your up-island getaway!

Listed by Compass

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Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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 Creek Hill Road, Menemsha Chilmark MA

MLS Number 35507

  • Residential
  • Square Feet 770
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.2

An opportunity to be right in the heart of Menemsha in one of the most iconic cottages over looking the harbor This sweet 2 bedroom home has been in the same family for generations. Some of you may remember Rasmus Klimm, famous local figure who displayed his wooden carvings and fishing floats on the shacks on the Harbor. This quintessential 770 square foot Chilmark cottage is right in the middle of it all. Walk to the beach, Dutcher's Dock, The Galley, Homeport, fish markets and of course the famous sunsets. Breathe in the simplicity of what this sweet fishing village has to offer. This feels like a genuine escape. With all the summer amenities you need to enjoy Menemsha during the quiet of spring, the warmth off summer and the buzz of derby season. Special location and opportunity !

Listed by Tea Lane Associates

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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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 Rockrose Path Chilmark MA

Price$1,695,000

Est. Mortgage: $/month

MLS Number 35538

  • Residential
  • Square Feet 2100
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1.6

This four bedroom, three bath home with ocean views and a private, south shore beach, is located on Rockrose Path off of Meetinghouse Road in Chilmark. This heated, year round house is sited on one and a half acres in a private setting with a large front yard and easy to care for landscaping. The open living room, dining area and kitchen have direct views to the Atlantic. The master bedroom and bath also have ocean views. The lower level of the home has one bedroom and one full bath (under construction), and plenty of storage space. This property is being sold with access to a private Atlantic Ocean beach, Thumb Cove, and access to a dock on Chilmark Pond for launching of a small boats, kayaks, and paddle boards. This home is being sold "as is"....bring your architect and builder for renovation and expansion plans! Furnishings available separately.

Listed by Russell Maloney Real Estate

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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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68 Meeting House Road Chilmark MA

Price$1,725,000

Est. Mortgage: $/month

MLS Number 35318

  • Residential
  • Square Feet 2300
  • Bedrooms 4
  • Bathroom 3
  • Acreage 6.16

Lovely four bedroom on six acres of rolling hills and meadow. Portion of land held in conservation, Open floor plan with a large screened in porch. New Windows installed in 2019.

Listed by Flanders Real Estate

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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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55 Bijahs Way Chilmark MA

Price$1,975,000

Est. Mortgage: $/month

MLS Number 35387

  • Residential
  • Square Feet 3776
  • Bedrooms 5
  • Bathroom 4
  • Half Bath 1

55 Bijah's Way is a custom designed post and beam home built by well-known and respected island builder Heikki Soikkeli. Sited on 3 private acres, this home features 5 bedrooms, 4 ½ baths, screened porch, 2 decks, fireplace, generator, and an attached two car garage. Native plantings, sweeping lawns, a lengthy stonewall, scattered glacial erratics, as well as specimen trees including red maples, beetlebungs, oaks, hollies and pines enhance the landscape. The first floor of this home features an open living and dining room, fireplace, screened porch, and a well appointed kitchen. There are two first floor bedrooms; the master suite with walk in closets and an outdoor shower and a second bedroom and bath. The second floor of this home contains three bedrooms, one of which is separate and accessed by its own staircase providing space for an au pair, in-laws, or an office. There are two bathrooms found on the second floor as well. Closet space is ample throughout the home. This property borders 50+ acres of land held under conservation restriction, and miles of walking and hiking trails can be found nearby. Neighborhood community tennis courts are available. Chilmark residents enjoy the ocean beaches of Lucy Vincent, Squibnocket, and Vineyard Sound beach at Menemsha.

Listed by Russell Maloney Real Estate

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Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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252 Middle Road Chilmark MA

Price$1,060,000

Est. Mortgage: $/month

MLS Number 35294

  • Residential
  • Square Feet 2106
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1.3

House and guest house on a hilltop sanctuary. The mid-century modern main house designed by Ronald Gourley offers open-living space with a glorious wall of windows that bring in dramatic light throughout the day. Main house has a first floor en suite master with private office space. Two upstairs bedrooms are connected by a loft hallway. The one-bedroom guest cottage is privately tucked away down the hill. Both houses offer expansive decks and outdoor showers. The large lower yard is hidden from the main road and surrounded by stone walls. Mature landscaping offers privacy and solitude.

Listed by Feiner Real Estate

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Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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28 Black Point Road Chilmark MA

Price$1,975,000

Est. Mortgage: $/month

MLS Number 35279

  • Residential
  • Square Feet 1719
  • Bedrooms 3
  • Bathroom 3
  • Acreage 5.4

Bright and airy retreat on Black Point complete with key to Black Point Beach. Set on 5.4 acres off Black Point Road in Chilmark, this charming cottage brings an immediate feeling of peace and levity. One can hear the ocean and walk, ride or drive to Black Point Beach as a key to this private south shore beach is included. The layout of the house is intelligent with an entry that brings one into an open and bright living, dining and kitchen area, as well as a screened porch and an open deck. The upper level offers a master bedroom and bath with water views, while the downstairs level offers another bedroom, full bathroom and living area. There is also a substantial independent garage with a newly finished bedroom and bath above. The current owners renovated both structures inside and out to include new appliances, heating and cooling systems, new roofing, an upgraded septic and so much more. They have enjoyed the property as is, but this generous lot has potential to support another home.

Listed by Tea Lane Associates

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$
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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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 Homeward Way Chilmark MA

Price$1,975,000

Est. Mortgage: $/month

MLS Number 34559

  • Residential
  • Square Feet 2444
  • Bedrooms 5
  • Bathroom 2
  • Acreage 6.7824

Vintage cape-style home, originally built in 1941 by renowned Chilmark builder, Roger Allen. This charming house was created using Chimark stones. A five bedroom home situated on a beautiful private 6.78 acre lot off North Road close to Menemsha. This extraordinary property abuts acres of Land Bank agricultural conservation property and is being offered for the first time in over 75 years. Within close proximity to Trustees of Reservations Menemsha Hills Preserve, a short drive to Land Bank Great Rock Bight preserve, Menemsha Beach and sunsets galore! This charming stone home welcomes you as you approach the property. A bright and cheery sun room addition lets you enjoy the spacious yard with ancient stonewalls and magnificent trees. Update this unique home or use your imagination to make it the home of your dreams, close to Menemsha yet a world away! To top it off there is a spacious two-car garage with attached workshop. Title V septic system recently installed. This property is very unique and must be seen to appreciate its value. Pictures do not do it justice. Being sold "as is".

Listed by Hancock Real Estate

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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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17 Chowder Kettle Lane Chilmark MA

Price$2,450,000

Est. Mortgage: $/month

MLS Number 19789

  • Residential
  • Square Feet 2384
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.2

Menemsha -- one of the most desirable locations on the Island. It is an easy walk to the village for a fish sandwich and a swim at the beach from this sweetly located property. Set at the end of a private cul-de-sac, this remodeled beach themed, sea view cottage oozes with charm. Three bedrooms and two baths are in the two story main house. The second floor consists of a master suite, dressing area, bathroom, water-view office and bonus room with ample storage. A screened in porch and upper and lower decks point the way to terrific sunsets! A one bedroom one bath guest cottage and outdoor shower complete this property. Agent has an ownership interest in home.

Listed by Kendall & Kendall

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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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$2,795,000

Est. Mortgage: $/month

MLS Number 35123

  • Residential
  • Square Feet 4100
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

This property exudes fine craftsmanship and a well rounded experience with pool, privacy and Menemsha Pond access nearby. Located in the Flanders Lane area near Menemsha, this post and beam home was built with only the best materials - red oak timberframe, quarter sawn red oak floors, radiant heat, Alaskan yellow cedar shakes, copper gutters and mahogany barn doors. It is solid, and elegant. This property needs to be experienced to be appreciated fully. The living spaces are generous and customized with built-ins. The bedrooms are large and private from each other. The 1000 s.f. garage and workshop space has radiant heat and beautiful timberframe structure and is ready for conversion to a first floor master suite, a rec room or whatever needs suit you. There is a new heated, Gunite saltwater pool which connects to the stone patio and the expansive lawn and gardens beyond. This is truly a hidden treasure.

Listed by Tea Lane Associates

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$
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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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13 Deerpath Lane Chilmark MA

Price$2,575,000

Est. Mortgage: $/month

MLS Number 34278

  • Residential
  • Square Feet 3194
  • Bedrooms 4
  • Bathroom 4
  • Half Bath 1

This impeccably built home is set on 3 private acres off of Old Farm Road in Chilmark. Open and light, the 4 bedroom house has an intelligent design that works well for quiet time or company. Upon entering one appreciates the sizable spaces that connect the living room, dining area, well appointed kitchen and study. The cathedral ceilings, large fireplace, and stunning glass doors ensure that you have everything you need in the center of the house. The left wing includes a master bedroom suite and sitting area that overlook the gardens and lush lawn, while the second floor offers another generous master bedroom suite. There are also two lovely bedrooms and one corresponding bathroom. Each room has its own orientation viewing the pool, or gardens- like an English country house with all the modern conveniences... The in ground pool was designed by Rosbeck and is nicely separated from the house but enjoys a refined pool house with full bath and outdoor shower. There is also a detached garage that continues the aesthetic while beautiful flowers, grasses and other plantings tie the property together and deepen the relationship of the structures to the land... This is a perfectionist's dream....must be experienced...

Listed by Tea Lane Associates

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$
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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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18 Henry Hough Lane Chilmark MA

Price$2,350,000

Est. Mortgage: $/month

MLS Number 34988

  • Residential
  • Square Feet 3770
  • Bedrooms 4
  • Bathroom 4
  • Acreage 3

A Large commanding residence set hilltop off Middle road with outstanding water views of the Atlantic and glimpses of Chilmark Pond. Inviting common room with cathedral ceilings, fireplace and gourmet kitchen seamlessly flows to the screened porch and lounging deck. Each wing of the house is comprised of a master bedroom en-suite including two additional bedrooms with private baths. Whether spread out in the family/media room, deck or porch this expansive home can accommodate the largest of families. Special and private with access a short walk away to Fulling Mill Brook Preserve offering 60 acres of walking trails

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

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$
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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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8B Clambelly Road Chilmark MA

Price$1,275,000

Est. Mortgage: $/month

MLS Number 34950

  • Residential
  • Square Feet 1978
  • Bedrooms 3
  • Bathroom 3
  • Half Bath 1

CHARMING IN CHILMARK - WITH FULLY PERMITTED COMMERCIAL KITCHEN! Nestled among the rolling hills of Chilmark, this expanded Cape welcomes those who wish to retreat to its magical comfort. The thoughtful design captures the southern light traversing the first floor living area as the day unfolds. The Chef's kitchen, open concept design and large deck allow for an exceptional space in which to entertain. Three outbuildings grace the property allowing for additional storage, gardening tools and a space for simple solitude, play or work. Just minutes away from Lucy Vincent and Squibnocket as well as Alley's and the famous Liz Lemon at 7A. See additional details below.

Listed by Point B Realty LLC

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$
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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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16 Trails End Chilmark MA

Price$1,550,000

Est. Mortgage: $/month

MLS Number 34723

  • Residential
  • Square Feet 1113
  • Bedrooms 3
  • Bathroom 2
  • Acreage 2

One of the unique aspects of this hilltop home is it's location at the top of a rise where it captures the stunning water views looking westerly over the Atlantic to Squibnocket point and the amazing sunsets. Connect with nature within the abutting Land Bank preserve. Several favorite vantage points are the new master suite/office again with those amazing views, the cathedral ceiling living room with gas wood stove and the expansive deck. Free wheeling with a beach Jeep included and a short drive to exclusive Lucy Vincent Beach.. Shed for storage, Out door shower, air conditioning and excellent rental history.

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

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$
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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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 Doctors Creek Path Chilmark MA

Price$1,700,000

Est. Mortgage: $/month

MLS Number 34870

  • Residential
  • Square Feet 989
  • Bedrooms 3
  • Bathroom 1
  • Half Bath 1

You can "see for miles and miles and miles and miles" from this uniquely located Chilmark cottage that includes a deeded beach lot on South Beach...a $300,000 value! . 180 degree water views looking easterly over Chilmark Pond, to the Barrier Beach and beyond and westerly over the Atlantic to Nomans Land. Simply Stunning! Colorful Sunsets! The cottage is a cozy camp with beach stone fireplace; used seasonally. This is a "one of kind" south shore location that is not often available for purchase. Short walk to the shores of Chilmark Pond from the cottage where you can wade across, in the summer, to the boardwalk that leads to your private access to South Beach!

Listed by RE/MAX on Island

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$
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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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22 Larsen Lane Chilmark MA

Price$1,199,000

Est. Mortgage: $/month

MLS Number 34809

  • Residential
  • Square Feet 1361
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.13

Unique opportunity to enjoy the Vineyard the way it use to be on this lovely country lane just steps from the Homeport and Menemsha Pond. Nestled in among vintage cottages this charming, fully renovated home offers all of the amenities buyers are looking for in an expanded Cape with three floors for entertaining family and summer guests. The home offers a beach theme design with its white beadboard wainscoting and offers rich wood floors, ceramic tile floors and baths. The home includes three spacious bedrooms and three full baths as well as a cozy sun room off the kitchen and a large finished basement. Winter water views from upstairs. This location offers your family and guests the unique ability to walk to a day at the beach, watch a Menemsha sunset, go to dinner and never have to get into a car or struggle to find a coveted parking space. Most Furnishings Included. There is over 600 additional sq feet of living space on the lower level that is not included in the square footage listed. Check out the 3D Virtual Tour.

Listed by Kelleher R.E.

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$
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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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20 Tennis Lane Chilmark MA

Price$1,995,000

Est. Mortgage: $/month

MLS Number 34314

  • Residential
  • Square Feet 2673
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

A thoughtfully appointed contemporary home in the center of Chilmark with 4 bedrooms and three and a half bathrooms all of which are newly renovated. This home has great entertaining spaces in and out. The large living room has a cathedral ceiling and a modern fireplace which is the focal point, there is lots of natural light provided by two sets of sliding doors to the deck . Another set of wide sliders opens up from the kitchen to the screened porch with dining area and door to the deck . The bright modern kitchen includes all high end appliances and central island. The 2 first floor bedrooms share a full bath while there is a half bath for guests and laundry room on this level. On the second floor there are two private master suites each with a private bath and one with private balcony. Large clean unfinished basement which could be finished for extra living space. A great second home or rental investment property with strong rental history. Chilmark residents have access to beautiful Lucy Vincent beach and a Squibnocket beaches and the home is within walking distance to lovely trails at Waskosims Rock land bank property.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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61 Stonewall Road Chilmark MA

Price$2,175,000

Est. Mortgage: $/month

MLS Number 34058

  • Residential
  • Square Feet 2537
  • Bedrooms 4
  • Bathroom 3
  • Acreage 4.5

Stonewall Association, one of the premier waterfront neighborhoods in Chilmark, is the location of this brilliant renovation. A wall of beautiful windows across the entire length of the house, white tile and light hardwood floors, create a delightful and stylish home. The renovation, completed this year, adds a clean, modern aesthetic that complements the strong post and beams of the original design. The 4.5-acre property is largely cleared providing a sweeping lawn and a setting for a whimsical outdoor dining gazebo. An Atlantic Ocean beach is the main allure of the neighborhood and this property is well situated for access to the beach and all the pleasures of Chilmark. Whether you are a fun-loving beach person or academic recluse, this property has broad appeal to a gamut of tastes. Virtually all furniture included for an additional fee.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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114 Middle Road Chilmark MA

Price$1,875,000

Est. Mortgage: $/month

MLS Number 33858

  • Residential
  • Square Feet 3951
  • Bedrooms 3
  • Bathroom 3
  • Half Bath 1

MOTIVATED SELLER! This masterfully-crafted home completed in 2014 was built with the highest quality materials, finishes, and mechanics. There is custom paneling, mill work, and cabinetry gracing each and every room. Start with the open concept floor plan - enter first the foyer with a coat closet, powder room, and gorgeous staircase. Then the living room with cathedral ceiling and impressive stone fireplace, a lovely dining area, and a spectacular chef's kitchen with top-tier appliances - Wolf stove top and microwave, 2 Viking ovens and warming drawer, Fisher Paykel refrigerator, dishwasher, and dryer. Off the living room is the master bedroom suite with its own library with fireplace, dressing room with fireplace, and stunning bathroom with a claw-foot soaking tub, double vanity, and tiled shower. Off the kitchen is the year-round sun room or den, a butler's pantry, laundry, and 2-car heated garage. Upstairs you have 2 more bedrooms each with high-end bathrooms. Outside there are stone walls and patios and a charming fountain - all designed for relaxing. Plus a deck perfect for outdoor dining. There is a 4-bedroom septic system so one of the dens could be used as a bedroom. All this plus a newly paved driveway. Furniture and furnishings negotiable - beds, nightstands, couches, rugs, TVs, office furniture, and more.

Listed by Viewpoints

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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
  • Half Bath 1

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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