Chilmark Classified Ad Listings

60 Bartimus Luce Rd. This North Shore beachfront estate represents one of the most breathtaking properties in all of New England. The newly built home was created on a 3.3-acre parcel of land, surrounded by specimen trees, rolling grassy meadows and is highly situated on a stable bank overlooking nearly 250 ft of sandy beach. The home, which celebrates and was imagined utilizing the 14 patterns...

13 West Ave. Embrace the ultimate Cape Cod lifestyle in this classic 1925 coastal home, offering spectacular water views and unbeatable rental or multi-generational family potential. Known affectionately as "Grandma's House," this charming 4BR/1.5BA property captures the essence of desirable New Silver Beach. The layout features a covered front porch and a spacious enclosed sunroom designed for...

41 Hagerty Drive. Single Family Home for sale in Tisbury, MA for $5,750,000 with 6 bedrooms and 6 full baths, 1 half bath. This 5,424 square foot home was built in 2026 on a lot size of 0.96.. Welcome to your Vineyard dream home in the highly sought-after West Chop neighborhood. This exceptional brand-new construction offers 6 bedrooms, 6 full baths, and 1 half bath, thoughtfully designed with ...

34 Edys Island Way. Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by an Island legacy family, this property is unique among Island estates for its combination of privacy yet convenience, seclusion yet expansive views. ...

38 Black Point Road. Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach. Magical expansive views of meadows, pond and ocean. This estate-sized property abuts 140 acres of Sheriff's Meadow conservation land, offering exceptional privacy. A simple 1041 square foot two bedroom home sits on one lot with two detached studios alongside. Close to nature...

16 Red Coat Hill. Single Family Home for sale in West Tisbury, MA for $6,500,000 with 6 bedrooms and 5 full baths, 2 half baths. This 4,753 square foot home was built in 2026 on a lot size of 4.85.. Private West Tisbury Oasis Modern Luxury on 4.85 Acres Built by the highly regarded Novo Builds and designed by acclaimed architect Zander Auerbach, this newly constructed estate in the heart of Wes...

31 Garrison Rd. West Falmouth, move in ready! This beautifully maintained and renovated 2 bedroom ranch enjoys a fantastic West Falmouth location, tucked back from the road on a small dead end street. The spacious primary suite addition, completed in 2014 features an en-suite bath. Sliders open to a private deck, an ideal spot for morning coffee or an afternoon book. Second bedroom with modern ...

0 Sandwich Lot 28. Land - just under an acre in convenient Sandwich Road location. This is nice opportunity to enjoy all the amenities that Falmouth has to offer. Buyers and agents responsible for due diligence.

5 Wauompauque Ch 213 Trl Unit 1. THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second flo...

Young; Availability Date * 10/21/2026; Location * Oak Bluffs MA, 02557, USA. Dog Breed: Poodle (Standard) / Mixed. This dog is up to date on vaccinations and is spayed or neutered. (Please note: Puppies under 3 months old may not be sterilized prior to adoption. If this is the case, your adoption coordinator will provide guidance on the process.) To adopt or learn more about this dog, you must ...

Adult; Availability Date * 10/21/2026; Location * Oak Bluffs MA, 02557, USA. Dog Breed: Shih Tzu. Meet Gordita! Our little burrito is a sweet 5-year-old Shih Tzu whose world changed suddenly when her devoted owner passed away unexpectedly while at work. Gordita and her housemates came into rescue together, and now she is adjusting to a brand-new life while looking for a family to call her own. ...

Baby; Availability Date * 10/21/2026; Location * Oak Bluffs MA, 02557, USA. Dog Breed: Chihuahua / Pomeranian / Mixed. This dog is up to date on vaccinations and is spayed or neutered. (Please note: Puppies under 3 months old may not be sterilized prior to adoption. If this is the case, your adoption coordinator will provide guidance on the process.) To adopt or learn more about this dog, you m...

Young; Availability Date * 10/21/2026; Location * Oak Bluffs MA, 02557, USA. Dog Breed: American Pit Bull Terrier. Meet Spice! Spice is a sweet, gentle 2-year-old girl who is slowly discovering what it feels like to relax, feel safe, and enjoy simply being part of a home. She can be shy and nervous at first, and her new family will need to give her time to decompress and adjust at her own pace....

Baby; Availability Date * 10/21/2026; Location * Oak Bluffs MA, 02557, USA. Dog Breed: Australian Shepherd. Meet Kiefer! If you're looking for an adventure buddy who will keep you active and shower you with affection, Kiefer is ready to be your perfect sidekick! This handsome 35-pound pup has an energetic spirit, a heart full of love, and is happiest when he's spending time with his favorite pe...

Senior; Availability Date * 10/21/2026; Location * Oak Bluffs MA, 02557, USA. Dog Breed: German Shepherd Dog. At 9 years old, Guinness may technically be a senior, but apparently no one has bothered to tell him. This handsome German Shepherd still has plenty of pep in his step, loves his daily adventures, and is always ready for a game of fetch. Guinness is the perfect example of why senior dog...

Baby; Availability Date * 10/21/2026; Location * Oak Bluffs MA, 02557, USA. Dog Breed: Great Pyrenees. This dog is up to date on vaccinations and is spayed or neutered. (Please note: Puppies under 3 months old may not be sterilized prior to adoption. If this is the case, your adoption coordinator will provide guidance on the process.) To adopt or learn more about this dog, you must complete an ...

Adult; Availability Date * 10/21/2026; Location * Oak Bluffs MA, 02557, USA. Dog Breed: Shih Tzu. Meet Lucia! Lucia is a sweet 7-year-old Shih Tzu whose world changed suddenly when her devoted owner passed away unexpectedly. Lucia and her housemates came into rescue together, and now this gentle girl is starting the next chapter of her life with us. One very special part of Lucia s life is her ...

Young; Availability Date * 10/21/2026; Location * Oak Bluffs MA, 02557, USA. Dog Breed: Schnauzer / Terrier / Mixed. Have you ever met a Tony you didn't like? We haven't. This dog is up to date on vaccinations and is spayed or neutered. (Please note: Puppies under 3 months old may not be sterilized prior to adoption. If this is the case, your adoption coordinator will provide guidance on the pr...

Young; Availability Date * 10/21/2026; Location * Oak Bluffs MA, 02557, USA. Dog Breed: Dachshund / Chihuahua / Mixed. Frieda is a lovable 1-year-old Chihuahua/Dachshund mix with a big personality packed into a small body! This sweet girl is full of energy and loves to spend her days playing, exploring, and soaking up attention from her people. When playtime is over, Frieda loves to curl up on ...

Baby; Availability Date * 10/21/2026; Location * Oak Bluffs MA, 02557, USA. Dog Breed: Pug / Chihuahua / Mixed. Meet Pretzel! Pretzel is a young pup who is bursting with happiness, playful energy, and affection. This cheerful boy has not stopped smiling since arriving in his foster home and is always eager to be part of whatever his people are doing. Pretzel does wonderfully with dogs of all si...