Welcome to 216 Hillsborough--an INCOME-GENERATING oasis in the heart of Safety Harbor! Located on one of the town's most sought-after streets, this stunning property is just a short stroll from vibrant Main Street and the breathtaking waterfront. The captivating curb appeal will draw you in, with a picturesque circular driveway that sets the stage for this coastal retreat. Inside, the main house showcases gorgeous vaulted wood ceilings, two beautifully appointed bedrooms, two full baths, a versatile office or bonus room, and a majestic wood-burning fireplace that creates a cozy focal point. The primary bedroom boasts two walk-in closets, providing generous storage and a cozy sitting area with French doors leading to the back deck. Skylights throughout the home bring in natural light, enhancing the inviting atmosphere. Enjoy peace of mind with a brand NEW ROOF (11/24) and a fresh exterior paint job (2021) giving the home a modern, welcoming look. But that's not all! A charming separate cottage awaits, complete with two additional bedrooms, a full bath, a cozy kitchen/living room combo, and a new water heater--perfect for guests, extended family, or rental income potential. Step outside to your private paradise: an expansive back deck ideal for entertaining, overlooking a serene, fenced yard that promises tranquility and privacy. With ample storage options, including an attached storage room and a detached shed, you'll have plenty of space for your golf cart and all your outdoor gear. This home exudes warmth, character, and income potential in one of Safety Harbor's most desirable neighborhoods. Don't miss your chance to make it yours!