65 Winter Ave, Deep River, CT 06417
OFF MARKET

65 Winter Ave
Deep River, CT 06417

Deep River Center
  • 2 Beds
  • 1 Bath
  • 1,188 sqft (on 0.69 acres)

$335,400

Trulia Estimate
as of Aug 16, 2026
Est. Refi. Payment $2,332/mo*
Refinance Your Home

$335,400

Trulia Estimate
as of Aug 16, 2026
Est. Refi. Payment $2,332/mo*
Refinance Your Home
2 Beds
1 Bath
1,188 sqft
(on 0.69 acres)

Home Value

Trulia Estimate
$335K
Since last month
Decreased$9K (-2.5%)
Since last year
Increased$22K (+7%)
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 +62% in the last 10 years
MonthEstimated value
2026
August 2026$337K
July 2026$336K
June 2026$345K
May 2026$341K
April 2026$320K
March 2026$317K
February 2026$303K
January 2026$303K
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
0.08
Single-Family Home
$366,000
12/29/25
2
1.5
1,081
79 Middlesex Avenue, Chester, CT
0.57
Single-Family Home
$410,000
04/30/26
2
1
1,470
138 River St, Deep River, CT
0.59
Single-Family Home
$359,000
09/04/25
2
1
1,032
8 Phelps Lane, Deep River, CT
0.54
Single-Family Home
$331,500
07/21/26
2
1
912
8 Prospect Hill, Deep River, CT
0.57
Single-Family Home
$345,000
07/24/26
2
1
912
21 East Liberty Street, Chester, CT
0.88
Single-Family Home
$252,500
11/17/25
2
1
1,012
61 Maple St, Chester, CT
0.61
Single-Family Home
$140,000
07/13/26
2
1
672
12 Jones Lane, Deep River, CT
0.88
Single-Family Home
$430,000
06/29/26
2
1
1,200
64 River Lane, Deep River, CT
0.64
Single-Family Home
$563,500
06/15/26
4
1.5
1,241
23 Spring Street, Chester, CT
0.83
Single-Family Home
$550,000
10/15/25
2
1.5
1,104

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
0.08
$366,000
2
1.5
1,081
Recently Sold
5 Mitchell Terrace, Deep River, CT 06417
0.08
$423,400
3
1.5
1,184
Off Market
16 Middlesex Avenue, Chester, CT 06412
0.15
$569,800
3
2
1,963
Off Market
32 Winter Avenue, Deep River, CT 06417
0.14
$389,600
4
2
1,598
Off Market
26 Middlesex Avenue, Chester, CT 06412
0.22
$490,200
4
1.5
1,496
Off Market
95 Castle Heights, Deep River, CT 06417
0.17
-
-
-
-
Off Market
17&21 Winter Avenue, Deep River, CT 06417
0.20
$325,000
2
1.5
1,061
For Sale
30 Middlesex Avenue, Chester, CT 06412
0.26
$427,000
2
1.5
1,362
Off Market
16 Winter Avenue, Deep River, CT 06417
0.20
-
5
2
1,553
Off Market
33 Castle Heights, Deep River, CT 06417
0.22
$35,000
-
-
-
Recently Sold
11 Winter Avenue, Deep River, CT 06417
0.23
$328,600
2
1
1,058
Off Market
15 Gilbert Hill Road, Chester, CT 06412
0.31
$1,087,400
4
3
3,054
Off Market

Local Information

  • Map ViewExplore the area around 65 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
1920
Lot Size
0.69 acres
Living Area
1,188 sqft
Price/Sqft
$282
Parking
Garage

About this House

This single-family home is located at 65 Winter Ave, Deep River, CT. 65 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 1,188 sqft of floor space. This property has a lot size of 0.69 acres and was built in 1920.
65 Winter Ave, Deep River, CT 06417 is a 2 bedroom, 1 bathroom, 1,188 sqft single-family home in Deep River Center, built in 1920. It is currently off market. The Trulia Estimate is $335,400, with a rent estimate of $2,377/month.

Home Details for 65 Winter Ave

Interior Features

Interior Details
BasementAtticNumber of Rooms: 5
Heating & Cooling
Heating: Forced Air, OilHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodPatio
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1920
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 0.69 acres

Price and Tax history

YearProperty taxTax assessment
2025
$4,932
$154,210
Home facts updated by county records

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
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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

Apartments for Rent

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Homes for sale near 65 Winter Ave

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Off Market Homes Near 65 Winter Ave

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Frequently asked questions about 65 Winter Ave

  • What is 65 Winter Ave estimated to be worth?
    Trulia's estimated value for 65 Winter Ave in Deep River, CT is $335,400.
  • 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.
  • What are the closest schools to 65 Winter Ave?
    The closest schools to 65 Winter Ave in Deep River, CT are Deep River Elementary School (Pre-K, rated 7/10), John Winthrop Middle School (rated 4/10), Valley Regional High School (rated 7/10).
  • How big is the lot at 65 Winter Ave?
    The lot at 65 Winter Ave in Deep River, CT is about 0.69 acres (30,056 sq ft).
  • Does 65 Winter Ave have a garage?
    Yes, 65 Winter Ave in Deep River, CT has a garage.