420 E Waterside Dr. #2303

in The Regatta
$550,000 Active · 1 day on market
2
beds
2
baths
1,177
sq ft
$467
per sq ft

About this unit

Located in the coveted Regatta at Lakeshore East, this sun-drenched southwest corner residence offers sweeping views of Lake Michigan, the Chicago River, and the city skyline from every angle. This beautifully designed 2-bedroom, 2-bath home features an open-concept floor plan with soaring ceilings, hardwood floors, and floor-to-ceiling windows that flood the space with natural light. The spacious living and dining area opens to a private balcony, perfect for enjoying skyline sunsets and park views. The split-bedroom layout provides ideal privacy, while the chef's kitchen includes granite countertops, custom cabinetry, stainless steel appliances, breakfast bar seating, and ample storage. The luxurious primary suite features a walk-in closet and spa-inspired bath with dual vanity, soaking tub, and separate shower. In-unit laundry and garage parking complete the home. Residents of the Regatta enjoy full-service luxury amenities including 24-hour door staff, indoor pool and spa, state-of-the-art fitness center, theater room, game room, library, sundeck with grills, children's playroom, and on-site management. Ideally located in the heart of Lakeshore East, steps from the lakefront, Riverwalk, Mariano's, Millennium Park, bike paths, dining, shopping, and all that downtown Chicago has to offer.

Amenities

Shared amenities included with the building.

  • 24/7 Front Desk
  • Fitness Center
  • Pool

Property details

The facts that decide a tour — straight from MRED.

Monthly costs
HOA$839 / mo
HOA includesHeat, Air Conditioning, Water, Gas, Parking, Insurance, Doorman, TV/Cable, Exercise Facilities, Pool, Exterior Maintenance, Scavenger, Internet
Annual tax$10,798 (2024)
Rules & parking
ParkingHeated Garage, Yes, Deeded, 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.

$550,000
$
20%$110,000
6.85%
30 years
Principal & interest$2,883 / mo
HOA$839 / mo
Property tax (est.)$900 / mo
All-in monthly$4,622

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.

Sep 5, 2026 Listed for sale $550,000current

About 420 E Waterside Dr.

A look at the building this unit is in.

420 E Waterside Dr.— The Regatta

Lakeshore East condo · 44 floors · built 2006
3 for sale · 0 for rent
For sale from $365K
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.

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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.

Similar units in this building

Other listings on the same line, same floor, or close in size.

Recently sold in this building

Last 12 months of closed sales at 420 E Waterside Dr. — straight from MRED. For pricing context, not for tour.

Listed by Karen Majerczak · Compass · MLS #MRD12752424 · MRED
Mino Conenna
Mino Conenna
Licensed IL broker · Chicago condo specialist
Online now · replies in minutes

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