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

$4,995,000

Original price: $5,995,000
  • 4 Beds
  • 4 Baths
  • 4,293 sqft (on 2.05 acres)

39 Chippechaug Trail, Mystic, CT 06355

Est. Mortgage $33,705/mo*
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Home Highlights

Single-Family Home
Built in 1968
2.05 acre lot
$1,164/sqft
3 Car Garage

Local Information

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

About this House

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.
Last check for updates: about 5 hours ago
Listing courtesy of Danielle Malloy, (203) 921-9987
Serhant Connecticut, LLC, (203) 921-9987
Co-Listing Agent: Jonathan Shockley, (860) 917-6016
Serhant Connecticut, LLC, (203) 489-7800
Source: Smart MLS, MLS#24172306
Also Listed on Smart MLS.

Home Details for 39 Chippechaug Trail

Interior Features

Interior Details
Basement: Full,UnfinishedNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom
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
Appliances & Utilities
Appliances: Oven/Range, Refrigerator, Dishwasher, Disposal, Washer, Dryer, Water HeaterDishwasherDisposalDryerRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,GeothermalHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
Windows, Doors, Floors & Walls
Door: French Doors
View
Has a ViewView: Water
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: OtherPatio / Porch: DeckExterior: GardenFoundation: Concrete PerimeterGardenNo Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageParking Spaces: 3Parking: Attached
Frontage
WaterfrontWaterfront: Waterfront, Beach, Dock or Mooring, Water CommunityOn Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 4293 Square Feet

Days on Market

Days on Market: 136

Property Information

Year Built
Year Built: 1968
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: French,Modern
Building
Construction Materials: OtherNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 2076943

Price & Status

Price
List Price: $4,995,000Price Per Sqft: $1,164
Status Change & Dates
Possession Timing: Immediate

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: StoningtonCommunity: Masons Island
School Information
Elementary School: Deans MillJr High / Middle School: StoningtonHigh School: Stonington

Agent Information

Listing Agent
Listing ID: 24172306

Building

Building Area
Building Area: 4293 Square Feet

Community

Community Features: Golf, Library, Park, Private School(s), Public Rec Facilities

HOA

HOA Fee Includes: Road MaintenanceHas an HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 2.05 Acres

Energy

Energy Efficiency Features: HVAC

Miscellaneous

BasementMls Number: 24172306Attic: NoneWater ViewWater View: WaterAttribution Contact: (203) 921-9987Above Grade Unfinished Area: 4293

Additional Information

GolfLibraryParkPrivate School(s)Public Rec Facilities

Around this home

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.
  • Trulia User
    "Great location 1/2 way between nyc and Boston. Need car to get to train stations "
    0
    Flag
  • 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. "
    1
    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 "
    3
    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
    Flag

Market trends in Stonington

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$633K
$88.5KMoM
Sale-to-List Price
100.7%
Price per sq ft
$377
$1MoM
Available listings
75
7MoM

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
19 Money Point Road, Mystic, CT
0.32
Single-Family Home
$1,285,000
02/17/26
4
4
3,335
6 Huckleberry Lane, Stonington, CT
0.06
Single-Family Home
$2,100,000
12/16/25
7
4.5
1,719
33 Nauyaug Point Road, Mystic, CT
0.36
Single-Family Home
$1,272,500
11/13/25
3
2.5
1,557
37 Nauyaug Point Road, Mystic, CT
0.41
Single-Family Home
$2,820,000
11/13/25
3
2.5
1,955
10 Osprey Lane, Mystic, CT
0.42
Single-Family Home
$1,150,000
08/17/26
4
2.5
2,190
27 Quarry Road, Mystic, CT
0.69
Single-Family Home
$1,675,000
09/30/25
3
3
3,651
1 Egret Road, Mystic, CT
0.64
Single-Family Home
$1,200,000
05/01/26
4
3
2,080
14 Quarry Road, Mystic, CT
0.87
Single-Family Home
$2,978,000
01/30/26
4
3
2,122
8 Osprey Lane, Mystic, CT
0.42
Single-Family Home
$1,200,000
04/15/26
3
2.5
1,900
83 Old North Road, Mystic, CT
0.69
Single-Family Home
$1,292,500
07/08/26
3
2.5
2,341

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
39 Chippechaug Trl, Mystic, CT 06355
0.05
$4,995,000
4
4
4,293
For Sale
6 Huckleberry Lane, Stonington, CT 06378
0.06
$2,100,000
7
4.5
1,719
Recently Sold
6 Bayberry Lane, Mystic, CT 06355
0.06
$1,116,800
3
2.5
2,141
Off Market
4 Huckleberry Lane, Stonington, CT 06378
0.08
$2,210,100
4
2.5
2,206
Off Market
13 East Forest Road, Mystic, CT 06355
0.16
$807,900
1
1
992
Off Market
7 Money Point Road, Stonington, CT 06378
0.19
$1,126,600
4
3
2,130
Off Market
2 Anchor Lane, Stonington, CT 06378
0.20
$1,451,100
5
3
3,550
Off Market
11 Nauyaug Point Road, Mystic, CT 06355
0.22
$1,592,100
4
2.5
2,643
Off Market
19 Chippechaug Trail, Stonington, CT 06355
0.31
-
-
-
-
Off Market
14 Skiff Lane, Mystic, CT 06355
0.27
$2,211,100
4
2.5
3,700
Off Market
14 Poggy Bay Lane, Mystic, CT 06355
0.28
$2,459,700
5
4.5
4,570
Off Market

Price and Tax history

DateEventPrice
Jul 7, 2026
Source: Smart MLS #24180978
PriceChange
$4,995,000
Price decreased by 17%
May 7, 2026
Source: Smart MLS #24172306
Listed For Sale
$5,995,000

LGBTQ Local Legal Protections

Danielle Malloy, Serhant Connecticut, LLC, (203) 921-9987
Agent Phone: (203) 921-9987
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.

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Frequently asked questions about 39 Chippechaug Trail

  • What is the estimated monthly payment for 39 Chippechaug Trail?
    Based on a $4,995,000 list price with 20% down at today's rates, the estimated monthly payment for 39 Chippechaug Trail in Mystic, CT is approximately $34,261 (about $27,276 principal & interest, $6,910 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 39 Chippechaug Trail compare to homes in Mystic?
    39 Chippechaug Trail in Mystic, CT is listed at $4,995,000, about 689% above the $633K median sale price in Mystic.
  • What do residents say about Mystic?
    Residents describe Mystic, CT as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See homes for sale in Mystic, CT.
  • What are the closest schools to 39 Chippechaug Trail?
    The closest schools to 39 Chippechaug Trail in Mystic, CT are Deans Mill School (Pre-K/Elementary, rated 9/10), Stonington High School (rated 7/10), Stonington Middle School (rated 7/10).
  • Does 39 Chippechaug Trail have air conditioning?
    Yes, 39 Chippechaug Trail in Mystic, CT has air conditioning.
  • Does 39 Chippechaug Trail have laundry facilities?
    Yes, 39 Chippechaug Trail in Mystic, CT has in-unit laundry.
39 Chippechaug Trail, 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 Smart MLS on May 7, 2026. The MLS # for this home is MLS# 24172306.