$5,995,000

39 Chippechaug Trail Mystic, CT 06355

Estimated payment $34,796/month

Total Views 14,754
4 Beds
5 Baths
4,293 Sq Ft
$1,396 Price per Sq Ft

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

Danielle Malloy

Serhant Connecticut, LLC Brokerage Phone: (203) 921-9987 License #REB.0794641 Listed on: 05/07/2026

Co-Listing Agent

Jonathan Shockley

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

Home Details

Home Type

Single Family

Est. Annual Taxes

$35,769

Year Built

Built in 1968

Lot Details

2.05 Acres

Listing Details

  • Neighborhood: Masons Island
  • Property Type: Single Family For Sale
  • Style: French, Modern
  • Sq Ft Est Heated Above Grade: 4293
  • Total Sq Ft: 4293
  • Year Built: 1968
  • New Construction: No/Resale
  • Nearby Amenities: Golf Course, Library, Park, Private School(s), Public Rec Facilities
  • Remarks Public Addendum: 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.
  • Direct Waterfront: Yes
  • Home Warranty Offered: No
  • Directions: Route 1 to mason island road
  • Spec Assoc Asses: No
  • Street Type: Trail
  • Office Attribution Contact: (203) 489-7800
  • Reserve Prospect: No
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Total Bedrooms: 4
  • Total Bathrooms: 5
  • Full Bathrooms: 3
  • Half Bathrooms: 2
  • Fireplaces: 2
  • Basement Description: Full, Unfinished
  • Interior Amenities: Security System
  • Appliances: Oven/Range, Refrigerator, Dishwasher, Disposal, Washer, Dryer
  • Attic: No

Exterior Features

  • Exterior Features: Deck, Garden Area, French Doors
  • Exterior Siding: Other
  • Foundation Type: Concrete
  • Roof Information: Other
  • Waterfront Description: L. I. Sound Frontage Beach Dock or Mooring Water Community View
  • Swimming Pool: No
  • Construction Description: Masonry

Garage/Parking

  • Garages Number: 3
  • Garage And Parking: Attached Garage

Utilities

  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Heat Fuel Type: Geothermal
  • Hot Water Description: Other
  • Water Source: Public Water Connected, Other
  • Sewer: Septic

Condo/Co-op/Association

  • Association Fee Includes: Road Maintenance

Green Features

  • Energy Features: Geothermal Heat

Lot Info

  • Acres: 2.05
  • Lot Description: Secluded Level Lot Water View
  • Zoning: RA-20
  • Parcel #: 2076943

Tax Info

  • Tax Year: July 2025-June 2026
  • Property Tax: 35769

MLS Schools

  • Elementary School: Deans Mill
  • Middle Jr High School: Stonington
  • High School: Stonington

Map

Range of Values:

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Value Increase
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Adjusted for Inflation
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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

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
Source: Public Records

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
Source: SmartMLS

About the Listing Agent

Danielle Malloy

Serhant Connecticut, LLC

(860) 846-4110

Section Image

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

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Source: SmartMLS

MLS Number: 24172306

SmartMLS

APN: STON-000177-000009-000004

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