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...

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 ...

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...

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...

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.

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...

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...

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 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...

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 ...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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 ...