Chilmark Classified Ad Listings

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...

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

131 State Rd. Magical waterfront Quitsa pond cottage with private dock will change your life living on the water. Every day is special when you have an intimate relationship with Quitsa Pond. Calm, safe and breathtaking, adventure is out the doorstep and the sunsets.... Designed with the setting in mind this sublime piece of architecture has wonderful spaces, fantastic detail and so much packed...

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...

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...

95 Rockville Ave. Cape style 3 bedroom 2 bath home. First floor living room has a fireplace and a grand Palladian-style window. Dining area has access to the delightful screened porch as well as to the kitchen. The kitchen has newer stainless steel appliances and a convenient center island. First floor bedroom with plenty of natural light and closets, and a full bathroom with shower finish the ...

29 And 33 Lagoon Pond Rd. Rare downtown Vineyard Haven compound offering! A unique opportunity to own two separate properties offered together just moments from the ferry, harbor, restaurants, and shops. 33 Lagoon Pond Road is a newly built 3BR/3BA home featuring an open floor plan, designer kitchen with quartz countertops, custom tile baths, water views, private backyard, spacious deck, attach...

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...

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...

16 Frog Holw. Downtown Vineyard Haven with Harbor Views. Positioned between the energy of Main Street and the quiet prestige of West Chop, this location delivers a rare balance of downtown access, privacy, and harbor frontage. Built in 2015, the three-bedroom, two-bath modern ranch is designed for easy first-floor living with expansive water views. Wide, harbor-facing windows showcase the meado...

33 Alyssa Ln. Country Living so close to Town! Lovely 4 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space. Open kitchen, dining and entertainment area. Sliders open to Large side deck. High Ceilings Wood floors Living Room with additional nook. Half bath. Interior stairs to lower level with office/bedroom, half bath, private exterior entrance and garage. 2nd floor has l...

Old Country Ln. Discover peace and privacy without sacrificing location. Nestled under a serene natural tree canopy, this central wooded parcel provides a quiet setting just minutes from local shops, dining, and beautiful beaches. Ready for your custom vision.

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...

27 Double Ox Rd. Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor...

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...

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 ...