About 81 Main Street
Discover the perfect blend of mid-century character and modern efficiency in the heart of Chester Village. This impeccably maintained home offers a vibrant "walk-to-everything" lifestyle, just steps from award-winning dining, boutiques, and the theater. Officially a 2-bedroom home per town records, the layout offers incredible flexibility. The main level features a stunning den currently utilized as a primary suite. This light-filled space features a private, fully renovated ensuite full bath and a handsome armoire for storage, offering a sophisticated retreat for those seeking first-floor living. Note: This serves as the primary bath for the main level, enhancing the "suite" feel of the space. Upstairs, you will find two additional well-appointed rooms and a second fully renovated full bath, providing ample space for guests or a home office. The home's infrastructure has been flawlessly upgraded, featuring a new 50-year roof, on-demand propane heat/hot water, and an electric heat pump for heating and cooling (A/C on the first floor). The updated eat-in kitchen is a chef's delight, while the professional landscaping and beautiful stone patio create a private oasis for outdoor entertaining. Rarely does a home combine such high-end mechanical peace of mind with the undeniable charm of a downtown location. Turn-key and ready for its next chapter-experience the best of Chester right outside your front door.
Features of 81 Main Street
| MLS® # | 24172804 |
|---|---|
| Price | $618,000 |
| Bedrooms | 2 |
| Bathrooms | 2.00 |
| Full Baths | 2 |
| Square Footage | 1,128 |
| Acres | 0.15 |
| Type | Single Family For Sale |
| Style | Cape Cod |
| Status | Closed |
Community Information
| Address | 81 Main Street |
|---|---|
| Area | N/A |
| City | Chester |
| County | Middlesex |
| State | Connecticut |
| Zip Code | 06412 |
Amenities
| Features | Storm Doors, Thermopane Windows |
|---|---|
| Is Waterfront | No |
| Waterfront | Not Applicable |
| Has Pool | No |
Interior
| Interior Features | Open Floor Plan |
|---|---|
| Appliances | Gas Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer |
| Heating | Heat Pump, Radiator, Electric, Propane |
| Cooling | Heat Pump, Window Unit |
| Fireplace | No |
Exterior
| Exterior | Wood |
|---|---|
| Exterior Features | Gutters, Garden Area, Patio |
| Lot Description | Treed, Level Lot, Professionally Landscaped |
| Roof | Asphalt Shingle |
| Foundation | Block |
School Information
| Elementary | Per Board of Ed |
|---|---|
| High | Per Board of Ed |
Additional Information
| Date Listed | May 8th, 2026 |
|---|---|
| Days on Market | 4 |
| Zoning | C |
| RE / Bank Owned | No |

