155 Winchester Road
Norfolk, Connecticut 06058
Reduced from $629,000
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 3,770
- Acres
- 2.26
- Year Built
- 1972
- Neighborhood
- South Norfolk
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Situated on 2.6 peaceful acres, this unique property offers exceptional space and flexibility for multigenerational living, rental potential, or a private guest residence. Offering 5 bedrooms, 3 full baths, and 1 half bath. The main residence features 3 bedrooms and 2 full baths, with the primary living quarters located above the oversized garage. This spacious upper level offers an open-concept living room, kitchen with dining area, the master bedroom has a walk-in closet and private bath, two additional bedrooms, a second full bath, and a private deck overlooking the peaceful surroundings. The in-law suite provides its own private living space with 2 bedrooms, 1.5 baths, spacious living room, dining room, kitchen, laundry room. Whether used for extended family, guests, or a private home office, this flexible layout offers endless possibilities. Car enthusiasts, hobbyists, and contractors will appreciate the impressive 40' x 40' heated garage, featuring radiant floor heat, a 12,000-pound two-post automotive lift, and abundant space for vehicles, equipment, or workshop projects. Additional year-round comfort is provided by a pellet stove and an energy-efficient mini-split system for supplemental heating and cooling. Minutes from the village center, hiking and biking trails, state parks, skiing, and dining.
Key Facts
- City/Town
- Norfolk
- Neighborhood
- South Norfolk
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1972
- Days on Market
- 25 days
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 3,770 sq ft
- Lot Size
- 2.26 acres
- Garage / Parking
- 6 garage
- Property Taxes
- $9,070 / Annually
Market Snapshot
The Norfolk Market
Single Family · trailing 12 months
Active Listings
10
6 under contract
Median List Price
$792,000
10 active listings
Median Closed Price
$305,000
10 sales
Median Days on Market
25
10 active listings
Median $ / Sq Ft
$256
10 active listings
Sale-to-List Ratio
96.7%
10 sales
How this home compares
List Price
$599,000
vs $792,000 median
24.4% below median
Price / Sq Ft
$159
vs $256 median
37.9% below median
Days on Market
25 days
vs 25 days median
In line with median
Based on 10 active and 10 closed sales (trailing 12 mo) of single family in Norfolk. Source: SmartMLS · As of July 28, 2026.
Location
155 Winchester Road, Norfolk, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$3,054
- Property Taxes$756
- Insurance$200
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Norfolk
- Neighborhood
- South Norfolk
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Cape Cod
- Year Built
- 1972
- New Construction
- No/Resale
- Living Area
- 3,770 sq ft
Schools
- Elementary
- Botelle
- High
- Regional District 7
Interior
- Heating
- Baseboard
- Heat Fuel
- Propane
- Cooling
- Ceiling Fans
- Laundry
- Main Level
- Appliances
- RefrigeratorElectric Range
- Basement
- Full
- In-Law Apartment
- YesFirst Floor
Exterior & Lot
- Lot Size
- 2.26 acres
- Zoning
- RU
- Garage / Parking
- 6 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $9,070 / Annually
- Days on Market
- 25
- MLS #
- 24184788
- MLS Status
- Active
- Financing
- FHA
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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 4:25 AM UTC.