New Eastside
New Eastside is framed by three of the most valuable pieces of Chicago real estate that aren't for sale: Millennium Park to the south, Lake Michigan to the east, and the Chicago River to the north. The neighborhood was largely built from scratch over the past 25 years, and the intentionality shows — in the building quality, in the consistency of demand, and in a price-per-square-foot that leads the downtown market. This is not a neighborhood people stumble into. They research it, compare it, and choose it deliberately. That buyer profile shapes everything about how the market here behaves, including what it looks like when it's time to sell.
Data current through Q2 2026 — updated quarterlyWhat this neighborhood is made of
The building stock is predominantly highrises — 86% of in-scope complexes — with newer construction ages relative to the rest of downtown and floor plans that skew toward larger configurations. Looking at trailing two-year sales, 2-bedrooms and 3-bedrooms together account for roughly 61% of what sells here. Studios are a small fraction at approximately 4% of closed sales, anchored largely by 400 E Randolph, a nearly 1,000-unit building whose scale shapes the smaller-unit data for the neighborhood.
At the upper end, St. Regis Chicago and Cirrus represent the newest premium product in the market, with pricing that reflects both building quality and their position as the addresses buyers choose when they've decided New Eastside is the answer and want the best of it.
What you're writing a check for every month
| Unit size | New Eastside | Downtown | ↑/↓ |
|---|---|---|---|
| Studio | $1,987 | $1,807 | ↑ $180 |
| 1BR | $3,103 | $2,625 | ↑ $478 |
| 2BR | $5,321 | $4,209 | ↑ $1,112 |
| 3BR | $10,214 | $8,256 | ↑ $1,958 |
| 4BR+ | $23,862 | $11,910 | ↑ $11,951 |
New Eastside covers a wide price range, from the smaller homes in very large buildings like 400 East Randolph up to the high-end towers such as St. Regis and Cirrus. The biggest change over the past year is in two-bedrooms: their monthly cost rose sharply as prices climbed 14.1% — the largest gain of any size anywhere downtown. Buyers at that size face a clearly more expensive market than a year earlier, while sellers are about as well positioned as anywhere downtown.
That two-bedroom strength was broad — prices rose across the whole range, from the more modest homes to the priciest, and on more sales than the year before. The larger homes went a different way: three- and four-bedroom costs eased, but only because fewer of the most expensive ones sold, not because typical large homes are worth less. If you're buying a fairly standard three- or four-bedroom, prices sit about where they did a year earlier; only the very top of the market sold for less.
What's selling and how New Eastside compares
| Unit size | #Sold | Share of Downtown |
|---|---|---|
| Studio | 24 | 6% |
| 1BR | 197 | 7% |
| 2BR | 236 | 7% |
| 3BR | 131 | 10% |
| 4BR+ | 14 | 6% |
| All units | 602 | 7% |
New Eastside generated 7.1% of all downtown closings in the trailing two years — 602 transactions from a limited number of complexes. The 3-bedroom segment is where the neighborhood's market share is most notable: 131 closings represent 9.6% of all downtown 3-bedroom sales. That concentration at the upper end reflects consistent demand for a level of building quality and location that doesn't exist elsewhere downtown.
Understanding the data requires keeping the building mix in mind. 400 E Randolph's scale shapes the smaller-unit figures. At the upper end, St. Regis Chicago and Cirrus drove higher closing volume this period — both buildings saw more transactions than a year earlier — and that activity is what moves the neighborhood's medians. When a meaningful share of a period's closings comes from those buildings, the neighborhood's price-per-square-foot and unit-level medians reflect their positioning more than any market-wide trend.
What's happening with values here
New Eastside's price per square foot ticked up to about $505, from $490 the prior period — the highest of any downtown neighborhood, and a genuine premium of roughly $125 a foot over the $380 downtown median, about a third higher. This is no rounding difference: it reflects what the neighborhood is, with newer towers, larger floor plans, and a lakefront position the rest of downtown can't match at scale. The figure widened its lead this period rather than drifting back toward the middle.
Median Sale Price by unit size
| Unit size | Median Sale Price | vs. Downtown | Price Growth |
|---|---|---|---|
| Studio | $218,000 | ↑ 9% | ↓ 5.8% |
| 1BR | $370,000 | ↑ 25% | ↑ 8.8% |
| 2BR | $650,000 | ↑ 31% | ↑ 14.1% |
| 3BR | $1,350,000 | ↑ 36% | ↓ 7.5% |
| 4BR+ | $3,352,500 | ↑ 128% | — |
The larger sizes softened at the very top rather than across the board. Three-bedrooms show a 7.5% dip to $1,350,000, but that's because fewer of the most expensive ones sold — prices for more typical three-bedrooms barely moved, and the size still sells about 36% above downtown. Four-bedroom-plus, on only a handful of sales, tells the same story: last year's sales reached past $6 million, this year's didn't, which pulled the median down without a real trend beneath it.
What this data can't tell you
Everything above is aggregate data, and aggregate data has a ceiling. It can tell you where New Eastside sits relative to the rest of downtown, how its pricing has moved, what carrying costs look like across the building stock. It cannot tell you whether a specific building is well-governed, whether its reserves are adequate, whether its amenity spend is efficient, or whether a particular floor plan holds value the way the building's median suggests it should.
Those questions don't resolve at the neighborhood level. They resolve at the building level — and in some cases, only in conversation.