First time available in over 50 years, this generational

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Home For Sale

39 Chippechaug Trl

Stonington, Connecticut 06378

New London County

Waterfront: Yes

Community: 

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$5,995,000 4 br, 4.0 bath 4293 sq. ft. 2.050 acres

First time available in over 50 years, this generational waterfront estate on Masons Island presents an extraordinary coastal offering. Set on two private acres with more than 250 feet of direct water frontage, deep water access, sweeping 180-degree unobstructed views, a private dock, majestic mature oak trees, and its very own sandy beach, 39 Chippechaug Trail is a rare convergence of acreage, privacy, and position. Set within a private island enclave, the property is defined by scale, serenity, and an uninterrupted connection to the water. Dappled light, coastal breezes, and a timeless natural landscape create an environment that feels both grounded and quietly spectacular. Expansive, ever-changing views stretch toward the horizon from one of the largest and most coveted waterfront parcels in the community. Deep water access and a private dock support an effortless yachting lifestyle, while the breadth of the acreage allows for a setback residence, maximized square footage, and the possibility of bountiful formal gardens. Morning light rises dramatically over the water, with breathtaking sunrises that define the daily experience of living here. Surrounding oaks provide privacy, shade, and a rare sense of established beauty not often found in waterfront offerings. Despite its quiet, retreat-like atmosphere, the property is just minutes from the heart of Mystic, with renowned dining, boutique shopping, marinas, and waterfront charm only a short distance away. Enhanced by geothermal efficiency and access to a private yacht club within the association, the offering is as functional as it is remarkable. A private coastal retreat. A legacy waterfront estate. One of Mason's Island's rarest holdings, offered for the first time in more than half a century.

Interior:
  • Bedrooms: 4
  • Baths: 4.0
  • Sq Ft: 4293
  • Year Built: 1968
  • Utilities: 
  • Fireplaces: Has Fireplace
  • Stories: 
  • Heat/AC: Forced Air, Geothermal (Heating)
  • Garage: Garage - Attached
Exterior:
  • Lot Size: 2.050 acre
  • Lot Dimensions: 
  • Waterfront: Yes
  • View Types: 
  • Yard: 
  • Siding: 
  • Roof: 
  • Property Taxes: $35,769
  • MLS #: 124927
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Contact Information:
Beach Home For Sale in Stonington, Connecticut
Listing Agent: Danielle Malloy, SERHANT CONNECTICUT LLC, 646-480-7665, 203-489-7800 Listing Site, Listing Status: Active
Copyright © 2026 Greenwich MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Ad Number: 7684203
Viewed 13 times.
Updated: May 08, 2026

This property is a Home located at 39 Chippechaug Trl, Stonington, Connecticut 06378, and is currently For Sale at $5,995,000. This Home has 4 bedrooms, 4.0 baths, 4293 sq ft.