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118 Meadow Street

Winchester, Connecticut 06098

PENDING$269,999

Reduced from $290,000

Beds
3
Baths
2
SqFt
1,652
Acres
0.17
Year Built
1860
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

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Price Reduced

About This Home

This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting and ample amounts of storage. The home sits on a flat, level yard with a huge storage shed, perfect for outdoor gatherings, storage, gardening, and play. Multiple decks off the home create inviting spaces to relax and take in the surroundings. Located just moments from a local boat launch, this property is ideal for those who love recreational water access. You're also close to the town green, shops, and everyday conveniences, making this home the perfect blend of historic charm and modern lifestyle. Schedule to view today!!

Key Facts

City/Town
Winchester
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1860
Days on Market
253 days
Beds
3
Baths
2 full
Living Area
1,652 sq ft
Lot Size
0.17 acres
Property Taxes
$2,949 / 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

$269,999

vs $524,900 median

48.6% below median

Price / Sq Ft

$163

vs $265 median

38.5% below median

Days on Market

253 days

vs 39 days median

214 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

118 Meadow Street, Winchester, Connecticut

Property + 10 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$1,713

per month

  • Principal & Interest$1,377
  • Property Taxes$246
  • Insurance$90
  • 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
Colonial
Year Built
1860
New Construction
No/Resale
Living Area
1,652 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Radiator
Heat Fuel
Oil
Cooling
None
Laundry
Main Level
Laundry Location
kitchen
Appliances
Oven/RangeRefrigeratorDishwasher
Basement
Full
In-Law Apartment
No

Exterior & Lot

Lot Size
0.17 acres
Zoning
R-3
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Shingle
Roof
Asphalt Shingle
Foundation
Block
Lot Description
Level LotCleared

Listing & Financials

Property Taxes
$2,949 / Annually
Days on Market
253
MLS #
24140514
MLS Status
Under Contract
Financing
FHA,VA,CHFA

Similar Properties

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

Listed By

Ashley Henry

(860) 776-6515

The Washington Agency

(860) 482-7044

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 6:55 AM UTC.