# 39 Chippechaug Trail, Stonington, CT 06355

> **TL;DR:** 4bd/5ba single family, $5,995,000 ($1396/sqft), built 1968, 4,293 sqft.
> Fireplace, Waterfront, A/C. Est. $25,978/mo. Listed 25 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $5,995,000 |
| Price/sqft | $1396 |
| Bedrooms | 4 |
| Bathrooms | 3 full, 2 half |
| Square Feet | 4,293 |
| Year Built | 1968 |
| Lot Size | 89,298 sqft (2.05 acres) |
| Property Type | Single Family (Other) |
| Status | For Sale |
| Days on Market | 25 |

## Why This Home Stands Out

- **Waterfront** - Direct water access

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $25,978 |
| **Total** | **$25,978** |

## Nearby Schools

- **Elementary:** Deans Mill
- **High:** Stonington

## Key Amenities

- Fireplace
- Waterfront
- A/C

## Property Highlights

- Built in 1968
- 2.05 acre lot
- Fireplace
- Waterfront

## Description

### Agent 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.

## Location

- **Address:** 39 Chippechaug Trail, Stonington, CT 06355
- **County:** New London
- **Coordinates:** 41.328767, -71.964427
- **Google Maps:** https://www.google.com/maps?q=41.328767,-71.964427

## Listing Agent

- **Name:** Danielle Malloy
- **Brokerage:** Serhant Connecticut, LLC
- **Phone:** 2039219987
- **Email:** Danielle@SerhantCT.com

## Primary Photo

![39 Chippechaug Trail - Primary Photo](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f1250989332r.jpg)

*36 total photos available on [listing page](https://www.propertysimple.com/listing/39-chippechaug-trail-stonington-ct-06355-24172306)*

---

**MLS#:** 24172306 | **Updated:** 2026-06-17
**Source:** listhub

*Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.com/listing/39-chippechaug-trail-stonington-ct-06355-24172306)

---

## Structured Data

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  "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",
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