About 226 Middlesex Avenue
Prominently set on over two picturesque acres in historic Chester, this custom-built and thoughtfully designed Saltbox Colonial offers the perfect blend of timeless New England charm and modern home comforts. Lovingly maintained by the original owner, a gracious entry leads to a cozy family room centered around the fireplace, creating a warm and welcoming atmosphere year-round. The formal living room and dining room with custom built-ins and gleaming hardwood floors is perfect for holiday gatherings or those special occasions with friends & family. The sun-filled kitchen with a center island and casual dining area leads to a private deck overlooking park-like grounds...ideal for outdoor entertaining. A half bath and laundry area complete the main level. Upstairs you'll find 4 bedrooms including the primary suite with its own private bath while the lower level features a bonus room and workshop. Bordered by mature trees and colorful perennials the spacious yard is ideal for gardening; a charming potting shed is perfect for all of your storage needs. A true highlight of this unique property is the 22 x 30 Country Carpenter carriage house barn/garage. Located just minutes from the Village, this quintessential New England home with seasonal views of the CT River, is close to Chester Boat Basin...offering easy access to boating and outdoor recreation. Whether you are looking for a full time residence or an ideal weekend retreat this is the perfect place to call home.
Features of 226 Middlesex Avenue
| MLS® # | 24165416 |
|---|---|
| Price | $695,000 |
| Bedrooms | 4 |
| Bathrooms | 2/1 |
| Full Baths | 2 |
| Half Baths | 1 |
| Square Footage | 2,029 |
| Acres | 2.33 |
| Type | Single Family For Sale |
| Style | Colonial |
| Status | Closed |
Community Information
| Address | 226 Middlesex Avenue |
|---|---|
| Area | N/A |
| City | Chester |
| County | Middlesex |
| State | Connecticut |
| Zip Code | 06412 |
Amenities
| Is Waterfront | No |
|---|---|
| Waterfront | Seasonal |
| Has Pool | No |
Interior
| Interior Features | Cable - Available |
|---|---|
| Appliances | Oven/Range, Refrigerator, Dishwasher, Washer, Dryer |
| Heating | Hot Water, Oil |
| Cooling | Split System |
| Fireplace | Yes |
| # of Fireplaces | 1 |
Exterior
| Exterior | Clapboard |
|---|---|
| Exterior Features | Shed, Deck, Garden Area |
| Lot Description | Lightly Wooded, Level Lot |
| Roof | Asphalt Shingle |
| Foundation | Concrete |
School Information
| Elementary | Chester |
|---|---|
| Middle | Winthrop |
| High | Valley |
Additional Information
| Date Listed | April 11th, 2026 |
|---|---|
| Days on Market | 5 |
| Zoning | R-2 |
| RE / Bank Owned | No |

