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39 Chippechaug Trail

Stonington, CT 06355
  • $4,995,000
  • STATUS: Active
  • ON SITE: 74 Days
  • MLS #: 24180978
UPDATED: 53 min ago
$4,995,000
  • 0
    BEDS
  • 2.05
    ACRES
  • 0
    BATHS
  • 0
    1/2 BATHS
Neighborhood:
Type:
Vacant Land / Lots
County:
Area:

School Information

Elementary School:
Middle School:
High School:

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 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.

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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc. Data last updated: 2026-08-18T22:09:55.927.
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39 Chippechaug Trail Stonington, CT 06355

  • Price: $4,995,000
  • Status: Active
  • On Site: 74 Days
  • Updated: 53 min ago
  • MLS #: 24180978
0
Beds
0
Baths
0
½ Baths
2.05
Acres
Neighborhood:
Masons Island
County:
New London
Area:
Stonington
Elementary School:
Deans Mill
Middle School:
Stonington
High School:
Stonington
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 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.
Exterior Features

Direct Waterfront YN Yes Lot Description SecludedRollingWater View Lot Improvements None Nearby Amenities Golf CourseLibraryParkPrivate School(s)Public Rec Facilities Road Frontage Approximate 260 Road Frontage Description Paved Road Waterfront Description BeachDock or MooringWater CommunityView

Property Features

Agent Owner YN No Bank Owned Property No Flood Zone YN No Home Owners Assocation No Location Suburban Potential Short Sale No Property Sub Type Residential Land Septic Approval YN No Septic Plan Available YN No Sewage System Septic Tax Year July 2025-June 2026 Under Agreement Yn No Utilities Available Electric Water Source Private Well Zoning RA-20

Listing information © 2026 Smart MLS
Listing provided courtesy of Danielle Malloy of Serhant Connecticut, LLC: (646) 480-7665.


The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc. Data last updated: 2026-08-18T22:09:55.927.
 
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