39 Chippechaug Trail - Stonington, CT

$4,995,000

Beds

5.00

Baths

4,293

SqFt

2.05

Acres

Pricing Insight: Originally listed for $5,995,000, the price was last adjusted to $4,995,000 on July 20, 2026, a –$1,000,000 (16.7%) change, approximately 0 days ago. This property has been on the market for approximately 74 days.

39 Chippechaug Trail, Stonington, CT is a 4-bed, 5-bath, 4,293 square foot home built in 1968 , featuring french,modern architecture. This home is part of a homeowners association. The HOA fee includes: road maintenance.

This home is within the Stonington school district. Local, with nearby schools including Deans Mill.

MLS #: 24172306

Offered Price: $4,995,000

Residence Type: Single Family

Architectural Style: French,Modern

Living Area: 4,293 Sq. Ft.

Lot Size: 2.05 Acres

Neighborhood: Masons Island

County: New London

Year Built: 1968

Design & Construction: Masonry

Heating: Hot Air

Cooling: Central Air

Garage Spaces: 3

Price per Sq Ft as listed: $1,164

Estimated Tax: $35,769

Days on Market: 74

$4,995,000

0 Beds · 0 Baths · 0 Sq Ft

39 Chippechaug Trail, Stonington

Home Automation: Not specified

Energy Features: Geothermal Heat

Solar Contract: Not specified

Heating Fuel: Geothermal

Fuel Type: Hot Air

Fuel Tank Location: Not specified

Cooling System: Central Air

Hot Water System: Other

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $1,164 / Sq. Ft.

Tax assessed value: $1,657,500

Estimated Tax: $35,769

Architectural Style: French,Modern

Design & Construction: Masonry

Residence Type: Single Family

Year Constructed: 1968

Living Area: 4,293 Sq. Ft.

Lot Size: 2.05 Acres

Fuel: Geothermal

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AUTOMATED VALUATION ESTIMATE

Note: Computer-generated estimate, not an appraisal.

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Understanding This Valuation

The RPR AVM considers:

Recent sales of comparable properties
Property characteristics and location
Market trends in Stonington
Statistical modeling algorithms

Local Market Context

Active Listings: 84

Average Price: $1,337,505

Average DOM: 74 days

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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.

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Flood Risk Assessment Water Body Detected Nearby

Water Proximity Detected: This property exhibits indicators suggesting nearby or referenced water features

Location Analysis:

Water features noted

Water Proximity:

Near water body

Topography:

Standard terrain • 2.1 acres

Water Indicators Found:

Water-related features referenced in listing details

Recommendations:

Professional flood assessment advised
Based on identified water-related indicators, flood insurance may warrant consideration
Consult FEMA Flood Maps for zone verification
Evaluate drainage systems
Review local flood history

Risk Level: Moderate

Property near water bodies. Consider flood insurance.

Walkability Score: calculating…
Motif Lifestyle Score: calculating…

Amenity Access Summary

Dining & Café Access: Low to Moderate
Daily Services: Limited
Recreational Space: Limited Nearby

How These Scores Are Calculated

These scores reflect the proximity and concentration of nearby amenities, measured against a typical town-center environment.

Walkability emphasizes access to daily necessities such as groceries, pharmacies, banking, and routine services.
Motif Lifestyle emphasizes dining, cafés, parks, and leisure destinations that contribute to neighborhood character and quality of life.

All scores are normalized on a 0–100 scale to allow consistent comparison across different locations.

84

Homes For Sale

$1,337,505

Average List Price

Mechanicals & Utilities: Hot Air • Geothermal • Central Air • Public Water Connected,Other water • 2 fireplaces

Exterior Features

Exterior Construction: Other

Roof Type: Other

Foundation: Concrete

Garage: Attached Garage (3 car)

Patio/Deck: Deck,Garden Area,French Doors

Utilities: Water: Public Water Connected,Other

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George Antonopoulos

Real Estate Advisor

Stonington • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

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(800) 555-0001

george@appzentric.com

Good afternoon George, I'm interested in
39 Chippechaug Trail, Stonington, Connecticut

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