About this home

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.

Facts and features

Schools

• Stonington Middle School

  middle · 6-8 · 2.3 mi

  7

• Stonington High School

  high · 9-12 · 6.0 mi

  7

• Deans Mill School

  elementary · K-5 · 3.1 mi

  9

• Pine Point School

  elementary · K-9 · 4.4 mi

• Ella T. Grasso Southeastern Technical High School

  high · 9-12 · 2.9 mi

  5

• Lighthouse Voc-Ed Center Groton

  elementary · 4.7 mi

Price history

• Oct 22, 2026 · Price Changed$3,995,000
• Aug 20, 2026 · Listing Removed—
• Jul 7, 2026 · Price Changed$4,995,000
• Jul 7, 2026 · Price Changed$4,995,000
• Jun 4, 2026 · Listed$5,995,000
• May 7, 2026 · Listed$5,995,000

Tax history

• 2026$37,460 tax · $1,657,500 assessed
• 2023$31,575 tax · $1,657,500 assessed
• 2022$27,955 tax · $1,072,700 assessed
• 2021$27,799 tax · $1,072,700 assessed
• 2020$26,989 tax · $1,072,700 assessed
• 2018$26,077 tax · $1,072,700 assessed
• 2017$27,775 tax · $1,128,600 assessed
• 2016$27,019 tax · $1,128,600 assessed

Home value

$4,797,060

• Quantarium$4,797,060
• Cotality$4,848,900
• Collateral Analytics$4,709,000

Where it is