A truly magical find in Wooster Square! Meticulously renovated with exceptional care and attention to detail, this unique three-unit compound blends historic charm with modern comfort and convenience. The freestanding brick house features 2 bedrooms and 1 full bath, a spacious eat-in kitchen, generous living and dining rooms, and a huge finished basement. High ceilings and beautiful original details add timeless character. Tucked at the rear of the property, the former carriage house has been thoughtfully converted into two additional residences. Unit #2 offers 3 bedrooms, 2 full baths, an open-concept living, dining, and kitchen area, a den, and an exceptional private terrace. Unit #3 features an inviting open living space, a well-appointed kitchen, a private bedroom, and a full bath, complemented by high ceilings. Each unit has its own washer/dryer. The charming courtyard provides off-street parking for up to five cars, and separately fenced off area for a dog run or a secure play area. Newer mechanicals; tankless water heaters; Central Air in #50 and #52; window units in #54. A rare opportunity for investors or owner-occupants seeking a distinctive property with multiple income possibilities or extended family living in one of New Haven's most beloved neighborhoods!