A Prospect Hill classic on a leafy side-street steps from Yale or Shakespeare in the Park, the 1915 Donald Prentice House was likely designed by Brown & Von Beren. Prentice taught mechanical engineering at Yale & literally wrote the book on home heating systems. His striking Colonial Revival home was built for the ages: 18" stone foundations, heavy beams, and a heating system (w/new furnace ca. 2010) that keeps the house snug. This lovingly preserved and generously proportioned 4-5 bedroom home has changed hands just a few times, most recently in 1979 (the wonderful writer & writing teacher Caroline Roberts Rosenstone lived here almost 45 years). A lovely entrance hall opens to a grand living room made for entertaining. Light pours in from three sides, including from an enlarged sunroom that leads to both a formal dining room and a 2021 deck with views of the private back garden & cityscape beyond. The charming St. Charles eat-in kitchen (with ca. 2016 reverse-osmosis drinking water filter) offers space for contemporary renovation if desired. A mud-room and renovated half-bath complete the 1st floor. 2nd floor features 4 generous bedrooms (1 with small private balcony facing the garden), laundry room and full bath. 3rd floor has a study/5th bedroom, 2nd full bath, and unfinished attic with room to expand. Full-height partly-finished basement offers further possibilities. Whole house protected by back-up generator.