104 Maloney Court
Winchester, Connecticut 06098
Reduced from $289,000
- Beds
- 3
- Baths
- 1
- SqFt
- 1,008
- Acres
- 0.31
- Year Built
- 1957
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Perched on desirable Wallens Hill with beautiful western sunset views, this lovingly maintained 3 bed 1957 ranch is full of warmth, charm, and pride of ownership. Bright and sunny throughout, the home offers 1,008 square feet of comfortable living space with hardwood floors, central air conditioning, and an easy-flow layout designed for everyday living. The spacious eat-in kitchen features oak cabinetry, abundant workspace, and a welcoming atmosphere perfect for gathering. A cozy three-season porch provides the ideal place to enjoy your morning coffee or unwind at the end of the day while overlooking the peaceful backyard. Outside, the gently tapered yard is a gardener's dream with mature perennial plantings, space for raised beds, and room to relax on the rear platform deck. The dry lower level includes laundry, interior access to the garage, and added convenience for bringing in groceries and storage. Clean, efficient, and beautifully cared for, this adorable ranch offers timeless character and broad appeal for buyers seeking comfort, simplicity, and a truly move-in ready home in the heart of Winchester. Don't miss this!
Key Facts
- City/Town
- Winchester
- Neighborhood
- N/A
- Property / Style
- Single Family · Ranch
- Year Built
- 1957
- Days on Market
- 81 days
- Beds
- 3
- Baths
- 1 full
- Living Area
- 1,008 sq ft
- Lot Size
- 0.31 acres
- Garage / Parking
- 1 garage · 3 total
- Property Taxes
- $3,142 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
12
12 under contract
Median List Price
$524,900
12 active listings
Median Closed Price
$325,000
103 sales
Median Days on Market
39
12 active listings
Median $ / Sq Ft
$265
12 active listings
Sale-to-List Ratio
100.0%
103 sales
How this home compares
List Price
$279,000
vs $524,900 median
46.8% below median
Price / Sq Ft
$277
vs $265 median
In line with median
Days on Market
81 days
vs 39 days median
42 days longer than median
Based on 12 active and 103 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of July 28, 2026.
Location
104 Maloney Court, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,423
- Property Taxes$262
- Insurance$93
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Ranch
- Year Built
- 1957
- New Construction
- No/Resale
- Living Area
- 1,008 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Baseboard
- Heat Fuel
- Oil
- Cooling
- Central Air
- Laundry Location
- Basement
- Appliances
- Oven/RangeRefrigeratorWasherElectric Dryer
- Basement
- FullUnfinishedInterior Access
- In-Law Apartment
- No
Exterior & Lot
- Lot Size
- 0.31 acres
- Zoning
- R-3
- Garage / Parking
- 1 garage space3 total parking spacesUnder House GarageDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- ShingleWood
- Roof
- Gable
- Foundation
- Concrete
- Lot Description
- Sloping Lot
Listing & Financials
- Property Taxes
- $3,142 / Annually
- Days on Market
- 81
- MLS #
- 24172219
- MLS Status
- Under Contract
Similar Properties
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Co-Listed By
Suzie Larson
Turning Point Realty, LLC
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/28/2026 at 7:55 AM UTC.