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4 Beds
5 Baths
4,293 sqft

$4,995,000

39 Chippechaug Trail, Stonington CT, 06378

Price per sqft$1,163.52
Built in1968
Property size4,293 sqft
Property typeResidential

Overview

Active

Listed May 7, 2026

Updated Aug 23

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.

$33,232/mo

Est. mortgage payment based on a $4,995,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
124927

Interior Features

Bedrooms
4
Bathrooms
5
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
2.05 Acres

Other Property Details

Taxes
$35,769
Tax Frequency
Annually
Garage
Yes
Waterfront
Yes
MLS provider logo

Listed by Danielle Malloy with Serhant Connecticut LLC
Listing Contact:  

The IDX display contains information sourced from the Greenwich Association of REALTORS® as of 8/23/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

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Data last updated on 8/23/2026 at 4:52 AM UTC

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