1930s GRAND VILLA SPANISH TROPHY TRIPLEX COMPOUND. Rare opportunity to own a character-rich Spanish compound in coveted Longwood Highlands, blending timeless architecture with thoughtful modern upgrades. The front duplex features two expansive 3-bedroom, 2-bath residences with oversized rooms, abundant natural light, and refined period details throughout. The rear 2-bedroom, 1-bath unit sits privately above the 4-car garage, offering separation and flexibility. Set behind a perimeter wall with an electronic gated driveway , this compound delivers privacy, security, views from the upper units and exceptional curb appeal. A private hedged front yard with mature, lush landscaping and intercom system welcomes you into a beautifully maintained courtyard setting with classic wrought iron detailing. High-end improvements include solid slab Italian marble wainscots, tile floors and countertops, designer fixtures, refurbished period lighting and energy-efficient systems. Major infrastructure upgrades include updated plumbing, electrical, and sewer lines. Additional features include beautiful oak hardwood floors, A/C, individual gas and electric meters, common area lighting as well as an abundance of off-street parking. The extra-large lot includes strong in-place rents, creating an attractive income profile with long-term upside potential. Upper level owner's 3 Bed unit will be delivered vacant, presenting an exceptional opportunity for an owner-user or investor. A rare blend of scale, character, privacy, and income in one of the area's most desirable neighborhoods.