32 Winter Avenue
Deep River, CT 06417
Deep River Center
4 Beds
2 Baths
1,598 sqft (on 0.29 acres)
4 Beds
2 Baths
1,598 sqft
(on 0.29 acres)
Local Information
- Map ViewExplore the area around 32 Winter Avenue.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Description
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 $366,400, with a rent estimate of $3,061/month.
Home Highlights
Parking
None
Outdoor
Porch
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 32 Winter Avenue
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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 |
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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 |
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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 |
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Price List Price: $349,000 |
Status Change & Dates Off Market Date: Mon Nov 04 2024Possession Timing: Immediate |
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MLS Status: Closed |
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Direction & Address City: Deep River |
School Information Elementary School: Per Board of EdHigh School: Per Board of Ed |
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Building Area Building Area: 1598 Square Feet |
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Community Features: Health Club, Library, Park, Playground, Stables/Riding |
Other Playground |
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No HOA |
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Lot Area: 0.29 acres |
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BasementMls Number: 24029886Attic: Walk-upAbove Grade Unfinished Area: 1598 |
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Health ClubLibraryParkPlaygroundStables/Riding |
Last check for updates: about 19 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
Price History for 32 Winter Avenue
| Date | Price | Event | Source |
|---|---|---|---|
| 12/20/2024 | $335,000 | Sold | Smart MLS #24029886 |
| 12/20/2024 | $349,000 | PendingToActive | William Raveis Real Estate, Mortgage & Insurance #24029886 |
| 11/04/2024 | $349,000 | Pending | William Raveis Real Estate, Mortgage & Insurance #24029886 |
| 11/01/2024 | $349,000 | PriceChange | Smart MLS #24029886 |
| 09/24/2024 | $360,000 | PriceChange | Smart MLS #24029886 |
| 09/09/2024 | $390,000 | PriceChange | Smart MLS #24029886 |
| 07/07/2024 | $399,000 | Listed For Sale | Smart MLS #24029886 |
| 09/02/2003 | $229,900 | Sold | Smart MLS #M9072291 |
| 11/05/1998 | $110,000 | Sold | N/A |
Market trends in Deep River
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
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Price per sq ft
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Available listings
14
1MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $5,478 |
| Assessment | $171,290 |
Home facts updated by county records
Comparable Sales for 32 Winter Avenue
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.08 | Single-Family Home | $366,000 | 12/29/25 | 2 | 1.5 | 1,081 | |
0.43 | Single-Family Home | $421,000 | 12/19/25 | 4 | 1.5 | 1,878 | |
0.49 | Single-Family Home | $393,000 | 11/21/25 | 3 | 2 | 1,352 | |
0.56 | Single-Family Home | $610,000 | 08/01/25 | 3 | 1.5 | 1,570 | |
0.63 | Single-Family Home | $563,500 | 06/15/26 | 4 | 1.5 | 1,241 | |
0.80 | Single-Family Home | $407,000 | 11/24/25 | 2 | 1.5 | 1,440 | |
0.69 | Single-Family Home | $780,000 | 01/15/26 | 3 | 2 | 1,772 | |
0.65 | Single-Family Home | $379,000 | 11/26/25 | 3 | 1 | 1,144 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
SOLDDEC 29, 2025William Raveis Real Estate
OFF MARKETCalcagni Real Estate
OFF MARKETDB Associates of CT, LLC
OFF MARKETWilliam Raveis Real Estate
OFF MARKETRe/Max Valley Shore
OFF MARKETWilliam Pitt Sotheby's Int'l
Assigned Schools
These are the assigned schools for 32 Winter Avenue.
- John Winthrop Middle School
- 7-8
- Public
- 197 Students
4/10GreatSchools RatingParent Rating AverageI think bullying was the worst problem that happened during my time at JWMS. The adult authorities at the school had a difficult time understanding situations and that often made it worse. I'm also not stating that it was just the kids at the school who would bully but it was also teachers. I remember my 8th grade science teacher would verbally bully girls and pick on them, and it was always girls he was picking on. I was one of them. It didn't help that I had a counselor who couldn't care less if one of there students just jumped off a bridge. They could care less of there students well being, and the same goes with the principles. I honestly would recommend going to a different school, I mean unless you want your child to become depressed.Other Review8y ago - Valley Regional High School
- 9-12
- Public
- 429 Students
7/10GreatSchools RatingParent Rating AverageI enjoyed going to Valley. It is different as a parent I see things differently. However compared to other schools I would say Valley is above the rest.Parent Review7y ago - Deep River Elementary School
- PK-6
- Public
- 189 Students
7/10GreatSchools RatingParent Rating AverageOutstanding teaching staff and principal! Very proactive in getting needed resources to each child with an awesome team approach. Focus on good citizenship. This school really fosters a great atmosphere for learning!Parent Review13y ago 
Check out schools near 32 Winter Avenue.
Neighborhood Overview
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.
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Homes for sale near 32 Winter Avenue
NEWOPEN SAT, 1-3PM0.68 ACRESRe/Max Valley Shore
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Off Market Homes Near 32 Winter Avenue
SOLDJUL 8, 2026William Pitt Sotheby's Int'l
SOLDJUL 6, 2026Berkshire Hathaway NE Prop.
SOLDJUN 29, 2026William Raveis Real Estate
SOLDJUN 22, 2026William Pitt Sotheby's Int'l
SOLDJUN 12, 2026Great Estates, CT
SOLDJUN 10, 2026Coldwell Banker Realty
SOLDJUN 9, 2026Berkshire Hathaway NE Prop.- See more homes for sale inDeep River
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