50 Winter Ave, Deep River, CT 06417
Property image
Property image
OFF MARKET

50 Winter Ave
Deep River, CT 06417

Deep River Center
  • 2 Beds
  • 1 Bath
  • 813 sqft (on 0.68 acres)

$352,500

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $2,438/mo*
Refinance Your Home

$352,500

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $2,438/mo*
Refinance Your Home
2 Beds
1 Bath
813 sqft
(on 0.68 acres)

Home Value

Trulia Estimate
$353K
Since last month
Increased$8K (+2.3%)
Since last year
Increased$28K (+8.7%)
Since last sale
Increased$143K (+67.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +106% in the last 10 years
MonthEstimated value
2026
August 2026$354K
July 2026$346K
June 2026$353K
May 2026$359K
April 2026$339K
March 2026$330K
February 2026$323K
January 2026$318K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5 Mitchell Lane, Deep River, CT
0.04
Single-Family Home
$366,000
12/29/25
2
1.5
1,081
8 Prospect Hill, Deep River, CT
0.51
Single-Family Home
$345,000
07/24/26
2
1
912
8 Phelps Lane, Deep River, CT
0.52
Single-Family Home
$331,500
07/21/26
2
1
912
138 River St, Deep River, CT
0.58
Single-Family Home
$359,000
09/04/25
2
1
1,032
61 Maple St, Chester, CT
0.59
Single-Family Home
$140,000
07/13/26
2
1
672
79 Middlesex Avenue, Chester, CT
0.61
Single-Family Home
$410,000
04/30/26
2
1
1,470
21 East Liberty Street, Chester, CT
0.91
Single-Family Home
$252,500
11/17/25
2
1
1,012
111 Union St, Deep River, CT
0.83
Single-Family Home
$275,000
12/02/25
2
2
1,172
12 Jones Lane, Deep River, CT
0.82
Single-Family Home
$430,000
06/29/26
2
1
1,200
54 Maple St, Chester, CT
0.74
Single-Family Home
$325,000
11/26/25
3
2
1,260

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
5 Mitchell Lane, Deep River, CT 06417
0.04
$366,000
2
1.5
1,081
Recently Sold
5 Mitchell Terrace, Deep River, CT 06417
0.04
$423,400
3
1.5
1,184
Off Market
32 Winter Avenue, Deep River, CT 06417
0.07
$387,800
4
2
1,598
Off Market
16 Middlesex Avenue, Chester, CT 06412
0.15
$569,800
3
2
1,963
Off Market
95 Castle Heights, Deep River, CT 06417
0.13
-
-
-
-
Off Market
17&21 Winter Avenue, Deep River, CT 06417
0.14
$325,000
2
1.5
1,061
For Sale
16 Winter Avenue, Deep River, CT 06417
0.14
-
5
2
1,553
Off Market
33 Castle Heights, Deep River, CT 06417
0.16
$35,000
-
-
-
Recently Sold
11 Winter Avenue, Deep River, CT 06417
0.17
$327,600
2
1
1,058
Off Market
26 Middlesex Avenue, Chester, CT 06412
0.24
$490,200
4
1.5
1,496
Off Market
38 Main Street, Deep River, CT 06417
0.22
$625,000
4
3
2,560
For Sale
30 Middlesex Avenue, Chester, CT 06412
0.28
$425,300
2
1.5
1,362
Off Market

Local Information

  • Map ViewExplore the area around 50 Winter Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1850
Lot Size
0.68 acres
Living Area
813 sqft
Price/Sqft
$434
Parking
Garage

About this House

This single-family home is located at 50 Winter Ave, Deep River, CT. 50 Winter Ave is in the Deep River Center neighborhood in Deep River, CT and in ZIP code 06417. This property has 2 bedrooms, 1 bathroom and approximately 813 sqft of floor space. This property has a lot size of 0.68 acres and was built in 1850.
50 Winter Ave, Deep River, CT 06417 is a 2 bedroom, 1 bathroom, 813 sqft single-family home in Deep River Center, built in 1850. It last sold for $211,000 on Jun 29, 2007. It is currently off market. The Trulia Estimate is $352,500, with a rent estimate of $2,186/month.

Home Details for 50 Winter Ave

Interior Features

Interior Details
BasementNumber of Rooms: 4Types of Rooms: Breakfast Nook, WorkshopCeiling Fan
Heating & Cooling
Heating: Baseboard, OilHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Softwood, Tile, Linoleum Vinyl
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodGardenLawnPatioPorch
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1850
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 0.68 acres

Mobile R/V

RV Parking
Rv Parking

Price and Tax history

DateEventPrice
Jun 29, 2007
Source: Smart MLS #M9102790
Sold
$211,000
Dec 12, 2003
Source: Smart MLS #M9078283
Sold
$162,000

Market trends in Deep River

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
20
1MoM

Around this home

Neighborhood Overview

Deep River Center
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Deep River Center

At least 10 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 94 % Say there's wildlife

  • 94 % Say car is needed

  • 86 % Say it's walkable to grocery stores

  • 85 % Say yards are well-kept

  • 84 % Say it's walkable to restaurants

  • 82 % Say streets are well-lit

  • 80 % Say parking is easy

  • 76 % Say kids play outside

  • 75 % Say people would walk alone at night

  • 75 % Say there's holiday spirit

  • 73 % Say there are sidewalks

  • 72 % Say neighbors are friendly

  • 60 % Say they plan to stay for at least 5 years

  • 42 % Say there are community events

  • 36 % Say it's quiet

Sourced by Trulia users. Learn more about our methodology.
  • Timothy Ballantyne
    "Friendly helpful neighbors community support for different kinds of groups volunteer firefighters and ambulance "
    0
    Flag
  • Dave M.
    "the deep river muster, all my friends and family, great community!! deep river day in September. Small town America in New England!!"
    4
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 50 Winter Ave

  • What is 50 Winter Ave estimated to be worth?
    Trulia's estimated value for 50 Winter Ave in Deep River, CT is $352,500.
  • What is the price history for 50 Winter Ave?
    50 Winter Ave in Deep River, CT last sold for $211,000 in June 2007.
  • Is Deep River a buyer's or seller's market?
    Deep River is currently a seller's market, based on recent for-sale activity.
  • What do residents say about the Deep River Center neighborhood?
    Residents describe the Deep River Center neighborhood in Deep River, CT as dog-friendly, walkable to grocery stores, and well-kept. See recently sold homes in Deep River Center, Deep River.
  • Does 50 Winter Ave have laundry facilities?
    Yes, 50 Winter Ave in Deep River, CT has in-unit laundry.
  • How big is the lot at 50 Winter Ave?
    The lot at 50 Winter Ave in Deep River, CT is about 0.68 acres (29,621 sq ft).

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