Chicago, IL·District 299
Homes in the
Lake View HS district.
Historic North Side high school in the heart of Lakeview, where Brown Line convenience meets classic Chicago two-flats and walkable Southport and Roscoe Village living.
- Homes for sale
- 122
- Typical list
- $614,950
- Most expensive
- $7,995,000
- Most affordable
- $130,000
3026 Lake Shore Drive →
3600 LAKE SHORE Drive →
Wildcats · Red & White · 1,289 students · Chicago Public League
Active listings
122 homes on the market
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Market snapshot
The Lake View 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
246
Typical list price
$675,000
Avg time on market
7 days
Sold in the last year
820
Typical sale price · last 90 days
$680,000
Living near Lake View HS
The area, not just the school
The blocks around Lake View High School sit in one of Chicago's most sought-after stretches of the North Side, where the Lakeview, North Center, and Roscoe Village neighborhoods run into one another. This is classic tree-lined, walk-everywhere Chicago. You are within strolling distance of Southport Avenue's shops and restaurants, the boutiques and cafes along Roscoe Street, and a quick ride from the lakefront and Wrigleyville. It is the kind of area where families put down roots and stay, drawn by the parks, the local schools, and a real main-street feel that is rare this close to downtown.
Getting downtown is easy, which is a big part of why buyers love it. The CTA Brown Line runs right through the area with stops at Paulina, Southport, and Addison, and a typical ride to the Loop lands in the 20 to 30 minute range. The Red Line at Addison and several bus routes give you more ways into the rest of the city without a car.
The housing here has real character and real range. You will find vintage greystone and brick two-flats and three-flats, plenty of converted and new-construction condos, classic frame and brick single-family homes, and townhouses tucked onto side streets. West Lakeview and Roscoe Village in particular lean toward two-flats and single-family homes with a more residential, family feel, while the condo inventory gives first-time buyers and downsizers a way into the same neighborhood.
🏫Oldest township HS in IL
Lake View opened in 1874 and is the oldest operating township secondary school in Illinois.
🔴Wildcats, Red and White
Teams compete as the Wildcats in the Chicago Public League.
🚆Brown Line at your door
Brown, Purple, and Red Line trains plus several bus routes serve the school's Ashland Avenue corner.
🔬STEM-designated
A STEM neighborhood school offering AP Capstone, Dual Credit, and electives like Forensic Science and Game Programming.
👥About 1,289 students
Serves grades 9 through 12 as a Chicago Public Schools neighborhood high school.
🏡Two-flats to condos
Surrounding Lakeview, North Center, and Roscoe Village mix vintage two-flats, greystones, single-family homes, and condos.
The school
About Lake View High School
Lake View High School is a public four-year high school in the Lakeview neighborhood on Chicago's North Side. While the current building opened in 1886, the school itself opened in 1874, when the Lake View community was a separate township not yet part of Chicago. Lake View was annexed into Chicago in 1889. Because it was created while Lake View was still its own township, the school is the oldest operating township secondary school in the state of Illinois. Parts of the 1980 film My Bodyguard were filmed at the school.
Lake View is a STEM-designated neighborhood high school. It teaches critical thinking across all courses and offers science and math electives including Forensic Science and Game Programming, plus AP Capstone. Through Early College options, students can earn college credit through AP and Dual Credit courses. AP participation is reported at roughly 55 percent.
Lake View competes as the Wildcats in the Chicago Public League and is a member of the Illinois High School Association. The boys track and field team finished second at the first IHSA state meet in 1892-93, and the boys soccer team finished fourth in the IHSA state tournament in 2008-09. In the era before World War Two the school even maintained a fifty-foot rifle range in the basement and fielded a rifle team.
- District
- District 299
- Founded
- 1874
- Principal
- Paul Joseph Karafiol
- Conference
- Chicago Public League
- Address
- 4015 N Ashland Ave, Chicago, IL 60613
Notable alumni
- Edgar Bergen. Ventriloquist, radio personality and actor, and father of actress Candice Bergen.
- Gloria Swanson. Golden Globe winning actress who played Norma Desmond in Sunset Boulevard.
- Tom Bosley. Tony Award winning actor best known as Howard Cunningham on Happy Days.
- Abe Saperstein. Founder, owner and coach of the Harlem Globetrotters.
- Sidney R. Yates. Long-serving U.S. Representative for Illinois across the mid and late 20th century.
- Vince Lawrence. Platinum-selling producer and a leading innovator of Chicago house music.
Facts on this page sourced from Wikipedia and the District District 299 website. Last verified 2026-06-25.
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
Lake View HS FAQ
The questions I get most from buyers shopping the Lake View HS district. If yours isn't here, text 224-385-8779, same-day reply.
- How is the commute downtown from this area?
- Very manageable. The CTA Brown Line stops at Paulina, Southport, and Addison are all near the school, and a typical ride to the Loop is about 20 to 30 minutes. The Red Line at Addison and several bus routes add more options.
- What kind of homes are around Lake View High School?
- A real mix. Expect classic Chicago brick and greystone two-flats and three-flats, single-family frame and brick homes, plus vintage and new-construction condos and the occasional townhouse. West Lakeview, North Center, and Roscoe Village lean more single-family and two-flat, while condos open the door for first-time buyers.
- Is Lake View a neighborhood school or a selective-enrollment school?
- Lake View is a neighborhood high school, which means CPS assigns students primarily by home attendance boundary. CPS also runs separate selective-enrollment high schools across the city that admit by test score regardless of address, so it is worth understanding both paths when you plan.
- Does living in a particular listing guarantee my child attends Lake View?
- Not automatically. CPS assigns neighborhood-school seats by attendance boundary, and boundaries can change, so a specific address should always be confirmed before you rely on it. Use the official CPS School Locator to check any address.
- Who should I contact to confirm a home is in the Lake View attendance area?
- Confirm directly with the source rather than a listing description. Check the address on the CPS School Locator and call the CPS or school office to verify the current boundary assignment. Your agent can pull the listing and walk through it with you.
Thinking of selling?
What's your home actually worth?
Not a Zestimate. A real CMA from someone who's sold this neighborhood, knows the floor plan premiums, and can tell you which upgrades the buyer pool here actually pays for.
- Pricing range with comp-by-comp logic
- Pre-list improvements that pay back, and the ones that don't
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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 16, 2025 through July 16, 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.