39 Chippechaug Trail Mystic, CT 06355
Stonington AreaEstimated payment $30,118/month
Total Views
45,233
2.05
Acres
$2,436,585
Price per Acre
89,298
Sq Ft Lot
Highlights
- Waterfront
- 2.05 Acre Lot
- Property is near golf course
- Stonington Middle School Rated A-
About This Lot
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.
Listing Agent
Serhant Connecticut, LLC Brokerage Phone: (203) 921-9987 License #REB.0794641 Listed on: 06/04/2026
Co-Listing Agent
Serhant Connecticut, LLC Brokerage Phone: (203) 921-9987 License #RES.0812681
Property Details
Property Type
- Land
Est. Annual Taxes
- $35,769
Lot Details
- 2.05 Acre Lot
- Waterfront
- Property is zoned RA-20
Schools
- Deans Mill Elementary School
- Stonington Middle School
- Stonington High School
Additional Features
- Property is near golf course
- Private Company Owned Well
Listing and Financial Details
- Assessor Parcel Number 2076943
Map
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area
Home Values in the Area
Average Home Value in this Area
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $35,769 | $1,657,500 | $1,018,300 | $639,200 |
| 2024 | $34,559 | $1,657,500 | $1,018,300 | $639,200 |
| 2023 | $31,575 | $1,657,500 | $1,018,300 | $639,200 |
| 2022 | $27,955 | $1,072,700 | $739,300 | $333,400 |
| 2021 | $27,799 | $1,072,700 | $739,300 | $333,400 |
| 2020 | $26,989 | $1,072,700 | $739,300 | $333,400 |
| 2019 | $26,882 | $1,072,700 | $739,300 | $333,400 |
| 2018 | $26,077 | $1,072,700 | $739,300 | $333,400 |
| 2017 | $27,775 | $1,128,600 | $824,600 | $304,000 |
| 2016 | $27,019 | $1,128,600 | $824,600 | $304,000 |
| 2015 | $25,901 | $1,128,600 | $824,600 | $304,000 |
| 2014 | $24,897 | $1,128,600 | $824,600 | $304,000 |
Source: Public Records
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 07/07/2026 07/07/26 | Price Changed | $4,995,000 | -16.7% | -- |
| 06/04/2026 06/04/26 | For Sale | $5,995,000 | -- | -- |
Source: SmartMLS
About the Listing Agent
Danielle Malloy is a leading real estate expert who has been providing first-class service to luxury buyers, sellers, developers, and investors for nearly two decades. The Managing Broker and Founding Partner of SERHANT. Connecticut, she has taken part in over $1B in sales and is one of the most successful brokers in Greenwich and neighboring communities like New Canaan, Westport, and Darien. Her vast industry experience and peerless knowledge are invaluable assets to her clients, and her
Danielle's Other Listings
Source: SmartMLS
MLS Number: 24180978
APN: STON-000177-000009-000004
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Nearby Homes
Your Personal Tour Guide
Ask me questions while you tour the home.