365 Winthrop Road
Deep River, Connecticut 06417
- Beds
- 3
- Baths
- 2
- SqFt
- 1,984
- Acres
- 1.20
- Year Built
- 1840
- Neighborhood
- Winthrop
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Welcome to 365 Winthrop Road in Deep River, where historic charm meets thoughtful updates. This beautifully maintained 3-bedroom, 2-bathroom home offers timeless character alongside the conveniences of modern living. The spacious main level features a large kitchen, formal dining room, inviting living room, cozy den, and a stunning great room with French doors leading to the backyard, perfect for entertaining or everyday living. Upstairs, you'll find a convenient laundry room, two bedrooms and a generous primary suite filled with natural light, featuring cathedral ceilings, exposed post-and-beam construction, ample closet space, and an en suite bathroom. Step outside to enjoy a picturesque setting with beautiful stonework, mature gardens, and a charming gazebo. A storage shed and a separate workshop with electricity and heating/cooling provide endless possibilities for hobbies, projects, or additional workspace. Recent improvements include hot water heater (December 2025) a new roof and well pump (April 2026). Don't miss this unique opportunity to own a home that seamlessly blends historic character and exceptional outdoor living in Deep River.
Key Facts
- City/Town
- Deep River
- Neighborhood
- Winthrop
- Property / Style
- Single Family · Colonial
- Year Built
- 1840
- Days on Market
- 20 days
- Beds
- 3
- Baths
- 2 full
- Living Area
- 1,984 sq ft
- Lot Size
- 1.20 acres
- Property Taxes
- $6,705 / Annually
Market Snapshot
The Deep River Market
Single Family · trailing 12 months
Active Listings
10
12 under contract
Median List Price
$887,000
10 active listings
Median Closed Price
$457,000
42 sales
Median Days on Market
33
10 active listings
Median $ / Sq Ft
$317
10 active listings
Sale-to-List Ratio
100.0%
42 sales
How this home compares
List Price
$475,000
vs $887,000 median
46.4% below median
Price / Sq Ft
$239
vs $317 median
24.6% below median
Days on Market
20 days
vs 33 days median
13 days fresher than median
Based on 10 active and 42 closed sales (trailing 12 mo) of single family in Deep River. Source: SmartMLS · As of July 28, 2026.
Location
365 Winthrop Road, Deep River, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,422
- Property Taxes$559
- Insurance$158
- 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
- Colonial
- Year Built
- 1840
- New Construction
- No/Resale
- Living Area
- 1,984 sq ft
Schools
- Elementary
- Deep River
- High
- Valley
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Upper Level
- Laundry Location
- laundry room located upstairs
- Appliances
- Oven/RangeMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- Crawl SpacePartialSump PumpPartial With Hatchway
- Interior Features
- Central Vacuum
- Additional Rooms
- Laundry Room
Exterior & Lot
- Lot Size
- 1.20 acres
- Zoning
- R60
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- ClapboardWood
- Color
- white
- Roof
- Asphalt Shingle
- Foundation
- ConcreteStone
- Exterior Features
- ShedGazeboGarden AreaLightingStone WallFrench DoorsPatio
- Lot Description
- Lightly WoodedLevel Lot
Listing & Financials
- Property Taxes
- $6,705 / Annually
- Days on Market
- 20
- MLS #
- 24189405
- MLS Status
- Under Contract - Continue to Show
Similar Properties
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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 7/28/2026. 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 7/28/2026 at 5:15 AM UTC.