55 Wig Hill Road, Chester, Connecticut

$499,900

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3

Beds

2

Baths

1,774

Square feet

1.43

Acres

About 55 Wig Hill Road

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.

Features of 55 Wig Hill Road

MLS® # 24202647
Price $499,900
Bedrooms 3
Bathrooms 2.00
Full Baths 2
Square Footage 1,774
Acres 1.43
Type Single Family For Sale
Style Raised Ranch
Status Under Contract - Continue to Show

Community Information

Address 55 Wig Hill Road
Area Wig Hill
City Chester
County Middlesex
State Connecticut
Zip Code 06412

Amenities

Features Thermopane Windows
Parking Under House Garage
# of Garages 2
Is Waterfront No
Waterfront Not Applicable
Has Pool No

Interior

Interior Features Cable - Available
Appliances Oven/Range, Refrigerator, Dishwasher, Washer, Dryer
Heating Hot Air, Propane
Cooling Central Air
Fireplace Yes
# of Fireplaces 1
Has Basement Yes
Basement Full, Apartment, Partially Finished, Walk-out

Exterior

Exterior Vinyl Siding
Exterior Features Shed, Deck, Gutters, Stone Wall
Lot Description Lightly Wooded, Level Lot
Roof Asphalt Shingle
Foundation Concrete

School Information

Elementary Chester
Middle Winthrop
High Valley

Additional Information

Date Listed August 30th, 2026
Days on Market 36
Zoning R-2
RE / Bank Owned No

Listing Details

OfficePuorro Realty Group

Listing Map

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Listing information last updated on October 6th, 2026 at 10:14pm EDT.