Experience the best of coastal living in the heart of Clearwater with this versatile, income generating property, nestled within a serene tropical landscape. Ideal for investors, multi generational living, or those seeking a live/work retreat, this rare gem features multiple residences, lush outdoor spaces, and direct access to the Pinellas Trail. The grounds feel like your own private resort, surrounded by mature shade oaks, swaying palms, and even your own mango tree. Brick walkways wind through cozy nooks and open gathering areas, perfect for enjoying Floridas outdoor lifestyle. Designed with Spanish inspired architecture, the main residence greets you with a circular brick driveway, clay tile roof accents, and a welcoming porch with Spanish tile flooring. Step inside through wood framed French doors to a charming living room featuring hardwood floors and a classic fireplace. The adjacent dining room is flooded with natural light from a picture window overlooking a lush garden, while the fully renovated kitchen is both stylish and functional, boasting granite countertops, white shaker style soft close cabinetry, hammered copper dishwasher (2024), Induction range (2025) and a "smart" refrigerator (2025). A laundry/storage room includes a stacked washer/dryer, utility sink, and shelving. A leaded glass door leads you to the rear patio and garden, where a private hot tub awaits. The primary bedroom offers newer luxury vinyl flooring and a private sunroom perfect for a home office, yoga space, or quiet reading nook with direct yard access. The second bedroom connects to an updated bath with basket weave stone tile flooring and a modern walk in shower. Accessible from both inside the home and via a wide outdoor staircase, this bright and spacious second floor suite is perfect as a primary ensuite, guest quarters, or rental unit. Features include an oversized private deck, kitchenette with butcher block counters, soft close cabinetry, and stainless sink, Murphy Bed for flexible living and a full bath with tiled tub/shower combo. Across from the main house, a charming standalone cottage offers a bright, open living area with large sliding windows, tile countertops, ample kitchen storage, and space for dining/game area. There is also a private bedroom with walk in closet and a full bath and private rear patio perfect for guests, short term rentals, or extended family stays. Features & Upgrades include high efficiency mini split HVAC systems in all residences, newer sewer lines and main water supply lines to both main house and cottage, a gas water heater (2019), Tesla charging station, and one car garage with newer garage door. NO HOA. FLOOD ZONE X. This unmatched location is situated directly on the Pinellas Trail, enjoy 47 miles of scenic biking and walking from your backyard. Ride north to Downtown Dunedins shops, microbreweries, and farmers markets, or head south to historic Clearwater and world famous Clearwater Beach. Just a block away, launch your kayak to explore uninhabited coastal islands or drop your boat in at the Seminole Boat Ramp. You're also minutes from award winning beaches, premier golf courses, top rated hospitals, airports, restaurants, retail, and live music venues. This is more than a home its a lifestyle. Whether you're looking for a profitable investment, a multi unit family property, or a peaceful tropical retreat, this Clearwater oasis has it all.