Steeped in history and timeless elegance, this exceptional circa 1927 Arts & Crafts residence is beautifully positioned on a terraced lakefront homesite overlooking picturesque Lake Highland in the heart of downtown Orlando. Rich in architectural character, the home showcases original craftsmanship thoughtfully preserved and enhanced through tasteful renovations that seamlessly blend historic charm with modern luxury. Authentic period details include impressive 7-inch moldings, picture rails, original built-ins and cabinetry, beautiful oak and heart pine flooring, and architectural elements that honor the home’s historic significance while creating an inviting atmosphere for contemporary living. Designed across multiple levels, the thoughtfully planned floor plan offers exceptional living and entertaining spaces, all enhanced by breathtaking lake views. The main level features an expansive family room, elegant formal dining room, and a European-inspired kitchen with adjoining lakefront dinette overlooking the water. The lower level is an entertainer’s dream, offering a spacious summer living room, dining area, wet bar, and versatile studio space that opens seamlessly to the outdoor living areas. The upper levels are dedicated to private living quarters with beautifully renovated bathrooms and generously sized bedrooms, including a luxurious primary suite featuring a private sitting area and a spa-inspired bath complete with a classic clawfoot soaking tub perfectly positioned to capture tranquil lake views. Outdoor living is equally extraordinary. A covered lanai with summer kitchen and outdoor dining area overlooks the beautifully terraced backyard featuring bubbling waterfalls, lush tropical landscaping, and multiple gathering spaces. Meandering steps lead to your private lakefront retreat where a lakeside fire pit and expansive waterfront deck create the perfect setting for enjoying spectacular sunsets, entertaining guests, or simply relaxing with a glass of wine while taking in the peaceful surroundings. Enjoy skiing, paddle boarding, or kayaking on private Lake Highland. Completing this one-of-a-kind estate is a detached one-bedroom, one-bath guest house, providing an ideal private retreat for guests, extended family, or a home office. This remarkable residence offers a rare opportunity to own one of downtown Orlando’s most distinctive historic lakefront homes—where timeless architecture, modern comfort, and resort-style outdoor living come together in an unforgettable setting.