Chilmark, MA Homes for Sale

The Beauty of Chilmark Real Estate

Nestled on the western edge of Martha's Vineyard, Chilmark is a charming coastal town known for its stunning beaches and rolling farmland. The real estate in Chilmark reflects the area's natural beauty, with many properties offering sweeping ocean views and private beach access. From quaint cottages to luxurious waterfront estates, there is a wide range of options for potential homebuyers in this picturesque town.

A Closer Look at Chilmark's Real Estate Market

The real estate market in Chilmark is unique compared to other areas on Martha's Vineyard. The town is known for its high-end properties, with many homes selling for millions of dollars. Despite the high prices, demand remains strong in Chilmark, as buyers are drawn to the area's exclusive feel and natural beauty. Whether you're looking for a vacation home or a permanent residence, Chilmark offers a wide variety of options for potential buyers.

Living in Chilmark: Lifestyle and Amenities

Living in Chilmark offers a laid-back and luxurious lifestyle, with plenty of outdoor activities to enjoy. Residents can spend their days lounging on the beach, exploring hiking trails, or sampling fresh local seafood at one of the town's charming restaurants. With its close-knit community and stunning natural surroundings, Chilmark is the perfect place to escape the hustle and bustle of city life and relax in a peaceful coastal setting.

Investing in Chilmark Real Estate

For those looking to invest in real estate in Chilmark, the potential for high returns is significant. The town's desirable location, limited supply of homes, and strong demand from buyers make it an attractive market for investors. Whether you're looking to purchase a vacation rental property or a permanent residence, investing in Chilmark real estate can be a smart financial decision that allows you to enjoy the town's natural beauty and tranquil lifestyle.

Conclusion

In conclusion, real estate in Chilmark, MA, offers a unique blend of coastal beauty, luxury amenities, and strong investment potential. With its stunning natural surroundings, exclusive feel, and range of high-end properties, Chilmark is a sought-after destination for homebuyers and investors alike. Whether you're looking for a vacation home, a permanent residence, or a lucrative investment opportunity, Chilmark's real estate market has something to offer for everyone.

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Newest Chilmark, MA Homes for Sale

$15,650,000

6 Beds ⋅ 6 Baths ⋅ 73248835 MLS

8 Snail Road, Chilmark

Listing courtesy of Listing Agent: Jen O'Hanlon from Listing Office: Compass.

$12,500,000

6 Beds ⋅ 6 Baths ⋅ 73225612 MLS

CHILMARK SOUTH SHORE WATER VIEW. This Squibnocket gem is a Hutker Arhictect-designed family compound, main house,& guest house on 4.5 acres. Live the ultimate up-Island life with captivating water views in every direction. The home is pristine and private, with many unique features. The chef's kitchen and dining area are serene, bright, and functional. Step up to what might be the best panorama in all of Chilmark, featuring views of the South Shore beach, Quitsa, Menemsha Pond, and Vineyard Sound. A stately wood-burning stone fireplace centers the one-of-a-kind living room that overlooks the oversized lap pool, expansive stone patio area, and dining space for outdoor enjoyment. The stunning main house has 4 bedrooms and 3 ½ baths. The primary bedroom is on the main level and has its own fireplace, ensuite bathroom, walk-in closet, and direct access to the outdoor shower. Take a quick walk down the hill to stunning Squibnocket Beach for a dip in the surf.

2 Squibnocket Rd, Chilmark

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Compass.

$21,000

3 Beds ⋅ 3 Baths ⋅ 73217527 MLS

WEEKLY RENTAL $21,000/WEEK. 3 bed, 3 bath + outdoor shower with chef's kitchen and top of the line appliances, this home was built in 2018. Home also has cold plunge as well as a sauna. The exquisite post & beam Allen Farm Hilltop Farmhouse perched 150 feet above Lucy Vincent Beach & the Atlantic Ocean in Chilmark has the best views on the island and provides unmatchable privacy. The 100+ acre property is surrounded by stone walls and nature. House has direct access to Lucy Vincent Beach & Chilmark Pond. Enjoy the fresh veggie garden & eggs provided by the farm, as well as the beautiful & historic farmland & pastures that have been owned by the Allen family since 1762! The 3 season screened in porch, chef's kitchen, and open layout are ideal for entertaining. Sleeps 10. 3+ bedrooms, 3 full bathrooms, + outdoor shower. The rental comes w kayaks/canoes, and views as far as the eye can see. Linens provided.

16 Allen Farm Road, Chilmark

Listing courtesy of Listing Agent: Jesse Greenstein from Listing Office: Douglas Elliman Real Estate - Park Plaza.

$4,250

2 Beds ⋅ 2 Baths ⋅ 73191193 MLS

**BOOKING SUMMER 2024** Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime location off North Road next to North Tabor Farm, Great Rock Bight Preserve, Menemsha Beach, The Chilmark Store, Library and Community Center. The gorgeous grounds are dotted with wild blueberries and embraced by tall trees alive with local birds. Bright, light, and easy. Perfect for a long summer stay, fall leaf peeping, visiting family and friends and retreating artists alike. Furnished, Kitchenware provided, Sheets, Bath & Beach Towels provided,Washer/Dryer. Beach Passes can be purchased for Lucy Vincent and Squibnocket. INQUIRE FOR AVAILABILITY. Taxes,Cleaning, Security Additional.

11 Hammett Lane, Chilmark

Listing courtesy of Listing Agent: Allison Cameron Parry from Listing Office: Douglas Elliman Real Estate - Nantucket.

$7,000

4 Beds ⋅ 4 Baths ⋅ 73176394 MLS

Weekly Rental The "Grapevine" is located on a private road next door to the Beach Plum Inn, It was completely rebuilt not to long ago it has 3 generous size bedrooms all with private baths, 2 of the bedrooms are located on the second floor, 1 bedroom is located on the first floor as well as the Open concept living with a chefs Kitchen, living room ,dining area and fireplace area. Walk out the Sliding doors to your spacious deck with propane gas grill, wonderful views to Vineyard sound and Elizabeth Islands . Private Outdoor shower in the back.The lower level has an extra living room/ bedroom equipped with sofa ,chairs and a flat screened tv. Take a stroll down the Private Trail, pass by a barn with animals, walk out to a meadow and to Menemsha Beach. fully air conditioned . All the amenities you could want. You will be able to get Beach Passes to the famous Lucy Vincent Beach in Chilmark. Walk to Menemsha Beach and Village, boat rentals, fishing, Eating, swimming and so much more..

27 Beach Plum Lane, Chilmark

Listing courtesy of Listing Agent: Bryan Hummel from Listing Office: Commonwealth Realty Group.

$1,885,000

3 Beds ⋅ 3 Baths ⋅ 73170658 MLS

CHARMING CHILMARK- This sweet, sunny home comes with deeded access to Chilmark Pond and South Shore Beach. Kayak, paddleboard, sail, or motor across the pond to one of Chilmark's most pristine private beaches. The location is also convenient, being centrally located and close to West Tisbury Center, Grey Barn, the Yoga Barn, Chilmark Center, Beetlebung Farm, Chilmark Store, and Chilmark Tavern. This three-bedroom post and beam has an efficient Viessmann heating system and a mini-split for AC. The three-acre lot has been thoughtfully landscaped, providing a serene and picturesque setting.Additionally, per Chilmark zoning regulations, there is potential for expansion, allowing for a total of 3,500 square feet and up to six bedrooms with the necessary permits and an upgraded septic system. If a pool is on the wishlist, there is also room for that with a special permit. This property has a lot of opportunities to create your vision, enjoying all Chilmark has to offer.

5 Meeting House Rd, Chilmark

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Compass.

$16,000

7 Beds ⋅ 4 Baths ⋅ 73121636 MLS

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite. Fully equipped kitchen with a six burner gas stove, double ovens and gorgeous granite countertops. Outdoor to indoor living is easy with a stone patio and large grassy lawn overlooking the Atlantic Ocean. Come, enjoy and relax!

5 Wauompauque Trail Unit 1 CH213, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$22,000

4 Beds ⋅ 2 Baths ⋅ 72850761 MLS

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four bedroom, 2 bath home has an expansive rear deck that offers panoramic water views. The main level offers an open kitchen and large living room complete with fireplace. An entire wall is floor to ceiling glass with French doors opening onto a large deck. All of the rooms on this floor offer stunning views, including the Master bedroom. The first level features a large family room and three ample sized bedrooms. Black Point Beach Key included with property!!!

36 Henry Hough Lane Ch206, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$36,000

3 Beds ⋅ 4 Baths ⋅ 72850912 MLS

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half bath, a master suite with private bath with jacuzzi tub and a private outside shower. The lower level offers 2 bedrooms, each with it's own bathroom and a living room with wet bar and sliders that open to a patio and rolling lawn. The house also has mini-spilt air conditioning for extra hot days. Just a short distance to a private association beach. Lucy Vincent and Squibnocket Beach access too.

29 Cemetery Rd Ch216, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$24,000

4 Beds ⋅ 4 Baths ⋅ 72851099 MLS

THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

44 Flanders Lane Ch237, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$7,900

3 Beds ⋅ 3 Baths ⋅ 73007684 MLS

2 Paddock Circle Ch210, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$40,000

6 Beds ⋅ 6 Baths ⋅ 72851050 MLS

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four bedrooms, and guest house, with two bedrooms, allow for comfortable space between family and guests. The gently rolling farm land and picturesque pond welcome cows and flocks of Canada geese. This excellent location is very close to Chilmark center and a quick drive, walk or hike to Lucy Vincent beach and Menemsha.

384 Middle Rd Ch222, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$50,700

4 Beds ⋅ 3 Baths ⋅ 72852603 MLS

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,675. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set atop a hill you will find this wonderful 4 bedroom home with distant views and a wonderful lap pool. Enjoy your days on the large deck or take a swim in the pool. This great vacation home is tastefully decorated and is located on one level with plenty of space for gatherings. The living room has a fireplace with built in seating areas overlooking the yard. Each room is decorated so nicely. You will find that this is the house you will come back to year after year. By renting this home you will have access to the private town beaches that are some of the best on the island.

6 Trails End Ch241, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$10,800

4 Beds ⋅ 2 Baths ⋅ 72843696 MLS

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a fully equipped kitchen, and a storybook bedroom complete with wonderful linens. This home is one of the most perfect spots to spend your vacation on the Vineyard. Also, renters have access to the private beaches of Lucy Vincent and Squibnocket. Great out door shower and wonderful patio complete the amenities. No pets allowed.

141 North Rd. Ch202, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$13,200

2 Beds ⋅ 2 Baths ⋅ 72854072 MLS

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room. On each side of the main living area are two one bedroom en suite areas that offers privacy between the two bedrooms. Each bedroom has a queen bed and a twin bed affording the possibility of sleeping six people. This home is set on a hill that provides privacy and tranquility PLEASE WASH AND DRY BEACH TOWELS PRIOR TO DEPARTURE.No pets allowed.

224 North Rd Ch248, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$4,500

2 Beds ⋅ 2 Baths ⋅ 73007753 MLS

THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

33 Menemsha Inn Rd Ch223 3, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$14,000

3 Beds ⋅ 2 Baths ⋅ 71300155 MLS

THIS IS A SUMMER RENTAL ONLY. This bright and cheerful, wooded retreat is truly tranquil, yet just a little over a mile from West Tisbury village, with its General Store (Alley's), Farmer's Market, Artisan's Festivals and Flea Market. This home has been recently updated by its new owners. They have chosen the loveliest colors and simple, appropriate cottage touches. There is a new expansive deck and large screened porch perfect for lounging and dining.

73 Quenames Rd, Ch205, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$24,000

4 Beds ⋅ 4 Baths ⋅ 72850821 MLS

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Relax and enjoy this majestic estate you will call home during your stay. This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and master bedroom. Only rents two weeks all summer.

56 Chilmark Rd Ch208, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$20,000

5 Beds ⋅ 3 Baths ⋅ 72712700 MLS

WEEKLY RENTAL $20,000/WEEK. Fully updated in 1998 1773 Allen Farm Farmhouse perched above Lucy Vincent Beach in Chilmark is one of the greatest properties Martha's Vineyard & New England. If you know about Allen Farm, then you already know how special and rare this property is. This home sleeps 10, has 5 bedrooms, 3 bathrooms, a jacuzzi, open concept chef's kitchen & dining room w two living rooms, screened in porch, outdoor shower, & master bed on main floor, 3 bedrooms on the 2nd floor & big bedroom w 3 beds on the 3rd floor. The property is surrounded by stone walls, & offers direct access to Lucy Vincent Beach, Chilmark Pond & pasture in the front yard, & farmland/pasture in your backyard w fresh organic veggie garden at your disposal, you simply will not find a better vacation home. Comes w Kayaks/Canoes. Linens Provided.

421 S Road, Chilmark

Listing courtesy of Listing Agent: Jesse Greenstein from Listing Office: Douglas Elliman Real Estate - Park Plaza.

$16,800

3 Beds ⋅ 2 Baths ⋅ 72850978 MLS

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and enjoy the view. Short drive to Alleys General Store, Lucy Vincent Beach and the Chilmark Store. You have access to Lucy Vincent beach. This house accepts pets with an additional deposit of $300.

31 South Ridge Rd Ch218, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$22,000

3 Beds ⋅ 3 Baths ⋅ 72850887 MLS

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable drip coffee maker with glass carafe. There is a coffee grinder provided in the house, too.The other two bedrooms are located on the second floor and share a full bath. There are french doors off the living room to a patio. The finishing touch a lovely deck complete with seating and grill for your cooking needs.

2 Strikers Way Ch211, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$12,500

3 Beds ⋅ 2 Baths ⋅ 71299593 MLS

THIS IS A SUMMER RENTAL ONLY. This newly remodeled 3 bedroom 2 bath has a spacious master bedroom suite, cozy sun room and updated kitchen. It has a great yard with garden landscaping, a perfect spot for outdoor dining. 1.5 miles from Alley's store. 3.3 miles to Lucy Vincent Beach.The bathrooms are fully remodeled. An easy, comfortable house in a central location. Three ceiling fans and 3 portable fans.

138 South Rd, Ch228, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$34,000

4 Beds ⋅ 3 Baths ⋅ 72850133 MLS

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Modern 4 bedroom home completed in 2019, in Menemsha. Located on a quiet road with waterviews from the upstairs bedrooms also offers views of the famous Menemsha sunsets from the deck. Sustainably harvested flooring features silky smooth and buttery hard wood floors from reclaimed red birch. A contemporary kitchen and clean lines throughout lead to the separate open concept dining/living room layout with sliding doors to the masterfully crafted deck. First floor main Queen bedroom and private bath with gorgeous walk in shower. Three additional bedrooms upstairs share a full bath. Powder room on the first floor and private outside shower. An extra fridge in the basement can hold anything you need for your guests.

15 Loon Lane Ch203, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$110,000

5 Beds ⋅ 5 Baths ⋅ 72852574 MLS

THIS IS A WEEKLY SUMMER RENTAL ONLY. See web site for pricing!! Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches and high speed internet wifi.

17 Round Pond Rd Ch240, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$42,000

5 Beds ⋅ 3 Baths ⋅ 72851010 MLS

THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all with views, two livingrooms, a deck with views south and to the west. Well maintained and cared for.

19 Lake Rd Ch220, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

$8,000

4 Beds ⋅ 5 Baths ⋅ 73007140 MLS

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and master bedroom. Two week minimum. Owner requires interim cleaning between weeks.

56 Chilmark Rd Ch208, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

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