Welcome to 5422 39th Street, a 1918 classic four-square in the coveted neighborhood of Chevy Chase DC. Situated on an impressive 8400 square foot lot, this home has been lovingly maintained and thoughtfully updated while retaining its original charm and character. Entering through the white picket gate, a slate walkway surrounded by mature plantings leads to the expansive porch, perfect for entertaining. The front door with stained glass detail and period trim opens to an impressive foyer with high ceilings and hardwood floors. The generous living room boasts a wood-burning fireplace and a wall of windows including a glass door with access to the back porch. A separate dining room is perfect for large gatherings, and the updated kitchen features reclaimed chestnut floors, soapstone counters, custom built-ins, and a tucked-away powder room with a pocket door. The kitchen provides direct access to the large back yard through a grapevine-covered back porch. Upstairs there is a hall bath and four generously-sized bedrooms, including a primary bedroom with an ensuite bath and walk-in closet. The third level features a fifth bedroom, full bath, and additional space perfect for a home office. The unfinished lower level with half bath awaits the imagination! An expansive backyard includes a back porch with ceiling fans and heater for year round enjoyment, two patios, a firepit, and raised vegetable gardens. This fully fenced oasis also boasts an outbuilding with potential as a fitness room, home office, or art studio. Beyond the fence is a garage, as well as two convenient parking spaces accessible via the rear alley. This prime location is just over a half mile to the red line metro, and blocks to Chevy Chase playground and all that upper Connecticut Ave has to offer: groceries, shops, restaurants and more. This is a rare gem and truly a special opportunity!