Hillcrest Condos for Sale. Hillcrest is San Diego’s first suburb, and today, is a colorful and diverse community brimming with coffee shops, restaurants and boutiques. The area got its start in the summer of 1906 when William Wesley Whitson received a business tip from his sister-in-law Laura Anderson that the George Hill Estate was for sale. Anderson purchased the hilly, tract just north of downtown from Whitson for $115,000, which was a bargain at the time. Hillcrest today more closely resembles a village than an urban center. The restored Hillcrest sign centers the area around University, and gives it a unique character. Streets are lined with antique stores, specialty shops, bookstores and specialty dining. Properties vary widely from early 1900’s historic homes to newer construction condo buildings.