Nestled on a desirable street in the heart of Chevy Chase, this charming colonial-style brick home at 3500 Shepherd Street has been meticulously cared for by its original owner. This exceptional property in a sought-after neighborhood with top-rated schools boasts timeless curb appeal and a welcoming warmth that extends from its classic brick facade to its well-maintained landscaping. What truly sets this property apart is the versatile attached apartment, offering unparalleled flexibility and significant value. This self-contained unit is perfectly designed for diverse needs: (1) Rental Income: Generate steady income with a highly desirable, independent rental unit; (2) Multi-Generational Living: Provide comfortable and private space for extended family; (3) Au Pair / Caregiver Suite: An ideal arrangement for live-in support; (4) Private Guest Retreat: Offer visitors their own dedicated amenities; (5) Executive Home Office: A professional and separate workspace. This bright apartment features its own kitchen with quartz countertops, a charming built-in bookcase, a sunny bay window, a full bath with accessible bathroom equipment/accessories, and a spacious bedroom with a large closet. For complete independence, it includes an in-unit washer and dryer and a separate entrance. Furthermore, it boasts its own electric panel, along with dedicated attic space for storage. The apartment is seamlessly connected to the main home by a light-filled entrance featuring a skylight, blending convenience with privacy. The main residence features 4 bedrooms and 3 full bathrooms. Its traditional layout showcases beautiful hardwood floors, a formal dining room, and a full kitchen equipped with granite countertops, stainless steel appliances, and a convenient outside entrance. The comfortable living room includes a cozy fireplace, and a versatile first-floor room offers flexibility as a bedroom, home office, or den. Upstairs, you'll find three bedrooms, including a primary suite with an en suite bathroom featuring a walk-in shower. The full guest bathroom offers a tub/shower combination. Adding significant living space is the fully finished walk-out basement, a true extension of the home. This lower level provides three separate rooms ideal for recreation, a home office, a gym, or guest quarters. The spacious rec room, complete with a wood-burning fireplace, is fantastic for teen space or entertaining. The walk-out offers easy access to the backyard, enhancing the functionality of this level. Situated on a sizable partially fenced lot with a raised deck, the property provides a wonderful setting for outdoor enjoyment, with ample potential for gardening, play areas, and entertaining. Its prime location offers easy access to vibrant downtown Bethesda, the shops and restaurants of Friendship Heights, beautiful parks, and convenient transportation options. Don't miss this opportunity to own a truly special Chevy Chase gem.