Dan Loves HousesCompass · Chicago

Neighborhoods · Far Southeast Side

Washington Heights

🏠

Why people love it

Washington Heights is 74 percent single family detached houses, and it feels like it: front lawns, brick bungalows, and neighbors who have been on the block for thirty years. The Carter G. Woodson Regional Library sits right here, holding the largest collection of African American history in the midwestern United States.

📈

What's drawing people

Three Metra Rock Island stations inside the community area at Brainerd, 95th Street Longwood and 103rd Street, plus full time CTA service on the 95, 103 and 112. The city and CTA ran a $1 million planning study for the 95th Street corridor aimed at transit oriented development, and buyers have noticed: the typical house went from $111,000 to $231,005 in twelve years.

👥

The value

At a $231,005 median with 2 bedrooms renting near $1,460, you are looking at roughly 7.6 percent gross rent to price before taxes, insurance, vacancy and repairs. That is a house you can own, live in and hold, on a block where the housing stock is already built and already good. Buy here to operate, not to flip.

What people say about Washington Heights

  • The typical house sale went from $111,000 to $231,005 across the 2013 to 2025 rolling windows, up 108 percent.
  • 2 bedroom rents average about $1,460 a month, up 9.9 percent year over year, which pencils to roughly 7.6 percent gross against the median house.
  • 527 bungalows sit in the Brainerd Bungalow Historic District, built 1915 to 1931, listed on the National Register in December 2016.

Washington Heights is 74 percent single family detached houses, and it feels like it: front lawns, brick bungalows, and neighbors who have been on the block for thirty years.

Washington Heights grew up where two rail lines crossed, incorporated as a village in 1874 and annexed by Chicago in 1890. The name goes back to 1869, when the post office opened and honored George Washington. Three neighborhoods live inside the community area: Brainerd, Fernwood and Washington Heights proper. Today it is home to about 25,000 people with a median age near 42, and the Carter G. Woodson Regional Library anchors it as a place that takes its own history seriously.

The housing is the story. Roughly 74 percent of it is single family detached, and most of it went up between 1940 and 1969, so you are buying real construction with real lot lines. The Brainerd Bungalow Historic District covers 527 Chicago bungalows built between 1915 and 1931, and even though forty two different architects worked on them, the streets read as one continuous idea with color and trim doing the individual work. That is a rare thing to find still intact.

The price line has been steady and strong. Typical house sales moved from $111,000 in the 2013 rolling window to $231,005 in the 2025 window, a 108 percent gain over twelve years. That is not a spike, it is a decade of consistent absorption by people who wanted to own here. With 2 bedroom rents averaging $1,460 and rising almost 10 percent year over year, the rent side is moving with it.

This fits a buyer who wants a real house on a real block and does not want to pay north side money for it. It also fits a long hold investor who values a Metra stop and a full time bus grid more than a flip margin. I would not send a quick turn speculator here. I would send someone who intends to still own the property in 2036.

Last updated August 2026.

Thinking about Washington Heights, or a neighborhood like it?

Reach out