Chilmark Classified Ad Listings

82 Edgewater Dr E. Waterfront on the Chid's River.. 2 Bedrooms. 1 Bathroom. 780 ft

9 Chickawaukee St. Offered fully furnished, this beautifully updated four-bedroom, two-bath home is a rare turnkey opportunity in Oak Bluffs. Thoughtfully updated and meticulously maintained, it is equally well suited as a year-round residence, vacation retreat, or investment property. Located just 0.8 miles from downtown Oak Bluffs, the home offers convenient access to beaches, restaurants, sh...

95 Hines Point Rd. JUST APPROVED FOR A 4 BDR SEPTIC SYSTEM. A rare opportunity, this Hines Point waterfront compound offers expansive views of the Lagoon and 100 feet of private beach. The home was built and has been enjoyed by the same family for gathering and summer recreation over generations. The main house offers an open first floor layout with high ceilings and large windows facing the wa...

12 Avalon Dr. Turnkey with Established Rental History! This inviting home is an excellent opportunity for a year-round residence, vacation retreat, or investment property. Successfully operated as a vacation rental for several years, the property offers a proven rental history and the convenience of a move-in-ready setup. The open-concept living and kitchen area creates a welcoming gathering sp...

224 North Rd # CH248. 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 th...

44 Brick Kiln Rd. There's something special about a home that feels connected to every season, and this charming 1949 Cape does just that. In summer, the wraparound mahogany deck becomes an extension of the living space, framed by beautiful perennial gardens; come fall, the half-acre setting transforms with the season; and when winter arrives, the wood stove creates a warm and inviting place to...

80 Gansett Rd. Privately set on 1.95 beautifully landscaped acres in the coveted Gansett neighborhood of Woods Hole, this distinguished 1930 Colonial estate captures the essence of refined Cape Cod living. Days unfold between the heated saltwater pool, expansive lawns, private association beach overlooking Quissett Harbor, and deeded access to Little Gansett Beach, while the restaurants, cafes,...

261 Quissett Ave. Proudly offered a rare opportunity for a legacy home to become uniquely your own. Originally built as part of the wave of "summer cottages" in 1890 in the Quissett area of Woods Hole, this shingle style Gambrel home sits high on a hill with a generous 2.62-acre private lot. Across the street, a deeded right of way leads you to your private stone dock on Quissett harbor. A year...

36 Baptiste Ln. This brand new 3-bed, 2.5-bath ranch-style home with a 2-car garage, sits on a level acre lot, overlooking nearly 7 acres of peaceful conservation land. Step inside to an open layout with high ceilings and custom moldings. Hardwood floor throughout the main living area and designer tile in the bathrooms. Luxury Thermador appliances in the kitchen and a living room with built-ins...

66 Woodland Trl Unit 66. If you love one floor living with soaring ceilings, great amenities and a Cape Cod lifestyle this home is for you! The sunlit country kitchen has a gas fireplace, wood floors, granite counters, loads of storage, and a slider to the spacious deck. The space is amazing! The unit is perched a short distance to the heated pool, 2 dinghy docks, clubhouse, tennis and pickleba...

22 Old Lighthouse Rd. This spacious 5-bedroom, 3-bathroom home is located in a quiet enclave off Main Street, Vineyard Haven. Just half a mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the hom...

9 Winchester Dr. Enjoy effortless single-level living in this beautifully updated home nestled within a desirable waterfront community offering an association beach and rights-of-way to the water. Thoughtfully refreshed throughout, this inviting three-bedroom residence offers the perfect blend of comfort, style, and relaxed Cape Cod living. The bright, open living area flows seamlessly into a w...

511 E Palmer Avenue. 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 ...

19 Perkins Ave. Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter - whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries, restaurants, and shops while creating your own vision in this classic Island sett...

6 Sailaway Ln. Discover the epitome of Coastal Charm in this exquisite New Construction farmhouse-style home. Nestled in the new subdivision of Sea Salt Estates, this stunning 4bedroom, 4.5 bathroom home with 2 car garage offers the perfect blend of modern comfort and classic Cape Cod elegance. Featuring spacious open-concept living bathed in natural light, ideal for entertaining family and fri...

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...

18 Allen Farm Rd. Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1+ bedroom cottage with screened porch. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, especially for solar designs. The cottage is offered full furnished with exception of...

7 Ploughshare Ln. Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dini...

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...