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Located at 420 E Waterside Drive, Chicago, Illinois 60601, New Eastside neighborhood, this Single Family Home is for Sale with a price of $1,399,000 USD. The property was built in 2006, includes 3 bedrooms, has 2 full baths and 1 partial baths. This listing has 2,642 Sq.Ft. of interior space. See all Homes for Sale in New Eastside.
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39. 420 E Waterside Drive
1. 420 E Waterside Drive
2. 420 E Waterside Drive
1 of 39
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ChicagoNew Eastside420 E Waterside Drive

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Description

420 E Waterside Drive,

Regatta on Waterside, #4010, Chicago, IL 60601

Experience luxury living high above the city at The Regatta in the peaceful Lakeshore East neighborhood. Perched in the penthouse tower of this iconic high-rise, Unit 4010 boasts an extraordinary amount of living space along with sweeping 360-degree views from wraparound floor-to-ceiling windows in every room. Two nice-sized private balconies offer outside space with gorgeous views of the river and lake. The extra-large living room incorporates space typically closed off in this tier as a third bedroom or den. It can be easily enclosed if desired. A spacious dining area could comfortably seat 8-12, and the stylish kitchen offers both a breakfast bar and space for a cafe table...with a river view, btw! The expansive primary suite features a dressing room-sized walk-in closet, and a spa-like bathroom with two vanities, soaking tub, walk-in shower, and water closet. The size of the primary bedroom offers the owner the possibility of also adding in an office area, workout space, or...? The split floor plan places the second bedroom almost in a "private wing" with its own entrance, full bath, and wall of double closets. High ceilings, hardwood floors, and panoramic views add to the elegance. (Make sure you see the stunning nighttime photos that were just taken from this unit that show the river, the lake, and the fireworks from Navy Pier.) A pretty powder room, side-by-side washer/dryer, and large front hall closet add to the convenience. The Regatta's 5000 square feet of top-tier amenities include an indoor pool with hot tub, well-appointed fitness center, newly remodeled party room, library, children's playroom, 13th floor sundeck with grills, and more. Set in the tranquil Lakeshore East neighborhood with its lovely park, you're moments from the vibrancy of Millennium Park, Grant Park, Michigan Avenue, the Theatre District, and of course, the lakefront. Mariano's is a 10-minute walk away. Deeded garage parking valued at $45K is included in the asking price-though you may never need to drive anywhere! This is easy city living at its best!

This is an Active listing.

Broker Office Phone Number: 773-466-7150

Copyright © 2025Midwest Real Estate Data, LLC. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Amenities

  • Dishwasher
  • Garbage Disposal
  • Refrigerator
  • Hardwood Flooring
  • Dryer Included
  • Washer / Dryer
  • Waterfront
Listing By: Compass via Data Source: Midwest Real Estate Data, LLC 
3
Bedrooms
2
Full Baths
1
Partial Bath
$1,399,000
price
$530
Price Per Sqft
$30,768
Annual taxes
Single Family Home
Property type
2006
Year Built
Chicago Public 299
School District
Chicago Public 299
School District
chicago-public-school-district-299-chicago-il
Schools
Ogden Elementary
Elementary
Ogden Elementary
Middle
16290115
Web Id
12488178
MLS ID
29
Days Posted

Price History

datepricevariancetype
10/21/2025$1,399,000 1.82 %decreased
9/9/2025$1,425,000 1.72 %decreased
8/11/2025$1,450,000-Listed
listing agent: Chris Stockwell
more info
2,642 Sq Ft.
interior
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    Reduced

    Regatta on Waterside, #4010
    New Eastside, Chicago, IL 60601

    $1,399,000
    3 bd2 ba