420 E Waterside Dr, Chicago, IL 60601
OFF MARKET

$587,400

Trulia Estimate
  • 2 Beds
  • 2 Baths
  • 1,182 sqft

420 E Waterside Dr, Chicago, IL 60601

New Eastside
Est. Refi. Payment $4,335/mo*
Refinance Your Home

Home Value

Trulia Estimate
$587K
Since last month
Decreased$15K (-2.5%)
Since last year
Decreased$107K (-15.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +29% in the last 10 years
MonthEstimated value
2026
October 2026$587K
September 2026$602K
June 2026$626K
May 2026$648K
April 2026$694K
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
195 N Harbor Dr #2508, Chicago, IL
0.14
Condo
$570,000
06/15/26
2
2
1,294
222 N Columbus Dr #1903, Chicago, IL
0.25
Condo
$430,000
07/20/26
2
2
1,225
474 N Lake Shore Dr #PS158, Chicago, IL
0.26
Condo
$30,000
08/28/26
2
2
1,225
400 E Randolph St #3419, Chicago, IL
0.17
Condo
$595,000
04/21/26
2
2
1,250
211 E Ohio St #2120, Chicago, IL
0.46
Condo
$3,500
05/14/26
2
2
1,100
155 N Harbor Dr #206, Chicago, IL
0.17
Condo
$489,000
10/22/25
1
2
1,050
512 N McClurg Ct #2804, Chicago, IL
0.33
Condo
$540,000
05/07/26
2
2
1,400
420 E Waterside Dr #509, Chicago, IL
0.00
Condo
$559,000
04/06/26
2
1.5
1,117
420 E Waterside Dr #709, Chicago, IL
0.00
Condo
$535,000
10/10/25
2
1.5
1,100
450 E Waterside Dr #808, Chicago, IL
0.04
Condo
$653,000
05/01/26
2
2
1,228

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
725 Brookvale Dr #C, Wheeling, IL 60090
0.00
$219,400
1
1
850
Off Market
420 E Waterside Dr #4310, Chicago, IL 60601
0.00
$1,769,200
3
2.5
1,900
Off Market
420 E Waterside Dr #P-225, Chicago, IL 60601
0.00
$96,800
Studio
-
-
Off Market
420 E Waterside Dr #910, Chicago, IL 60601
0.00
$470,500
1
1.5
1,141
Off Market
420 E Waterside Dr #P-320, Chicago, IL 60601
0.00
-
Studio
-
80
Off Market
420 E Waterside Dr #702, Chicago, IL 60601
0.00
$316,500
1
1
826
Off Market
420 E Waterside Dr #307, Chicago, IL 60601
0.00
$344,300
1
1
900
Off Market
420 E Waterside Dr #P-270, Chicago, IL 60601
0.00
-
Studio
-
-
Off Market
420 E Waterside Dr #P-191, Chicago, IL 60601
0.00
-
Studio
-
-
Off Market
420 E Waterside Dr #P-122, Chicago, IL 60601
0.00
-
Studio
-
-
Off Market
420 E Waterside Dr #P-183, Chicago, IL 60601
0.00
-
Studio
-
-
Off Market
420 E Waterside Dr #3901, Chicago, IL 60601
0.00
$1,126,700
Studio
-
-
Off Market
420 E Waterside Dr #2812, Chicago, IL 60601
0.00
$847,300
2
2
1,586
Off Market
420 E Waterside Dr #P-45, Chicago, IL 60601
0.00
-
Studio
-
-
Off Market
420 E Waterside Dr #703, Chicago, IL 60601
0.00
$567,600
2
2
1,182
Off Market
420 E Waterside Dr #P-302, Chicago, IL 60601
0.00
-
Studio
-
-
Off Market
420 E Waterside Dr #2503, Chicago, IL 60601
0.00
$499,700
2
2
1,182
Off Market
420 E Waterside Dr #1401, Chicago, IL 60601
0.00
$640,000
2
2
1,546
Recently Sold
420 E Waterside Dr #1302, Chicago, IL 60601
0.00
$367,000
1
1
826
Off Market
420 E Waterside Dr #P-163, Chicago, IL 60601
0.00
-
Studio
-
-
Off Market

Local Information

  • Map ViewExplore the area around 420 E Waterside Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Condo
Built in 2006
1,182 sqft
$497/sqft
Garage

About this House

What's unique:Views overlooking chicago riverGas rangesMaple cabinetryHardwood floorsWalk-in closetsCustomer granite countertops
SPECTACULAR REGATTA OFFERS THIS 2 BEDROOM, 2 BATH, CONDO WITH A COMFY AND COZY SOUTHERN EXPOSURE OVERLOOKING LAKE SHORE EAST. JUST A STEP OUTSIDE THE BALCONY WILL MAKE YOU FEEL A PART OF IT ALL. HARDWOOD FLRS. , GRANITE COUNTER TOPS, KITCHEN WITH S/S APPLIANCES, FRENCH DOORS, CEILING FAN, IN-UNIT WASHER/DRYER, AND GARAGE PARKING INCLUDED. MANY AMENITIES WITHIN. MINUTES AWAY FROM RESTAURANTS, SHOPS, AND THE LAKE.
420 E Waterside Dr, Chicago, IL 60601 is a 2 bedroom, 2 bathroom, 1,182 sqft condo in New Eastside, built in 2006. More recently, it was listed as a rental in July 2026 with an asking price of $2,800 per month. That rental listing was removed on July 22, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $587,400, with a rent estimate of $4,119/month.

Home Details for 420 E Waterside Dr

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
Number of Rooms: 6Types of Rooms: Walk In Closet, Dining Room, Laundry Room, Master Bath
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Hot Tub or Spa
Levels, Entrance, & Accessibility
ElevatorFloors: Tile, Hardwood

Property Information

Year Built
Year Built: 2006
Property Type / Style
Property Type: Condo

Exterior Features

Exterior Home Features
DeckExterior: Other, Brick, Cement Concrete, Metal
Pool
Pool
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 0.84 acres

Additional Information

DoormanDoorman

Building

Community rooms
Fitness Center

Price and Tax history

DateEventPrice
Jul 22, 2026
Source: MRED as distributed by MLS GRID #12703289
ListingRemoved
$2,800
Jul 14, 2026
Source: MRED as distributed by MLS GRID #12703289
Listed For Rent
$2,800

Market trends in New Eastside

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$623K
$63.5KMoM
Sale-to-List Price
—
Price per sq ft
—
Available listings
94
1MoM

Around this home

Neighborhood Overview

New Eastside
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about New Eastside

This October

Trick-or-Treat Score

Built from what locals say about New Eastside.
  • 100% say there are sidewalks
  • 88% say neighbors are friendly
  • 75% say there's holiday spirit
Trulia Trick or TreatStart Ghost Hunt
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
    "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
    "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
    "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
    "The variety of restaurants, shops, and people. The convenience of public transportation options. The architecture. "
    1
    Flag
  • Keyia M.
    "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.
    "Pedway is a life saver during those winter days! Easy access to the pedway, trains, bus and ride-shares. "
    0
    Flag
  • Lisa O.
    "There are lots of family in this area with wonderful parks, restaurants, close to shopping and right near the lake! "
    0
    Flag
  • Norman Roeber
    "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
    "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
    "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
    "Great park for kids and adults alike. The Park at Lakeshore east is a great place to live. Very convenient "
    0
    Flag
  • Andy C.
    "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
    "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

Frequently asked questions about 420 E Waterside Dr

  • What is 420 E Waterside Dr estimated to be worth?
    Trulia's estimated value for 420 E Waterside Dr in Chicago, IL is $587,400.
  • Is Chicago a buyer's or seller's market?
    Chicago is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Chicago?
    The median sale price in Chicago is $623K. That is up $63.5K from the prior month.
  • What are the closest schools to 420 E Waterside Dr?
    The closest schools to 420 E Waterside Dr in Chicago, IL are Ogden Elementary School (Pre-K/Middle, rated 4/10), Wells Community Academy High School (rated 1/10).
  • Does 420 E Waterside Dr have air conditioning?
    Yes, 420 E Waterside Dr in Chicago, IL has air conditioning.
  • Does 420 E Waterside Dr have a pool?
    Yes, 420 E Waterside Dr in Chicago, IL has a pool.

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