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173 Gilbert Avenue

Winchester, Connecticut 06098

ACTIVE - NEW$289,900
Beds
4
Baths
1 | 1
SqFt
1,664
Acres
0.23
Year Built
1927
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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1 Fireplace

About This Home

Welcome to this charming 4-bedroom, 1.5 bath home in Winsted, where classic character meets comfortable everyday living. Built in 1927, this well-maintained home features beautiful hardwood floors, original woodwork, detailed trim, and spacious rooms filled with natural light. The main level offers generous living and dining spaces while the bright kitchen features ample cabinetry, stainless steel appliances, and plenty of counter space. A convenient half bath completes the main level. Upstairs, you'll find four well sized bedrooms, a full bath, and additional built-in storage, along with preserved woodwork and charm throughout. This property offers a private yard with mature trees and established landscaping, providing a nice outdoor space to enjoy. A wonderful opportunity to own a character-filled home with space, charm, and comfort in the heart of Winsted!

Key Facts

City/Town
Winchester
Neighborhood
Winsted
Property / Style
Single Family · Colonial
Year Built
1927
Days on Market
0 days
Beds
4
Baths
1 full · 1 half
Living Area
1,664 sq ft
Lot Size
0.23 acres
Property Taxes
$4,628 / Annually

Market Snapshot

The Winchester Market

Single Family · trailing 12 months

Median Days on Market

32

23 active listings

Median $ / Sq Ft

$256

23 active listings

Sale-to-List Ratio

100.0%

92 sales

How this home compares

List Price

$289,900

vs $410,000 median

29.3% below median

Price / Sq Ft

$174

vs $256 median

32.0% below median

Days on Market

0 days

vs 32 days median

32 days fresher than median

Based on 23 active and 92 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of September 27, 2026.

Location

173 Gilbert Avenue, Winchester, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,031

per month

  • Principal & Interest$1,548
  • Property Taxes$386
  • Insurance$97
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Winchester
Neighborhood
Winsted
County
Litchfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1927
New Construction
No/Resale
Living Area
1,664 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Water
Heat Fuel
Natural Gas
Cooling
None
Fireplaces
1
Appliances
Oven/RangeRefrigeratorWasherElectric Dryer
Basement
Full

Exterior & Lot

Lot Size
0.23 acres
Zoning
TSF
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Stone
Lot Description
Sloping Lot

Listing & Financials

Property Taxes
$4,628 / Annually
Days on Market
0
MLS #
24210073
MLS Status
Active

Similar Properties

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Listed By

Taylor Anderson

(413) 262-0147

Tier 1 Real Estate

(860) 578-2016

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/27/2026. 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 9/27/2026 at 3:20 AM UTC.