Welcome to 220 North Road, Chilmark, an idyllic, up-island retreat featuring a 4-BR, post-and-beam, main house and 3-BR guest cottage. Set on three private acres, this verdant oasis is surrounded by preserves, walking trails and even an ancient way that leads directly from the property to Middle Line Woods Preserve, and then all the way to Tea Lane Farm. A two-thirds of an acre conservation buffer runs along the length of the back of the property for further privacy. Just across North Road from the ancient way is the walking entrance to Great Rock Bight. If you enjoy the splendid rural nature of upisland Chilmark, then this is your place. MAIN HOUSE: The rich wooden interior radiates warmth and relaxation and is enhanced by the living room's floor-to-cathedral-ceiling natural stone fireplace. A large deck wraps around nearly half the house, giving you treehouse-like views and a magical setting for outdoor entertaining. GUEST COTTAGE: This intimate log-home is a separate getaway, hidden by a clutch of tall trees nearly 100 yards away from the main house which creates highly protected privacy. Flowers and herb gardens surround its sunny deck, creating a peaceful nook for reading and relaxation. A detached bedroom is like a honeymoon retreat that guests will love. A new, 3BR septic system was just installed (July 2026). EACH HOUSE HAS its own septic system and well, making them truly separate and independent. There's room for a swimming pool. Leave the congestion of down-island comfortably behind, while enjoying easy recreation access to public lands and beaches (Lucy Vincent, Squibnocket), sailing on Quitsa & Menemsha ponds, and proximity to Menemsha and the Chilmark Store, community center and famed Chilmark Tavern. ASK ABOUT partial Seller financing. Also, ASK ABOUT about Seller lease-back of the Guest Cottage which could significantly reduce the purchase price.

View Property Details >

Rare Chilmark compound with beach access, barn, horse stalls, and fenced pasture on 1.6 acres. Set just over the West Tisbury line, this restored 1885 farmhouse offers a compelling blend of authentic Vineyard character, modern comfort, and access to Chilmark’s coveted south shore beaches, including Lucy Vincent and Squibnocket. The property unfolds as a small country compound with a distinctly pastoral sensibility. A classic barn, two run-in horse stalls, a fenced field, and a coop support equestrian pursuits or a small gentleman’s farm—an increasingly uncommon offering in Chilmark at this price point. The open acreage invites outdoor living, from summer entertaining and gardening to quiet enjoyment of the surrounding landscape and privacy. Inside, the home balances antique charm with thoughtful updates. Four bedrooms and three full baths include two main-level bedrooms and two second-floor en-suite guest rooms, creating a comfortable and flexible layout for hosting family and friends. Living spaces are warm and inviting, with a masonry double fireplace, preserved period details, and an updated kitchen and baths. Recent improvements include HVAC, windows, insulation, and a five-bedroom septic system, offering flexibility for future expansion and barn renovation. Located steps from West Tisbury village, Alleys General Store, the library, the Yoga Barn, the Grange Hall and nearby conservation trails, the setting combines convenience with the privacy and natural beauty that define Chilmark. A distinctive Vineyard offering with uncommon versatility—equally suited as a summer retreat, year-round residence, or small-scale farmstead.

View Property Details >

This Chilmark 3 bedroom, 2 bath home has been meticulously maintained inside and out. A major addition and reconstruction of the original house was completed in 1991 and included a 22 x 43 addition. The completely new second floor added over 1,500 square feet and the work included entirely new heating, plumbing, electrical, central AC, septic and well! Many nice features include spacious living spaces, a modern kitchen with breakfast bar, open living and dining room with cathedral ceiling, oversized windows and a slider that leads out to a spacious deck. There is a second floor primary with ensuite bath, walk-in closet and private deck. Large family room with skylights and built-ins. There are two first floor bedrooms that share a bath, full basement, wood floors, a whole house generator and Oil FHW heat and new A/C. Privately sited 1.20 acres bordered by stone walls, beautifully landscaped grounds, mature gardens and plantings. There are also beautiful fruit trees; peach, pear and apple! The property is gated and entirely enclosed with deer fencing. There is also a storage shed and a detached garage. Easy access to Menemsha, Chilmark Store and Chilmark Beaches. Outdoor surveillance system on premises, audio and video.

View Property Details >

Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to discover a custom circular staircase with dramatic floor to ceiling windows, leading to the upper living area flooded with natural light from the wall of south-facing windows. The living area with high ceilings and woodstove is a comfortable place to congregate, while the kitchen and open dining areas lend themselves to modern day living. Glass sliding doors open onto a spacious 2nd story deck giving the entire living space an intimate relationship with the outdoors. On the first floor there are three total bedrooms; two bedrooms sharing a full bath plus a primary bedroom with a full bath en-suite. Total square footage represents house (1,400 sq. ft.) and guest house (518 sq. ft.). A shared six (6) bedroom septic system services both houses.

View Property Details >

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 some art and a few other items and has everything you need to enjoy your summers in Chilmark as you plan for your future. The property has a 4-bedroom septic system. Broker has ownership interest. TENANTS IN PLACE; 48 HOURS ADVANCE NOTICE FOR SHOWINGS PLEASE

View Property Details >

Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and projects. Wood working area in the basement is a plus. Enjoy the outdoors via the screened porch, large deck and the rolling lawn. Come see this property to truly appreciate it.

View Property Details >

Tucked away on a quiet country road in a serene Chilmark setting, this beautifully crafted home, built in 2023, offers modern comfort surrounded by natural beauty. The thoughtfully designed main level features an open, light-filled floor plan where the living, dining, kitchen, and family areas flow seamlessly together. A wall of glass doors opens to the outdoors, creating an effortless indoor-outdoor lifestyle. Additional first-floor amenities include a full bathroom, laundry area, mudroom, screened porch off the kitchen, and an attached one-car garage. Upstairs, the spacious primary suite is complemented by two additional bedrooms, a full bathroom, a comfortable sitting room or flex space, and a second laundry and storage room for added convenience. The grounds are equally enchanting, featuring expansive lawn areas, a picturesque pond, and mature trees that provide privacy and character, some beautifully draped in flowering wisteria. Offering the perfect blend of contemporary living and timeless Vineyard charm, this classic Chilmark property is ideally suited for year-round enjoyment or a peaceful summer retreat.

PC

View Property Details >

A rare opportunity to build a private retreat awaits at this 15 acre land parcel centrally located in Chilmark. Once part of the High Mark estate, the property features groves of mature trees planted more than 100 years ago, creating a wondrous, secluded and private setting rarely found anywhere on the island today. The parcel directly abuts the nearly 80 acres of conservation land at the Martha’s Vineyard Land Bank Peaked Hill Reservation. This unique adjacency significantly enhances the sense of scale while ensuring that the surrounding landscape remains protected and preserved. Buyer is responsible for due diligence including engineering, utilities and permitting. Some wetlands are present. This is a rare chance to secure substantial acreage in Chilmark with historic character, enduring privacy, and direct connection to preserved conservation land — an ideal setting for a legacy Vineyard property.

View Property Details >

Set on a private 3.5-acre wooded parcel surrounded by conservation land, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees and protected open space, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring comfortable living spaces ideal for year-round living or seasonal enjoyment. With 3 bedrooms and 2 full baths, the layout offers flexibility for family, guests, or a home office. Custom soapstone countertops add to this home's beauty. Expansive outdoor space invites relaxation, exploration, and the potential for future enhancements, all within a serene woodland environment. An increasingly rare opportunity to own a conservation-abutting property on Martha’s Vineyard—perfect as a primary residence, vacation home, or long-term investment in one of the island’s most desirable natural settings.

View Property Details >

Nestled in Chilmark, this four-bedroom home blends classic Vineyard charm with modern comfort. The sunlit eat-in kitchen features dual ovens, granite countertops, and custom cherry built-ins, flowing seamlessly to a living room with a Vermont Castings wood stove and access to a covered porch and spacious deck. The first-floor primary suite offers two en-suite baths and two walk-in closets, while two second floor bedrooms boast wood floors, built-ins, and a shared hall bath. A bonus room above the garage provides additional space for a home office, workout space, or studio. The private backyard, outdoor shower, garage, basement, and generator complete this exceptional property. A separate studio with an open floor plan, bath, and loft, separate from the main house, adds further versatility. Close to Lucy Vincent Beach, the center of Chilmark, and all West Tisbury has to offer, this property is ideal as a year-round home, seasonal retreat, or investment.

PC

View Property Details >

Escape to your own getaway with mature landscaped gardens and privacy in the heart of Chilmark. Walk to the Chilmark Store, library, Chilmark Community Center, Beetlebung Farm and bank. Access to Chilmark beaches - Lucy Vincent and Squibnocket - and Menemsha Public Beach are a plus. This four bedroom, two bath home has hardwood floors throughout. The living room and eat-in kitchen separate the bedrooms from one another providing privacy for all. There is a very large two bay garage with plenty of storage space and work area. This home has character and should be seen to be appreciated. Property is being SOLD AS IS.

View Property Details >

This versatile Chilmark property offers a rare combination of privacy, flexibility, and investment potential. The main residence features 4 bedrooms and 4 bathrooms, complemented by a detached 1-bedroom, 1-bath suite with an attached garage—ideal for guests, extended family, or rental income. Two separate parking areas provide ample space and convenience. Abutting over 200 acres of protected conservation land of Menemsha Hills, the property enjoys a natural buffer along with direct access to scenic walking trails and some of Chilmark’s most iconic views. Ideally located just a short distance from Menemsha and Chilmark Center, it offers both seclusion and accessibility. Homeowners will also have access to Lucy Vinecent and Squibnocket beaches as Chilmark property owners. With an established rental history and full winterization for year-round use, this home is well-suited for both personal enjoyment and income generation. For those seeking a foothold in one of Martha’s Vineyard’s most desirable towns, this is a compelling opportunity not to be missed.

View Property Details >