Behind a gated drive and lush hedges in Longwood Highlands lies a rare 1930s Spanish triplex compound that marries old-world charm with modern comfort. The upper-level 3-bedroom owner's unit delivered vacant at closing invites you to move in, while the rest of the property continues to generate strong income. The front structure is a true duplex: two expansive 3-bedroom, 2-bath residences with oversized rooms, abundant natural light, and lovingly preserved period details.Tucked quietly at the rear, a separate 2-bedroom, 1-bath unit crowns the 4-car garage, providing exceptional privacy and flexibility for guests, tenants, or home office use. A hedged front yard, mature landscaping, and an intercom entry open to a classic courtyard anchored by wrought-iron railings and timeless Spanish character. The home's authenticity is complemented by thoughtful upgrades: Italian marble countertops, designer tile and fixtures, refurbished original lighting, and energy-efficient systems. Major building systems including plumbing, electrical, and sewer have been updated. Throughout, you'll find beautiful oak hardwood floors, central A/C, individual gas and electric meters, common-area lighting, and generous off-street parking. Set on an extra-large lot with strong existing rents and clear room for upside, this property offers scale, character, privacy, and income in one of the neighborhood's most sought-after enclaves.