Oakland was once nothing more than a general store, a church, a town hall and a strip of wood-frame homes. During this simple time, the area was referred to as "Cleaverville" in honor of its first factory owner, Charles Cleaver. It was only a matter of years, however, before the Illinois Central Railroad stepped into the picture (in 1871) and made the neighborhood a more desirable living destination, bringing with it a completely new name that remains today.

Oakland fell into a rough spot shortly after a population boom in the 1940s and ended up making way for large, low-income housing projects. Most of these buildings have been torn down and Oakland is in the process of bringing in new constructions and making renovations to older homes. It's only a matter of time before the place is once again brimming with its old mid-19th century charm.

Part of that charm, though, can already be found in the neighborhood's popular recreational spot known as Mandrake Park. Constructed in the late 1990s, this outdoor locale proudly boasts a multi-purpose athletic field, a running track and attractive landscaped grounds. Participating with Chicago Park District's well-loved family-oriented programs, Mandrake Park offers evening entertainment in the form of Movies in the Park, which takes place throughout the summer months. Nobody misses a chance to sprawl out on a blanket with their favorite snacks to watch a film out under the stars (that might have a little something to do with the free admission, but by the smiling faces you see here, the experience is most certainly priceless).

When you're not veggin' out with popcorn and classic flicks, Mandrake Park is a great spot to get physical. Bring a group of friends and hit up the softball field, or go one-on-one at the park's tennis court. If you stray east of the park, you'll hit the beautiful lakefront just off Oakwood Avenue, lined with walking and bike trails. Strolling along the water watching the waves crash up against the shore is great, but if you're up for a self-guided architectural tour, stick to Oakland's residential blocks where you'll find pockets of century-old homes and Victorian mansions. Queen Anne-style cottages, Romanesque houses and Classical Revival structures are among the best. Most of these older homes have large porches and intricate architectural details that remind of classic 19th century life and instill a sense of Oakland's historic past.

Recent years have seen a rise in new developments and rehabbed condominiums in Oakland, with the average two-bedroom attached residence valued in the mid $200,000s. Tack on an extra room and you're looking at prices in the low $300,000s. Oakland real estate also includes a selection of detached single-family houses. Home buyers can find deals starting at $200,000, but the average price is in the low $400,000s. Still got your eyes set on one of those renovated older homes? How about a large and lavish new construction? Start saving up because some of these properties are already valued at over a million dollars.