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Chicago Luxury Real Estate in 2025: Elevated Living in the City of Big Shoulders

Joe Kotoch

Chicago Luxury Real Estate in 2025: Elevated Living in the City of Big Shoulders

Chicago’s Luxury Market: Classic Architecture Meets Modern Lifestyle

Chicago’s high-end market blends pre-war grandeur and cutting-edge design—think landmark co-ops and limestone single-families in the Gold Coast and Lincoln Park, glassy skyline penthouses in Streeterville and River North, and architect-led new builds across the West Loop, Bucktown/Wicker Park, and along
the iconic 606 elevated trail. Momentum at the top end is real: $4M+ sales hit a record high in the first half of 2025 across the Chicago area, underscoring deep demand for trophy properties. X (formerly Twitter)

What’s Fueling Demand in Chicago?
● Relative value vs. coasts + diversified economy. Chicago remains more attainable than NYC/LA/Miami while offering global-city amenities, a deep cultural scene, and major-market employment. In fact we are seeing an increasing number of out-of-state investors seeking Chicago’s attractive cap rates and relative affordability by major-market standards.

● Tight luxury supply. In April 2025, Redfin’s luxury tier (top 5% of sales) showed active listings down ~16% year-over-year in Chicago, even as prices rose (see
below). Redfin

● Lifestyle draws. Buyers want proximity to the lakefront, parks and trails (Lincoln Park, 606 Trail), Michelin-level dining (West Loop), and private-school corridors—all within 20–30 minutes door-to-door.

2025 By the Numbers in Chicago
● Citywide trend: July 2025 median sale price $385,000, up 5.5% YoY; median 54 days on market. (Macro health check that underpins the upper tiers.) Redfin

● Luxury tier (top 5%, Redfin): April 2025 median luxury price $1.45M (+11.9% YoY); active listings −16.4% YoY; median days on market 57. Translation: quality, well-priced luxury listings still move. Redfin

● Ultra-luxury color: May’s top city sales clustered in Lincoln Park and River North—multiple $4M–$6.7M closings—illustrating where buyers are concentrating for space, privacy, and finishes. Redfin

● Outlook: Local economists and CAR’s 2025 outlook continue to flag more inventory and slightly lower mortgage rates supporting higher transaction volume into year-end. chicagorealtor.com

Where Affluent Buyers Are Focusing
● Single-Family Standouts: Lincoln Park, Lakeview, Bucktown/Wicker Park, Old Town—extra-wide lots, new builds, and designer gut-rehabs with attached/EV-ready garages. Recent $4M+ activity is concentrated here. Redfin

● Luxury Condo/Penthouse Living: Gold Coast, River North, Streeterville, West Loop—full-amenity towers, protected sightlines, private terraces, and concierge buildings ideal for lock-and-leave lifestyles. Redfin

● North Shore and Western Suburb Extensions: Winnetka, Kenilworth, Glencoe, Lake Forest, and Hinsdale for estate properties with acreage and schools; often paired with in-city pieds-à-terre.

2025 Luxury Buyer Priorities in Chicago
● Modern-meets-classic design: Limestone façades and steel-window additions, chef’s kitchens with sculleries, integrated indoor-outdoor living (roof decks, terraces, four-season rooms).

● Wellness & privacy: Saunas/cold plunges, gyms, massage rooms; secure elevators, discreet entries, and boutique full-service buildings.

● Work-from-anywhere: Dual offices, sound-treated studios, and garden-level flex spaces for staff or guests.

● Parking & infrastructure: Heated, EV-ready garages; snow-melt and radiant systems; backup power.

● Location lifestyle: Walkability to parks, lakefront, dining, private clubs, training facilities, and easy airport access.

Why Work with Joe Kotoch & The Joe Kotoch Group | Compass Chicago
● Negotiation DNA: Former NBA agent and attorney—battle-tested negotiator with meticulous contract control and confidentiality.

● Sports & Entertainment + Compass Commercial: Discreet representation for athletes, entertainers, and executives, with access to off-market opportunities and investment-grade assets.

● Developer’s eye: We source, evaluate, and optimize value—whether it’s a limestone on Burling, a Fulton Market penthouse, or a gut-rehab in Wrigleyville. As an investor and developer too, I have an eye for opportunities and projected ROI.

● Bespoke marketing: Black-and-white, Chicago-forward branding, cinematic video, and targeted digital to reach qualified buyers locally and nationally.

● Compass horsepower: Private Exclusives, Coming Soon, and national referral reach to relocate buyers moving from the coasts and Sun Belt.

Looking Ahead
Chicago luxury remains supply-constrained with firm pricing at the top, while broader city metrics show steady appreciation and normalizing market times. Expect selective, data-driven pricing to outperform as turnover improves into late 2025 with slightly better rates and more listing flow—particularly in core luxury neighborhoods and best-in-class buildings. Redfin+1chicagorealtor.com