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4 Beds
5 Baths
4,293 sqft

$4,995,000

39 Chippechaug Trail, Stonington CT, 06355

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

Overview

Active

Listed May 7, 2026

Updated Aug 25

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.

$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
24172306

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
$37,460
Tax Frequency
Annually
Garage
Yes
Waterfront
Yes
MLS provider logo

Listed by Danielle Malloy with Serhant Connecticut, LLC (203) 921-9987

The IDX display contains information sourced from SmartMLS, Inc. as of 8/25/2026. This information is for personal, non-commercial use only and may not be used for any purpose other than identifying properties the viewer may be interested in purchasing. MLS data is generally considered reliable but is not guaranteed accurate by the MLS. Buyers are responsible for verifying all information and should conduct their own investigation or consult a professional. Some MLS data may have been provided by sources other than the listing agent. Unless stated in writing, the Broker/Agent has not verified information obtained from outside sources. The Broker/Agent may or may not have been the listing and/or selling agent, and cannot guarantee the accuracy of any property location shown on a map. Any offer of compensation is made only to participants of the MLS where the listing is filed.

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Data last updated on 8/25/2026 at 3:42 AM UTC.

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