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.
For sale
$4,995,000
39 Chippechaug Trail, Stonington, CT 06355
4beds
4,293sqft
Single Family Residence
Built in 1968
2.05 Acres Lot
$-- Zestimate®
$1,164/sqft
$-- HOA
What's special
Own dockGeothermal heatingThree-car garagePrivate sandy beachSpectacular waterfront residenceExpansive lawnsExpansive windows
- 156 days
- 768
- 32
Zillow last checked:
Listing updated:
Listed by:
CT LUXE TEAM AT SERHANT CONNECTICUT,
Danielle Malloy (203)921-9987,
Serhant Connecticut, LLC 203-489-7800,
Co-Listing Agent: Jonathan Shockley 860-917-6016,
Serhant Connecticut, LLC
Source: Smart MLS,MLS#: 24172306
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 3
- 1/2 bathrooms: 2
Primary bedroom
- Level: Upper
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Heating
- Forced Air, Geothermal
Cooling
- Central Air
Appliances
- Included: Oven/Range, Refrigerator, Dishwasher, Disposal, Washer, Dryer, Water Heater
Features
- Doors: French Doors
- Basement: Full,Unfinished
- Attic: None
- Number of fireplaces: 2
Interior area
- Total structure area: 4,293
- Total interior livable area: 4,293 sqft
- Finished area above ground: 4,293
Video & virtual tour
Property
Parking
- Total spaces: 3
- Parking features: Attached
- Attached garage spaces: 3
Features
- Patio & porch: Deck
- Exterior features: Garden
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront, Beach, Dock or Mooring, Water Community
Lot
- Size: 2.05 Acres
- Features: Secluded, Level
Details
- Parcel number: 2076943
- Zoning: RA-20
Construction
Type & style
- Home type: SingleFamily
- Architectural style: French,Modern
- Property subtype: Single Family Residence
Materials
- Other
- Foundation: Concrete Perimeter
- Roof: Other
Condition
- New construction: No
- Year built: 1968
Utilities & green energy
- Sewer: Septic Tank
- Water: Public, Other
Green energy
- Energy efficient items: HVAC
Community & HOA
Community
- Features: Golf, Library, Park, Private School(s), Public Rec Facilities
- Security: Security System
- Subdivision: Masons Island
HOA
- Has HOA: Yes
- Services included: Road Maintenance
Location
- Region: Mystic
Financial & listing details
- Price per square foot: $1,164/sqft
- Tax assessed value: $1,657,500
- Annual tax amount: $37,460
- Date on market: 5/7/2026
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 7/7/2026 | Price change | $4,995,000-16.7%$1,164/sqft |
Source: | ||
| 5/7/2026 | Listed for sale | $5,995,000$1,396/sqft |
Source: | ||
Public tax history
Tax history is unavailable.
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 06355
Nearby schools
Schools provided by the listing agent
- Elementary: Deans Mill
- Middle: Stonington
- High: Stonington
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.






