Chicago, IL·Chicago Public Schools
Homes in the
Roosevelt HS district.
Historic brick homes, unmatched diversity, and a one-seat Brown Line ride downtown from the heart of Albany Park.
- Homes for sale
- 27
- Typical list
- $379,000
- Most expensive
- $1,499,000
- Most affordable
- $189,900
Chicago, IL →
4606 MONTICELLO Avenue →
Rough Riders · Blue & Gold · 1,016 students · Chicago Public League
Active listings
27 homes on the market
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Market snapshot
The Roosevelt HS 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
42
Typical list price
$459,000
Avg time on market
14 days
Sold in the last year
88
Typical sale price · last 90 days
$420,000
Living near Roosevelt HS
The area, not just the school
Roosevelt High School sits in the heart of Albany Park, one of the most genuinely diverse neighborhoods in the country, where more than 40 languages are spoken and Lawrence Avenue carries a mix of Korean, Mexican, and Middle Eastern shops. This is a neighborhood of classic Chicago brick two-flats, greystones, and courtyard buildings, with the tree-lined enclave of Ravenswood Manor just across the river offering some of the most sought-after single-family homes on the Northwest Side. Prices here stay more approachable than the lakefront neighborhoods to the east, which is a big part of the draw for families and first-time buyers who want character and space without leaving the city.
The commute is a quiet superpower. The CTA Brown Line terminates right at the Kimball station in Albany Park, so residents get a reliable one-seat ride into the Loop, with the Kedzie and Francisco stops, the Montrose Blue Line, and the Edens Expressway all close by. Everyday errands are walkable, and a Metra stop in nearby Mayfair adds another fast option downtown.
What ties it together is the North Branch of the Chicago River, which curves along the neighborhood's east and north edges and feeds a green ribbon of parks. River Park and Ronan Park put riverfront trails and open space steps from home, and the campuses of Northeastern Illinois University and North Park University lend the area a steady, grounded energy.
🎓Grades 9-12
A four-year Chicago Public Schools high school in Albany Park.
🌍40+ languages
Albany Park is one of the most diverse neighborhoods in the country.
🚆Brown Line terminal
The CTA Brown Line ends at Kimball, a one-seat ride to the Loop.
🛠️Five CTE pathways
Culinary, teaching, health careers, game design and coding, and IT networking.
🏫Founded 1922
Opened in 1922 and renamed for President Theodore Roosevelt in 1927.
🌳Riverfront parks
River Park and Ronan Park line the North Branch of the Chicago River.
The school
About Theodore Roosevelt High School
Roosevelt opened in 1922 as William G. Hibbard High School, then moved into a new building and was renamed in honor of Theodore Roosevelt, the 26th president, in 1927. By 1930 the surrounding Albany Park neighborhood had grown to roughly 55,000 residents, and Roosevelt's overcrowding was so severe that nearby Von Steuben was pressed into service as a high school to absorb the demand. Today the school remains an anchor institution of Albany Park, serving students from one of the most ethnically diverse neighborhoods in the United States.
Roosevelt offers five Career and Technical Education pathways: culinary arts, teaching and education, health careers, game design and coding, and IT and computer networking. It is one of a small number of Chicago high schools with a Spanish dual-language program, and it also offers honors, Advanced Placement, and dual-credit coursework, with about half of students graduating with college credit or on track for a technical certification.
The Rough Riders compete in the Chicago Public League and are members of the IHSA. The school had a banner year in 1952, capturing the city basketball championship over Tilden Tech and a tennis championship over Senn, and the football team were Public League champions in the 1960-61 season.
- District
- Chicago Public Schools
- Founded
- 1922
- Principal
- Dr. Daniel Kramer
- Conference
- Chicago Public League
- Address
- 3436 W. Wilson Avenue, Chicago, IL 60625
Notable alumni
- Shel Silverstein. Poet, cartoonist, and Grammy-winning songwriter, author of The Giving Tree.
- Nelson Algren. Author of The Man with the Golden Arm and Chicago: City on the Make.
- Carl Foreman. Academy Award-winning screenwriter of High Noon and The Bridge on the River Kwai.
- Leo Melamed. Former chairman of the Chicago Mercantile Exchange and pioneer of currency futures.
- Adolph Kiefer. Olympic gold medal swimmer at the 1936 Games.
Facts on this page sourced from Wikipedia and the District website. Last verified 2026-07-02.
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
Roosevelt HS FAQ
The questions I get most from buyers shopping the Roosevelt HS district. If yours isn't here, text 224-385-8779, same-day reply.
- What high school serves the Albany Park area?
- Theodore Roosevelt High School at 3436 W. Wilson Avenue is the neighborhood public high school, part of Chicago Public Schools, drawing students from Albany Park, Ravenswood Manor, and Irving Park.
- What academic programs does Roosevelt offer?
- Roosevelt offers five CTE career pathways, a Spanish dual-language program, and honors, AP, and dual-credit courses, with about half of students graduating with college credit or a technical certification track.
- How is the commute downtown from the area around Roosevelt?
- It is easy. The CTA Brown Line terminates at Kimball in Albany Park for a direct ride to the Loop, with the Kedzie and Francisco stops, the Montrose Blue Line, the Edens Expressway, and a Metra stop in Mayfair adding more options.
- What kind of housing will I find near the school?
- The area is known for classic Chicago brick two-flats, greystones, and courtyard buildings, with the tree-lined Ravenswood Manor enclave nearby offering desirable single-family homes, generally at more approachable prices than the lakefront neighborhoods.
- How do I find homes near Roosevelt High School?
- The listings here are filtered to homes whose MRED listing agent assigned Roosevelt as the high school. For alerts on new homes in the area, text 224-385-8779.
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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.