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$2,800,000
4 Beds ⋅ 4 Baths ⋅ 73533644 MLS
Tucked away on 4.4 spectacular acres just off North Road, this one-of-a-kind Chilmark retreat blends timeless Vineyard charm with exceptional privacy. A shaded driveway leads to classic stone walls and cedar gates opening into a beautifully landscaped courtyard. The inviting porch overlooks lush gardens, creating a peaceful outdoor sanctuary. Inside, warm, light-filled living spaces and the primary suite enjoy sweeping meadow views framed by granite boulders and stately oaks. The main level offers additional sleeping accommodations, while a spacious finished lower level with a private entrance provides ideal guest quarters. Across the courtyard, an unfinished outbuilding with a screened porch offers exciting potential as a bunkhouse, studio, or office. Two garage bays accommodate cars or boats. Ideally located less than 2 miles from Menemsha Village and Beach, 1 mile from Great Rock Bight, and just 3 miles from Lucy Vincent Beach.

300 North Rd/18 Belhaven Way, Chilmark

Listing courtesy of Listing Agent: Bonnie Pierce from Listing Office: Wallace & Co. Sotheby's International Realty.
$3,710,000
3 Beds ⋅ 6 Baths ⋅ 73418123 MLS
CHILMARK BLISS – Refined Retreat | 15 Old Farm Road. Set on 3+ acres of manicured grounds, this 2020 Peter Breese–redesigned home blends elegance and tranquility. A serene pond, stream, and custom hardscape set the tone. Inside, a dramatic open kitchen/living area boasts high-end appliances, stone countertops, and a striking fireplace, with a pantry leading to a screened porch. The main-level primary suite opens to a private deck; also on this floor are a library and media room. Upstairs offers a guest room and bath plus a separate suite with fireplace, lounge, and patio. The lower level features storage, a bonus room, and a walk-out to gardens, fenced flower beds, and a post-and-beam artist studio. Designed for a future pool with a 5-bedroom septic. Includes access to Lucy Vincent & Squibnocket beaches.

15 Old Farm Rd, Chilmark

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Donnelly + Co..
$2,225,000
4 Beds ⋅ 3 Baths ⋅ 73379215 MLS
Beautifully sited on 3.4 acres, this distinctive Chilmark home offers a rare blend of privacy, comfort, and expansive living space, ideal for entertaining, both inside and outside. From the welcoming foyer, step into the dramatic vaulted living room, where wood-paneled ceilings, a gas fireplace, and abundant natural light from skylights and picture windows create a warm and inviting atmosphere. Adjacent to the living area, the dining room and well-appointed kitchen flow effortlessly into a fabulous screened porch. The primary suite is on the main level, featuring a large walk-in closet, a full bath, and a striking double-sided stone gas fireplace connecting the bedroom to an adjoining sitting area with a shiplap ceiling. With direct access to a wrap-around deck, this space is truly the crown jewel of the home. Upstairs, you’ll find a large bedroom with a private deck, two additional bedrooms, and a shared full bath. A quintessential Chilmark property!

9 Beetlebung Grove Way, Chilmark

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
$37,000,000
8 Beds ⋅ 6 Baths ⋅ 73371283 MLS
One of the most exclusive estates in the Northeast, Blue Heron Farm on Martha's Vineyard is set on nearly 30 acres of lush landscaping along the shores of Tisbury Great Pond. The former summer residence of President Obama and family, chosen for its privacy, serenity and significance, this multi-generational compound is protected by surrounding farmland and mature trees. Approached by a long gated drive and a 150-year-old barn relocated from Pennsylvania, the beautiful Main House with bespoke interiors and a wraparound porch overlooks rolling lawns and a quintessential boat house with dock and private beach. A separate guest house, design studio, gym, tennis court, garages, additional guest accommodations and staff housing are thoughtfully sited around the property. Multiple riding rings and paddocks for equestrians and gentleman farmers, while the stunning Norman Foster-designed pool house is a true work of art, ideal for personal relaxation or sophisticated entertaining.

41 Cobbs Hill Road, Chilmark

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.
$9,725,000
6 Beds ⋅ 6 Baths ⋅ 73225612 MLS
CHILMARK SOUTH SHORE WATER VIEW. This Squibnocket gem is a Hutker Arhictect-designed family compound, main house,& guest house on 4.5 acres. Live the ultimate up-Island life with captivating water views in every direction. The home is pristine and private, with many unique features. The chef's kitchen and dining area are serene, bright, and functional. Step up to what might be the best panorama in all of Chilmark, featuring views of the South Shore beach, Quitsa, Menemsha Pond, and Vineyard Sound. A stately wood-burning stone fireplace centers the one-of-a-kind living room that overlooks the oversized lap pool, expansive stone patio area, and dining space for outdoor enjoyment. The stunning main house has 4 bedrooms and 3 ½ baths. The primary bedroom is on the main level and has its own fireplace, ensuite bathroom, walk-in closet, and direct access to the outdoor shower. Take a quick walk down the hill to stunning Squibnocket Beach for a dip in the surf.

2 Squibnocket Rd, Chilmark

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Compass.
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 73170658 MLS
CHARMING CHILMARK- This sweet, sunny home comes with deeded access to Chilmark Pond and South Shore Beach. Kayak, paddleboard, sail, or motor across the pond to one of Chilmark's most pristine private beaches. The location is also convenient, being centrally located and close to West Tisbury Center, Grey Barn, the Yoga Barn, Chilmark Center, Beetlebung Farm, Chilmark Store, and Chilmark Tavern. This three-bedroom post and beam has an efficient Viessmann heating system and a mini-split for AC. The three-acre lot has been thoughtfully landscaped, providing a serene and picturesque setting.Additionally, per Chilmark zoning regulations, there is potential for expansion, allowing for a total of 3,500 square feet and up to six bedrooms with the necessary permits and an upgraded septic system. If a pool is on the wishlist, there is also room for that with a special permit. This property has a lot of opportunities to create your vision, enjoying all Chilmark has to offer.

5 Meeting House Rd, Chilmark

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Compass.

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