New Listing - 05/07/2026
Listing courtesy of Danielle Malloy (203) 921-9987, Serhant Connecticut, LLC (203) 489-7800
39 Chippechaug Trail, Stonington, (Masons Island), CT, 06355
9 rooms
4 beds
3 Full / 2 Half baths
1968
French, Modern
4,293 sqft
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 drive 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.
Status:
Active
Town:
Stonington
Type:
Single-family residential
Zoning:
RA-20
Garage:
3-car Attached Garage
Heating:
Hot Air
Cooling:
Central Air
Energy Features:
Geothermal Heat
Basement:
Full, Unfinished
Acreage:
2.05
Est. Taxes:
$35,769
Assessment
$1,657,500
Lot Description:
Secluded,Level Lot,Water View
Waterfront:
Yes
Elementary School:
Deans Mill
Middle School:
Stonington
High School:
Stonington
Days on Market:
12
Appliances:
Oven/Range, Refrigerator, Dishwasher, Disposal, Washer, Dryer
MLS #:
24172306
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