Chilmark Classified Ad Listings

24 Katama Bay View Rd. This classic New England home in Katama offers a refined blend of timeless architecture and modern comfort, set on a spacious, beautifully landscaped lot. The main house features three well-appointed bedrooms, including a light-filled primary suite and inviting guest rooms designed for comfort and privacy. The open-concept living area is ideal for entertaining, highlighte...

25 Lelands Path. YOUR OWN PRIVATE WATERFRONT OASIS: CAPTIVATING ESTATE LIVING. This extraordinary Katama Bay waterfront retreat blends timeless coastal architecture, refined interiors, and the natural beauty of Chappaquiddick in unforgettable fashion. Designed by noted architect Patrick Ahearn, this magnificent residence is privately sited at the end of a winding drive on 16.4 acres, offering m...

10-A Saint Andrews Way Unit 10A. Beautiful end-unit townhouse condo, offering comfort ,privacy and picturesque golf course views.The inviting main level features hardwood floors, a large eat- in kitchen. Stainless steel appliances , refrigerator is 2 years old, microwave is fairly new as well. The generously sized bedrooms with ample closets, both bedrooms newly carpeted. Added bonus walk up at...

331 Falmouth Woods Rd. Here is that most desired - but elusive - property, the "Goldilocks" of a Cape house, i.e., not too big, not too small, just right! And the ultimate in stylish, sophisticated, move-in condition! To be specific, this light and bright home is a beautiful, efficient 2100 sf for everyday living and gracious entertaining. The full height ceilings and wide openings between room...

3 Viber Ln. Live, work, and create in this beautifully remodeled, move-in-ready 3-bedroom, 2-bath Cape Cod home. Offering over 2,400 sq. ft. of living space on a 22,000+ sq. ft. level lot with a rolling lawn, this property combines versatility with exceptional peace of mind.The unique19' x 23' studio/office, with separate entrance, adds exceptional flexibility for a home-based business, profess...

14 Nickerson St. Charming Cape-style home ideally located in the heart of Falmouth, offering three bedrooms and two full bathrooms. The first floor features two bedrooms, a full bathroom, and a welcoming living room with a wood-burning fireplace and beamed cathedral ceiling. The renovated kitchen, completed in 2017, features stainless steel appliances, a farmhouse sink, and granite countertops....

51 Cliff Rd. Welcome to The Cliffs, one of West Falmouth's premier coastal neighborhoods, offering a private sandy association beach on Buzzards Bay. This stunning new construction combines contemporary shingle-style architecture with a fresh, refined coastal design. Offering approximately 3,700 sq. ft., the home features 4 bedrooms, 3.5 baths, hardwood floors, high ceilings, custom built-ins a...

14 Cow Bay Rd. Set within the prestigious Cow Bay Association, one of the island's most exclusive and sought-after enclaves, this extraordinary 1.5-acre estate embodies the pinnacle of refined coastal living. Accessed via private road through protected land, the property includes access to over 2,000 feet of private shoreline, beach cabanas, Trapps Pond and potential mooring. Despite its remark...

87 Acapesket Rd # 3B. Condo for sale in Falmouth, MA for $499,900 with 2 bedrooms and 1 full bath. This 780 square foot condo was built in 2026.. New Construction in East Falmouth MA! A great neighborhood, only minutes to everything you would hope for on Cape Cod...beaches, shopping, dining, downtown Falmouth and boats to the Vineyard. This one level living condominium features 2 bedrooms and 1...

9 Thaxter Ed Ln # 310. THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $14,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Enjoy the pool with this Stunning custom designed and professionally decorated Tri Level contemporary home with open floor plan. Once inside you will be captivated by the dramatic open spaces, soaring ceiling and walls of glass. Located in a high...

14 Donaldbin Close. Tucked into a quiet neighborhood and surrounded by mature trees, this home sits elevated on a 0.84-acre lot. With an open floorplan, the kitchen, dining, and living areas flow comfortably together, enhanced by vaulted ceilings, a stone gas fireplace, and French doors that bring in abundant natural light and provide easy access to the outdoors. A custom-designed open staircas...

274 Seaward Bend UNIT 274. Property for Rent in East Falmouth, MA for $3,000 with 2 bedrooms and 2 full baths, 1 half bath. This 1,344 square foot property was built in 1977.. Year-Round Rental-Furnished or Not You Decide. Two bedroom, 2.5 bath attractive townhouse condominium located in the highly desirable Falmouth Port community, conveniently situated to all that Falmouth has to offer. This ...

76 Mattakesett Ed Way # 313. THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,325. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This upside-down house was built in 2007. Sit out on the upper deck to panoramic ocean views or grill your favorite seafood while taking in the view. Watch the sun set to a new and beautiful aurora each night on either of the decks or while ...

25 Deepwood Dr. Welcome to this charming 3 bedroom, 1 bath ranch nestled in a sought-after neighborhood with room to make it your own. Filled with warmth and potential, this home offers comfortable one-level living with spacious bedrooms, hardwood floors, and a bright kitchen featuring stainless steel appliances. A full basement provides excellent storage, workshop space, or future expansion po...

63 Division Rd. LOT #4 - The last lot available in this 5-lot Edgartown subdivision! Division Road is located between Meshacket and Meetinghouse Way, less than 1 mile from the center of town. This concept was thoughtfully and creatively developed in an effort to create a new and upcoming neighborhood. The new residences will be able to accommodate up to 7 bedrooms, and offer the opportunity to ...

63 Seatucket Rd. Charming Cape Cod retreat with beautiful Green Pond views in the desirable Davisville area of East Falmouth. This inviting year-round home offers a peaceful setting, abundant natural light, and timeless coastal charm. The open living area features vaulted wood-beamed ceilings, a skylight, hardwood floors, and large windows overlooking the water. The bright enclosed porch provid...

10 Woodhaven Dr. Edgartown - Room to Live. Space to Breathe. Tucked into more than an acre of peaceful woodland, 10 Woodhaven Drive is the kind of Vineyard home that invites you to settle in and stay awhile. Generous rooms, multiple gathering spaces and an easy connection to the outdoors create a home that feels equally suited to quiet Island weekends, a house full of summer guests or comfortab...

32 Marthas Rd. Nestled within Edgartown's coveted Katama/Island Grove enclave, 32 Martha's Road is a masterfully crafted 2023 modern farmhouse where elevated design meets the effortless elegance of Vineyard living. Built by renowned island builder Shawn Chapps, this five-bedroom residence is a study in sophistication-rich with architectural intention, bathed in natural light, and thoughtfully c...

44 Prices Way. Contemporary Island Retreat - A smart opportunity for buyers seeking a low-maintenance Vineyard home near Edgartown Village, this contemporary retreat offers convenient access to shopping, services and the bike path connecting the three down-Island towns. Ideal as a year-round residence, seasonal getaway or potential vacation rental, the home features an open living and dining ar...

25 Coffins Field Rd. This 1.0-acre parcel is approved by the West Tisbury Board of Health for the construction of a six-bedroom dwelling. Seller is offering a $40,000 credit at closing to assist with costs associated with the design, permitting, and installation of the septic system.The property is located in a centrally situated neighborhood and abuts conservation land, providing a private set...