Classic Elegance in the Heart of Sought-After Leonardtown! Nestled at the end of a quiet cul-de-sac in the desirable Academy Hills community, this stunning 5-bedroom, 3.5-bath Colonial offers nearly 4,000 square feet of beautifully finished living space surrounded by peaceful wooded views and open pastureland. Step outside to enjoy the private, fenced backyard featuring split-rail fencing, a spacious composite deck with vinyl railings, and a patio perfect for entertaining or relaxing in a serene setting. Inside, the traditional floor plan is both timeless and functional, highlighted by a grand two-story foyer, formal living and dining rooms, and a spacious eat-in kitchen with open sightlines into the inviting family room. Upstairs, you'll find four generously sized bedrooms, two full baths, and a conveniently located laundry room. The sun-filled primary suite is a true retreat, featuring vaulted ceilings, a custom walk-in closet system, and a luxurious en-suite bath complete with dual vanities, a newly updated shower, and a soaking tub. The fully finished walk-out basement offers exceptional versatility and previously served as an in-law suite. Complete with a private bedroom and full bath, French doors leading to the patio, separate stackable washer/dryer hookup, propane line for an additional fireplace, and abundant storage space with added shelving, it's ideal for extended family, guests, or multi-generational living. This home has been thoughtfully updated with numerous improvements, including a new roof, newly renovated primary bathroom, new refrigerator and dishwasher, washer and dryer, updated second-floor bathroom vanity, new flooring in the basement bathroom, and a new HVAC system for the second floor installed in 2022. Fresh interior paint adds a bright, move-in-ready feel throughout. Conveniently located within walking distance to historic downtown Leonardtown and just 25 minutes to NAS Patuxent River, this home perfectly blends timeless charm, modern updates, and an unbeatable location.