Chilmark Classified Ad Listings

41 And 0 Cook Rd. Included in the asking price are two separate parcels: a beautifully updated 3-bedroom home and an adjacent 16,000 square foot buildable lot. No subdivision is required. The lot is ready for your plans or may be sold separately after closing, offering exceptional flexibility for a family compound, second home, or future investment. An easement is being established along the ex...

87 Central Ave. Bring your vision to this rare East Falmouth opportunity with space, privacy, and potential! Set on just under an acre, this well-maintained four-bedroom Cape offers an exceptional amount of land. Conveniently located near some of Falmouth's beautiful beaches, including Menauhant Beach and Falmouth Heights, as well as the area's shops, restaurants, and other amenities. Whether y...

19 Moniz Way. Cozy Winter Getaway in Falmouth Escape to Cape Cod this winter and enjoy a spacious 4-bedroom, 2-bathroom home designed for families and friends looking for comfort, relaxation, and plenty of space to enjoy time together. The home features a fully stocked kitchen, cozy living and dining areas, and comfortable sleeping arrangements. Dogs are welcome, so your furry family members ca...

15 Childs River Rd Apt 5. Waterfront Condominium with Deeded Boat Slip at White's Landing! Discover the exceptional opportunity to own a wonderful waterfront condominium at White's Landing, directly overlooking the harbor and the East Falmouth Marina. This two-bedroom, one-and-a-half-bath residence offers the perfect combination of comfortable coastal living, beautiful harbor views, and an outs...

100 Gosnolds Way. Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound and the Elizabeth Islands. Short walk to the Brickyard Beach on the North Shore, rights are included with ...

528 Main St. Expanded cottage with in-law suite, garage, and detached studio. On the way to West Chop, it is equidistant to Downtown Vineyard Haven, the flagpole at West Chop, Mink Meadows Golf Club, and Vineyard Haven Yacht Club. This 4 bedroom, 4 bathroom property offers a flexible floor plan, including a private inlaw wing complete with its own entrance, kitchen, living room, full bathroom, ...

30 Norris Path. Just half a mile from Great Pond Beach and minutes to Bristol Beach, this spacious Falmouth home offers exceptional flexibility for year-round living, a Cape Codgetaway, multigenerational use, or potential short-term rental. Multiple bedrooms and distinct living areas allow everyone to gather comfortably while still enjoying privacy,creating an ideal setup for extended family, g...

30 Shore St. Welcome to this beautiful historic 4-bedroom, 3-bath home in the heart of downtown Falmouth, just steps from everything downtown has to offer and ideally situated just moments from Surf Drive Beach and the Shining Sea Bikeway. The home has been completely remodeled and thoughtfully updated, with a new addition completed in 2026 and a brand-new septic system. The custom-built kitche...

101 Brigantine Dr. Still in TIME to ENJOY your SUMMER in YOUR own backyard OASIS in sought after CAPE COD!!! After a good day at the BEACH, it's precious to RELAX around the FIRE pit in those cooling nights! WELCOME to your lovely OVERSIZED ranch with 3 bedrooms and 2 FULL baths. Primary SUITE offers an AMPLE walk-in closet and a full bath. The other 2 bedrooms also have very spacious WALK-IN c...

27 Beach Plum Ln. September Availability weekly rental rate negotiable, cost $600-$975 per night depending on season and month 3 night min stay The "Grapevine" is located on a private road.The house 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 Kitche...

25 Duck Blind Rd. WATERFRONT ESTATE | HEATED POOL/HOT TUB | BOAT SLIP | 1.3 ACRES. An exceptional retreat, this magnificent 6,293 sq ft home offers breathtaking water views; 5 bedrooms, 6 bath, 3 fireplaces, and 3 decks, the home blends elegant interiors with the beauty of its surroundings. Exceptional craftsmanship is evident: cherry hardwood floors, elegant millwork, and expansive windows cre...

119 Seacoast Shores Blvd. Price reduction! This Cape Cod Darling offers deeded ownership and membership rights to The Seacoast Shores Clubhouse, offering a pool, tennis, dining, bar and many more community activities. The home is also located less than 1/2 mile to the sandy Association Beach. Just bring your toothbrush and bathing suit and enjoy summer life in one of the most desirable ocean si...

25 Brickyard Rd. Perched on an elevated 10.69-acre site just off picturesque North Road in Chilmark, this exceptional private compound brings together natural beauty and architectural distinction. Designed by renowned architect Patrick Ahearn, the residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, along with superb sunsets. Spanning 7,691 ...

Elsies Way. This exceptional 11.79-acre parcel in East Falmouth offers a rare opportunity to own a significant piece of land on Cape Cod. It directly abuts the manicured fairways of the Falmouth Country Club, one of the Upper Cape's finest golf courses. Despite its private feel, the property offers convenience with access to major routes and is just minutes from Falmouth and Mashpee beaches, po...

26 Qaushnet Way. OFFER DEADLINE 9/9 5PM Set in a desirable Falmouth location, 26 Quashnet Way offers four bedrooms and a flexible layout designed to accommodate a variety of living arrangements. An attached apartment located off the garage provides separate space for guests, a home office, extended living, or other potential uses. The main home offers comfortable living areas with access to a d...

156 Teaticket Hwy. Unique Cape Cod property. Post and beam/farmhouse style building with proven short term rental history. Newly renovated in 2022. Approximately 4000 square feet in the main rental space. 6000 square feet overall with fully finished basement. Basement has two full bathrooms. Large, light filled one bedroom apartment upstairs together with a lofted 800 square foot office area. G...

11 Hammett Ln. BOOKING SUMMER 2027 AND FALL/SPRING '26 SPRING '27 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 wi...

6 Trails End # CH241. 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 wit...

511 Palmer Ave. Multi-Family Home for sale in Falmouth, MA for $849,000 with 4 bedrooms and 2 full baths, 1 half bath. This 2,373 square foot home was built in 1934 on a lot size of 0.99.. Welcome to this highly desirable, move-in-ready property offering the perfect blend of charm, space, and versatility! Featuring a spacious 3-bedroom, 1.5-bath main house and a separate 1-bedroom, 1-bath cotta...

2 Strikers Ch Way # 211. 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 gr...