5738-40 S Kenwood Avenue #3

About this unit
Rarely does an opportunity like this come along in the heart of Hyde Park. Located just a few doors from the University of Chicago Laboratory Schools and moments from the University of Chicago campus, this extraordinary penthouse residence offers an unmatched combination of space, character, and convenience. Created by combining two top-floor condominiums into one spectacular home, this expansive residence lives like a single-family home while offering the ease of condominium living. With five bedrooms and three full baths, the thoughtfully designed floor plan provides incredible flexibility for everyday living, working from home, and entertaining. The beautiful and bright kitchen features abundant cabinetry, generous prep space, and extensive counter seating that invites family and friends to gather. A gracious living room and a huge library provide inviting spaces to relax or work, while the stunning primary suite includes a remarkable dressing room and tons of built-in storage rarely found in city living. Vintage charm abounds throughout, with beautiful original details, elegant millwork, and multiple fireplaces adorned with unique antique tile surrounds that add warmth and distinction to the home. Step outside to enjoy the expansive rear deck spanning the entire width of the building-an exceptional outdoor retreat with ample space for dining, gardening, and entertaining. Completing this remarkable offering are in-unit laundry, basement storage and two exterior parking spaces, an invaluable convenience in this sought-after neighborhood. Perfectly positioned near the University of Chicago, the Obama Presidential Center, neighborhood parks, acclaimed dining, shopping, and public transportation, this truly one-of-a-kind Hyde Park penthouse offers the very best of historic character and modern city living.
Property details
The facts that decide a tour — straight from MRED.
What it costs each month
Live estimate. Tax based on Cook County 2024 effective rate. HOA pulled from the listing.
Estimate. Real rate depends on your lender, credit, and reserves. We'll connect you to a Chicago-based broker once you tour.
Listing history
The MLS trail for this unit — list events and price changes only.
About 5738-40 S Kenwood Avenue
A look at the building this unit is in.
Where it is
FAQ
Where do these listings come from?
Straight from the Midwest Real Estate Data (MRED) MLS, refreshed regularly — the same listings your buyer's agent sees, no curated subset.
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Can I rent in this building?
If owners are leasing units, the For Rent tab shows them. These are individual condo owners listing through the MLS, so lease terms and pet rules vary by unit.
How is this different from Redfin or Zillow?
Same MLS feed, different model — we don't sell your contact info or turn every click into a lead. One Dibze condo expert handles your whole search and represents you, not the seller.

We'll email you the moment the price changes or it goes under contract. Nothing else.