420 E Waterside Dr #503, Chicago, IL 60601
Property image
Property image
OFF MARKET
  • 2 Beds
  • 2 Baths
  • 1,182 sqft
  • 2 Beds
  • 2 Baths
  • 1,182 sqft

420 E Waterside Dr #503, Chicago, IL 60601

New Eastside

Home Highlights

Property Type
Apartment
Living Area
1,182 sqft

Local Information

  • Map ViewExplore the area around 420 E Waterside Dr #503.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Spacious and bright corner 2bed/2bath in luxurious full amenity building in the heart of Lakeshore East. The home is south facing with ample natural sunlight. The unit features a desirable split floor plan layout with a massive private balcony offering breathtaking city and park views. The kitchen is open to the living room complete with stainless steel appliances, breakfast bar, and pantry. Entertain and relax in the spacious living/dining room with private balcony access. Retreat to a large primary bedroom suite offering a generous walk-in closet and en-suite bath offering a dual vanity. The 2nd bedroom is sizable with brand new carpeting. In-unit washer/dryer. The Regatta is a full amenity building offering 24hr door-staff, onsite management, newer state-of-the-art fitness center/yoga room, indoor pool & jacuzzi, multiple media & party rooms, game room, sundeck, library, & play area. The Regatta is located within highly desirable Lakeshore East and is steps away from Mariano's, multiple parks, river-walk, lakefront path, DuSable Harbor, endless restaurants, nightlife, Michigan Ave, Loop, Pedway, & more! Heat, AC, Gas, Basic Cable, Internet, and additional storage are all included in the monthly rent. Parking options available for rent in the building.
420 E Waterside Dr #503, Chicago, IL 60601 is a 2 bedroom, 2 bathroom, 1,182 sqft apartment in New Eastside. It last sold for $420,000 on Mar 4, 2016 (13,025% above the $3,200 asking price). More recently, it was listed as a rental in March 2026 with an asking price of $3,800 per month. That rental listing was removed on April 4, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $4,025/month.

Home Details for 420 E Waterside Dr #503

Property Information

Property Type / Style
Property Type: Apartment

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Interior Features

Appliances & Utilities
DryerWasher
Heating & Cooling
Air Conditioning

Comparable Sales for 420 E Waterside Dr #503

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
195 N Harbor Dr #4305, Chicago, IL
0.13
Apartment
$480,000
10/16/25
2
2
1,225 sqft
680 N Lake Shore Dr #715, Chicago, IL
0.52
Apartment
$414,000
07/21/26
2
2
1,400 sqft
201 N Westshore Dr #P-34, Chicago, IL
0.07
Apartment
$40,000
11/04/25
2
2.5
1,285 sqft
155 N Harbor Dr #4305, Chicago, IL
0.17
Apartment
$300,000
07/15/26
1
1
858 sqft
360 E Randolph St #2006, Chicago, IL
0.18
Apartment
$280,000
01/27/26
1
1
770 sqft
10 E Ontario St #4908, Chicago, IL
0.72
Apartment
$560,000
05/19/26
2
2
-
33 W Ontario St #36EN, Chicago, IL
0.79
Apartment
$479,000
05/07/26
2
2
1,325 sqft
222 E Pearson St #1502, Chicago, IL
0.78
Apartment
$499,000
07/24/26
2
2
1,350 sqft
512 N McClurg Ct #2112, Chicago, IL
0.33
Apartment
$295,000
01/26/26
1
1
920 sqft
512 N McClurg Ct #5607, Chicago, IL
0.33
Apartment
$800,000
07/21/26
3
3
2,200 sqft
Home facts updated by county records

Nearby homes

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Around this home

Neighborhood Overview

New Eastside
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
    "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

Price and Tax history

DateEventPrice
Apr 4, 2026
Source: MRED as distributed by MLS GRID #12593694
ListingRemoved
$3,800
Mar 17, 2026
Source: MRED as distributed by MLS GRID #12593694
Listed For Rent
$3,800
Nov 5, 2024
Source: Zillow Rentals
ListingRemoved
$3,200
Nov 2, 2023
Source: Zillow Rentals
ListingRemoved
Oct 3, 2023
Source: Zillow Rentals
Listed For Rent
$3,200

Frequently asked questions about 420 E Waterside Dr #503

  • What is the price history for 420 E Waterside Dr #503?
    420 E Waterside Dr #503 in Chicago, IL last sold for $420,000 in March 2016.
  • 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 $574K.
  • What are the closest schools to 420 E Waterside Dr #503?
    The closest schools to 420 E Waterside Dr #503 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 #503 have laundry facilities?
    Yes, 420 E Waterside Dr #503 in Chicago, IL has in-unit laundry.

Homes for rent near 420 E Waterside Dr #503

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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