39 Chippechaug Trail

Private Island Waterfront Estate

A spectacular waterfront residence on Masons Island, 39 Chippechaug Trail captures the very best of coastal New England living. Set on 2.05 private acres with more than 250 feet of direct waterfront, this custom-built, move-in ready 4,300 square-foot home enjoys sweeping 180-degree water views, a private sandy beach, deep-water access and its own dock all within one of the Mystic/Stonington area’s most coveted waterfront settings.

Beautifully maintained and thoughtfully positioned to embrace its extraordinary surroundings, the residence offers comfortable, inviting interiors designed to be enjoyed from day one. Expansive windows and water-facing spaces create a natural connection between the home, grounds and shoreline, while mature oaks frame the property with exceptional privacy and an established coastal landscape.

Designed for both relaxed everyday living and entertaining, the property transitions effortlessly from the house to expansive lawns, beach and dock. Boating, swimming, kayaking and days on the water begin right outside your door, while the breadth of the property creates a remarkable sense of openness, privacy and connection to the shoreline.

A three-car garage and geothermal heating add comfort and functionality, while the private island setting feels worlds away yet remains just minutes from downtown Mystic’s acclaimed restaurants, boutiques, marinas and waterfront attractions.

There is an ease to life here that is difficult to replicate... a home where mornings begin on the water, afternoons unfold along the shoreline and evenings are framed by the beauty of the surrounding landscape. Equally suited as a year-round residence or an exceptional coastal retreat, 39 Chippechaug Trail is a rare opportunity to experience Mason’s Island living at its finest.

Mason's Island: Mystic, Connecticut

Set at the mouth of the Mystic River where the water opens toward Fishers Island Sound, Masons Island is one of coastal Connecticut’s most quietly coveted enclaves. Originally known as Chippachaug, an Algonquin name often translated as “a separated place,” the island has long carried the feeling of a world slightly apart. Connected to the mainland by causeway, it offers the rare combination of privacy, boating access, natural beauty, and proximity to village life. Once a summer retreat reached by boat from nearby Noank, Masons Island has evolved into a distinguished waterfront community defined by serenity, mature landscape, protected coves, marina access, and an enduring connection to the sea.

Just beyond the island, Mystic offers one of New England’s most compelling coastal settings, a place where maritime history, contemporary dining, independent shops, and year-round cultural life meet with unusual ease. The Mystic River runs through the heart of the village, past historic homes, working docks, sailboats, galleries, cafés, and the iconic bascule bridge. The town’s deep nautical heritage remains central to its identity, anchored by Mystic Seaport Museum, one of the nation’s leading maritime museums, with historic vessels, a recreated coastal village, exhibition galleries, and a working preservation shipyard. Nearby, Mystic Aquarium adds another major cultural and family draw, home to thousands of marine animals and a strong conservation mission.

Mystic has also become one of the most talked-about small coastal destinations in the Northeast, praised for its walkable downtown, waterfront setting, fresh seafood, craft beer, boutique lodging, and increasingly celebrated restaurant scene. Publications have noted its growing culinary reputation, with local chefs, fishermen, farmers, brewers, and makers giving the village a character that feels both polished and deeply authentic. It is the kind of place that works beautifully as a summer escape, yet never feels closed for the season. Autumn brings foliage and quieter weekends, winter brings lights and a softer coastal calm, and spring returns the village to boats, gardens, patios, and the rhythm of the water.

Its location is part of the appeal. Mystic sits approximately 130 miles from New York City and 100 miles from Boston, making it an elegant midpoint between two major metropolitan centers, close enough for a weekend retreat yet removed enough to feel like a true escape. Watch Hill, Rhode Island, with its beaches, harbor, and classic seaside atmosphere, is roughly 20 minutes away by car, adding another layer of coastal lifestyle within easy reach. For those seeking a vacation home, Masons Island offers privacy and waterfront access in one of Mystic’s most distinctive settings. For those seeking a year-round residence, it offers something even rarer: the quiet of an island, the culture of a historic village, and the convenience of a well-connected New England coastal address.