Charming South Tampa Gem with Guest House & Saltwater Pool, A Rare Find! Welcome to this captivating 1939 Craftsman-style Airplane Bungalow, nestled on one of South Tampa's most iconic, tree-lined streets. This gorgeous property blends timeless character with modern luxury, offering a truly unique lifestyle in one of the city's most desirable neighborhoods. The main home features 2 spacious bedrooms, 2 bathrooms, and a cozy den, while the detached 2-story guest house provides a private 1 bed 1 bath suite perfect for visitors, a home office or creative studio. Step onto the inviting front porch and into a warm, light-filled living room showcasing original heart-pine hardwood floors, a classic wood-burning fireplace, and stunning architectural details. The den, ideal for reading or remote work, features custom built-in bookshelves that elevate the charm even further. The renovated eat-in kitchen is a chef's dream outfitted with high-end Sub-Zero and KitchenAid appliances, solid cherry wood cabinetry, and an adjacent formal dining room that's perfect for hosting dinner parties or intimate meals. French doors in the primary suite open to your own private backyard oasis complete with a sparkling saltwater pool and spa, lush landscaping, and ample space for lounging or entertaining. A beautifully updated en-suite bath (2019) and convenient first-floor laundry room add to the effortless livability. Upstairs, discover a light-filled third bedroom with windows on all four sides, creating a serene, sun-drenched retreat. The guest house, completed in 2000, offers its own living area, full bath, and kitchenette downstairs, with a versatile bedroom upstairs plus a private balcony overlooking the pool. It's a perfect escape for guests or a stylish work-from-home setup. Throughout the property, you'll find timeless details like extensive wood trim, plantation shutters, and handcrafted finishes all complemented by modern upgrades including a gorgeous paved driveway. Enjoy the best of South Tampa living just minutes from Bayshore Boulevard, top-rated restaurants, boutique shopping, and scenic walking and biking paths. Don't miss your chance to own a piece of South Tampa history with income potential and resort-style amenities! Schedule your private tour today.