39 Chippechaug Trail
Stonington, Connecticut 06355
Reduced from $5,995,000
- Beds
- 4
- Baths
- 3 | 2
- SqFt
- 4,293
- Acres
- 2.05
- Year Built
- 1968
- Neighborhood
- Masons Island
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
45
35 under contract
Median List Price
$1.35M
45 active listings
Median Closed Price
$650,000
193 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per 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
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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.