# 39 Chippechaug Trail, Stonington, CT 06355 > **TL;DR:** 4bd/5ba single family, $3,995,000 ($931/sqft), built 1968, 4,293 sqft. > Fireplace, Waterfront, A/C, 3-car garage. Est. $21,366/mo. Listed 175 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $3,995,000 | | Price/sqft | $931 | | Bedrooms | 4 | | Bathrooms | 3 full, 2 half | | Square Feet | 4,293 | | Year Built | 1968 | | Lot Size | 89,298 sqft (2.05 acres) | | Garage | 3-car | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 175 | ## Why This Home Stands Out - **Waterfront** - Waterfront location listed - **Large Garage** - 3-car garage ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $20,201 | | Estimated Insurance | $1,165 | | **Total** | **$21,366** | ## Nearby Schools - **Elementary:** Deans Mill - **High:** Stonington ## Key Amenities - Fireplace - Waterfront - A/C - 3-car garage ## Property Highlights - Built in 1968 - 2.05 acre lot - Fireplace - Waterfront ## Description ### Agent Description 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. ## Location - **Address:** 39 Chippechaug Trail, Stonington, CT 06355 - **County:** New London - **Coordinates:** 41.328767, -71.964427 - **Google Maps:** https://www.google.com/maps?q=41.328767,-71.964427 ## Virtual Tour & Media - **Video Tour:** https://www.masonsislandestate.com/mls ## Listing Agent - **Name:** Danielle Malloy - **Brokerage:** SERHANT CONNECTICUT LLC - **Broker Phone:** (646) 480-7665 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/39-Chippechaug-Trl_Mystic_CT_06355_M47690-50828?f=listhub&s=CTMLS&m=24172306&c=propsimple) ## Photos ![39 Chippechaug Trail - Photo 1](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f1250989332r.jpg) ![39 Chippechaug Trail - Photo 2](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f2364430691r.jpg) ![39 Chippechaug Trail - Photo 3](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f2398905048r.jpg) ![39 Chippechaug Trail - Photo 4](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f1747680708r.jpg) ![39 Chippechaug Trail - Photo 5](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f3273275676r.jpg) ![39 Chippechaug Trail - Photo 6](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f1867650r.jpg) ![39 Chippechaug Trail - Photo 7](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f913118601r.jpg) ![39 Chippechaug Trail - Photo 8](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f1808932777r.jpg) ![39 Chippechaug Trail - Photo 9](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f427422025r.jpg) ![39 Chippechaug Trail - Photo 10](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f1596071041r.jpg) ![39 Chippechaug Trail - Photo 11](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f2773950056r.jpg) ![39 Chippechaug Trail - Photo 12](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f169422204r.jpg) ![39 Chippechaug Trail - Photo 13](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f2721111217r.jpg) ![39 Chippechaug Trail - Photo 14](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f3957032997r.jpg) ![39 Chippechaug Trail - Photo 15](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f2723456046r.jpg) ![39 Chippechaug Trail - Photo 16](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f3959513275r.jpg) ![39 Chippechaug Trail - Photo 17](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f1429340843r.jpg) ![39 Chippechaug Trail - Photo 18](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f951496839r.jpg) ![39 Chippechaug Trail - Photo 19](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f909507002r.jpg) ![39 Chippechaug Trail - Photo 20](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f1911681338r.jpg) ![39 Chippechaug Trail - Photo 21](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f3293329135r.jpg) ![39 Chippechaug Trail - Photo 22](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f917898735r.jpg) ![39 Chippechaug Trail - Photo 23](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f621167350r.jpg) ![39 Chippechaug Trail - Photo 24](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f1199610282r.jpg) ![39 Chippechaug Trail - Photo 25](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f3741626390r.jpg) ![39 Chippechaug Trail - Photo 26](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f2124849056r.jpg) ![39 Chippechaug Trail - Photo 27](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f4238302772r.jpg) ![39 Chippechaug Trail - Photo 28](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f622644736r.jpg) ![39 Chippechaug Trail - Photo 29](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f2971587322r.jpg) ![39 Chippechaug Trail - Photo 30](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f1527211400r.jpg) ![39 Chippechaug Trail - Photo 31](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f2838912277r.jpg) ![39 Chippechaug Trail - Photo 32](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f4135170389r.jpg) ![39 Chippechaug Trail - Photo 33](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f1465887678r.jpg) ![39 Chippechaug Trail - Photo 34](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f3129709747r.jpg) ![39 Chippechaug Trail - Photo 35](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f3557254418r.jpg) ![39 Chippechaug Trail - Photo 36](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f4232325984r.jpg) ![39 Chippechaug Trail - Photo 37](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f205127489r.jpg) ![39 Chippechaug Trail - Photo 38](http://lh.rdcpix.com/976004773c44091c7c5b6b75e1e5075cl-f1631035872r.jpg) --- **MLS#:** 24172306 | **Updated:** 2026-10-25 **Source:** listhub *Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://staging.propertysimple.ai/listing/39-chippechaug-trail-stonington-ct-06355-db35d195e87d4e76a7763c32c6cadc6a) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/39-chippechaug-trail-stonington-ct-06355-db35d195e87d4e76a7763c32c6cadc6a#listing", "url": "https://staging.propertysimple.ai/listing/39-chippechaug-trail-stonington-ct-06355-db35d195e87d4e76a7763c32c6cadc6a", "name": "39 Chippechaug Trail, Stonington, CT 06355", "description": "A spectacular waterfront residence on Masons Island, 39 Chippechaug Trail captures the very best of coastal New England living. 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