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2 Pinewood Trail

Deep River, Connecticut 06417

ACTIVE - NEW$685,000
Beds
3
Baths
3 | 1
SqFt
2,403
Acres
1.96
Year Built
1990
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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About This Home

Discover this dramatic modern Cape-style living in this beautifully appointed 3-bedroom, 3-bath home nestled in the scenic Connecticut River Valley. Set on a peaceful dead-end street, with your own private pond, this exceptional property blends contemporary design, inviting spaces, and picturesque natural surroundings. Hardwood floors and a soaring cathedral ceiling create an impressive, open first-floor living area centered around a cozy fireplace. The modern kitchen features stainless steel appliances and flows seamlessly into the main living and entertaining spaces. A desirable first-floor primary suite offers comfort and convenience, while two additional bedrooms on the upper floor provide flexible accommodations for family, guests, or a home office. The fully finished lower level expands your living space with an above-grade walkout, creating the perfect setting for recreation, relaxation, or entertaining. Step outside to enjoy professionally landscaped grounds, along your tranquil pond, and an inviting outdoor firepit-ideal for gathering with friends or unwinding under the stars. A two-car garage adds everyday convenience and storage. Enjoy the serenity of a beautiful natural setting and experience the best of Historic Connecticut River Valley!

Key Facts

City/Town
Deep River
Neighborhood
Winthrop
Property / Style
Single Family · Cape Cod
Year Built
1990
Days on Market
0 days
Beds
3
Baths
3 full · 1 half
Living Area
2,403 sq ft
Lot Size
1.96 acres
Property Taxes
$9,554 / Annually

Market Snapshot

The Deep River Market

Single Family · trailing 12 months

Median Days on Market

36

12 active listings

Median $ / Sq Ft

$306

12 active listings

Sale-to-List Ratio

101.1%

51 sales

How this home compares

List Price

$685,000

vs $734,450 median

6.7% below median

Price / Sq Ft

$285

vs $306 median

6.9% below median

Days on Market

0 days

vs 36 days median

36 days fresher than median

Based on 12 active and 51 closed sales (trailing 12 mo) of single family in Deep River. Source: SmartMLS · As of October 19, 2026.

Location

2 Pinewood Trail, Deep River, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,818

per month

  • Principal & Interest$3,794
  • Property Taxes$796
  • Insurance$228
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Deep River
Neighborhood
Winthrop
County
Middlesex

Residence

Property Type
Single Family
Style
Cape Cod
Year Built
1990
New Construction
No/Resale
Living Area
2,403 sq ft
Below Grade
757 sq ft

Schools

Elementary
Deep River
High
Valley

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Window Unit
Fireplaces
1
Laundry
Main Level
Appliances
Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
Basement
FullHeatedSump PumpFully FinishedInterior AccessWalk-out
In-Law Apartment
PossibleLower Level
Interior Features
Open Floor Plan

Exterior & Lot

Lot Size
1.96 acres
Zoning
R80
Waterfront
Direct waterfront
Waterfront Details
Pond
Water Source
Private Well
Sewer
Septic
Construction
Clapboard
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
DeckGutters
Lot Description
Professionally LandscapedWater ViewOpen Lot

Listing & Financials

Property Taxes
$9,554 / Annually
Days on Market
0
MLS #
24212188
MLS Status
Active

Similar Properties

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Listed By

Angela Ruel

(860) 575-0754

Berkshire Hathaway NE Prop.

(860) 388-3411

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 10/19/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 10/19/2026 at 2:05 PM UTC.