Welcome to 29 Pleasant Street, a charming two-family home in Cumberland offering the perfect blend of classic New England character, modern updates, and investment potential. Built in 1910, this well-maintained property features two spacious units, each offering two bedrooms, one full bathroom, comfortable living spaces, and the convenience of in-unit laundry. Recent improvements include beautifully refinished hardwood floors and fresh paint throughout, creating bright, inviting interiors while preserving the home's original charm. The first-floor unit features a kitchen with granite countertops, newer appliances, and private basement access, while the second-floor unit offers a spacious kitchen and functional layout. Outside, an inviting farmer's porch adds timeless appeal, while vinyl siding, updated windows, and a detached two-car garage provide added convenience. Ideally situated near shopping, dining, and major commuter routes, this property offers both accessibility and neighborhood charm. Whether you're looking to expand your investment portfolio, enjoy the benefits of owner-occupied living with rental income, or accommodate multigenerational living, 29 Pleasant Street offers versatility and opportunity in a convenient Cumberland location.