
About this unit
Set in the exclusive Lakeshore East, Penthouse Residence 4114 at The Regatta is the definition of elevated city living. Highest 14-tier unit in the building! Step into a grand foyer highlighted by a timeless chandelier that sets the tone for classic elegance and quality craftsmanship. Soaring 10-foot ceilings and rich oak flooring guide you into a sunlit living space, where floor-to-ceiling windows deliver panoramic views of Lake Michigan, Navy Pier, and the Chicago River. The layout is ideal for both social gatherings and quiet relaxation; enjoy the ambiance of a contemporary fireplace or prepare gourmet meals in the upgraded kitchen, complete with peninsula granite counters, Brookhaven cabinetry, KitchenAid appliances, a dual-temperature wine cooler, and ample hosting space. Take advantage of the balcony to relax with your favorite drink and watch Navy Pier's summer fireworks. Three separate heating and cooling zones provide personalized comfort throughout the home. The primary suite serves as a private retreat with a custom walk-in closet and a luxurious bathroom featuring double vanities, a walk-in shower, and a deep soaking tub. With a split-bedroom design, one en-suite bedroom is set apart with its own marble bath with heated floors, perfect for guests or extended stays. A spacious third bedroom offers a unique view of Lake Michigan and comes furnished with custom designed closets that enhance convenience. A necessary third marble bathroom boasts heated floors and a custom walk-in shower. Practical features include ample closet space throughout the home and a spacious laundry room with side-by-side appliances. Located on the penthouse level, this residence stands out for its abundant sunlight, architectural flair, and modern touches. Amenities at The Regatta encompass everything from a 24-hour doorman, indoor pool, whirlpool, gym, landscaped sun deck, children's play area, theater, game and lounge rooms, event spaces, library, on-site dry cleaning, and two deeded parking garage spaces. This unit offers more than just luxurious accommodations, it's a serene escape above the city, yet steps away from the opera, events, shopping, and parks; presenting an unparalleled opportunity to experience Chicago at its finest.
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.
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 420 E Waterside Dr.
A look at the building this unit is in.

420 E Waterside Dr.— The Regatta
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.
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.

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