Welcome to 39 Pitney Ave, a beautifully maintained, detached legal two-family home in the heart of Pleasant Plains! This spacious side-hall Colonial offers three bedrooms and three bathrooms in the main residence, plus a separate one-bedroom, one-bathroom apartment. Combining comfort, style, and versatility, this home offers an exceptional opportunity for homeowners and investors alike. Recent updates include a renovated kitchen, updated flooring, windows, roof, garage door, two-zone baseboard heating, and a new pool liner. Enter through the steel entry doors into a welcoming living room featuring hardwood floors and a charming balcony overlooking the front yard. This level also offers a convenient half bath and a dedicated laundry room. The spacious, renovated eat-in kitchen is truly the heart of the home, showcasing stainless steel appliances, quartz countertops, an oversized island, and abundant cabinetry and pantry storage. Sliding glass doors lead to a large deck overlooking the backyard, complete with an above-ground pool—perfect for entertaining, relaxing, and enjoying the warmer months. Upstairs, you'll find three bedrooms and a full bathroom. The primary suite features a spacious walk-in closet and a beautifully renovated private three-quarter bathroom, creating a comfortable retreat at the end of the day. Adding exceptional value and flexibility, the property features a separate, legal one-bedroom apartment with its own utilities and a full bathroom. Whether you're looking for additional living space for extended family or the opportunity for rental income, this versatile property offers wonderful possibilities.