29 W Chestnut St. #5A

About this unit
SOLD BEFORE PRINT. Rarely available and full of character, this distinctive three-story, 3-bedroom, 2.5-bath residence at 29 W Chestnut offers a truly unique Gold Coast living experience. Originally built in 1889, the home blends historic charm with a flexible, non-cookie-cutter floor plan and exceptional indoor-outdoor living. The main level features an open layout with kitchen, living area, dining room, and powder room, creating an inviting space for everyday living and entertaining. A separate bedroom and full bath on the first floor provide excellent flexibility for guests, a home office, or a true live/work setup. The top floor includes a spacious primary bedroom, an additional bedroom, and a full bath, offering privacy and separation from the main living spaces. North and east exposures bring in natural light throughout the home. One of the property's most special features is its outdoor setting, including a European-style courtyard and shared garden patio that create a charming, tucked-away atmosphere in the heart of the city. An attached one-car garage adds convenience that is especially rare in this location. With low assessments and outstanding proximity to Michigan Avenue, Oak Street, neighborhood restaurants, shopping, and the lakefront, this is a one-of-a-kind Gold Coast home for someone looking for character, versatility, and something truly different.
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 29 W Chestnut St.
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.
Can I work with Dibze to buy?
Yes. A licensed Chicago buyer's agent lines up tours, writes offers, and handles the close. The seller pays the commission, so it's free to you — and we rebate part of it back at closing.
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.