Tucked into the heart of Roland Park on picturesque Deepdene Road, this enchanting storybook cottage blends timeless charm with thoughtful updates. Set against a lush, terraced backdrop, this detached home offers 4 spacious bedrooms, 2 full baths, and a versatile floor plan perfect for modern living. The main level features a warm, formal living room with a wood-burning fireplace, a gracious dining room, and a bright four-season sunroom — ideal for year-round enjoyment. The cozy den, complete with custom built-ins, provides the perfect spot for working from home or unwinding with a good book. A delightful butler’s pantry with a sink and additional cabinetry connects to the refreshed kitchen, which now boasts new quartz counters, updated flooring, and modern lighting. Upstairs, the primary suite includes a private full bath, while three additional bedrooms share a second updated bath. Original hardwood floors throughout have been beautifully refinished, and the entire home has been freshly painted for a crisp, clean look. Out back, the large rear deck offers a peaceful place to relax or entertain while enjoying the beautifully landscaped hillside—lush, green, and full of character. While there’s little traditional yard space, the surrounding greenery creates a private, serene atmosphere that’s both low-maintenance and visually stunning. With a classic slate roof meticulously maintained by Fick Bros, this charming home is a rare value in Roland Park—offering the character you love, the updates you need, and a location that can’t be beat.