Active

39 Chippechaug Trail

Stonington, CT 06355

$4,995,000 $21,059/Mo

Get Pre-Approved Check your credit

Overview

Bed

Bath

4,293

Sqft

2.05

Acres(Lot)

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 e stablished 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.

Property Details

Property Type : Residential

Price : $4,995,000

AD Id : 78215473

MLS Id : 24172306

Beds : 4

Lot Size : 2.05 Acres

Living Area Size : 4,293

Tax Amount : 37460.00

Year Built : 1968

Garage : 3

County : New London

Map

What's Nearby

Nearby Areas

Features

Bedroom Information

Total beds: 4

Bathroom Information

Total Baths: 5 Full Baths: 3 Half Baths: 2

Room Information

Rooms Total: 9 Has Basement: Yes Basement: Full, Unfinished
Interior Features

Appliances: Dishwasher, Disposal, Dryer, Range, Oven, Refrigerator, Washer
Heating & Cooling

Has Heating: Yes Heating: Geothermal, Forced Air Has Cooling: Yes Cooling: Central Air Water front: 1

Building Information

Year Built: 1968 Building Area Total: 4293 Construction Materials: Other Patio And Porch Features: Deck Private Pool: No Water front Features: Beach Front View: Water
Exterior Features

Exterior Features: Garden, Dock

Lot Information

Lot Size Acres: 2.05 Lot Description: Level, Waterfront

Listing Price Information

Listing Price: $4995000 Original Price: $5995000

Tax Information

Parcel Number: 2076943 Annual Tax: $37460

Virtual Tour

Virtual Tour (External Link)

Parking Information

Attached

Garage Information

Has Garage: Yes Has Attached Garage: Yes Garage Space: 3

Homeowners Association Information
Has Association: Yes Community Features: Golf

School Information

Elementary School: Deans Mill

Junior High School: Stonington

Senior High School: Stonington
Location Information

Direction: Route 1 to mason island road WaterSource: Public Security Features: Security System

Sell a home like this and save $299,201 Find out How

How much is this property worth?

Curious about this home's true market value? Use our free Home Evaluation Tool to instantly get a personalized Comparative Market Analysis (CMA) report. Make smarter, data-driven decisions before you buy.

Loading, please wait...

Nearby Home Value

Address	Estimate	Bed	Bath	Sq. Ft	Lot Size
29 Dubois Drive, Stonington, CT, 06355	$2,950,000	4	4	3,360	0.19 Acre
7 Osprey Lane, Stonington, CT, 06355	$1,200,000	3	2	1,877	0.32 Acre
2 Stafford Street, Stonington, CT, 06355	$800,000	4	2	1,692	0.18 Acre
152 Whitehall Avenue, Stonington, CT, 06355	$4,350,000	4	6	7,000	2.06 Acres
40 Holmes Street, Stonington, CT, 06355	$1,600,000	3	3	2,402	0.30 Acre
152 & 156 Whitehall Ave.., Stonington, CT, 06355	$4,350,000	10	10	9,872	4 Acres
32 E Main Street, Stonington, CT, 06355	$1,749,000	5	3	4,259	0.25 Acre
32 Money Point Road, Stonington, CT, 06355	$1,975,000	6	3	2,899	0.66 Acre
31 N Stonington Road, Stonington, CT, 06355	$515,000	2	2	1,490	0.48 Acre

Similar Homes To 39 Chippechaug Trail

Nearby For Sale

$1,120,100

Home For Sale

23 Summertime Circle,
Stonington, CT, 06379

Bed

Bath

Sqft

Acre(Lot)

417 River Road,
Stonington, CT, 06379

Bed

Bath

Sqft

Acre(Lot)

3 Lamberts Lane,
Stonington, CT, 06378

Bed

Bath

Sqft

Acre(Lot)

1189 Pequot Trail,
Stonington, CT, 06378

Bed

Bath

Sqft

Acres(Lot)

1189 Pequot Trail,
Stonington, CT, 06378

Bed

Bath

1,170

Sqft

77.88

Acres(Lot)

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

ByOwner last updated this listing 09/09/2026 @ 22:23

MLS: 24172306 LISTED BY: Danielle Malloy, Serhant Connecticut, LLC SOURCE: SmartMLS