Peyton Wallace

Perched on an elevated 10.69-acre site off picturesque North Road in Chilmark, this exceptional private compound pairs natural beauty with architectural distinction. Designed by renowned architect Patrick Ahearn and built by Rosbeck Builders, the 7,691-square-foot residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, with spectacular sunsets.

An Inspirational Oasis -- Nestled along the gentle slopes of Indian Hill, this secluded three-dwelling compound offers more than three acres of exceptional privacy where rural tranquility meets effortless island living. Centered around a heated saltwater pool, the main house, studio barn, and guest house provide 4,464 square feet of living space surrounded by wildflower meadows, perennial

Breathtaking property at the tip of a prominent peninsula on Sengekontacket Pond's western shoreline. Set beautifully at high elevation above the shore, this charming home and guest cottage includes jaw-dropping views of the pond, barrier dunes and Nantucket Sound. Direct from the property take your whaler or other watercraft out into the sound and beyond for endless recreational pursuits. Aside

This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience --

Set privately in one of Vineyard Haven's most tranquil enclaves, 30 Water Gate Road is a rare legacy offering defined by pastoral beauty and access to Lake Tashmoo. The nearly 5,000-square-foot residence offers five bedrooms and generous living spaces designed for gathering and quiet retreat, with an effortless indoor-outdoor flow. Bedrooms are thoughtfully arranged in separate wings, with a

NEW CONSTRUCTION: Experience modern Katama luxury in this thoughtfully designed home by Morgan Studio, a husband-and-wife-led boutique design firm. Created for effortless indoor-outdoor living, the residence features soaring ceilings, a flowing floor plan, oversized windows, and exceptional materials and finishes throughout. A private interior courtyard, envisioned as an edible garden, anchors

Located on the edge of downtown Vineyard Haven, just steps from the ferry, harbor, shops, restaurants, and beaches, this two-family property presents a rare opportunity. With full-floor residences offering a combined five bedrooms, the home provides exceptional flexibility for owner occupancy with rental income, investment, employee housing, or multigenerational living. Ready for thoughtful