39 Chippechaug Trl, Mystic, CT 06355
Property image
Property image
FOR SALE
3D VIEW
2.05 ACRES

39 Chippechaug Trl
Mystic, CT 06355

  • 4 Beds
  • 4 Baths
  • 4,293 sqft (on 2.05 acres)

$4,995,000

Original price: $5,995,000
Est. Mortgage $32,585/mo*
Get Pre-Qualified

$4,995,000

Original price: $5,995,000
Est. Mortgage $32,585/mo*
Get Pre-Qualified
4 Beds
4 Baths
4,293 sqft
(on 2.05 acres)

Home Highlights

Parking
Garage
Climate Control
Heating & Cooling
Price/Sqft
$1,164
Listed
91 days ago

Local Information

  • Map ViewExplore the area around 39 Chippechaug Trl.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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 distance away. 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.

Home Details for 39 Chippechaug Trl

Interior Features

Interior Details
Basement: Full,Unfinished
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 5Number of Bathrooms (full): 3Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 4293 Square Feet
Heating & Cooling
Heating: Forced Air,GeothermalHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
View
Has a ViewView: Water
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: OtherNo Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3Has a GarageParking Spaces: 3Parking: Garage
Frontage
WaterfrontWaterfront: Deep Water, LI Sound, WaterfrontOn Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Days on Market: 91

Property Information

Year Built
Year Built: 1968
Property Type / Style
Property Type: ResidentialProperty Subtype: Residential, Single Family ResidenceArchitecture: Post Modern
Building
Construction Materials: See Remarks
Property Information
Included in Sale: Washer/Dryer, All Kitchen ApplncsParcel Number: 00449800

Price & Status

Price
List Price: $4,995,000Price Per Sqft: $1,164

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: Stonington
School Information
Elementary School: Out of TownJr High / Middle School: Out of Town

Agent Information

Listing Agent
Listing ID: 124927

Building

Building Area
Building Area: 4293 Square Feet

Lot Information

Lot Area: 2.05 Acres

Mobile R/V

Mobile Home Park
Mobile Home Units: Feet

Miscellaneous

BasementMls Number: 124927Water ViewWater View: Water
Last check for updates: about 3 hours ago
Listing courtesy of Danielle Malloy, (203) 921-9987
Serhant Connecticut LLC
Source: Greenwich MLS, Inc., MLS#124927
Also Listed on Greenwich MLS, Inc..

Market trends in Stonington

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
79
2MoM

Price History for 39 Chippechaug Trl

DatePriceEventSource
07/07/2026$4,995,000PriceChange
Greenwich MLS, Inc. #124927
05/07/2026$5,995,000Listed For SaleGreenwich MLS, Inc. #124927

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Comparable Sales for 39 Chippechaug Trl

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
19 Money Point Road, Mystic, CT
0.27
Single-Family Home
$1,285,000
02/17/26
4
4
3,335
33 Nauyaug Point Road, Mystic, CT
0.34
Single-Family Home
$1,272,500
11/13/25
3
2.5
1,557
6 Huckleberry Lane, Stonington, CT
0.08
Single-Family Home
$2,100,000
12/16/25
7
4.5
1,719
37 Nauyaug Point Road, Mystic, CT
0.39
Single-Family Home
$2,820,000
11/13/25
3
2.5
1,955
7 Egret Road, Mystic, CT
0.68
Single-Family Home
$1,917,500
08/19/25
3
3.5
3,570
27 Quarry Road, Mystic, CT
0.66
Single-Family Home
$1,675,000
09/30/25
3
3
3,651
1 Egret Road, Mystic, CT
0.63
Single-Family Home
$1,200,000
05/01/26
4
3
2,080
14 Quarry Road, Mystic, CT
0.84
Single-Family Home
$2,978,000
01/30/26
4
3
2,122
8 Osprey Lane, Mystic, CT
0.41
Single-Family Home
$1,200,000
04/15/26
3
2.5
1,900
83 Old North Road, Mystic, CT
0.67
Single-Family Home
$1,292,500
07/08/26
3
2.5
2,341

Nearby homes

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Assigned Schools

These are the assigned schools for 39 Chippechaug Trl.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Stonington

At least 138 Trulia users voted on each feature.

  • 88 % Say it's dog friendly

  • 84 % Say yards are well-kept

  • 81 % Say there's holiday spirit

  • 81 % Say people would walk alone at night

  • 79 % Say car is needed

  • 78 % Say parking is easy

  • 70 % Say kids play outside

  • 66 % Say it's walkable to restaurants

  • 64 % Say they plan to stay for at least 5 years

  • 62 % Say streets are well-lit

  • 62 % Say there's wildlife

  • 62 % Say neighbors are friendly

  • 59 % Say it's quiet

  • 56 % Say there are sidewalks

  • 35 % Say it's walkable to grocery stores

  • 32 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Bill
    "It very safe here for all age of children.."
    0
    Flag
  • Joseph Witherell
    "Low speed limits and quiet side streets. Great dog parks in westerly and Stonington. Many options for affordable walkers and boarders in the area. "
    0
    Flag
  • Anna.mazgelis066
    "A car is needed if living in this area. The train is handy for traveling to and from NYC, Providence or Boston "
    2
    Flag
  • Trulia User
    "people here are very friendly, amicable and trusting. they are not aggressive when they drive as in nyc."
    0
    Flag
  • Trulia User
    "the people are friendly , I love how quiet it is. the kids in the neighborhood are sweet . they always have gatherings. "
    0
    Flag
  • Trulia User
    "Nothing. I love dogs and there are so many cute ones. Everyone picks up after their dogs and majority of the dogs are well behaved"
    0
    Flag
  • Cookeint
    "the Mystic Art festival Concerts on the green in the summer Irish parade is loads of fun with fire trucks and lots of drum and fife groups. People are from everywhere. "
    0
    Flag
  • Daphne
    "Beautiful neighborhood so close to velvet mill and all the awesome shops inside and restaurants. You walk to stores and also neighbors are friendly but allow you your privacy. It is a slice of heaven!"
    1
    Flag
  • Michaela S. C.
    "Downtown Westerly RI is around the corner and has many holiday and seasonal events and fairs. Most are family friendly and free to attend. "
    4
    Flag
  • Srbranson
    "The people are kind and friendly. There is so much to do that most small towns don’t have: an art museum , the aquarium, the Seaport, an vital downtown with lots of restaurants and shopping. And all with a historical, small town feel."
    6
    Flag
  • Justine W.
    "People walk their dogs all the time in my neighborhood! There are a few sharp turns but switching sides of the street so cars can see you is easy. "
    5
    Flag
  • Laura C. R.
    "Dog friendly and they seem to all cleanup after themselves. Nice neighborhood with sidewalks and great lawns. Trees line some of the trees. "
    2
    Flag
  • Crystal S.
    "My neighborhood is very quiet and friendly, I have lived here 21 years. Lots of children no traffic "
    2
    Flag
  • Trulia User
    "There are dogs everywhere, it’s great. Everyone seems to pick up, and is generally respectful. The neighborhood offers many loops as well, it’s ideal."
    0
    Flag
  • Sharon M.
    "Little to no traffic, quick access to the highway. Short commute to Rhode Island beaches. Only 2 hours to Boston or New York. "
    4
    Flag
  • Cyork5
    "Dogs are welcome. Most families in our neighborhood have pets. The neighborhood streets are quiet however Lantern Hill is too busy a road to walk your dog. Downtown Mystic has a beautiful green space and lots of people walk their dogs there."
    3
    Flag
  • Sharon M.
    "It’s a great neighborhood to walk your dog. Everyone is dog friendly and there are is a field close by where people like to exercise their dogs. "
    2
    Flag
  • ka
    "Great school system for children with and without special needs. Love my town. Anyone would. It’s perfect. "
    1
    Flag
  • Sharon M.
    "It’s a safe neighborhood, close to schools and Plenty of open play space. Location is close to elementary, middle and high school. "
    1
    Flag
  • Michaela C.
    "This area is friendly and extremely safe. There are not a lot of homes with yards however there are playgrounds, court yards and is a 10 minute walk to a child friendly beach."
    0
    Flag
  • Rory.douthit
    "Very dog friendly neighborhood. All are expected to pick up after their pets, but dogs are seen being walked regularly."
    2
    Flag
  • Jcottrel
    "Anything I need is within 5-10 drive. Although beautiful, the area is not walk or bike friendly EXCEPT in downtown Westerly, Stonington Borough, and Downtown Mystic. Public transportation is much needed with frequent stops and regular and late service including ‘express routes’ Public transportation with frequent stops, regular service, late service between Westerly and Mystic and New London"
    0
    Flag
  • Courtney
    "It's close to the highways but does not feel like it. Downtown Westerly is 5 minutes away and downtown mystic is less than 15 minutes away. "
    1
    Flag
  • Tompurdy7
    "Beautiful area! Love living in Connecticut near the ocean and a short train ride to Boston and New York. "
    1
    Flag
  • Lshanleyfpt
    "The walk to downtown is wonderful and easy. The area is beautiful and the people are wonderfully friendly"
    0
    Flag
  • Scottjohnson71
    "Lived here over 10 years. Great schools and very family oriented. Property values have come back up so taxes are high"
    0
    Flag
  • Adams n. t.
    "It’s a nice family neighborhood within walking distance of restaurants, bars, grocery stores, and the library. "
    0
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LGBTQ Local Legal Protections

Danielle Malloy, Serhant Connecticut LLC
Agent Phone: (203) 921-9987
Listing data courtesy of Greenwich MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by the MLS.
39 Chippechaug Trl, Mystic, CT 06355 is a 4 bedroom, 5 bathroom, 4,293 sqft single-family home built in 1968. This property is currently available for sale and was listed by Greenwich MLS, Inc. on May 7, 2026. The MLS # for this home is MLS# 124927.