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104 Maloney Court

Winchester, Connecticut 06098

PENDING$279,000

Reduced from $289,000

Beds
3
Baths
1
SqFt
1,008
Acres
0.31
Year Built
1957
Matt Caiola

Matt Caiola

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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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$1,778

per 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

Homes with a close match in area, property type, and price.

Listed By

Lisa Garten Johnson

(203) 768-2150

Turning Point Realty, LLC

(860) 909-1162

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.