39 Chippechaug Trail Mystic, CT 06355
Estimated payment $34,796/month
Highlights
- Waterfront
- 2.05 Acre Lot
- French Architecture
- Stonington Middle School Rated A-
- Deck
- 2 Fireplaces
About This Home
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.
Listing Agent
Serhant Connecticut, LLC Brokerage Phone: (203) 921-9987 License #REB.0794641 Listed on: 05/07/2026
Co-Listing Agent
Serhant Connecticut, LLC Brokerage Phone: (203) 921-9987 License #RES.0812681
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $35,769
Year Built
- Built in 1968
Lot Details
- 2.05 Acre Lot
- Waterfront
- Garden
- Property is zoned RA-20
Home Design
- French Architecture
- Modern Architecture
- Concrete Foundation
- Masonry
Interior Spaces
- 4,293 Sq Ft Home
- 2 Fireplaces
- French Doors
- Unfinished Basement
- Basement Fills Entire Space Under The House
- Home Security System
Kitchen
- Oven or Range
- Dishwasher
- Disposal
Bedrooms and Bathrooms
- 4 Bedrooms
Laundry
- Dryer
- Washer
Parking
- 3 Car Garage
- Parking Deck
Schools
- Deans Mill Elementary School
- Stonington Middle School
- Stonington High School
Utilities
- Central Air
- Geothermal Heating and Cooling
Additional Features
- Deck
- Property is near golf course
Community Details
- Association fees include road maintenance
Listing and Financial Details
- Assessor Parcel Number 2076943
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| 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 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 05/07/2026 05/07/26 | For Sale | $5,995,000 | -- | $1,396 / Sq Ft |
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: 24172306
APN: STON-000177-000009-000004
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Ask me questions while you tour the home.