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Ad #7829267
MLS #24180978
Listing photo

First time available in over 50 years, this generational

39 Chippechaug Trl, Stonington, CT 06355
$4,995,000
--Beds
--Baths
--Sqft
2.05Acres

About this property

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.

Property Features

0 Beds
0 Baths
0 Sqft
2.05 Acres
On Beachfront
$35,769 / yr property tax
New London County

Additional Photos

Additional listing photo 1
Additional listing photo 2
Additional listing photo 3
Additional listing photo 4

Contact Information

Danielle Malloy

SERHANT CONNECTICUT LLC

203-921-9987

Location

Map
Listing Agent: Danielle Malloy 203-921-9987
Broker: SERHANT CONNECTICUT LLC 646-480-7665 Listing Site
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.
BeachHouse.com
Printed Aug 11, 2026

Photo Gallery

First time available in over 50 years, this generational - photo 1
First time available in over 50 years, this generational - photo 2
First time available in over 50 years, this generational - photo 3
First time available in over 50 years, this generational - photo 4
First time available in over 50 years, this generational - photo 5
First time available in over 50 years, this generational - photo 6
First time available in over 50 years, this generational - photo 7
First time available in over 50 years, this generational - photo 8
First time available in over 50 years, this generational - photo 9
First time available in over 50 years, this generational - photo 10
First time available in over 50 years, this generational - photo 11
First time available in over 50 years, this generational - photo 12
First time available in over 50 years, this generational - photo 13
First time available in over 50 years, this generational - photo 14
First time available in over 50 years, this generational - photo 15
First time available in over 50 years, this generational - photo 16
First time available in over 50 years, this generational - photo 17
First time available in over 50 years, this generational - photo 18
First time available in over 50 years, this generational - photo 19
First time available in over 50 years, this generational - photo 20
First time available in over 50 years, this generational - photo 21
First time available in over 50 years, this generational - photo 22
First time available in over 50 years, this generational - photo 23
First time available in over 50 years, this generational - photo 24
First time available in over 50 years, this generational - photo 25
First time available in over 50 years, this generational - photo 26
First time available in over 50 years, this generational - photo 27
First time available in over 50 years, this generational - photo 28
First time available in over 50 years, this generational - photo 29
First time available in over 50 years, this generational - photo 30

$4,995,000

--
Beds
--
Baths
--
Sqft

39 Chippechaug Trl, Stonington, CT 06355

By contacting this agent you agree to these Terms and Conditions.
Home Connecticut Stonington
First time available in over 50 years, this generational - photo 1
First time available in over 50 years, this generational - photo 2
First time available in over 50 years, this generational - photo 3
First time available in over 50 years, this generational - photo 4
First time available in over 50 years, this generational - photo 5
MLS# 24180978
Acreage For Sale

First time available in over 50 years, this generational

$4,995,000

39 Chippechaug Trl, Stonington, CT 06355

--
Beds
--
Baths
--
Sqft
2.05
Acres
$4,995,000
39 Chippechaug Trl, Stonington, CT 06355
-- Beds
-- Baths
-- Sqft
2.05 Acres
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.
68 days
on BeachHouse.com
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0
saves

Property Details

HOME DETAILS

0 Beds
0 Baths
0 Sqft
2.05 Acres

BEACH & VIEW

On Beachfront

FINANCIAL & COMMUNITY

$35,769 / yr property tax
New London County
See More Details

Location

Map
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Ad Statistics

Ad Number
7829267
Viewed
76 times
Listing Status
Active
Added
Jun 04, 2026
Last Refreshed
Jul 03, 2026 06:17:28 PM

Listing Information

Data Source
SmartMLS, Inc.
Source Property ID
24180978
Listing Agent: Danielle Malloy 203-921-9987
Broker: SERHANT CONNECTICUT LLC 646-480-7665 Listing Site
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.

Request Information

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Added: 01/14/2026 • Updated: 06/28/2026
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This consent applies even if you are on a corporate, state or national Do Not Call list. Dream Home Network Inc. may share information about your recent and future site activity with its affiliates and service providers (including real estate professionals such as Brokers, Listing Agents, Buyers Agents, and local referral partners) to help them better understand what I am looking for in a property. To opt-out at any time you can reply "STOP" or contact Dream Home Network Inc. at  csv@dreamhomenetwork.com.
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SERVICES
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Dream Home Network Inc.

is committed to ensuring digital accessibility and property listings for individuals with disabilities. All information provided is deemed reliable but is not guaranteed and should be independently verified. We are continuously working to improve the accessibility of our web experience for everyone, and we welcome feedback and accommodation requests. If you wish to report an issue or seek an accommodation, please let us know.

Dream Home Network Inc. Sells leads to DHN Realty Inc. who holds real estate brokerage licenses in Alabama. Listing agents will be sent notification copy of leads on their listings where Dream Home Network Inc. is provided listings via our Feed Provider as required.

© 1997 - 2026 BeachHouse.com
Part of Dream Home Network, Inc.
Last updated on 2026.08.11
Terms & Policy