195 Reaching Hill Road
Winchester, Connecticut 06098
- Beds
- 3
- Baths
- 2
- SqFt
- 1,324
- Acres
- 0.93
- Year Built
- 1979
- 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
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
Active Listings
12
12 under contract
Median List Price
$524,900
12 active listings
Median Closed Price
$325,000
103 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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.