32 Winter Avenue, Deep River, CT 06417
OFF MARKET

32 Winter Avenue
Deep River, CT 06417

Deep River Center
  • 4 Beds
  • 2 Baths
  • 1,598 sqft (on 0.29 acres)

$392,800

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $2,706/mo*
Refinance Your Home

$392,800

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $2,706/mo*
Refinance Your Home
4 Beds
2 Baths
1,598 sqft
(on 0.29 acres)

Home Value

Trulia Estimate
$393K
Since last month
Increased$9K (+2.4%)
Since last year
Increased$50K (+14.6%)
Since last sale
Increased$58K (+17.3%)
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 +79% in the last 10 years
MonthEstimated value
2026
August 2026$393K
July 2026$384K
June 2026$366K
May 2026$358K
April 2026$362K
March 2026$365K
February 2026$359K
January 2026$354K
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
2 Crescent Street, Deep River, CT
0.43
Single-Family Home
$421,000
12/19/25
4
1.5
1,878
15 Prospect Street, Deep River, CT
0.49
Single-Family Home
$393,000
11/21/25
3
2
1,352
15 Grove Street, Deep River, CT
0.62
Single-Family Home
$415,000
07/24/26
4
1.5
1,080
64 River Lane, Deep River, CT
0.63
Single-Family Home
$563,500
06/15/26
4
1.5
1,241
69 High Street, Deep River, CT
0.80
Single-Family Home
$407,000
11/24/25
2
1.5
1,440
8 Prospect Hill, Deep River, CT
0.45
Single-Family Home
$345,000
07/24/26
2
1
912
8 Phelps Lane, Deep River, CT
0.51
Single-Family Home
$331,500
07/21/26
2
1
912

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
17+21 Winter Avenue, Deep River, CT 06417
0.02
$289,900
3
2.5
1,061
For Sale
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
$436,900
3
1.5
1,184
Off Market
16 Winter Avenue, Deep River, CT 06417
0.08
-
5
2
1,553
Off Market
11 Winter Avenue, Deep River, CT 06417
0.10
$326,600
2
1
1,058
Off Market
33 Castle Heights, Deep River, CT 06417
0.11
$35,000
-
-
-
Recently Sold
95 Castle Heights, Deep River, CT 06417
0.12
-
-
-
-
Off Market
16 Middlesex Avenue, Chester, CT 06412
0.18
$569,800
3
2
1,963
Off Market
38 Main Street, Deep River, CT 06417
0.15
$625,000
4
3
2,560
For Sale
57 Main Street, Deep River, CT 06417
0.20
$523,000
5
3
2,000
Off Market
26 Middlesex Avenue, Chester, CT 06412
0.27
$488,300
4
1.5
1,496
Off Market

Local Information

  • Map ViewExplore the area around 32 Winter Avenue.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1900
Lot Size
0.29 acres
Living Area
1,598 sqft
Price/Sqft
$246
Parking
None

About this House

This 18th century rumored home of Billy Winters, and many travelers passing through the Underground Railroad, is rich with history. If the walls could talk, they could surely tell a story or two! Throughout the years this loved home was once a 2-family, the laundry room on the 2nd floor was the kitchen - perhaps it could be once again. Upstairs has three bedrooms and a full bath, and the first floor boasts a bedroom, a full bath, an office or another bedroom, with second laundry hookups in the basement. The location is ideal, off the main road but walking distance to downtown Deep River, Chester, and the infamous High Nine Brewery! From the beautiful curb appeal of the Victorian-esque front porch, to the shining, vintage hard wood floors, and the walk-up attic - this home is simply one of a kind. With the recent price reductions, home is selling As-is.
32 Winter Avenue, Deep River, CT 06417 is a 4 bedroom, 2 bathroom, 1,598 sqft single-family home in Deep River Center, built in 1900. It last sold for $335,000 on Dec 20, 2024 (4% below the $349,000 asking price). It is currently off market. The Trulia Estimate is $392,800, with a rent estimate of $3,006/month.
Last check for updates: about 11 hours ago
Listed by Rachel Welch, (860) 304-6896
William Raveis Real Estate, (860) 388-3936
Bought with: Cindy Breckheimer, (860) 690-3141, Forever Homes Real Estate LLC, (860) 690-3141
Source: Smart MLS, MLS#24029886

Home Details for 32 Winter Avenue

Interior Features

Interior Details
Basement: Partial,Sump PumpNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom, Dining Room, Kitchen, Office
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1598 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Refrigerator, Dishwasher, Water Heater, Electric Water HeaterDishwasherLaundry: Upper LevelRefrigerator
Heating & Cooling
Heating: Baseboard,Forced Air,Zoned,Electric,OilNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
No Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: PorchFoundation: StoneNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageParking: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1598 Square Feet

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial,Antique
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 961883

Price & Status

Price
List Price: $349,000
Status Change & Dates
Off Market Date: Mon Nov 04 2024Possession Timing: Immediate

Active Status

MLS Status: Closed

Location

Direction & Address
City: Deep River
School Information
Elementary School: Per Board of EdHigh School: Per Board of Ed

Building

Building Area
Building Area: 1598 Square Feet

Community

Community Features: Health Club, Library, Park, Playground, Stables/Riding
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 0.29 acres

Miscellaneous

BasementMls Number: 24029886Attic: Walk-upAbove Grade Unfinished Area: 1598

Additional Information

Health ClubLibraryParkPlaygroundStables/Riding

Price and Tax history

DateEventPrice
Dec 20, 2024
Source: Smart MLS #24029886
Sold
$335,000
Dec 20, 2024
Source: William Raveis Real Estate, Mortgage & Insurance #24029886
PendingToActive
$349,000
Nov 4, 2024
Source: William Raveis Real Estate, Mortgage & Insurance #24029886
Pending
$349,000
Nov 1, 2024
Source: Smart MLS #24029886
PriceChange
$349,000
Price decreased by 3%
Sep 24, 2024
Source: Smart MLS #24029886
PriceChange
$360,000
Price decreased by 8%

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

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Frequently asked questions about 32 Winter Avenue

  • What is 32 Winter Avenue estimated to be worth?
    Trulia's estimated value for 32 Winter Avenue in Deep River, CT is $392,800.
  • What is the price history for 32 Winter Avenue?
    32 Winter Avenue in Deep River, CT last sold for $335,000 in December 2024.
  • 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 32 Winter Avenue have laundry facilities?
    Yes, 32 Winter Avenue in Deep River, CT has laundry facilities.
  • How big is the lot at 32 Winter Avenue?
    The lot at 32 Winter Avenue in Deep River, CT is about 0.29 acres (12,632 sq ft).

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