**First time on the market!** Lovingly owned and meticulously maintained by one family, this custom 4-bedroom, 2.1-bath residence is nestled on 2.2 acres at the end of a quiet cul-de-sac street in the highly sought-after Chester community. A newly stained redwood exterior welcomes you to a warm, light-filled interior featuring solid oak hardwood floors, wood beam accents, retro style bathrooms, large hearth fireplace, abundant windows, and beautiful views of the surrounding retreat-like property. Two expansive decks extend the living space outdoors, offering the perfect setting for dining, entertaining, or simply unwinding in nature. Numerous important updates provide peace of mind, including a new oil burner and water heater, holding tank, water mitigation system, newer windows and garage doors, and a built-in generator. The walk-out basement with wood burning fireplace provides easy yard access and flexible space for storage, hobbies, recreation, or future finishing. Located in a top-rated school district with an attractive International Baccalaureate (IB) program, around the corner from the neighborhood preschool The Dogwood School of Chester and just minutes from charming historical Main Street, shopping, restaurants, local farms, walking trails and major highways. A distinctive custom home with a wonderful feeling of privacy and place, ready to welcome its next chapter.