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195 Reaching Hill Road

Winchester, Connecticut 06098

PENDING$353,500
Beds
3
Baths
2
SqFt
1,324
Acres
0.93
Year Built
1979
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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About This Home

Please submit your client's highest and best offer by Sunday 07/19 at 3:00 PM. Beautifully remodeled and move-in ready, 195 Reaching Hill Rd in Winsted, CT features modern updates, comfort, and functionality throughout. This 3-bedroom, 2-bath conventional-style home sits on nearly one acre of land and showcases a bright open-concept layout with beautiful hardwood floors, a spacious living area, and a dedicated dining space with large sliding glass doors overlooking the backyard. The main floor includes a bedroom and full bathroom, providing flexibility for a variety of uses such as a guest room, home office, or convenient one-level living arrangement. The finished lower level with a walk-out entrance and full basement adds valuable additional space with endless possibilities for a recreation room, home gym, playroom, workshop, or additional storage. Enjoy the comfort of central air conditioning, along with a relaxing porch, outdoor shed, and a private backyard with plenty of space to relax, garden, or entertain. Located near Highland Lake, this property provides convenient access to outdoor recreation throughout the seasons. With thoughtful renovations, spacious rooms, and a great indoor-outdoor connection, this home is ready for its next owner. Schedule your private showing today and see everything this beautifully updated Winsted property has to provide.

Key Facts

City/Town
Winchester
Neighborhood
Winsted
Property / Style
Single Family · Contemporary
Year Built
1979
Days on Market
17 days
Beds
3
Baths
2 full
Living Area
1,324 sq ft
Lot Size
0.93 acres
Property Taxes
$3,688 / 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

$353,500

vs $524,900 median

32.7% below median

Price / Sq Ft

$267

vs $265 median

In line with median

Days on Market

17 days

vs 39 days median

22 days fresher 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

195 Reaching Hill Road, Winchester, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,227

per month

  • Principal & Interest$1,802
  • Property Taxes$307
  • Insurance$118
  • 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
Contemporary
Year Built
1979
New Construction
No/Resale
Living Area
1,324 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Water
Heat Fuel
Electric
Cooling
Central Air
Appliances
Electric RangeOven/RangeRange HoodRefrigeratorDishwasher
Basement
FullWalk-outFull With Walk-Out

Exterior & Lot

Lot Size
0.93 acres
Zoning
RU-1
Waterfront Details
Walk to Water
Water Source
Private Well
Sewer
Septic
Construction
Vinyl Siding
Color
Blue
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
Lightly WoodedTreedLevel Lot

Listing & Financials

Property Taxes
$3,688 / Annually
Days on Market
17
MLS #
24190790
MLS Status
Under Contract - Continue to Show
Financing
FHA,VA,CHFA

Similar Properties

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

Listed By

Nicolle Estrella

(860) 710-9086

eXp Realty

(866) 828-3951

Co-Listed By

Michael Disla

eXp Realty

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.