A truly rare opportunity in the heart of Midtown Ocean City! Just one block from the beach, 104 Bering Rd offers an exceptional property featuring two separate homes on one lot—a unique offering that's seldom available in Ocean City. Whether you're looking for a primary residence with guest accommodations, a vacation retreat for extended family, or an investment with incredible flexibility, the possibilities are endless. Each home can be rented individually under 1 rental license, or use 1 home and rent the other. Lovingly maintained by a caring owner, this property blends classic Old Ocean City coastal charm with thoughtful modern updates. Its prime Midtown location puts you within walking distance of restaurants, shopping, entertainment, 94th Street Park, and just around the corner from the Caribbean Dr. public boat ramp. The MAIN HOME offers approximately 1,508 sq. ft. with 3 bedrooms and 2.5 baths. Step inside to a bright sunroom with tile flooring and abundant natural light. The cozy living room features a gas fireplace, while the beautifully updated kitchen (2021) boasts granite countertops, white cabinetry, and stainless steel appliances. The spacious first-floor primary suite offers hardwood flooring and a beautifully updated bath with a large vanity and tiled shower. A second full bath with a tiled shower, washer & dryer, and hardwood flooring throughout most of the first floor completes the main level. Upstairs you'll find two generously sized bedrooms and a convenient half bath. The GUEST HOME offers approximately 1,000 sq. ft. with 4 bedrooms and 1.5 baths, along with a welcoming front deck. The first floor includes three bedrooms with hardwood flooring, a full bath, half bath, and a washer & dryer. Upstairs features an open living and dining area with hardwood flooring, a fully equipped kitchen with tile flooring, an additional bedroom, and a spacious screened porch overlooking the backyard. The outdoor space is truly something special. Tucked behind the main home is a private, fenced backyard area that feels like your own personal retreat, complete with a large paver patio, covered patio, side yard, multiple storage sheds with lighting, and plenty of room to entertain, eat crabs, BBQ, relax, and create lasting memories with family and friends. Additional highlights include a large driveway providing ample parking. Whether you're searching for a beach getaway, multi-generational living, rental income potential, or simply a one-of-a-kind Ocean City property, 104 Bering Rd is an opportunity you won't want to miss.