Discover this charming and spacious two-family home nestled in the heart of Chester. Recently refreshed with new flooring throughout and thoughtful cosmetic updates, this well-maintained property is ready for its next owner. Each unit offers 3 comfortably sized bedrooms, 1.5 bathrooms, a large living room, dining area, kitchen, first-floor laundry, and a bonus room that can be used as an office, playroom, or additional storage. The property sits on a generous lot—close to 1 acre—with a large front yard and expansive backyard that accommodates parking for approximately 6 additional vehicles. Ideal for anyone seeking a tranquil setting with strong rental income potential or a reliable investment opportunity. A barn with a 2-car garage and upstairs loft adds even more versatility and is being sold as is. The home also includes a new septic system, offering added peace of mind.
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| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 06/03/2026 | ↓ Price Reduced | $389,900 | $5,000 | - | From $394,900 to $389,900 (-1.3%) |
| 04/09/2026 | ↓ Price Reduced | $394,900 | $10,000 | - | From $404,900 to $394,900 (-2.5%) |
| 03/04/2026 | ↓ Price Reduced | $404,900 | $10,099 | - | From $414,999 to $404,900 (-2.4%) |
| 12/11/2025 | 🏠 Listed for Sale | $414,999 | - | - | Original listing |
| Year | Taxes | Assessment |
|---|---|---|
| 2025 | $4,264 | $236,100 |
56 Middlefield Rd, Chester MA 01011
Chester, MA 01011
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