173 Gilbert Avenue
Winchester, Connecticut 06098
- Beds
- 4
- Baths
- 1 | 1
- SqFt
- 1,664
- Acres
- 0.23
- Year Built
- 1927
- Neighborhood
- Winsted
- 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
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
Active Listings
23
11 under contract
Median List Price
$410,000
23 active listings
Median Closed Price
$340,500
92 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per 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
Homes with a close match in area, property type, and price.
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.