Chicago, IL·District 299
Homes in the
Kelly College Prep district.
Green and white pride in the heart of Brighton Park, one of Chicago's most connected Southwest Side neighborhoods.
- Homes for sale
- 26
- Typical list
- $361,500
- Most expensive
- $719,000
- Most affordable
- $150,000
3818 Paulina Street →
3307 37th Place →
Trojans · Green & White · 1,339 students · Chicago Public League
Active listings
26 homes on the market
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Market snapshot
The Kelly College Prep area, by the numbers
Live MRED data, refreshed daily. What this market is actually doing right now, sales included, not a portal estimate.
Homes for sale now
28
Typical list price
$361,500
Avg time on market
16 days
Sold in the last year
11
Typical sale price · last 90 days
$462,000
Living near Kelly College Prep
The area, not just the school
Living around Kelly College Prep puts you in the heart of Brighton Park, one of Chicago's most tight-knit Southwest Side neighborhoods. Rows of classic brick bungalows and two-flats line the side streets, Archer Avenue carries the local pulse of taquerias, panaderias, and family-owned shops, and a strong Mexican-American community gives the area its warmth. It is residential and hardworking, with generations of families who have put down roots here.
The commute is a big part of the appeal. The CTA Orange Line gives you a straight shot to the Loop and to Midway Airport, and Archer Avenue plus the nearby Stevenson Expressway make getting around by car easy too. You are close to McKinley Park and Archer Heights, which share that same mix of solid bungalow housing and neighborhood character. For buyers who want an affordable, well-connected Chicago neighborhood with real community feel, this pocket of the Southwest Side is hard to beat.
🏫Opened 1928
One of the largest high schools in Chicago Public Schools.
👥1,339 students
Grades 9 to 12 (Chicago Public Schools, 2025-26).
🏈Trojans, Green & White
Chicago Public League (IHSA).
🚆CTA Orange Line
Straight shot to the Loop and Midway Airport.
🧱Brighton Park bungalows
Classic brick bungalows and two-flats on the Southwest Side.
The school
About Thomas Kelly College Preparatory High School
Thomas Kelly opened on December 3, 1928 as a junior high school serving grades six through nine in Chicago's Brighton Park neighborhood. After the Chicago Board of Education abolished junior high schools in 1933, Kelly reopened as a senior high school for the 1933-34 year. The school is named for Irish nationalist Thomas J. Kelly and today is one of the largest high schools in the city, serving a community that is more than 80 percent Hispanic.
Now known as Kelly College Prep, the school combines International Baccalaureate, Advanced Placement, Honors, and college-prep tracks with a dedicated freshman academy. It runs award-winning performing-arts programs and offers bilingual services in both Spanish and Chinese, and it is accredited by the North Central Association of Colleges and Schools.
Kelly competes as the Trojans in the Chicago Public League and is a member of the Illinois High School Association, playing in green and white. Athletics run alongside the school's strong performing-arts tradition on the Southwest Side.
- District
- District 299
- Founded
- 1928
- Principal
- Raul Magdaleno
- Conference
- Chicago Public League
- Address
- 4136 S California Ave, Chicago, IL 60632
Notable alumni
- Lenny Gomulka. Professional polka bandleader and musician.
- Kevin Hickey. Major League Baseball pitcher for the Chicago White Sox and Baltimore Orioles.
- Ron Masak. Actor best known for the series Murder, She Wrote.
Facts on this page sourced from Wikipedia and the District District 299 website. Last verified 2026-07-05.
Listings filtered by the school the MRED listing agent assigned. Roughly 7 in 10 active listings have this field populated; the remaining listings will surface once the school-district boundary pipeline ships. School assignment is not a guarantee. Always verify with the district before writing an offer.
The questions buyers actually ask
Kelly College Prep FAQ
The questions I get most from buyers shopping the Kelly College Prep district. If yours isn't here, text 224-385-8779, same-day reply.
- What neighborhood is Kelly College Prep in?
- Kelly is at 4136 S California Ave in Brighton Park, a residential Southwest Side neighborhood known for its brick bungalows, the Archer Avenue business corridor, and a strong Mexican-American community.
- How is the commute to downtown from around the school?
- The area is very well connected. The CTA Orange Line runs straight to the Loop and to Midway Airport, and Archer Avenue plus the nearby Stevenson Expressway make driving easy too.
- What kind of homes are near Kelly High School?
- The streets around the school are lined with classic Chicago brick bungalows and two-flats, most built in the early 20th century, which gives the area a consistent architectural character.
- Is Kelly a good academic fit for my student?
- Kelly offers International Baccalaureate, Advanced Placement, Honors, and college-prep programs, a freshman academy, award-winning performing arts, and bilingual services in Spanish and Chinese, so it serves a wide range of learners.
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What's your home actually worth?
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This representation is based in whole or in part on data supplied by Midwest Real Estate Data, LLC for the period July 21, 2025 through July 21, 2026. Midwest Real Estate Data, LLC does not guarantee nor is it in any way responsible for its accuracy. Data maintained by Midwest Real Estate Data LLC may not reflect all real estate activity in the market.