Welcome to this beautifully maintained Winter Park gem, offering exceptional curb appeal and bursting with charm, character and timeless style. Located in the highly desirable Dubsdread Heights neighborhood, bordering Little Lake Fairview and the Dubsdread Golf Course, this home places you just minutes from the boutique shops, dining options and festivals of Park Avenue, with easy access to I-4. As you step inside, you're greeted by a bright sunroom with warm, stylish Saltillo tile flooring which seamlessly flows into the spacious living room featuring stunning Red Oak hardwood floors. The eat-in kitchen boasts sleek quartz countertops, modern cabinets with crown molding, a built-in pantry with convenient slide-out drawers and newer appliances. This home has been thoughtfully updated with double-paned windows, a 2018 roof replacement and updated plumbing, ensuring peace of mind for years to come. Both bedrooms are generous in size and feature Red Oak wood flooring and modern ceiling fans, with a full bath conveniently situated in between that retains timeless charm with original custom tiling, a pedestal sink, and shower/tub combo. The private, fully fenced backyard is a true tropical retreat, perfect for relaxation or entertaining guests. The recently replaced wood deck with sail awnings and a concrete patio create ideal spaces to enjoy Florida's year-round beauty. A charming brick paver walkway leads to a separate laundry and storage shed, with additional cabinets and space to meet your storage needs. This home has gutters installed along with a rain barrel designed to capture and conserve water for your landscaping watering needs. Kitchen appliances, washer, dryer and lawn mower, edger, and blower are all included in sale. Combining the perfect blend of modern updates and original character, this home is a must-see in the heart of Winter Park!