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39 Chippechaug Trail

Stonington, Connecticut 06355

ACTIVE$4,995,000

Reduced from $5,995,000

Beds
4
Baths
3 | 2
SqFt
4,293
Acres
2.05
Year Built
1968
Matt Caiola

Matt Caiola

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WaterfrontDock / Mooring3-Car Garage2 FireplacesVirtual TourPrice Reduced

About This Home

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.

Key Facts

City/Town
Stonington
Neighborhood
Masons Island
Property / Style
Single Family · French,Modern
Year Built
1968
Days on Market
128 days
Beds
4
Baths
3 full · 2 half
Living Area
4,293 sq ft
Lot Size
2.05 acres
Garage / Parking
3 garage
Property Taxes
$37,460 / Annually

Market Snapshot

The Stonington Market

Single Family · trailing 12 months

Median Days on Market

50

45 active listings

Median $ / Sq Ft

$510

45 active listings

Sale-to-List Ratio

99.2%

193 sales

How this home compares

List Price

$5.00M

vs $1.35M median

3.7× the median

Price / Sq Ft

$1,164

vs $510 median

2.3× the median

Days on Market

128 days

vs 50 days median

78 days longer than median

Based on 45 active and 193 closed sales (trailing 12 mo) of single family in Stonington. Source: SmartMLS · As of September 12, 2026.

Location

39 Chippechaug Trail, Stonington, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$30,732

per month

  • Principal & Interest$25,945
  • Property Taxes$3,122
  • Insurance$1,665
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Stonington
Neighborhood
Masons Island
County
New London

Residence

Property Type
Single Family
Style
French,Modern
Year Built
1968
New Construction
No/Resale
Living Area
4,293 sq ft

Schools

Elementary
Deans Mill
High
Stonington

Interior

Heating
Hot Air
Heat Fuel
Geothermal
Cooling
Central Air
Fireplaces
2
Appliances
Oven/RangeRefrigeratorDishwasherDisposalWasherDryer
Basement
FullUnfinished
Interior Features
Security System

Exterior & Lot

Lot Size
2.05 acres
Zoning
RA-20
Garage / Parking
3 garage spacesAttached Garage
Waterfront
Direct waterfront
Waterfront Details
L. I. Sound FrontageBeachDock or MooringWater CommunityView
Water Source
Public Water ConnectedOther
Sewer
Septic
Construction
Other
Roof
Other
Foundation
Concrete
Exterior Features
DeckGarden AreaFrench Doors
Lot Description
SecludedLevel LotWater View

Listing & Financials

Property Taxes
$37,460 / Annually
Days on Market
128
MLS #
24172306
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Danielle Malloy

(203) 921-9987

Serhant Connecticut, LLC

(203) 489-7800

Co-Listed By

Jonathan Shockley

Serhant Connecticut, LLC

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/12/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 9/12/2026 at 8:10 PM UTC.