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FOR SALE

420 E Waterside Dr #4114
Chicago, IL 60601

New Eastside

3 Beds
3 Baths
1,887 sqft

$1,199,000

Est. Mortgage $9,841/mo*

Get Pre-Qualified

$1,199,000

Est. Mortgage $9,841/mo*

Get Pre-Qualified

3 Beds

3 Baths

1,887 sqft

Home Highlights

Parking

2 Car Garage

Outdoor

Pool

Climate Control

Heating & Cooling

HOA

$1,614/Monthly

Price/Sqft

$635

Local Information

Map ViewExplore the area around 420 E Waterside Dr #4114.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

About this House

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.

Home Details for 420 E Waterside Dr #4114

Active Status
MLS Status: Active

Interior Features
Interior Details Basement: NoneNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Dining Room, Family Room, Kitchen, Laundry, Living Room
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout Living Area: 1887 Square Feet
Appliances & Utilities Utilities: Cable AvailableAppliances: Range, Dishwasher, RefrigeratorDishwasherLaundry: Washer Hookup,In UnitRefrigerator
Heating & Cooling Heating: Natural Gas,Forced Air,Radiant FloorHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Natural Gas
Fireplace & Spa Number of Fireplaces: 1Fireplace: Living RoomHas a FireplaceNo Spa
Gas & Electric Electric: Circuit Breakers
Windows, Doors, Floors & Walls Window: ScreensFlooring: Hardwood
Levels, Entrance, & Accessibility Number of Stories: 44Accessibility: No Disability AccessFloors: Hardwood
View Has a ViewView: Water, Front of Property

Exterior Features
Exterior Home Features Exterior: BalconyFoundation: Concrete Perimeter
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2Has a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Garage Door Opener,Yes,Garage Owned,Attached,Garage
Pool Pool: In GroundPool
Frontage WaterfrontWaterfront: River FrontOn Waterfront
Water & Sewer Sewer: Public Sewer

Property Information
Year Built Year Built: 2006
Property Type / Style Property Type: ResidentialProperty Subtype: Condominium, Single Family Residence
Building Construction Materials: Brick, Glass, ConcreteNot a New ConstructionHas Additional Parcels
Property Information Parcel Number: 17104000351312Additional Parcels Description: 17104000351438, 17104000351439

Price & Status
Price List Price: $1,199,000Price Per Sqft: $635
Status Change & Dates Possession Timing: Close Of Escrow

Location
Direction & Address City: ChicagoCommunity: Regatta
School Information Elementary School District: 299Jr High / Middle School District: 299High School District: 299

Agent Information
Listing Agent Listing ID: 12632003

HOA
HOA Fee Includes: Heat, Air Conditioning, Water, Gas, Parking, Insurance, Doorman, Cable TV, Exercise Facilities, Pool, Exterior Maintenance, Lawn Care, Scavenger, Snow Removal, InternetHas an HOAHOA Fee: $1,614/Monthly

Listing Info
Special Conditions: List Broker Must Accompany

Business
Business Information Ownership: Condo

Miscellaneous
Mls Number: 12632003Water ViewWater View: Water, Front of Property

Additional Information
HOA Amenities: Bike Room/Bike Trails,Door Person,Elevator in Residence,Exercise Room,Storage,On Site Manager/Engineer,Party Room,Sundeck,Indoor Pool,Receiving Room,Service Elevator(s),Valet/Cleaner,Spa/Hot TubSource Internet Entire Listing DisplayMRD IDX Comments Reviews: NoMRD Listing On IDX Display: YesMRD AVM On IDX Display: NoMRD Address On VOW Display: YesMRD Price History On IDX Display: NoMRD Market Time On IDX Display: NoSource Internet Address DisplayMRD REMARKSINTERNET: YesHide Days On Site DisplayHide Price History DisplayMRD Remarks On VOW Display: Yes

Additional Information

HOA Amenities: Bike Room/Bike Trails,Door Person,Elevator in Residence,Exercise Room,Storage,On Site Manager/Engineer,Party Room,Sundeck,Indoor Pool,Receiving Room,Service Elevator(s),Valet/Cleaner,Spa/Hot TubSource Internet Entire Listing DisplayMRD IDX Comments Reviews: NoMRD Listing On IDX Display: YesMRD AVM On IDX Display: NoMRD Address On VOW Display: YesMRD Price History On IDX Display: NoMRD Market Time On IDX Display: NoSource Internet Address DisplayMRD REMARKSINTERNET: YesHide Days On Site DisplayHide Price History DisplayMRD Remarks On VOW Display: Yes

Last check for updates: about 23 hours ago

Listing courtesy of: Andres Yepez, (773) 437-7330

Chicagoland Brokers, Inc.

Source: MRED as distributed by MLS GRID, MLS#12632003

Also Listed on MRED as distributed by MLS GRID, MRED as distributed by MLS GRID.

Market trends in New Eastside

Last updated June 2026

Avg. sale price

$782K

$156KMoM

Sale-to-List Price

—

Price per sq ft

—

Available listings

119

20MoM

Price History for 420 E Waterside Dr #4114

Date	Price	Event	Source
03/31/2016	$311,000	Sold	N/A
Recording Date 03/31/2016 County Transfer Tax N/A Total Transfer Tax N/A
10/25/2011	$815,000	Sold	MRED as distributed by MLS GRID #07894322
Recording Date 10/25/2011 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2024
Tax	$17,602
Assessment	$935,440

Home facts updated by county records

Comparable Sales for 420 E Waterside Dr #4114

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
420 E Waterside Dr #1814, Chicago, IL	0.00	Condo	$975,000	11/12/25	3	3	1,887
420 E Waterside Dr #1514, Chicago, IL	0.00	Condo	$1,010,000	02/25/26	3	3	1,887
450 E Waterside Dr #2708, Chicago, IL	0.04	Condo	$921,000	06/15/26	3	2.5	1,900
201 N Westshore Dr #1701, Chicago, IL	0.07	Condo	$849,000	11/17/25	3	2.5	1,800
201 N Westshore Dr #801, Chicago, IL	0.07	Condo	$854,000	06/10/26	3	2.5	1,800
195 N Harbor Dr #203, Chicago, IL	0.14	Condo	$665,000	01/27/26	3	2.5	1,600
195 N Harbor Dr #802, Chicago, IL	0.14	Condo	$675,000	09/11/25	3	2.5	1,600
420 E Waterside Dr #1108, Chicago, IL	0.00	Condo	$735,000	02/05/26	2	2.5	1,488
450 E Waterside Dr #402, Chicago, IL	0.04	Condo	$1,150,000	11/07/25	3	2.5	2,215

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $847,700
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1,586 sqft
420 E Waterside Dr #2812,
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Concentric Realty Inc., Closed
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MAY 29, 2026
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420 E Waterside Dr #1401,
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420 E Waterside Dr #1302,
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420 E Waterside Dr #3410,
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OFF MARKET
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420 E Waterside Dr #508,
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420 E Waterside Dr #2203,
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420 E Waterside Dr #511,
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Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 420 E Waterside Dr #4114.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

New Eastside

121 Homes For You
Buy: $229k - $11.5m

See Local Highlights

Neighborhood stats provided by third party data sources.

What Locals Say about New Eastside

At least 3 Trulia users voted on each feature.

100 % Say it's dog friendly
100 % Say they plan to stay for at least 5 years
100 % Say there's wildlife
100 % Say it's walkable to grocery stores
100 % Say it's walkable to restaurants
100 % Say there are sidewalks
100 % Say kids play outside
88 % Say neighbors are friendly
83 % Say streets are well-lit
75 % Say there's holiday spirit
60 % Say it's quiet
50 % Say people would walk alone at night
50 % Say parking is easy
25 % Say car is needed
20 % Say there are community events
17 % Say yards are well-kept

Sourced by Trulia users. Learn more about our methodology.

Jim Kepple
Resident
2y ago
"All concerts at Pritzker Pavillion and festivals in Grant park close by as well as many events in our park here; "
0
Flag
Jaimerubio.rgv
Visitor
6y ago
"This is downtown Chicago. What else can you say most of the area around the hotel are clean but other are in need of repair."
2
Flag
Kpritscher
Resident
6y ago
"It IS downtown so I can walk to work, using the Pedway when weather is bad. Alternately, there is easy access to buses and the El."
0
Flag
Dana
Prev. Resident
6y ago
"The variety of restaurants, shops, and people. The convenience of public transportation options. The architecture. "
1
Flag
Keyia M.
Resident
6y ago
"THIS IS A DOG OWNERS DREAM NEIGHBORHOOD, DOGS GET PRIORITY IN THIS AREA! THE DOG PARK IS GREAT, THE CONDOS ARE DOG FRIENDLY "
4
Flag
Brenda P.
Resident
6y ago
"Pedway is a life saver during those winter days! Easy access to the pedway, trains, bus and ride-shares. "
0
Flag
Lisa O.
Resident
6y ago
"There are lots of family in this area with wonderful parks, restaurants, close to shopping and right near the lake! "
0
Flag
Norman Roeber
Resident
7y ago
"I've lived here for 19-years - although many buildings have been built since moving here, it's really a nice community that is IN the City, yet just far enough off of Michigan Ave to be less busy. A Mariano's, eateries and coffee shops very walkable."
2
Flag
Alexis.jones
Resident
7y ago
"Great private school in the neighborhood. Walking distance to everything, however the neighborhood itself is removed from the loud moving parts of the city. You enter the park and you have left the city behind. "
0
Flag
Alexis.jones
Resident
7y ago
"Our park is the neighborhood hang out all Summer. Movies in the park, people hosting birthday parties, neighborhood soccer lessons. Our building also hosts a lot of activities for families. It’s a great quiet neighborhood! "
0
Flag
Luhrkelly
Resident
7y ago
"Great park for kids and adults alike. The Park at Lakeshore east is a great place to live. Very convenient "
0
Flag
Andy C.
Resident
8y ago
"Easy access to Magnificient Mile, Millenium Park, Riverwalk, Lake, and all the conviniences of urban life. Vividness of living brings vigor and mental health also!"
2
Flag
Dianrey
Resident
8y ago
"In summer you can walk to go to the beach, to attend concerts or movies at Maggie Daley park, or next to the river. In winter you have everything you need, very closed or in your building. "
1
Flag

LGBTQ Local Legal Protections

Andres Yepez, Chicagoland Brokers, Inc.

Agent Phone: (773) 437-7330

Based on information submitted to the MLS GRID as of 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Click here for more information

420 E Waterside Dr #4114, Chicago, IL 60601 is a 3 bedroom, 3 bathroom, 1,887 sqft condo built in 2006. 420 E Waterside Dr #4114 is located in New Eastside, Chicago. This property is currently available for sale and was listed by MRED as distributed by MLS GRID. The MLS # for this home is MLS# 12632003.

420 E Waterside Dr #4114
Chicago, IL 60601

$1,199,000