Kenwood · Cook County · IL
Homes for sale in
Kenwood.
- Active listings
- 8
- Median list
- $217K
- Avg time on market
- 58 days
- Sold · last year
- 0
Active listings
8 homes on the market
About the community
Living in Kenwood.
Kenwood is one of Chicago's 77 community areas, set on the shore of Lake Michigan on the South Side, with boundaries at 43rd Street, 51st Street, Cottage Grove Avenue, and the lakefront, tucked between Oakland to the north and Hyde Park to the south. It was once one of Chicago's most affluent neighborhoods and still holds some of the largest single-family homes in the city, with mansion-lined blocks in the northern half giving way to a broader housing mix of condos, vintage apartments, and rowhomes. The area contains two Chicago Landmark districts, Kenwood and North Kenwood, protecting an architectural heritage of Queen Anne, Romanesque Revival, and Georgian Revival residences built largely between the 1870s and 1920s. Kenwood gained national attention as the home of former President Barack Obama, whose Georgian-style residence stands on South Greenwood Avenue. The neighborhood is anchored by Kenwood Academy, a comprehensive Chicago Public Schools high school with a citywide gifted magnet program. Commuters reach downtown via the Metra Electric District, whose 47th Street and 51st/53rd Street Hyde Park stations run north to Millennium Station. Residents are minutes from the Lake Michigan shoreline and the institutions of adjacent Hyde Park and the University of Chicago. It suits buyers drawn to historic architecture, quiet tree-lined streets, an easy rail commute, and proximity to South Side cultural and university life.
At a glance
About 18,100 residents
Kenwood has roughly 18,138 residents as of 2023 in a community area of about 1.1 square miles.
Grand mansions
Two Chicago Landmark districts protect some of the city's largest single-family homes, built mostly between the 1870s and 1920s for Chicago's elite.
Frank Lloyd Wright
The George Blossom House on South Kenwood Avenue, designed by Wright in 1892 as one of his early bootleg commissions, sits in Kenwood.
Obama residence
Former President Barack Obama's Georgian-style home stands on South Greenwood Avenue.
Kenwood Academy
A comprehensive Chicago Public Schools high school serving roughly 2,300 students in grades 7 to 12, with a citywide gifted magnet program.
Metra Electric
The 47th Street and 51st/53rd Street Hyde Park stations connect Kenwood north to Millennium Station in the Loop.
Lakefront access
Kenwood fronts Lake Michigan on the South Side, with lakeside condominiums and quick reach to the shoreline near Promontory Point.
About $346,000 median
Homes in Kenwood sold for a median of roughly $346,000 as of March 2026.
What it’s actually like to live here
Kenwood is a quiet, predominantly residential neighborhood whose tree-lined streets and landmarked mansions make it a destination for architecture enthusiasts, including admirers of Frank Lloyd Wright's 1892 George Blossom House on South Kenwood Avenue. The southern portion of the community area, often called Hyde Park-Kenwood, places residents within walking distance of Hyde Park's institutions and the University of Chicago, just to the south. The Lake Michigan shoreline and the South Side lakefront parks are close at hand, with lakeside condominiums viewing the water near Promontory Point.
The neighborhood's cultural draws include the historic KAM Isaiah Israel synagogue on East Hyde Park Boulevard, home to the oldest Jewish congregation in Illinois, founded in 1847. Just beyond Kenwood in adjacent Jackson Park, the Obama Presidential Center is opening to the public on June 19, 2026, a roughly 19-acre campus with a museum, library branch, athletic facility, and gardens expected to draw up to a million visitors a year. Together with its landmark blocks and lakefront, this gives Kenwood a settled, community-minded character anchored in South Side history.
Neighborhoods
Detailed Kenwood community pages coming soon.
Browse the listings above. Detailed neighborhood pages with market stats, school info, and lifestyle take-downs land here as we roll them out.
Around town
What there is to do in Kenwood.
A handful of the places people who live here actually use. Not a directory.
- Parks
Burnham Park and the South Side Lakefront
A historic lakefront park on the Lake Michigan shoreline just east of Kenwood, offering open green space, a trail, and skyline views.
- Culture
Obama Family Home
The former President's Georgian-style residence on South Greenwood Avenue, a private home that visitors view only from a distance since the block is restricted.
- Culture
KAM Isaiah Israel
A landmark synagogue on East Hyde Park Boulevard, home to the oldest Jewish congregation in Illinois, founded in 1847.
- Culture
George Blossom House
Frank Lloyd Wright's 1892 bootleg house on South Kenwood Avenue anchors a walkable district of landmarked mansions.
- Family
Blackstone Library
The 1902 Beaux-Arts Blackstone Library, a neighborhood landmark and active branch of the Chicago Public Library.
- Culture
Obama Presidential Center
Opening June 19, 2026 in adjacent Jackson Park, this campus houses a museum, gardens, and a public library branch.
How Kenwood got here
A bit of history.
Kenwood was settled in the 1850s by wealthy Chicagoans seeking respite from the growing congestion of the city, the first being John A. Kennicott, who built his home near the Illinois Central Railroad around 48th Street and named it Kenwood after his ancestral land in Scotland. When the railroad opened a small depot near 47th Street, it adopted the Kenwood name, and the name soon spread to the whole area. Through the 1870s, large single-family mansions rose on Ellis and Woodlawn avenues, followed by Drexel Boulevard in the 1880s, drawing Chicago's elite including lumber merchant Martin Ryerson, meatpacker Gustavus Swift, and Sears Roebuck executive Julius Rosenwald. Originally part of Hyde Park Township, Kenwood was annexed to the city of Chicago in 1889 yet retained its suburban, low-density residential character.
Over the 20th century the northern and southern halves of Kenwood diverged, with the stately mansion blocks of the southern half remaining more stable while North Kenwood saw greater change. The area's architectural legacy of Queen Anne, Romanesque Revival, and Georgian Revival homes is now safeguarded by two Chicago Landmark districts, Kenwood and North Kenwood, with much of the southern half also falling within the Hyde Park-Kenwood Historic District. In recent years the neighborhood drew renewed national attention as the home of former President Barack Obama.
The questions buyers actually ask
Kenwood FAQ
The questions I get most from buyers shopping Kenwood. If yours isn't here, text 815-355-0582, same-day reply.
- What are the schools like in Kenwood?
- Kenwood Academy is the neighborhood's comprehensive Chicago Public Schools high school, serving roughly 2,300 students in grades 7 to 12 and running a citywide gifted magnet program admitting students by exam into 7th grade. The neighborhood also sits next to Hyde Park, home to the University of Chicago and its Laboratory Schools.
- How is the commute downtown?
- The Metra Electric District serves Kenwood at the 47th Street and 51st/53rd Street Hyde Park stations, running north to Millennium Station in the Loop.
- What kinds of homes can I buy here?
- Kenwood offers a wide range, from some of the largest single-family mansions in Chicago in its landmark districts to vintage apartments, condominiums, and lakefront high-rises. As of March 2026, the median sale price was about $346,000.
- Are there restrictions on historic homes?
- Much of Kenwood lies within Chicago Landmark districts, Kenwood and North Kenwood, and part of the southern half is in the Hyde Park-Kenwood Historic District, so exterior changes to many properties are subject to historic-preservation review.
- What is the character of the neighborhood?
- Kenwood is a quiet, largely residential South Side enclave known for tree-lined streets, historic mansions, and proximity to the lakefront and Hyde Park institutions, and it draws architecture visitors to its landmark blocks.
Your local agent
Joe knows Kenwood
Most agents will list anything. I focus on the places I actually know, and the things that move value here don't show up in the MLS write-up: which streets and buildings hold demand, what the HOA or assessments really cover, how the comps read once you account for condition and location, and where buyers consistently want to be.
When you're ready to tour or list, you want someone who has read the last 50 closed comps in this specific market, not a national average, and can tell you what they actually mean for your price. That's how I work. Text or call any time, and I'll give you a real take, not a brochure.
- Licensed Illinois broker
- Comp-driven pricing
- Kenwood specialist
- Honest local market take
- Brokerocity
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
- No obligation, no spam, no auto-dialer