Chicago · Cook County · IL
Homes for sale in
The Regatta.
- Active listings
- 1
- Median list
- $550K
- Avg time on market
- 84 days
- Sold · last year
- 7
Active listings
1 home on the market
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About the community
Full-service tower living in Lakeshore East on the New Eastside.
The Regatta is a 44-story luxury condominium tower in the Lakeshore East master-planned neighborhood on the New Eastside, at the edge of the Loop where the Chicago River meets the lake. Developed by Magellan Development Group with initial occupancy in 2006, the tower is wrapped in dual elliptical glass curtain walls and sits steps from the neighborhood's six-acre park. Studios through three-bedroom residences share a large Shore Club amenity floor and professional on-site management, with deeded parking sold separately.
At a glance
44-story Lakeshore East tower
About 320 to 325 residences in a 44-story tower delivered in 2006 by Magellan Development, the second condo tower built in Lakeshore East.
Dual curved-glass walls
A signature pair of elliptical glass curtain walls, with studios through three-bedroom layouts and penthouses on the upper floors.
Shore Club amenities
Over 5,000 square feet of amenities: an indoor pool and spa, a fitness center, a 13th-floor sundeck with grills, a party room, a game room, a theater, and a library.
Deeded parking, sold separately
The attached heated garage has deeded spaces that carry their own assessment and tax bill. Confirm whether a space conveys per unit.
Park, river, and lake views
Steps from the six-acre Lakeshore East park, with outlooks over Lake Michigan, the river, Maggie Daley and Millennium Park, and the skyline.
Utilities bundled in assessments
Assessments typically cover gas, heat, air, water, and cable plus staff and amenities, while deeded parking is billed separately. Confirm the figure per unit.
Chicago Public Schools
Assignments are set by boundary, and the neighborhood's former private GEMS academy has closed. Confirm current options by address with CPS.
What’s close
The Regatta sits inside Lakeshore East, a master-planned neighborhood organized around a six-acre park between the Loop, the river, and the lake.
- Parks and lakefront
- Steps to the Lakeshore East park, the Riverwalk, Maggie Daley Park, and Millennium and Grant Parks.
- Building amenities
- The Shore Club floor with an indoor pool, a fitness center, a sundeck, party and game rooms, a theater, and a library.
- Everyday needs
- A Mariano's grocery and other retail within the neighborhood, and the Pedway links parts of the New Eastside to the Loop.
- Transit and driving
- Quick access to Lower and Upper Wacker and Lake Shore Drive, with CTA and Metra connections in the nearby Loop.
- Schools
- Chicago Public Schools. Confirm current public and private options by address, since the neighborhood's GEMS academy has closed.
- Shopping and culture
- A short walk to the Art Institute, the Magnificent Mile, and the theater district.
What it’s actually like to live here
The Regatta suits a buyer who wants a full-service, amenity-rich high-rise in one of downtown Chicago's quietest yet most central pockets. From here you can walk to the lakefront, the Riverwalk, and two of the city's marquee parks, and reach the cultural spine of Michigan Avenue without dealing with the density and nightlife noise of River North or the core of the Loop. The building's staffed front desk, indoor pool, sundeck, and long-tenured management give it the day-to-day ease of a hotel, which is a large part of the appeal for professionals, downsizers, and lock-and-leave second-home owners.
The New Eastside's design is its own personality. Streets stack on multiple levels around the central park, which keeps through-traffic low and gives many residences open park and water views, but it also means the neighborhood can feel insular and can confuse first-time visitors and delivery drivers. Grocery, coffee, and a handful of restaurants are built into the neighborhood, though the densest dining and shopping still sit a walk away in the Loop or across the river in Streeterville.
The honest tradeoffs are the ones common to full-amenity glass towers of this era. Monthly assessments are meaningful because they bundle most utilities and a large staff and amenity floor, so the all-in monthly cost matters as much as price. Parking is usually a separate deeded purchase with its own carrying cost, and views and light vary dramatically by exposure and floor, so two same-size units can live very differently. For current pricing and market conditions, see the live Market snapshot on this page.
The questions buyers actually ask
The Regatta FAQ
The questions I get most from buyers shopping The Regatta. If yours isn't here, text 224-385-8779, same-day reply.
- What does the HOA actually cover?
- Monthly assessments at The Regatta commonly cover gas, heat, air conditioning, water, and cable along with the staffed front desk, the amenity package, common-area maintenance and insurance, and professional on-site management. Deeded parking spaces carry their own separate assessment and tax bill, and as a home inside the Lakeshore East master plan, owners are also subject to the neighborhood association framework. Request the current figure for the specific unit and a copy of the reserve study, since assessments vary by unit size.
- When was The Regatta built?
- Developed by Magellan Development Group; architecture by Loewenberg Architects built the community between 2004 and 2007.
- Where exactly is The Regatta and what neighborhood is it in?
- It is at 420 East Waterside Drive, in the New Eastside, inside the Lakeshore East master-planned neighborhood at the edge of the Loop near the Chicago River and Lake Michigan.
- How tall is the building and how many condos are there?
- It rises 44 stories. The developer lists 325 residential units, and some listing sites report figures in the 319 to 322 range, so plan on about 320 to 325. It was the second condominium tower completed in Lakeshore East.
- What amenities does the building have?
- A staffed front desk, an indoor pool, a fitness center, a 13th-floor sundeck and rooftop garden with grills, a party room, a billiards and game room, a theater room, a library, a yoga room, a kids' playroom, and bike and receiving rooms, all under professional on-site management.
- Is parking included, and how does it work?
- The Regatta has an attached heated garage with deeded spaces. Spaces are deeded real estate with their own assessment and tax bill. Some units include a space in the price and some do not, so confirm per unit.
- What do the monthly assessments cover?
- Assessments typically bundle gas, heat, air conditioning, water, and cable, plus staff, amenities, insurance, and management. Deeded parking is assessed separately. Ask for the exact figure and the reserve study for the specific unit.
- What do units cost and how is the market right now?
- Prices vary widely by size, floor, exposure, and whether parking is included, and the market moves over time, so this page does not quote a fixed number. See the live Market snapshot for current pricing and market conditions at The Regatta.
- Who is the real estate agent for The Regatta?
- Joe Keegan is the local licensed Illinois real estate broker who covers The Regatta in Chicago, IL through Subdiview, a neighborhood-first home search for the Chicago suburbs and collar counties. Joe prices and negotiates from the live MRED sold comps for The Regatta specifically, not national averages, and can help you buy or sell here. Reach Joe at 224-385-8779 or joe@joekeeganhomes.com.
Your local agent
Joe knows The Regatta
Most agents will list anything. I focus on the places I actually know, and the things that move value here don't show up in the MLS write-up: which streets and buildings hold demand, what the HOA or assessments really cover, how the comps read once you account for condition and location, and where buyers consistently want to be.
When you're ready to tour or list, you want someone who has read the last 50 closed comps in this specific market, not a national average, and can tell you what they actually mean for your price. That's how I work. Text or call any time, and I'll give you a real take, not a brochure.
- Licensed Illinois broker
- Comp-driven pricing
- Chicago specialist
- Honest local market take
- Brokerocity
Market snapshot
The Regatta, by the numbers
Live MRED data, refreshed daily. The numbers below tell you what this market is doing today, not what Zillow's algorithm thinks it might be doing six weeks from now.
Typical list price
$550,000
Typical sale price · last 90 days
$420,000
Homes for sale right now
1
Avg time on market
84 days
Sold in the last year
7
This representation is based in whole or in part on data supplied by Midwest Real Estate Data, LLC for the period August 5, 2025 through August 5, 2026. Midwest Real Estate Data, LLC does not guarantee nor is it in any way responsible for its accuracy. Data maintained by Midwest Real Estate Data LLC may not reflect all real estate activity in the market.
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