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.

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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

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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.

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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.

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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.

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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.

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Nestled on a serene 3.32-acre parcel between North Road and Tabor House in Chilmark, this property blends privacy, charm, and great potential. A sweet 2 bedroom guest house—beautifully maintained and offering excellent rental income—sits amid rolling stone walls and mature trees, creating a peaceful woodland setting. Recent updates include a new roof, siding, and HVAC system, ensuring comfort and ease for seasonal and year-round living. The land offers room to grow, with exciting expansion possibilities subject to town approvals. Whether you envision a quiet island retreat, an investment opportunity, or a future compound, this Chilmark gem offers endless possibilities and timeless Vineyard appeal. **abutting 4.28 acre parcel is also for sale, please inquire***

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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.

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On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural woodland setting. With strong rental income, currently generating $2,500 month to month year-round, and expansion opportunities subject to town approvals, the property is conveniently located near South Road, West Tisbury’s village center, and Chilmark’s iconic Lucy Vincent and Squibnocket Beaches. Passed Title V in December 2025 for 3 Bedrooms. #47 is shown as Lot 1-C on a new subdivision not yet reflected on the assessments and public records - approved survey is attached. 45 Quenames Lot 1-B is also available.

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Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with utility sink. Well system updated in 2011. With strong rental income, currently generating $2,500 month to month year-round, and expansion potential, this outstanding value is located close to South Road, West Tisbury's village center, and Chilmark's iconic town beaches Squibnocket and Lucy Vincent. Town records indicate a 4 bedroom septic, passed Title V Inspection in December 2025. #45 is shown as Lot 1-B on a new subdivision not yet reflected on the assessments and public records - approved survey is attached. 47 Quenames Lot 1-C is also available.

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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.

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Nestled on a beautiful lot in the heart of Chilmark, this charming cottage is framed by mature blueberry bushes just off the deck — a true slice of island life. Perfectly positioned to enjoy the quiet calm of up-island living while remaining close to town, beaches, and all that the Vineyard has to offer. Step inside through sliding glass doors into a cozy living area, where an arched entryway leads to the kitchen. Double sliding doors and circular windows provide the space with natural light, creating an open, airy atmosphere throughout. The layout features two guest bedrooms — one off the living area and one off the kitchen — sharing a full bathroom with a shower/tub combo. The primary bedroom, situated just beyond the kitchen, enjoys its own full bathroom and a private exterior door to the deck. A laundry/utility room next to the primary bedrooms provides access to an outdoor shower— a beloved Martha's Vineyard staple. Near the laundry room is a staircase leading to a bonus room upstairs. A large two room shed with a loft to store your beach/fishing gear or to use as a workshop rounds out the property. Whether you're searching for a summer retreat or a forever home, this is a rare opportunity to plant roots in Chilmark. Property offered "AS IS".

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