Active

39 Chippechaug Trail

Stonington, CT 06355

$5,995,000 $25,275/Mo

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Overview

Bed

Bath

4,293

Sqft

2.05

Acres(Lot)

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 parce ls 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.

Property Details

Property Type : Residential

Price : $5,995,000

AD Id : 78215473

MLS Id : 24172306

Beds : 4

Lot Size : 2.05 Acres

Living Area Size : 4,293

Year Built : 1968

Garage : 3

County : New London

Map

What's Nearby

Nearby Areas

Features

Bedroom Information

Total beds: 4

Bathroom Information

Total Baths: 5 Full Baths: 3 Half Baths: 2

Room Information

Rooms Total: 9 Has Basement: Yes Basement: Full, Unfinished
Interior Features

Appliances: Dishwasher, Disposal, Dryer, Range, Oven, Refrigerator, Washer
Heating & Cooling

Has Heating: Yes Heating: Geothermal, Forced Air Has Cooling: Yes Cooling: Central Air Water front: 1

Building Information

Year Built: 1968 Building Area Total: 4293 Construction Materials: Other Patio And Porch Features: Deck Private Pool: No Water front Features: Beach Front View: Water
Exterior Features

Exterior Features: Garden, Dock

Lot Information

Lot Size Acres: 2.05 Lot Description: Level, Waterfront

Listing Price Information

Listing Price: $5995000

Tax Information

Parcel Number: 2076943 Annual Tax: $35769

Virtual Tour

Virtual Tour (External Link)

Parking Information

Attached

Garage Information

Has Garage: Yes Has Attached Garage: Yes Garage Space: 3

Homeowners Association Information
Has Association: Yes Community Features: Golf

School Information

Elementary School: Deans Mill

Junior High School: Stonington

Senior High School: Stonington
Location Information

Direction: Route 1 to mason island road WaterSource: Public Security Features: Security System

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Nearby Home Value

Address	Estimate	Bed	Bath	Sq. Ft	Lot Size
152 & 156 Whitehall Ave.., Stonington, CT, 06355	$4,350,000	10	10	9,872	9,872 SqFt
39 Gled Hill Street, Stonington, CT, 06355	$1,895,000	4	3	3,688	3,688 SqFt
29 Dubois Drive #29, Stonington, CT, 06355	$2,950,000	4	4	3,360	3,360 SqFt
8 Ivy Road, Stonington, CT, 06355	$925,000	3	2	2,512	2,512 SqFt
16 School Street, Stonington, CT, 06355	$859,000	3	2	1,386	1,386 SqFt
83 Old North Road, Stonington, CT, 06355	$1,349,000	3	3	2,341	2,341 SqFt
152 Whitehall Avenue, Stonington, CT, 06355	$4,350,000	4	6	7,000	7,000 SqFt
40 Holmes Street, Stonington, CT, 06355	$1,795,000	3	3	2,402	2,402 SqFt
32 E Main Street, Stonington, CT, 06355	$1,895,000	5	3	4,259	4,259 SqFt
32 Money Point Road, Stonington, CT, 06355	$2,275,000	6	3	2,899	2,899 SqFt

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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. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

ByOwner last updated this listing 06/06/2026 @ 21:10

MLS: 24172306 LISTED BY: Danielle Malloy, Serhant Connecticut, LLC SOURCE: SmartMLS