39 Chippechaug Trail, Mystic, CT 06355
Local realty services provided by:Better Homes and Gardens Real Estate Gaetano Marra Homes
Listed by: danielle malloy, jonathan shockley(203) 921-9987
Office: serhant connecticut, llc(203) 489-7800
MLS#:24172306
Source:CT
Price summary
- Price:$4,995,000
- Price per sq. ft.:$1,163.52
About this home
First time available in over 50 years, this generational waterfront estate on Masons Island presents an extraordinary coastal offering. Set on two private acres with more than 250 feet of direct water frontage, deep water access, sweeping 180-degree unobstructed views, a private dock, majestic mature oak trees, and its very own sandy beach, 39 Chippechaug Trail is a rare convergence of acreage, privacy, and position. Set within a private island enclave, the property is defined by scale, serenity, and an uninterrupted connection to the water. Dappled light, coastal breezes, and a timeless natural landscape create an environment that feels both grounded and quietly spectacular. Expansive, ever-changing views stretch toward the horizon from one of the largest and most coveted waterfront parcels in the community. Deep water access and a private dock support an effortless yachting lifestyle, while the breadth of the acreage allows for a setback residence, maximized square footage, and the possibility of bountiful formal gardens. Morning light rises dramatically over the water, with breathtaking sunrises that define the daily experience of living here. Surrounding oaks provide privacy, shade, and a rare sense of established beauty not often found in waterfront offerings. Despite its quiet, retreat-like atmosphere, the property is just minutes from the heart of Mystic, with renowned dining, boutique shopping, marinas, and waterfront charm only a short drive away....
Contact an agent
Home facts
- Year built:1968
- Listing ID #:24172306
- Added:98 day(s) ago
- Updated:August 13, 2026 at 06:56 PM
Rooms and interior
- Bedrooms:4
- Total bathrooms:5
- Full bathrooms:3
- Half bathrooms:2
- Rooms Total:9
- Kitchen Description:Dishwasher, Disposal, Oven/Range, Refrigerator
- Basement Description:Full Basement, Unfinished
- Living area:4,293 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Hot Air
- Central air:Yes
Structure and exterior
- Year built:1968
- Building area:4,293 sq. ft.
- Lot area:2.05 Acres
- Lot Features:Level Lot, Secluded, Water View
- Architectural Style:French, Modern
- Exterior Features:Deck, French Doors, Garden Area
Schools
- High school:Stonington
- Middle school:Stonington
- Elementary school:Deans Mill
Utilities
- Water:Public Water Connected
- Sewer:Septic
Finances and disclosures
- Price:$4,995,000
- Price per sq. ft.:$1,163.52
- Tax amount:$35,769 (July 2025-June 2026)
Features and amenities
- Appliances:Dishwasher, Disposal, Dryer, Oven/Range, Refrigerator, Washer
- Amenities:Golf Course, Library, Park, Private School(s), Public Rec Facilities, Security System
Parking
- Parking description:Attached Garage
- Garage:Yes
- Garage spaces:3
New listings near 39 Chippechaug Trail
- Open Sat, 12 to 2pmNew
$1,195,000Active2 beds 2 baths1,314 sq. ft.15-1/2 Water Street #4, Groton, CT 06355
MLS# 24198104Listed by: William Pitt Sotheby's Int'l - New
$1,300,000Active5 beds 4 baths2,598 sq. ft.2 Ashby Street, Groton, CT 06355
MLS# 24197394Listed by: CENTURY 21 Shutters & Sails - New
$1,749,000Active5 beds 3 baths4,259 sq. ft.32 East Main Street, Stonington, CT 06355
MLS# 24196733Listed by: William Pitt Sotheby's Int'l - New
$400,000Active3 beds 1 baths1,037 sq. ft.6-1/2 Fort Rachel Place, Groton, CT 06355
MLS# 24196467Listed by: CENTURY 21 Shutters & Sails
$365,000Active2 beds 1 baths900 sq. ft.10 Masons Island Road #8, Stonington, CT 06355
MLS# 24195364Listed by: William Pitt Sotheby's Int'l
$799,000Pending3 beds 4 baths2,411 sq. ft.14 Brandon Lane #14, Stonington, CT 06355
MLS# 24191344Listed by: Coldwell Banker Realty
$895,000Active4 beds 5 baths2,729 sq. ft.14 New London Road, Groton, CT 06355
MLS# 24189185Listed by: Switz Real Estate Associates
$2,795,000Active4 beds 3 baths2,972 sq. ft.23 Gravel Street, Groton, CT 06355
MLS# 24193728Listed by: William Pitt Sotheby's Int'l
$550,000Pending1 beds 1 baths833 sq. ft.60 Willow Street #304, Stonington, CT 06355
MLS# 24190398Listed by: Compass Connecticut, LLC
$930,000Pending3 beds 3 baths2,645 sq. ft.6 Griffen Drive, Stonington, CT 06355
MLS# 24189877Listed by: RE/MAX Coast and Country