$5,995,000
Stonington, CT 06378
MLS# 124927
4 beds | 3.2 baths | 4293 sqft
1 / 36
Property Description
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
Details
Maps
Location & Property Info
List Price/SqFt: 1396.46
Zoning: OT - Out of Town
Owner Financing: No
Section: Out of Town
For Rent: No
CIOA: Yes
# HBths: 2
# FPs: 2
General Property Info
Acres +/-: 2.05
Elementary School: Out of Town
Middle School: Out of Town
Pool: No
Year Built: 1968
Garage #: 3
SqFt +/-: 4293
Tax & Misc Info
Assessment: 1657500
Mill Rate: 21.58
Taxes: 35769
Exterior
See Remarks: 1
Design
Post Modern: 1
Heat System
Forced Air: 1
Entry Hall Level/FP
1st: 1
Heat Fuel
Geothermal: 1
Entry Hall Comments
Entrance Foyer: 1
Front to Back: 1
Tile Floor: 1
Living Room Level/FP
1st: 1
FP: 1
Attic
None: 1
Living Room Comments
Built-in Features: 1
Step Down: 1
Lot Description
Formal Gardens: 1
Level: 1
Roof
Other: 1
Dining Room Level/FP
1st: 1
Waterfront Descrip
Deep Water: 1
LI Sound: 1
Waterfront: 1
Waterviews: 1
Cooling System
Central Air: 1
Library/Den Level/FP
1st: 1
Water Source
Public: 1
Sanitation Source
Septic Tank: 1
Library/Den Comments
Bookcases: 1
Built-Ins: 1
Family Room Level/FP
1st: 1
FP: 1
Family Room Comments
Wet Bar: 1
Powder Room Level/FP
1st: 2
Kitchen Level/FP
1st: 1
Parking Description
Attached Garage: 1
Kitchen Comments
Breakfast Room: 1
Eat-in Kitchen: 1
Pantry: 1
Primary Bdrm Level/FP
2nd: 1
Included
All Kitchen Applncs: 1
Washer/Dryer: 1
Primary Bdrm Comments
Primary Bedroom Suite: 1
Primary Bath Level/FP
2nd: 1
Dbl Bdrms Level/FP
2nd: 3
Bath Level/FP
2nd: 3
Hot Water
See Remarks: 1
Basement Type
Full: 1
Unfinished: 1
Features
Security System: 1
Location Property Info
List Price: $5,995,000
Type: Single Family Residence
Street #: 39
Street Name: Chippechaug
Street Suffix: Trail
State: CT
Zip Code: 06378
County: New London
Area: 16 - Out of Town
Property ID: 00449800
# Bdrms: 4
# FBths: 3
Baths: 3.2
OfficeContract Info
Status: Active
List Date: 2026-05-07
Property Features
Entry Hall Comments: Entrance Foyer; Front to Back; Tile Floor
Living Room Comments: Built-in Features; Step Down
Family Room Comments: Wet Bar
Kitchen Comments: Breakfast Room; Eat-in Kitchen; Pantry
Primary Bdrm Comments: Primary Bedroom Suite
Design: Post Modern
Cooling System: Central Air
Heat System: Forced Air
Heat Fuel: Geothermal
Hot Water: See Remarks
Attic: None
Basement Type: Full; Unfinished
Water Source: Public
Sanitation Source: Septic Tank
Exterior: See Remarks
Parking Description: Attached Garage
Roof: Other
Lot Description: Formal Gardens; Level
Waterfront Descrip: Deep Water; LI Sound; Waterfront; Waterviews
Features: Security System
Included: All Kitchen Applncs; Washer/Dryer
Supplements
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.
Listing Office: Serhant Connecticut LLC
Last Updated: May - 19 - 2026
Listing information comes from various sources and may not always be accurate. No representation or warranty is made as to the accuracy of this information. You should verify any information that is important to your buying decision. Greenwich Multiple Listing Service, Inc.