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Chilmark Homes for Sale

Explore the latest single family homes for sale in Chilmark below. Search through a variety of residential listings to find your new home. Be sure to create an account to save your search and receive notifications when new listings matching your criteria come onto the market. Already have an account? Sign in here!

Homes for Sale in Chilmark

If you have questions or would like to schedule a tour, contact Sandpiper Realty. You might be interested in searching waterfront homes or luxury listings for sale in Chilmark. 

2 Rockrose Path Chilmark MA

Chilmark, MA2 Rockrose Path

Price$1,395,000

Est. Mortgage: $/month

MLS Number 36863

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

This four bedroom, three bath home with ocean views is located on Rockrose Path off 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, large laundry room and plenty of storage space. Furnishings available separately. Access to a deeded, private Atlantic Ocean beach at Thumb Cove is also available separately (follow this link: http://vineyard.mylinkmls.com/Listings/36865).

Listed by Russell Maloney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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277 North Road Chilmark MA

Chilmark, MA277 North Road

Price$8,950,000

Est. Mortgage: $/month

MLS Number 36813

  • Residential
  • Square Feet 2914
  • Bedrooms 6
  • Bathroom 3
  • Half Bath 2

The James Cagney Estate - A vast 70-acre estate with multiple building sites on the north shore of Chilmark. This is possibly the last time a real estate asset of this scale ever becomes available on Martha's Vineyard. The property is a world unto itself offering so much of what Chilmark and Martha's Vineyard are rightly famous for - water views, beach access, sun-dappled meadows, shaded forests through which streams and brooks wend, and lichen-covered stone walls. Exploring this estate - actually made up of three contiguous pieces of property - is like traveling through time and offers a window into a Chilmark of days gone by. The property was at one time the summer retreat of movie star Jimmy Cagney whose affection for this place is legendary. The Cagney house dates from the 1700s and is still in its original location along with a second house, studio, and barn. The prime waterview building site is located a distance away and is completely private. Located on a ridge and surrounded by acres of meadows and stone walls, this site offers views of Vineyard Sound and the mainland in the distance. A third building site is situated in another area of wide open meadows. The opportunities to develop this estate are many and varied and are limited only by a buyer's vision. This rare property could be yours to be treasured now and for generations of your family to come - truly a refuge from the exigencies of modern city living.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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138 & 138B State Road Chilmark MA

Chilmark, MA138 & 138B State Road

Price$4,950,000

Est. Mortgage: $/month

MLS Number 36861

  • Residential
  • Square Feet 2558
  • Bedrooms 5
  • Bathroom 4
  • Acreage 4

This is an amazing Chilmark waterfront property that sits between Stonewall and Nashaquitsa ponds just past Hariffs Bridge. A 3 bedroom main house and 2 bedroom guest house occupy 4 acres of private natural land, and include access to Stonewall pond and Stonewall beach. The "Lenom" property has been in the same family since the 1970's and is being offered for the first time in over 50 years. The year-round main home has been lovingly maintained over the years and AC was added in 2017, the whole house interior was painted in 2020 which has transformed the space and emphasizes the cathedral height living room and the impressive central stone fireplace. Glass doors and three large picture windows surround the dining area to maximize the water views and summer indoor/outdoor living and entertaining. There's also a lovely patio directly off from the dining area to enjoy the outdoor space. The open kitchen has views over to 'Quitsa pond and was fully renovated in 2013 and painted in 2020. Upstairs there's a loft/TV space and also a great viewing roof deck to enjoy sunrises and sunsets and 360 degree water views all day long. The master bedroom is nicely separated from the other 2 guest bedrooms and there are three bathrooms in total, plus an outdoor shower. The guest cottage was converted from the original boathouse to a comfy one bed plus loft bedroom escape right at the water's edge. The upstairs living room with deck that overlooks the pond, bathroom, (with a second water view outdoor shower), and compact open kitchen/dining make this a great space for extra guests or extended family to stay. A new 2 bed septic has been designed and approved for this building. The property has been a popular rental with many repeat families enjoying the homes for generations.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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

Chilmark, MA8 Boston Hill Road

Price$2,850,000

Est. Mortgage: $/month

MLS Number 36621

  • 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 which leads 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 provides for 2 additional bedrooms or guest house.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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

Chilmark, MA8B Clambelly Road

Price$1,195,000

Est. Mortgage: $/month

MLS Number 36736

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

Charming Chilmark residence with 3+ br main home, a barn and two more outbuildings on 3.6 acres with perennial gardens, mature plantings, stonewalls and plenty of privacy. This property is off the meandering, historic Tea Lane and a stones' throw to the new Paint Mill Brook Preserve and down the road from treasured hiking trails at Waskosims' Rock and Tea Lane Farm. The first floor offers a sun filled, open kitchen and expanded living area with beautiful hardwood flooring, a foyer, and a first-floor en suite master bedroom. The second floor offers another living area with two more bedrooms and a partially finished 'bonus' room that could be converted to a fourth, future bedroom. The finished, lower level offers an abundance of additional space and potential! Presently operating as a fully-equipped, commercial kitchen, a dream opportunity for caterers and food enthusiasts, yet could easily be converted to its own in-law apartment with private entrance for your guests, parents or older children. Commercial Kitchen equipment to be sold separately or removed from the property by closing.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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 Quitsa Lane Chilmark MA

Chilmark, MA22 Quitsa Lane

Price$9,995,000

Est. Mortgage: $/month

MLS Number 36756

  • Residential
  • Square Feet 3888
  • Bedrooms 6
  • Bathroom 4
  • Half Bath 1

Spectacular and charming; this cottage style home and guest annex is located in one of the most picturesque parts of Martha's Vineyard. This home is full of character with access to private beach just steps from the home and unforgettable ocean views from nearly every vantage point on the property. The main house offers a large gourmet kitchen, amazing patio space for outdoor dining, quaint bedrooms and several entertainment and gathering space. The recently constructed guest annex and garage space is tastefully done with room for overflow family and friends.

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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 Greenhouse Lane Chilmark MA

Chilmark, MA18 Greenhouse Lane

Price$997,000

Est. Mortgage: $/month

MLS Number 36663

  • Residential
  • Square Feet 2100
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.4

Quintessential waterfront cottage overlooking Martha's Vineyard's hottest surf destination on the south shore. What a great place to spend some time and enjoy this classic and wonderful home listening to the sounds of the surf and sea. 3 comfortable bedrooms and a delightful kitchen lead to a living room centered around a great field stone fireplace with views from every room. The property may be used as is for some time and then be converted into a private beach access ideal for surfers and beach goers alike. This is a magical location where time stands still.

Listed by Feiner Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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 Azalea Lane Chilmark MA

Chilmark, MA11 Azalea Lane

Price$4,000,000

Est. Mortgage: $/month

MLS Number 36676

  • Residential
  • Square Feet 3750
  • Bedrooms 5
  • Bathroom 4
  • Half Bath 1

With 425 ft of private ocean beach, this offering deserves its reputation as the "ultimate beach house". The 5-bedroom home has been completely renovated to the highest specifications with a focus on bold contemporary choices to take advantage of the views and setting. The beach stairs provide access to a wide swath of sand that many consider the most beautiful stretch of beach on Martha's Vineyard. The property is being offered mostly furnished. To fully appreciate this extraordinary setting, view the images in the "photo gallery" and watch this drone video: https://vimeo.com/175588276

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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

Chilmark, MA7 Clambelly Road

Price$1,475,000

Est. Mortgage: $/month

MLS Number 36342

  • 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 an expansive view of the Sound. The main house has two bedrooms, both facing the water, and two bathrooms, designed with a warm 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 offering the possibility for expansion. The house was built to be a three season home, but the Seller is currently installing additional insulation and a heat pump. This is a wonderful investment opportunity for a Chilmark Buyer looking for a special view at a great price.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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 Tabor Hills Chilmark MA

Chilmark, MA22 Tabor Hills

Price$1,450,000

Est. Mortgage: $/month

MLS Number 36441

  • Residential
  • Square Feet 2375
  • Bedrooms 3
  • Bathroom 2
  • Half Bath 1

Beautifully kept three bedroom contemporary home, set amongst 3 acres of rolling Chilmark land. The first floor is all wood floors, a spacious first floor master bedroom, with large bathroom and walk-in closet space as well as an open layout plan for the living/dining and spacious kitchen area all add to the comfort of this home. Enjoy dinners on the screened in porch, or reading a back on the back deck overlooking the large yard and wooded surroundings. A First floor laundry area, a half bathroom, a small office area, as well as a 2 car garage complete the first floor. Upstairs you will find 2 more large bedrooms that share a full bathroom. This home gets amazing light, the living room is lined with windows, making it a wall of glass to enjoy the Chilmark landscape. This home has a 5 bedroom septic in place, yet it is only a 3 bedroom home so the potential already exists to add more bedrooms either by finishing the walk out basement area, an addition or a detached bedroom, so many options!

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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

Chilmark, MA15 Doctors Creek Path

Price$1,500,000

Est. Mortgage: $/month

MLS Number 36279

  • 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 beach cottage that includes deeded access to 7 acres of pristine South Beach on the Atlantic Ocean! 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 distance 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! Included is an approved septic design for a 3 bedroom system. Buyer is responsible for installation. Enjoy the "camp" as it is or use your vision to rebuild/remodel. A special place on this beautiful island.

Listed by RE/MAX on Island

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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260 South Road Chilmark MA

Chilmark, MA260 South Road

Price$4,195,000

Est. Mortgage: $/month

MLS Number 32807

  • Residential
  • Square Feet 2604
  • Bedrooms 6
  • Bathroom 2
  • Half Bath 2

Waterview Chilmark estate sprawling over 6.1 acres with access to Chilmark Pond and an Atlantic Ocean beach. Known as The James Allen House, this historic home has been lovingly maintained by the same family for generations. The landscape is like no other with stonewalls, various species of trees, expansive lawn, and an open field with paths that lead you to Chilmark Pond and beyond. The classic floor plan of the main house offers multiple living spaces with 3 bedrooms, several fireplaces, and beautiful waterviews. This property features multiple other buildings including a 2 bedroom guest cottage, 1 bedroom bunkhouse, garage and garden shed. This is a unique opportunity for a new owner to carry on the proud legacy of this home's historic past. An extraordinary and rare find in the heart of Chilmark.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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, 30, 31 Tower Lane Chilmark MA

Chilmark, MA27, 30, 31 Tower Lane

Price$2,950,000

Est. Mortgage: $/month

MLS Number 35757

  • Residential
  • Square Feet 4967
  • Bedrooms 6
  • Bathroom 3
  • Acreage 63.3

Over 63 acres in Chilmark. As you turn off of Middle Road you are met by a cobblestone driveway that leads you through 7+acres of conservation land and up to the towering Carriage House archway that is the entryway to this majestic property. Emerging through the archway you are greeted by a unique assemblage of structures including the contemporary main house, guest house, and studio. These are surrounded by old stonewalls and newer detailed stonework that creates a harmonious balance between old farmland and new modern design. The Main House contains 4-bedrooms, large open living space and a rooftop deck. The nearby Guest House with 2-bedrooms and full kitchen overlooks raised bed gardens and rolling hills. Also located on the property is another 2-bedroom cottage with a full kitchen and an unfinished pool with pool house. On the far side of the property is over 45 acres of conservation land including portions of the Tiasquam River, all creating the utmost in privacy. There is potential to build one more single-family home on a portion of the property, or simply update the existing structures and enjoy the pristine land that surrounds you. The options for this property are many and varied.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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 Jethro Lane Chilmark MA

Chilmark, MA8 Jethro Lane

Price$15,000,000

Est. Mortgage: $/month

MLS Number 35593

  • Residential
  • Square Feet 7000
  • Bedrooms 7
  • Bathroom 6
  • Half Bath 1

Stunning Chilmark north shore 4 acre waterfront paradise with wonderful sunsets and unique privacy nestled between a large wooded hill and a 200 acre private estate. The 5 bedroom 4 1/2 bath TWO kitchen main house and 2 bedroom (with 2 dormers) 2 bath guest house enjoy dramatic views of the Elizabeth Islands from the Gay Head Lighthouse to Woods Hole from every room. The property is beautifully manicured with an enchanting contour stretching to the bluff overlooking a dreamy private cove and sandy beach. Four cleared acres are very rare on the heavily wooded north shore. Waterfront values on the rugged, elevated and protected Vineyard north shore are attracting more interest after Hurricane Sandy damaged the low elevation fragile south shore NY, NJ and New England coast line. The property is in the highly desirable 335 acre Spring Point community with 38 home sites with 135 acres of common land, 3/4 mile of private beach, 2 tennis courts and endless dirt roads and trails.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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 Austin Pasture Road Chilmark MA

Chilmark, MA18 Austin Pasture Road

Price$8,900,000

Est. Mortgage: $/month

MLS Number 34345

  • Residential
  • Square Feet 4000
  • Bedrooms 5
  • Bathroom 3
  • Acreage 16.38

A magical setting on Squibnocket Pond with endless waterviews of Squibnocket Pond, Atlantic Ocean and Nomans Land Island. Perched high up on a hill on over 16 acres of untouched land, sits this inviting Chilmark home that has been crafted to take in the beautiful surroundings and private landscape. The home features wonderful wood throughout, a generous main level with an open living room and a stone fireplace, a built-in window seat, a spacious dining room and a large gourmet kitchen with an over-sized island. The master suite includes a spacious bath and access to a lovely porch overlooking Squibnocket Pond and beyond. A separate guest wing includes 2 additional bedrooms and full guest bath. Oversized windows allow for spectacular waterviews in every direction. The lower level features a comfortable sitting room with a wood stove, 2 guest bedrooms, full bath and access to a one car garage and storage area. Venture down a peaceful footpath to the water's edge and boat, kayak, or paddle board with ease on Squibnocket Pond. With over 16 acres of grounds, this home is sited to take in mesmerizing waterviews and its serene setting is the perfect retreat to create memories for a lifetime.

Listed by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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

Chilmark, MA13 Deerpath Lane

Price$2,425,000

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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

Chilmark, MA15 Lake Road

Price$3,000,000

Est. Mortgage: $/month

MLS Number 25297

  • Residential
  • Square Feet 1980
  • 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: 3.07% last updated on Jul 2, 2020
* 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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