Chilmark Classified Ad Listings

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...

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...

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...

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...

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 ...

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...

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...

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...

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...

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...

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...

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...

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 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...

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...

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 ...

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...

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 ...

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...

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, ...