39 Chippechaug Trail
Stonington, CT 06355
$4,995,000 - Masons Island
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.
| Listing Id: | 24172306 |
|---|---|
| List Price: | $4,995,000 |
| Property Type: | Single Family |
| Status: | Active |
| Bank Owned Property: | No |
| Beds Total: | 4 |
| Baths Full: | 3 |
| Baths Half: | 2 |
| Living Area Sqft Per Public Record: | 4,293 |
| Property Tax: | $37,460 |
| Acres: | 2.05 |
| Style: | French,Modern |
| Direct Waterfront Yn: | Yes |
| City: | Stonington |
| Neighborhood: | Masons Island |
| County: | New London |
| Postal Code: | 06355 |
| Year Built: | 1968 |
| Acres Source: | Public Records |
| Agent Owner Yn: | No |
| Appliances Included: | Oven/Range, Refrigerator, Dishwasher, Disposal, Washer, Dryer |
| Assessed Value: | $1,657,500 |
| Association Fee Includes: | Road Maintenance |
| Attic Yn: | No |
| Basement Description: | Yes |
| Basement Description: | Full,Unfinished |
| Baths Total: | 5 |
| Comp Only Manual Yn: | No |
| Cooling System: | Central Air |
| Current Price: | $4,995,000.00 |
| Directions: | Route 1 to mason island road |
| Display Fair Market Value Yn: | Yes |
| Elementary School: | Deans Mill |
| Energy Features: | Geothermal Heat |
| Exterior Features: | Deck, Garden Area, French Doors |
| Exterior Siding: | Other |
| Fireplaces Total: | 2 |
| Foundation Type: | Concrete |
| Garage & Parking: | Attached Garage |
| Garages Number: | 3 |
| Heat Fuel Type: | Geothermal |
| Heat Type: | Hot Air |
| High School: | Stonington |
| Home Owner's Assocation: | Yes |
| Home Warranty Offered Yn: | No |
| Hot Water Description: | Other |
| Interior Features: | Security System |
| Listing Contract Date: | 2026-05-07 |
| Lot Description: | Secluded, Level Lot, Water View |
| Middle Jr High School: | Stonington |
| Mil Rate Total: | $22.60 |
| Status: | Active |
| Nearby Amenities: | Golf Course, Library, Park, Private School(s), Public Rec Facilities |
| New Construction Type: | No/Resale |
| Occupied By: | Owner |
| Original List Price: | $5,995,000 |
| Parcel Number: | 2076943 |
| Parking Total Spaces: | 3 |
| Possession Availability: | Immediate |
| Potential Short Sale: | No |
| Preferred Phone: | (203) 921-9987 |
| Price: | $4,995,000 |
| Remarks Public Addendum: | 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. |
| Roof Information: | Other |
| Sewage System: | Septic |
| Sign Yn: | No |
| Special Association Assessment: | No |
| Sq Ft Est Heated Above Grade: | 4,293 |
| Sq Ft Total: | 4,293 |
| Swimming Pool Yn: | No |
| Tax Year: | July 2026-June 2027 |
| Total Rooms: | 9 |
| Under Agreement Yn: | No |
| Waterfront Description: | L. I. Sound Frontage, Beach, Dock or Mooring, Water Community, View |
| Water Source: | Public Water Connected, Other |
| Year Built Source: | Public Records |
| Zoning: | RA-20 |
Listing Courtesy of: Serhant Connecticut, LLC
Listing Agent: Danielle Malloy
(203) 921-9987
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Smart MLS Inc. data last updated on October 08, 2026 06:45 PM - ET
Property Last Updated: October 08, 2026 06:45 PM - ET