Chilmark Real Estate

Types of homes in Chilmark include ranch style homes, charming cottages, traditional farmhouses, vacation homes, and old family homesteads. Real estate in Chilmark offers access to fishing, beaches, and miles of trails. Chilmark's coastline is very dramatic, ranging from the sloping sandy beaches of the south shore to the rocky coast of the north shore.

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8 Jethro Lane Chilmark MA 02535

Chilmark, MA8 Jethro Lane

Price$11,995,000

Est. Mortgage: $/month

MLS Number 35593

  • Residential
  • Mls Status Active
  • Village North
  • Bedrooms 8
  • Bathroom 6.5

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

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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1 Pondmark Chilmark MA 02535

Chilmark, MA1 Pondmark

Price$4,700,000

Est. Mortgage: $/month

MLS Number 38183

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 4.7

Turn onto country lane and make first turn to right. Drive past Norwegian Pine and many mature plantings and follow stately stone walls up past an open field overlooking the pond. The gentle slope takes you past the garden to a parking area. The white cottage sits on top of the knoll with sweeping views looking out over Keith farm and beyond to the ocean. From the living room the light brightens the large room with vaulted ceilings and a fireplace with a copper chimney hood.You can walk out on the deck for breakfast and watch the cows, geese, horses or the calming motion of the sea. You can lay in bed and take it all in from the king size bed and wall of windows facing south. There is room for a guest house or barn in this private setting. There are walking trails on Old North Road or a trail to Menemsha Crossroads. Go back in time to a slower way of life in this old style Chilmark retreat.

Listed by Gay Head Realty

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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39 Prospect Hill Road Chilmark MA 02535

Chilmark, MA39 Prospect Hill Road

Price$3,750,000

Est. Mortgage: $/month

Pending

MLS Number 38968

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathroom 2
  • Acreage 3.3

Stunning sunset water views from this hilltop home will delight the senses from morning to night. At 207 feet above sea level, the rolling and interesting 3.3 acre parcel has spectacular views overlooking many acres of gorgeous stonewall lined fields, a small duck pond, and a glimpse of Noman's and includes Menemsha bight and the Vineyard Sound. On the top of the hill it is perched high enough that the views actually go almost 40 miles over the tops of the Elizabeth Islands to the Newport bridge and mainland north. A comfortable 4 bedroom home designed to accommodate family and friends has an open kitchen living room area walking out to the deck. Great for parties and gatherings the heart of the home is an updated kitchen and a great place to meet and of course the sunsets are exquisite- as is watching the weather patterns over Aquinnah and the Islands. This is the first time this home has been for sale since its construction and there is plenty of room to envision improvements and additions. Built by Island builder Colin White in 1980, this family home has been a cherished heirloom for 4 generations of the current owners family and it will be for you as well.

Listed by Feiner Real Estate

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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135 Middle Road Chilmark MA 02535

Chilmark, MA135 Middle Road

Price$2,950,000

Est. Mortgage: $/month

Active With Contract

MLS Number 37541

  • Residential
  • Bedrooms 5
  • Bathroom 2
  • Acreage 7.1

A quintessential 1950s cottage situated on the highly sought after area of Middle Road in Chilmark. Consisting of a main house, guest house, garage and storage shed on 7.1 total acres. Would make a great family compound. A Landbank walking trail abuts property. Property is being sold "AS IS." Septic upgrade plan completed, but not installed.

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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 Cedar Lane Chilmark MA 02535

Chilmark, MA4 Cedar Lane

Price$2,250,000

Est. Mortgage: $/month

MLS Number 39029

  • Land
  • Mls Status Active
  • Acreage 3.58

South shore beachy living in Stonewall Association. Private parking and access to a lovely swim and surf beach in a beloved area of Chilmark. Super sunny lot fully engineered and ready to go. Single family dwelling and guest house allowed according to the Chilmark by-laws. This lot includes rights to the private association beach. Great location in Chilmark, close to the Quitsa landing, Chilmark Center and Menemsha. Really a dream location. The lot offers interesting topography and flexibility. A rare opportunity in Chilmark.

Listed by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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5 Tree Frog Lane Chilmark MA 02575

Chilmark, MA5 Tree Frog Lane

Price$1,595,000

Est. Mortgage: $/month

Pending

MLS Number 39074

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathroom 2
  • Acreage 4

This tastefully designed post & beam home is privately sited on 4 acres overlooking a peaceful & pastoral setting with stone walls a charming vegetable garden with raised beds. Many nice features include wide pine wood floors, a living and dining room with fireplace, a country kitchen breakfast area, cathedral ceiling and first floor master. The second floor includes a small loft, 3 bedrooms and bath. Outside shower off the back deck. Being sold fully furnished, turnkey. There is also a large storage shed and barn. A guest house can be permitted in 5 years. Close to beaches, Menemsha and Chilmark Village. A must see!

Listed by Karen M. Overtoom R.E.

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$
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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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0 Eliot Avenue Chilmark MA 02535

Chilmark, MA0 Eliot Avenue

Price$155,000

Est. Mortgage: $/month

MLS Number 33176

  • Land
  • Mls Status Active
  • Village South
  • Acreage 0.8

Enjoy access to lovely stonewall Beach, south shore Atlantic beach with great swimming and fishing! - not a buildable lot.

Listed by Flanders Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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South Shore Water View with Pool

South Road Chilmark MA 02535
For Rent

Listing Number X64844175

  • Non-MLS Vacation Rentals
  • Bedrooms 5
  • Maximum Occupants 10
  • Bathroom 4
  • Type Vacation Rental

Spectacular five bedroom, water view home with pool. Open living /dining area with walk out to large deck with a well furnished outdoor dining area.   Plenty of outdoor living to be enjoyed whether in the pool or poolside, sitting around the fire pit at night or playing tennis on the private court.   Rental also comes with Chilmark Pond access and south shore beach access across the Pond. Please call for rates and availability.  

Listed by Hancock Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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Amazing Menemsha Waterfront

State Road Chilmark MA 02535
For Rent

Listing Number 2-MWF

  • Non-MLS Vacation Rentals
  • Bedrooms 4
  • Village Chilmark
  • Maximum Occupants 8
  • Bathroom 4

An unspoiled paradise ~ 140 acres with a mile of waterfront on Menemsha and Quitsa Ponds. Spectacular panoramic views of Menemsha Pond, Vineyard Sound and the Elizabeth Islands. Private walking trails and beautiful private beaches. The privacy, views and sunsets are unparalleled. Lovely, three bedroom home with spacious screened porches, fireplaces, central AC and all the comforts of home. A detached one bedroom studio with screened porch completes the package. A unique opportunity to enjoy a vacation paradise with your family on the beautiful island of Martha's Vineyard. Offered Exclusively through Hancock Real Estate. Please call for rates and availability...

Listed by Hancock Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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Menemsha Bridge House

North Road Chilmark MA 02535
For Rent

Listing Number 2-MBH

  • Non-MLS Vacation Rentals
  • Bedrooms 4
  • Bathroom 3
  • Maximum Occupants 8
  • Type Vacation Rental

Beautiful four bedroom home near Menemsha Village.  Open living/dining/kitchen area on first floor along with full bath and king bedroom.   Second floor has primary bedroom with king size bed, full bath and private deck, along with two other bedrooms, one queen and one with twin beds, that share a full bath.   Enjoy the outdoor living areas whether your on one of the decks, screened in porch or the patio.  House is well equipped, central AC, outdoor shower and propane grill.   Please contact office for availability and rates. Owner/Broker

Listed by Hancock Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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Spectacular Colonial Home ~ South Road

South Road Chilmark MA 02535
For Rent

Listing Number 1-SCHSR

  • Non-MLS Vacation Rentals
  • Bedrooms 5
  • Maximum Occupants 10
  • Type Vacation Rental
  • Sleeps 10

This is an updated 5-bedroom, 3½ bath, farmhouse set back behind ancient Chilmark stonewalls with a key to Hancock Beach!  The house lies between West Tisbury (Alley’s General Store, 7A Foods, Farmer’s Market, Artisan’s Market, galleries, etc.) and Chilmark (Chilmark Store, Chilmark Tavern, Chilmark Community Center, etc.).  It is also a short ride to Menemsha Village (fishing, fish markets, galleries, restaurants, and sunsets on the beach). This 1713 Mayhew farmhouse underwent a complete gut-renovation in 2017 and was reborn to honor its past while embracing today’s contemporary lifestyle.  The house is fully air- conditioned and has Wi-Fi, high speed Internet and cable TV.  A beautiful three-season porch was added to the back of the house.  It is a relaxing place to sit, read, play a game, watch TV, or simply observe what is going on outside.  The porch leads to a bluestone patio with a teak dining table with seating for 8 under a market umbrella along with a number of chairs to relax in and a gas grill.  Adjacent to the patio is a large private outdoor shower.  The house is surrounded by an expansive lawn bordered by stonewalls.    The house is remarkably open on the first floor.  The porch leads into a fully equipped cook’s kitchen with high-end appliances, quartz countertops and an island with seating.  The dining room has a farmer’s table that seats up to 10 along with an additional sitting area by the fireplace. The library/media room is a cozy place to sit and talk, read by the fireplace, or binge watch that show you just never got to last year on a large flat screen TV. The final room downstairs is the first, of two, en suite bedrooms (queen bed).  It has a fireplace, flat screen TV, and a marble and tile bathroom.  A French door leads from this bedroom to the bluestone patio.  The central hallway contains a half bath and two stairways that lead to the second floor where you will find four additional bedrooms, (two queens, one twin and an en suite king), a full laundry and a large bathroom with an oversized tub/shower.  The 2nd floor primary bedroom (king bed) has a flat screen TV, an attached walk-in closet and en suite marble and tile bath.  High quality linens and towels are provided throughout the house. The real bonus of this house is its key to Hancock Beach—located approximately 1.5 miles from the house down a private road.  Hancock Beach is a premier private South Shore ocean beach adjacent to Chilmark Pond so that both can be enjoyed.  Tenants can bring kayaks to the pond to explore this beautiful, unspoiled environment. Tenants also have access to Chilmark town beaches—Lucy Vincent and Squibnocket.  Beach chairs, towels, umbrellas and coolers are all provided. Please call for availability and rates.    

Listed by Hancock Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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Panoramic Water Views

North Road Chilmark MA 02535
For Rent

Listing Number 1-PWV

  • Non-MLS Vacation Rentals
  • Bedrooms 6
  • Bathroom 5
  • Type Vacation Rental

Spectacular six bedroom contemporary home with panoramic views of the Vineyard Sound. Please call for availability and rates. THIS HOME IS RENTED FOR THE 2022 SEASON

Listed by Hancock Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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"Based on information submitted to MA_LINKMV as of January 21, 2022 . All data is obtained from various sources and has not been, and will not be, verified by broker or MA_LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing."