39 Chippechaug Trail Stonington, CT $ 4,995,000
39 Chippechaug Trail
$ 4,995,000
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39 Chippechaug Trail

Stonington, CT, 06355
$ 4,995,000
Bedrooms4 Baths3.2 Sq 4,293

Monthly Estimate*

$ 31,539

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Single Family Home for sale in Stonington, CT

for $4,995,000 with 4 bedrooms and 3 full baths, 2 half baths. This 4,293 square foot home was built in 1968 on a lot size of 2.05.

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.

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Single Family Active

Price

$ 4,995,000

Bedrooms

4

Full Bath

3

Half Bath

2

Property Type

Single Family

Taxes

$ 37,460

Style

Lot Size

2.05

Year Built

1968

Town/City

Stonington

MLS | Web ID

24172306

Features
General
Zoning RA-20
Neighborhood Masons Island
County New London
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Active
Acres 2.05
Directions Route 1 to mason island road
High School Stonington
City Stonington
Elementary School Deans Mill
Sq Ft Total 4293
DOM 109
Year Built 1968
Style French Modern
Year Built Source Public Records
Energy Features Geothermal Heat
Association Fee Includes Road Maintenance
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Interior
Cooling System Central Air
Total Rooms 9
Basement Description Full Unfinished
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Exterior
Water Source Public Water Connected Other
Lot Description Secluded Level Lot Water View
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* Excluded Features
List By
Danielle Malloy

Listing Agent

Serhant Connecticut, Llc

Broker

Danielle@SerhantCT.com

Email

Affordability Calculator

$34,661
Per Month
91%
9%
0%
Monthly Principal & Interest
$31,539
Monthly Property Taxes
$3,122
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
895183 Elementary School
3042667 Middle School
Stonington High School High School
Pricing History
DatePricePrice ChangeDescription
7/7/2026$4,995,000 -16.68% Price Down
5/7/2026$5,995,000 Listed Price

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39 Chippechaug Trail, Stonington, CT, 06355 is a Single Family Home for sale at $4,995,000 with 4,293 sqft and a lot size of 2.05. 39 Chippechaug Trail has 4 bedrooms, 3.2 baths, and was built in 1968. The property's zip code is 06355 which is in Stonington, CT