420 E Waterside Dr #4414, Chicago, IL 60601
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Property image
OFF MARKET

420 E Waterside Dr #4414
Chicago, IL 60601

New Eastside
  • 3 Beds
  • 3 Baths
  • 1,900 sqft

$1,065,500

Trulia Estimate
as of Jul 24, 2026
Est. Refi. Payment $7,275/mo*
Refinance Your Home

$1,065,500

Trulia Estimate
as of Jul 24, 2026
Est. Refi. Payment $7,275/mo*
Refinance Your Home
3 Beds
3 Baths
1,900 sqft

Local Information

  • Map ViewExplore the area around 420 E Waterside Dr #4414.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Apartment
Living Area
1,900 sqft
Price/Sqft
$561
Parking
Attached Garage

About this House

**Video of the unit available upon request.

Very rare 3-bedroom, 3-bath penthouse now available at the coveted Regatta! This stunning home features unobstructed panoramic views of the lake, river, and Navy Pier clearing the Chandler for truly breathtaking sightlines.

The spacious open-concept living, dining, and kitchen area is ideal for both everyday living and entertaining. The upgraded kitchen includes 1.5" granite countertops, 42" walnut cabinetry, and stainless steel appliances. Floor-to-ceiling 10' windows flood the space with natural light and lead to a large private balcony.

The expansive primary suite offers a huge walk-in closet, automatic shades, and a spa-like bathroom with dual vanities, separate soaking tub, and walk-in shower. Two additional generously sized bedrooms feature organized closets and access to two additional full stone bathrooms.

Additional highlights include:
 - Recently added wide-plank hardwood flooring throughout
 - In unit washer/dryer
 - Two premium side-by-side garage parking spaces available ($200 per month each, located directly across from elevator)

The Regatta offers full-service, resort-style amenities including:
 - 24-hour door staff
 - Indoor pool & hot tub
 - Updated fitness center
 - Sundeck
 - Theater room
 - Party room
 - Game room/lounge

Unbeatable location just steps from Michigan Avenue, Mariano's, the lakefront, Riverwalk, and Lakeshore East Park.

Available as early as May 15th. 12-15 month lease. Rent includes gas, heat, internet, and cable. Tenant pays electric. Two side-by-side garage parking spot available for $200 p/m each. Pet rent $100 p/m (if applicable). $2500 admin fee. Renters insurance required. Application Link available upon request. Minimum Credit 720+. No Airbnb or short term rentals.
420 E Waterside Dr #4414, Chicago, IL 60601 is a 3 bedroom, 3 bathroom, 1,900 sqft apartment in New Eastside. More recently, it was listed as a rental in March 2026 with an asking price of $7,200 per month. That rental listing was removed on May 17, 2026. It is currently off market. The Trulia Estimate is $1,065,500, with a rent estimate of $6,739/month.

Home Details for 420 E Waterside Dr #4414

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Hot Tub or Spa
Levels, Entrance, & Accessibility
Floors: Hardwood, Tile

Property Information

Property Type / Style
Property Type: Apartment

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Pool
Pool
Parking & Garage
Parking: Attached, On Site

Building

Community rooms
Fitness Center

Additional Information

Pool

Price History for 420 E Waterside Dr #4414

DatePriceEventSource
05/17/2026$7,000ListingRemovedZillow Rentals
05/07/2026$7,000PriceChange
Zillow Rentals
04/09/2026$6,950PriceChange
Zillow Rentals
03/25/2026$7,200Listed For RentZillow Rentals
03/30/2016$5,500ListingRemovedAgent Provided
01/25/2016$5,500Listed For RentAgent Provided

Market trends in New Eastside

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$782K
$156KMoM
Sale-to-List Price
—
Price per sq ft
—
Available listings
119
20MoM
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Property Tax and Assessment

Year2024
Tax
Assessment$955,000
Home facts updated by county records

Comparable Sales for 420 E Waterside Dr #4414

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
201 N Westshore Dr #P-34, Chicago, IL
0.07
Apartment
$40,000
11/04/25
2
2.5
1,285
195 N Harbor Dr #4305, Chicago, IL
0.14
Apartment
$480,000
10/16/25
2
2
1,225
250 E Pearson St #2605, Chicago, IL
0.76
Apartment
$925,000
04/03/26
3
3
2,075
420 E Ohio St, Chicago, IL
0.40
Apartment
$89,000,000
12/18/25
2
2
650
60 W Erie St #1010, Chicago, IL
0.88
Apartment
$785,000
10/10/25
3
2.5
2,406
360 E Randolph St #2006, Chicago, IL
0.18
Apartment
$280,000
01/27/26
1
1
770
6 N Michigan Ave #13, Chicago, IL
0.56
Apartment
$35,000
12/04/25
4
4
6,400
33 W Ontario St #36EN, Chicago, IL
0.79
Apartment
$479,000
05/07/26
2
2
1,325
474 N Lake Shore Dr #2204, Chicago, IL
0.26
Apartment
$250,000
09/04/25
1
1
741
512 N McClurg Ct #2112, Chicago, IL
0.33
Apartment
$295,000
01/26/26
1
1
920
Home facts updated by county records

Nearby homes

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Assigned Schools

These are the assigned schools for 420 E Waterside Dr #4414.
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
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

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Off Market Homes Near 420 E Waterside Dr #4414

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