29 W Chestnut St. #5A

$849,900 Pending · 1 day on market
3
beds
3
baths
2,000
sq ft
$425
per sq ft

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.

Monthly costs
HOA$150 / mo
HOA includesWater, Insurance, Security, Scavenger
Annual tax$12,840 (2025)
Rules & parking
ParkingGarage Door Opener, Yes, Garage Owned, Attached, Garage
PetsCats OK, Dogs OK

What it costs each month

Live estimate. Tax based on Cook County 2024 effective rate. HOA pulled from the listing.

$849,900
$
20%$169,980
6.85%
30 years
Principal & interest$4,455 / mo
HOA$150 / mo
Property tax (est.)$1,070 / mo
All-in monthly$5,675

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.

Oct 22, 2026 Pending Pendingcurrent
Oct 19, 2026 Listed for sale $849,900

About 29 W Chestnut St.

A look at the building this unit is in.

29 W Chestnut St. building

29 W Chestnut St.

River North condo
1 for sale · 0 for rent
For sale from $850K
View the building

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.

Listed by Millie Rosenbloom · Baird & Warner · MLS #MRD12786560 · MRED
Mino Conenna
Mino Conenna
Licensed IL broker · Chicago condo specialist
Online now · replies in minutes

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