Date
Details
Price
Change
Source
5/07/2026
Listed
$5,995,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Property Description
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.
Full Property Details
Full Property Details for 39 Chippechaug Trail
General
- Price: $5,995,000
- Taxes: (July 2025-June 2026)
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24172306
- Updated: 5/8/2026
- Added to Site: 16 day(s) ago
Interior
- Number of Rooms: 9
- Interior Features: Security System
- Fireplace: Yes
- Number of Fireplaces: 2
- Appliances: Oven/Range, Refrigerator, Dishwasher, Disposal, Washer, Dryer
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 3
- Half Bathrooms: 2
Bedrooms
- Total Bedrooms: 4
- Primary Suite: Upper
- Bedroom 1: Bedroom, Upper
- Bedroom 2: Bedroom, Upper
- Bedroom 3: Bedroom, Upper
Exterior
- Exterior Features: Deck, Garden Area, French Doors
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Parking: Attached Garage
Location
- County: New London
- Neighborhood: Masons Island
- Driving Directions: Route 1 to mason island road
School Information
- Elementary School: Deans Mill
- Middle School: Stonington
- High School: Stonington
Community
- Community Name: Masons Island
- Association: Yes
- Home Owners Assn.: 1
- Assoc. Fees Include: Road Maintenance
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Hot Air, Geothermal
- Heating Fuel: Geothermal
- Water Heater: Other
Utilities
- Sewer: Septic
- Water: Public Water Connected, Other
Structural Information
- Architectural Style: French, Modern
- Construction Status: No/Resale
- Exterior Const.: Other
- Basement Desc.: Full, Unfinished
- Roof: Other
- Square Feet: 4,293
- Above Ground: 4,293 Sq. Ft.
- Year Built: 1968
Lot Features
- Lot Size (Acres): 2.05
- Zoning: RA-20
- Lot Description: Secluded, Level Lot, Water View
Water Features
- Water Front: Yes
- Water View: Yes
- Water Front Desc.: L. I. Sound Frontage, Beach, Dock or Mooring, Water Community, View
Green Features
- Energy Features: Geothermal Heat
Financial Considerations
- Assessment Amount: $1,657,500
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Property ID: 2076943
Listed by Serhant Connecticut, LLC, CT LUXE TEAM, Danielle Malloy and Serhant Connecticut, LLC, Jonathan Shockley
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agents
— 39 Chippechaug Trail —
Danielle Malloy
Serhant Connecticut, LLC
Jonathan Shockley
Serhant Connecticut, LLC
Agent Contact: (203) 921-9987 Office Contact: (203) 489-7800
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 39 Chippechaug Trail
School District:Stonington School District
| Name | Grades | Distance |
|---|---|---|
Deans Mill School 35 Deans Mill Road, Stonington, CT 06378 | K-5 | 3.1 mi |
Stonington Middle School 204 Mistuxet Avenue, Stonington, CT 06355 | 6-8 | 2.3 mi |
Stonington High School 176 South Broad St., Stonington, CT 06379 | 9-12 | 6 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 39 Chippechaug Trail
Tax History
Tax History for 39 Chippechaug Trail
Year
Property Taxes
Change
Tax Assessment
Change
2025
$35,769
4%
$1,657,500
—
2023
$34,559
9%
$1,657,500
—
2023
$31,575
13%
$1,657,500
55%
2022
$27,955
1%
$1,072,700
—
2021
$27,799
3%
$1,072,700
—
2020
$26,989
—
$1,072,700
—
2019
$26,882
3%
$1,072,700
—
2018
$26,077
-6%
$1,072,700
-5%
2017
$27,775
3%
$1,128,600
—
2016
$27,019
4%
$1,128,600
—
2015
$25,901
4%
$1,128,600
—
2014
$24,897
3%
$1,128,600
—
2011
$24,276
—
$1,128,600
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 39 Chippechaug Trail
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- Single Family
- Active
- Updated 4 hours ago
- 4Beds
- 5Total Baths
- 4,293Sq. Ft.
Listed by Serhant Connecticut LLC
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- Single Family
- Active
- Updated 1 hour ago
- 4Beds
- 2Total Baths
- 1,990Sq. Ft.
- Single Family
- Active
- Updated 3 days ago
- 3Beds
- 2Total Baths
- 2,078Sq. Ft.
- Single Family
- Active
- Updated 4 hours ago
- 2Beds
- 1Total Bath
- 621Sq. Ft.
- Single Family
- Active
- Updated 19 hours ago
- 3Beds
- 3Total Baths
- 2,307Sq. Ft.
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- Land Residential
- Active
- Updated 5 days ago
- 8.31Acres
- Single Family
- Active
- Updated 5 days ago
- 2Beds
- 1Total Bath
- 3,588Sq. Ft.
39 Chippechaug Trail, Stonington, CT 06355 (MLS# 24172306) is a Single Family property with 4 bedrooms, 3 full bathrooms and 2 partial bathrooms. 39 Chippechaug Trail is currently listed for $5,995,000 and was received on May 07, 2026. Want to learn more about 39 Chippechaug Trail? Do you have questions about finding other Single Family real estate for sale in Masons Island? You can browse all Masons Island real estate or contact a Coldwell Banker agent to request more information.