This neighborhood is up-and-coming and a great investment.

Welcome to Woodlawn 

Is Woodlawn going to be one of Chicago's next exciting neighborhoods?
Located on the South Side of Chicago, IL, the Woodlawn community houses a substantial wealth of locally-owned up-and-coming businesses, historic parks, organizations that are worthy of thorough exploration, and cultural institutions.
This neighborhood is up-and-coming and a great investment.

What to Love 

  • Historic parks
  • Cultural institutions
  • Walk on 63rd St Beach
  • Neighboring community of Jackson Park

Local Lifestyle 

Most residents of the Woodlawn community own their homes. The neighborhood gives residents a sort of combined suburban-rural feel to it. There are many young inspiring professionals and entrepreneurs living in Woodlawn.
With more and more residents moving into the neighborhood over the last few years, Woodlawn has seen a bit of a renaissance. A lot of its growth has been due to how close it is to Hyde Park; on top of that, Woodlawn has public transportation options that give it ease of access to the Loop, direct access to Lake Michigan, and a couple of extremely notable up-and-coming developments.
Jackson Park makes up much of Woodlawn's eastern portion. Woodlawn's northern edge contains a section of the University of Chicago's campus.

Dining, Entertainment & Shopping 

First on the list is Robust Coffee Lounge, a favorite hangout spot and beloved study area for community members and students alike. This indie coffeehouse not only offers fair-trade coffee, but it also offers the Woodlawn community a varied menu of different types of sandwiches, Belgian waffles, and a whole lot more. 
Next is Daley's Restaurant. This is a historic diner that serves a variety of soul and homestyle classics, from pork chops to waffles. It's been proudly serving the Woodlawn neighborhood since 1892.
If you're looking for some fun on the waterfront, you don't want to miss Reggies on the Beach over on 63rd St. Beach. The Reggies family is well-known for their Music Joint and venue Rock Club. If you're hungry, they also serve bar bites like quesadillas and burgers.
If you get a craving for some Caribbean food, you'll want to give Jerk 48 a try. They proudly serve Caribbean-inspired specialties in an industrial-style, roomy restaurant. Taste marinated steak, chicken, fresh seafood, lamb, and other blends of authentic jerk spices all grilled up fresh daily.

Things to Do 

For a little peace and tranquility, you can enjoy Jackson Park which boasts over 540 acres of fun, relaxation, and enjoyment. It features indoor and outdoor fitness facilities, gardens, and a beach. The park's green features include Wooded Island, which hosts the Japanese Garden, the Columbian Basin which is surrounded by cherry blossom trees, Bobolink Meadows, and a flower and vegetable garden. 
Located in Jackson Park you'll find the popular 63rd Street Beach. Here, beachgoers have a wide range of amenities they can enjoy. For instance, if you're hungry, you can stop by Leave With a Smile for some quick snacks and drinks or at the Belly Up if you're in the mood for something more satisfying like some Jamaican food. The historic beach house provides various amenities to beachgoers like showers, restrooms, interactive water fountains, and meeting rooms. Beachgoers can also rent the beach house if desired.


Woodlawn schools are managed and operated by the Woodlawn Unit School District 209. A few include:
  • Woodlawn community elementary school, Grades Pk-6, received a 2021 Thrive Award
  • Carter G. Woodson Middle School, Grades K-12, rigorous instructional program
  • Hyde Park Academy High School, Grades 9-12

Search All Homes

Work With Us

Our team culture is extremely important to us. Outside of real estate we workout together, explore the city and celebrate team wins, milestones, and family.

Follow Us on Instagram