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.
All offers need to be submitted by Tuesday 7/14 at 10am.
Est. $2,887 per month, based on comparable rentals
Sale and tax history for 365 Winthrop Rd
Sale History
Tax History
Date
Event
Price
Smart MLS #24189405
Aug 14, 2026
Sold
$568,000
$286/sq ft
Aug 11, 2026
Pending
—
Jul 15, 2026
Contingent
—
Jul 10, 2026
Listed
$475,000
$239/sq ft
Jul 8, 2026
Coming Soon
$475,000
$239/sq ft
Public Records
Jun 16, 1993
Sold
$95,000
$48/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$6,264 (+3.1%)
$49,840 + $159,810
$209,650
2022
$6,076 (−2.0%)
$49,840 + $159,810
$209,650
2021
$6,201 (−1.9%)
$49,840 + $159,810
$209,650
2020
$6,319 (+1.9%)
$49,840 + $160,860
$210,700
2019
$6,199
$49,840 + $160,860
$210,700
2018
$6,199 (+1.7%)
$49,840 + $160,860
$210,700
2017
$6,093 (+5.0%)
$49,840 + $160,860
$210,700
2016
$5,801 (+10.8%)
$49,840 + $160,860
$210,700
2014
$5,234 (+3.2%)
$50,540 + $151,690
$202,230
2011
$5,072
$50,540 + $151,690
$202,230
Public record
Beds
3
Baths
2
Stories
2
Lot width
—
Lot depth
—
Lot size
1.2 Acres
Year renovated
—
Sq. Ft.
1,984
Year built
1840
Style
Single Family Residential
County
Middlesex County
APN
960975
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 13, 2023.
Property details
Interior
Interior Information
Total Rooms: 8
Laundry Room Location: laundry room located upstairs
Laundry Room Info: Upper Level
Interior Features: Central Vacuum
Fireplaces Total: 2
Cooling System: Central Air
Appliances Included: Oven/Range, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer
Bathroom Information
# of Baths (Full): 2
Bedroom Information
Beds Total: 3
Room Information
Rooms Additional: Laundry Room
Basement Description: Crawl Space, Partial, Sump Pump, Partial With Hatchway
Exterior
Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Clapboard, Wood
Exterior Features: Shed, Gazebo, Garden Area, Lighting, Stone Wall, French Doors, Patio
Lot Information
Lot Description: Lightly Wooded, Level Lot
Building Information
Foundation Type: Concrete, Stone
Construction Description: Frame
Color: white
Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 1984
Financial
Assessments Information
Assessed Value: $209,650
Utilities
Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Electric, 50 Gallon Tank
Heat Type: Hot Air
Heat Fuel Type: Oil
Fuel Tank Location: In Basement
Location
School Information
High School: Valley
Elementary School: Deep River
Location Information
State: Connecticut
Directions: per gps
County: Middlesex
Public facts
Beds: 3
Baths: 2.0
Sq. Ft.: 1,984
Stories: 2.0
Lot Size: 1.2 acres
Style: Single Family Residential
Year Built: 1840
Year Renovated: —
County: Middlesex County
APN: 960975
Home facts updated by county records on Jul 13, 2023
Other
Documents & Disclosures
Supplement Count Public: 1
Around this home
Schools
Deep River Elementary School
Public PreK-6 • Assigned • 3.1mi
7/10
John Winthrop Middle School
Public 7-8 • Assigned • 1.6mi
4/10
Valley Regional High School
Public 9-12 • Assigned • 2.0mi
7/10
Provided by GreatSchools
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
5/10 Heat Factor
7 days above 93° expected this year, 17 days in 30 years
6/10 Wind Factor
77% chance of strong winds in next 30 years
4/10 Air Factor
3 unhealthy days expected this year, 5 days in 30 years
Provided by First Street
Historical weather
Deep River, CT • 06417
Average low and high temperatures (°F)
34
21
36
22
51
33
60
42
68
51
80
60
83
66
80
59
76
57
65
47
54
38
39
25
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
97/ 100
Exceptional sunlight
Sunscore
This home ranks in the top 16% for direct sun exposure in Deep River. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.3 hrs
5.5 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$487,000 – $589,000
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