About This Home

This 4-bedroom, 5-bathroom single family at 39 Chippechaug Trail in Stonington, CT is listed for $3,995,000 ($931 per sqft). Built in 1968, the home offers 4,293 sqft of living space on a 2.05 acres lot.

Key Features

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

Property Details

3 full, 2 half
3-car garage
1968

Amenities

FireplaceWaterfrontA/C
Listing Description

A spectacular waterfront residence on Masons Island, 39 Chippechaug Trail captures the very best of coastal New England living. Set on 2.05 private acres with more than 250 feet of direct waterfront, this custom-built, move-in ready 4,300 square-foot home enjoys sweeping 180-degree water views, a private sandy beach, deep-water access and its own dock all within one of the Mystic/Stonington area's most coveted waterfront settings.

Beautifully maintained and thoughtfully positioned to embrace its extraordinary surroundings, the residence offers comfortable, inviting interiors designed to be enjoyed from day one. Expansive windows and water-facing spaces create a natural connection between the home, grounds and shoreline, while mature oaks frame the property with exceptional privacy and an established coastal landscape.

Designed for both relaxed everyday living and entertaining, the property transitions effortlessly from the house to expansive lawns, beach and dock. Boating, swimming, kayaking and days on the water begin right outside your door, while the breadth of the property creates a remarkable sense of openness, privacy and connection to the shoreline.

A three-car garage and geothermal heating add comfort and functionality, while the private island setting feels worlds away yet remains just minutes from downtown Mystic's acclaimed restaurants, boutiques, marinas and waterfront attractions. There is an ease to life here that is difficult to replicate...

A home where mornings begin on the water, afternoons unfold along the shoreline and evenings are framed by the beauty of the surrounding landscape. Equally suited as a year-round residence or an exceptional coastal retreat, 39 Chippechaug Trail is a rare opportunity to experience Mason's Island living at its finest.

Monthly Cost Estimate

$21,366/mo

20% down · 6.5% · 30 years

Principal$2,889
Interest$17,312
Insurance$1,165

Estimates only. Actual payments may vary.

Location

39 Chippechaug Trail

Stonington, CT 06355

Features & Amenities

Interior Features

Security System

Exterior Features

Deck,Garden Area,French Doors

Property Details

Outdoor Features

Deck

Cooling

Central Air

Appliances

Oven/RangeRefrigeratorDishwasherDisposalWasherDryer

Questions & Answers

This 4-bedroom, 5-bathroom single family at 39 Chippechaug Trail is listed at $3,995,000 ($931/sqft). The estimated monthly payment is $21,366 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1968, 2.05 acre lot, Fireplace, Waterfront. Interior Features: Security System. Exterior Features: Deck,Garden Area,French Doors.

This property is listed by Danielle Malloy.

DM

Danielle Malloy

Agent at SERHANT CONNECTICUT LLC

Listed by SERHANT CONNECTICUT LLC · Broker phone: (646) 480-7665 · View on Broker Site · Broker website

MLS# 24172306· Source: SmartMLS, Inc.· 174 days on PropertySimple

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.

39 Chippechaug Trail, Stonington, CT 06355

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