2 Pinewood Trail
Deep River, Connecticut 06417
- Beds
- 3
- Baths
- 3 | 1
- SqFt
- 2,403
- Acres
- 1.96
- Year Built
- 1990
- Neighborhood
- Winthrop
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
12
10 under contract
Median List Price
$734,450
12 active listings
Median Closed Price
$480,000
51 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 15, 2026per 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
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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.