55 Wig Hill Road
Chester, Connecticut 06412
- Beds
- 3
- Baths
- 2
- SqFt
- 1,774
- Acres
- 1.43
- Year Built
- 1983
- Neighborhood
- Wig Hill
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Set in the charming town of Chester, this three-bedroom, two-bath home offers a versatile layout with thoughtfully updated spaces throughout. The main level features an updated kitchen, wood floors, and an inviting living room anchored by a striking raised gas fireplace that serves as a beautiful focal point. Recent improvements include a new roof and new central air conditioning condenser, adding to the home's appeal. Step outside to a multilevel deck overlooking the private backyard, creating a wonderful extension of the living space. The lower level adds exceptional flexibility with an ADU featuring its own private entrance, along with a separate laundry room and access to the two-car garage. Whether used for additional living space, guests, a home office, or other needs, the layout offers plenty of possibilities. Just a short distance from Chester Village, known for its acclaimed restaurants, independent shops, galleries, and distinctive small-town atmosphere. A unique opportunity to enjoy flexible living, outdoor space, and all that Chester has to offer.
Key Facts
- City/Town
- Chester
- Neighborhood
- Wig Hill
- Property / Style
- Single Family · Raised Ranch
- Year Built
- 1983
- Days on Market
- 54 days
- Beds
- 3
- Baths
- 2 full
- Living Area
- 1,774 sq ft
- Lot Size
- 1.43 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $6,596 / Annually
Market Snapshot
The Chester Market
Single Family · trailing 12 months
Active Listings
10
6 under contract
Median List Price
$707,000
10 active listings
Median Closed Price
$549,000
37 sales
Median Days on Market
29
10 active listings
Median $ / Sq Ft
$261
10 active listings
Sale-to-List Ratio
100.0%
37 sales
How this home compares
List Price
$499,900
vs $707,000 median
29.3% below median
Price / Sq Ft
$282
vs $261 median
8.0% above median
Days on Market
54 days
vs 29 days median
25 days longer than median
Based on 10 active and 37 closed sales (trailing 12 mo) of single family in Chester. Source: SmartMLS · As of October 23, 2026.
Location
55 Wig Hill Road, Chester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 22, 2026per month
- Principal & Interest$2,747
- Property Taxes$550
- Insurance$167
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Chester
- Neighborhood
- Wig Hill
- County
- Middlesex
Residence
- Property Type
- Single Family
- Style
- Raised Ranch
- Year Built
- 1983
- New Construction
- No/Resale
- Living Area
- 1,774 sq ft
- Below Grade
- 600 sq ft
Schools
- Elementary
- Chester
- High
- Valley
Interior
- Heating
- Hot Air
- Heat Fuel
- Propane
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Lower Level
- Appliances
- Oven/RangeRefrigeratorDishwasherWasherDryer
- Basement
- FullApartmentPartially FinishedWalk-out
- In-Law Apartment
- YesLower LevelSeparate Entry
- Interior Features
- Cable - Available
- Additional Rooms
- FoyerLaundry Room
Exterior & Lot
- Lot Size
- 1.43 acres
- Zoning
- R-2
- Garage / Parking
- 2 garage spacesUnder House Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- ShedDeckGuttersStone Wall
- Lot Description
- Lightly WoodedLevel Lot
Listing & Financials
- Property Taxes
- $6,596 / Annually
- Days on Market
- 54
- MLS #
- 24202647
- MLS Status
- Under Contract - Continue to Show
- Financing
- FHA,VA,CHFA
Similar Properties
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Co-Listed By
Brandon Puorro
Puorro Realty Group
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/23/2026. 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 10/23/2026 at 6:01 PM UTC.