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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114 Middle Road, Chilmark, MA

Price$2,375,000

Est. Mortgage: $/month

MLS Number 33858

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

This masterfully-crafted home was built in 2010 with high quality materials, equipment, and finishes. 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 name appliances including Wolf, Viking, and Fisher Paykel. 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, butler's pantry; laundry and 2-car heated garage. Upstairs you have 2 more bedrooms each with a top-notch bathrooms. Outside there are stone walls and patios and a charming fountain - all designed for relaxing. Plus a deck perfect for outdoor dining. This unique home is a must see!

Listed by Viewpoints

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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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$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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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130 South Road, Chilmark, MA

Price$1,295,000

Est. Mortgage: $/month

MLS Number 33794

  • Residential
  • Square Feet 2746
  • Bedrooms 4
  • Bathroom 3
  • Acreage 2.19

Once a two story barn, this 2200 square foot space was converted to a 3-br residence some years ago and still retains much of its original character. Formerly known as the Fenner barn, the exposed beams, trusses and original wood walls and ceiling were thoughtfully preserved to retain the antiquity and essence of the original Barn. An open style living concept, the residence offers two sunrooms, open kitchen/living dining area with stone fireplace and a main level master bedroom. Two more bedrooms on the second floor and another loft style living area with book cases and another stone fireplace - known as 'the music room'. Surrounding gardens and mature plantings on 2.3 acres complement the simplicity and charm of the interiors. A 1-br guest house (556 sf) at the rear of the property offers additional sleeping space for guests, family or an income producing property.

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: 4.57% last updated on Jun 21, 2018
* 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 North Slope Lane, Chilmark, MA

Price$1,475,000

Est. Mortgage: $/month

MLS Number 33844

  • Residential
  • Square Feet 1640
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1

Sweet location with surprising views over the Vineyard Sound. The lot is a form A which has not been recorded given the Seller would like the future owner to determine if they want the property in its entirety (6.7 acres) or this 3.9 acre parcel which has already been surveyed. A new well would need to be installed for this home. The septic has a Title V system for four bedrooms however this can be expanded with additional soil testing. The house could be used spiffed up for seasonal use until a new owner has time to design a new home with strong Elizabeth Island and sunset views.

Listed by Tea Lane Associates

{$office->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: 4.57% last updated on Jun 21, 2018
* 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$1,950,000

Est. Mortgage: $/month

MLS Number 33760

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

Charming four bedroom Cape with beach key to the sandy shores of Black Point. Sited on over six pristine acres, some of which is held in conservation, complete with stone walls, rolling hills, and meadow. The well-built home offers the perfect layout for comfortable summer living, with an open floor plan and large screened in porch. Distant water views and endless star gazing is achieved from the rooftop deck. The epitome of Island living.

Listed by Sandpiper Realty

{$office->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: 4.57% last updated on Jun 21, 2018
* 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 High Mark, Chilmark, MA

Price$1,950,000

Est. Mortgage: $/month

MLS Number 33598

  • Residential
  • Square Feet 2100
  • Bedrooms 4
  • Bathroom 2
  • Acreage 1.8

Enter into this home and be immediately stunned by the wide open expansive South Shore Atlantic views! This vintage home is reminiscent of mid century architecture and offers a lovely open floor plan with an expansive deck facing the views. The master bedroom and a full bathroom is also on this level. The lower level of the home features 3 more bedrooms and a full bathroom as well as an additional living room space, great for the kids! Glass doors and windows to let the natural light flow in. Only a short distance to Chilmark center, Menemsha and Lucy Vincent beach.

Listed by Flanders Real Estate

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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: 4.57% last updated on Jun 21, 2018
* 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$1,960,000

Est. Mortgage: $/month

MLS Number 33729

  • Residential
  • Square Feet 2120
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1

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 Point B Realty LLC

{$office->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: 4.57% last updated on Jun 21, 2018
* 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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30 Huntington Way, Chilmark, MA

Price$2,100,000

Est. Mortgage: $/month

MLS Number 32883

  • Residential
  • Square Feet 1100
  • Bedrooms 3
  • Bathroom 1
  • Acreage 3.02

A wonderful Chilmark opportunity on the Tisbury Great Pond with view and pond access. This sweet single level cottage is surrounded by 3 plus acres of land. Large dwelling and building site location formerly approved. A quick trail leads to the edge of a sandy swim spot where you can keep a sailboat, kayak or zodiac to enjoy all that the Tisbury Great Pond and the Atlantic ocean beach offers. Sunny deck, outdoor shower and pond views. Inside you will find a large eat in kitchen, cozy living room with fireplace plus a bonus sun room/den to the rear. Two bedrooms plus stairs to another attic bed/room. There's one bathroom and an outdoor shower. There's a large storage shed onsite and a septic for 6 bedrooms in and ready to go.

Listed by Tea Lane Associates

{$office->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: 4.57% last updated on Jun 21, 2018
* 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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12 & 24 North Slope Lane, Chilmark, MA

Price$2,100,000

Est. Mortgage: $/month

MLS Number 33341

  • Residential
  • Square Feet 1448
  • Bedrooms 3
  • Bathroom 2
  • Acreage 6.7

A fabulous property located off North Road, with sweeping protected water views of the North Shore and the Elizabeth Islands. The house sits on an enchanting piece of property with mature trees, pretty pathways, glacial boulders and of course the water views. The existing 2 bedroom seasonal home and detached studio bedroom was built in the late 1960's to a 1965 Stanmar design and partially re constructed in 1995 by the architect owner. There's a 4 bedroom septic on the property. Renovate this single level contemporary structure or start again in this location or further back on the property to maximize the land and water views - the property is staked and ready for your imagination.

Listed by Tea Lane Associates

{$office->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: 4.57% last updated on Jun 21, 2018
* 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$1,950,000

Est. Mortgage: $/month

MLS Number 33369

  • 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.

{$office->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: 4.57% last updated on Jun 21, 2018
* 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 33362

  • Residential
  • Square Feet 2500
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

Within walking distance to Chilmark center and Quitsa boat landing,this 4 bedroom home with beautiful grounds and water views of Menemsha Pond 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.

{$office->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: 4.57% last updated on Jun 21, 2018
* 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$1,395,000

Est. Mortgage: $/month

MLS Number 33322

  • Residential
  • Square Feet 3166
  • 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

{$office->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: 4.57% last updated on Jun 21, 2018
* 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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156 South Road, Chilmark, MA

Price$1,550,000

Est. Mortgage: $/month

MLS Number 33282

  • Residential
  • Square Feet 2084
  • Bedrooms 3
  • Bathroom 2
  • Acreage 5

This quintessential Vineyard retreat is located just 1.5 miles to West Tisbury on a large 5 acre lot on South Road. Upon entering this charming Cape you are immediately greeted with a warm yet dramatic post and beam living room with cathedral ceilings and a wood burning fireplace encased in a custom made floor to ceiling wood surround. This room sets the tone for the rest of the home which is very unique in both layout and architecture.The kitchen includes a small island and an additional room which could be used as a more casual eating area or sitting room. There is a bedroom and a den and bath in this section of the house leading to an inviting long corridor which provides access to the second bedroom and finally the master en suite. Placing a couple of the bedrooms away from the main living areas' is great for groups with small children or elders who might prefer to retire a bit earlier then the rest of the family offering peace and quiet from a busy summer day. The home has a full house generator which is a must have for winter use.The house is sited on a dramatic, park like setting lot which offers many options in terms of landscaping or expansion to the house. In season it offers a large lawn area as well as an expansive area of wild flowers, grape vines and vegetable garden. The large lot enables the buyer to add a guest house, barn, garage, pool, etc with town approvals.The home is only 1 mile to beautiful Hancock Beach and 3 miles to Lucy Vincent Beach. The Seller's do have a beach key to Hancock Beach that could be purchased separately.

Listed by Kelleher R.E.

{$office->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: 4.57% last updated on Jun 21, 2018
* 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 Smith Lane, Chilmark, MA

Price$1,175,000

Est. Mortgage: $/month

MLS Number 33196

  • Residential
  • Square Feet 2089
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1

If location is important this is the spot. Just a short drive off State road, this house is an easy bike ride to both town beaches and walking distance to the Chilmark Store and the community center. 2.5 wonderful rolling acres with a large west facing meadow affording tons of privacy and sun. This home has been rented for many years and is available for the first time. Nice sized bedrooms with a real master en-suite, huge living room with sliders out to a very large and almost new mahogany deck, great for lounging and grilling. The super-sized kitchen has tons of potential and would benefit from some updating of appliances and counter tops. This home is a diamond in the rough presenting real opportunity to someone with vision who appreciates a property with special qualities. There is a 2 car garage with plenty of storage and a wonderful palate of interesting land on which to create your vision.

Listed by Feiner Real Estate

{$office->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: 4.57% last updated on Jun 21, 2018
* 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$2,950,000

Est. Mortgage: $/month

MLS Number 33171

  • Residential
  • Square Feet 4000
  • Bedrooms 4
  • Bathroom 3
  • Half Bath 1

No detail was forgotten in this meticulously maintained Post and Beam custom home down Flanders Lane. A peaceful setting where you can hear the Menemsha bell chiming in the distance. With four spacious bedrooms, 2 of which are master bedrooms, gracious living areas, beautiful outdoor spaces and deeded rights to 200' of Menemsha Pond frontage, this home is a rare find. From the Alaskan cedar shake roof, to the soapstone kitchen counters and sink, the level of quality and craftsmanship is supreme. The finish work of the oversized living room with huge brick fireplace is an ideal resting place for those chilly winter evenings. The cozy TV/Dining area off the kitchen serves as the perfect entertaining space that can spill out onto the stone patio. A brand new 18 x 36 gunnite heated saltwater in-ground pool currently being added to this unique gem of a property, will enhance the already well maintained and beautiful landscapes and gardens surrounding this home. A must see property, too many details and qualities to list. An unparalleled find!

Listed by Flanders Real Estate

{$office->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: 4.57% last updated on Jun 21, 2018
* 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
  • Half Bath 1

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. Get your beach passes to Lucy Vincent and enjoy Summer 2018 season!

Listed by Carroll & Vincent R.E.

{$office->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: 4.57% last updated on Jun 21, 2018
* 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$1,020,000

Est. Mortgage: $/month

MLS Number 30444

  • Residential
  • Square Feet 1652
  • Bedrooms 3
  • Bathroom 2
  • Half Bath 1

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. Small stained glass insert in front door to be replaced with clear glass. Check out the 3D Tour - https://livetour.istaging.com/590cc123becd360054078dae?ui=true

Listed by Kelleher R.E.

{$office->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: 4.57% last updated on Jun 21, 2018
* 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

{$office->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: 4.57% last updated on Jun 21, 2018
* 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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