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$1,199,000 Just Listed

  • For Sale
  • Active
  • Condo
  • 3 Beds
  • 3 Full Baths
  • 1,887 Sq. Ft.
  • 2 Car Garage
  • Updated 15 hours ago
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Set in the exclusive Lakeshore East, Penthouse Residence 4114 at The Regatta is the definition of elevated city living. Step into a grand foyer highlighted by a vintage 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, 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 maximize storage. A convenient third marble bathroom includes heated floors and a custom walk-in shower. Practical features boast ample closet space throughout the home and a spacious laundry area 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.

Full Property Details for 420 E Waterside Dr #4114

General

  • Price: $1,199,000
  • HOA FEE: $1,614/month
  • Taxes: $19,310 (2024)
  • Status: Active
  • Type: Condo
  • Source: MRED
  • MLS ID: 12632003
  • Updated: 5/1/2026
  • Added to Site: 1 day(s) ago

Interior

  • Basement: None
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Living Room
  • Appliances: Range, Dishwasher, Refrigerator
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Bathroom Features: Separate Shower, Double Sink, Soaking Tub

Bedrooms

  • Total Bedrooms: 3

Additional Information

  • Shared Amenities: Bike Room/Bike Trails, Door Person, Elevator(s), Exercise Room, Storage, On-Site Manager/Engineer, Party Room, Sundeck, Indoor Pool, Receiving Room, Service Elevator(s), Valet/Cleaner, Spa/Hot Tub

Exterior

  • Exterior Features: Balcony

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Features: Garage Door Opener, Yes, Garage Owned, Attached, Garage

Location

  • Area: CHI - Loop
  • County: Cook
  • Township: South Chicago
  • Subdivision: Regatta
  • Driving Directions: RANDOLPH EAST OF MICHIGAN AVE, NORTH TO HARBOR, WEST TO 420 WATERSIDE.

School Information

  • School District: 299
  • Elem School District: 299
  • Midd School District: 299
  • High School District: 299

Community

  • Assoc. Fees Include: Heat, Air Conditioning, Water, Gas, Parking, Insurance, Doorman, TV/Cable, Exercise Facilities, Pool, Exterior Maintenance, Lawn Care, Scavenger, Snow Removal, Internet
  • Pets Allowed: Yes
  • Pets: Cats OK, Dogs OK
  • Pet Restrictions: Cats OK, Dogs OK, / 999lbs.
  • Mgmt. Company: Sudler Property Management

Heating & Cooling

  • Cooling Type: Central Air Conditioning
  • Heating Type: Natural Gas, Forced Air, Radiant Floor

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Onsite: Cable Available

Structural Information

  • Structure Type: Condo
  • Construction: Brick, Glass, Concrete
  • Exterior Const.: Brick, Glass, Concrete
  • Basement Desc.: None
  • Foundation: Concrete Perimeter
  • Windows: Screens
  • Sub-Flooring: Hardwood
  • Entry Floor Number: 41
  • Stories/Levels: 44
  • Square Feet: 1,887
  • Sq. Ft. Source: Other
  • Year Built: 2006

Unit Information

  • Units in Building: 320

Lot Features

  • Lot Dimensions: COMMON

Animals

  • Animals Allowed: Cats OK, Dogs OK

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: River Front
  • Water Front View: Front of Property

Financial Considerations

  • Association Fee: $1,614
  • Assoc Fee Freq.: Monthly
  • Parking Included: Yes
  • Assessment Year: 2006
  • Tax Amount: $19,310.51
  • Tax Year: 2024
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Condo
  • Special Conditions: List Broker Must Accompany
  • Property ID: 17104000351312

Listed by Chicagoland Brokers, Inc.

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— 420 E Waterside Dr #4114 —

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Schools serving 420 E Waterside Dr #4114

School District:Chicago Public School District 299
NameGradesDistance
Ogden Elementary School
24 West Walton Street, Chicago, IL 60610
K-81.1 mi
Wells Community Academy High School
936 North Ashland Avenue, Chicago, IL 60622
9-112.8 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 420 E Waterside Dr #4114 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/01/2026
Listed
$1,199,000
23.61%
MLS
9/17/2010
Sold
$970,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 420 E Waterside Dr #4114

Year
Property Taxes
Change
Tax Assessment
Change
2023
$23,251
3%
$110,199
—
2022
$22,666
2%
$110,199
—
2021
$22,160
—
$110,199
10%
2020
$22,243
2%
$99,847
-8%
2019
$21,856
2%
$108,783
—
2018
$21,488
-24%
$108,783
25%
2017
$28,310
62%
$86,992
—
2016
$17,424
9%
$86,992
—
2015
$15,941
8%
$86,992
9%
2014
$14,784
2%
$79,683
—
2013
$14,492
1%
$79,683
—
2012
$14,299
—
$79,683
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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420 E Waterside Drive #4114, Chicago, IL 60601 (MLS# 12632003) is a Condo property with 3 bedrooms and 3 full bathrooms. 420 E Waterside Drive #4114 is currently listed for $1,199,000 and was received on May 01, 2026. Want to learn more about 420 E Waterside Drive #4114? Do you have questions about finding other Condo real estate for sale in The Loop? You can browse all The Loop real estate or contact a Coldwell Banker agent to request more information.

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