Chilmark Classified Ad Listings

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...

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...

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...

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...

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,...

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...

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.

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...

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...

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...

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...

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...

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 ...

384 Middle Ch Rd # 222. 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 ...

35 S Bowl Rd. Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by acclaimed architects Jane and Christian Langmuir, this exceptional home is nestled on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace warmth, natural light, and its surrounding environment, the three-bedroom residence seamlessly blends natural elements with contemporary archit...

141 North Rd # CH202. 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 beaut...

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...

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...