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Homebuyers and sellers are navigating a slow and expensive housing market, with rising prices and stagnant demand on the sidelines. This comes amid rising and growing . But luxury homes—multimillion-dollar estates, sleek penthouses, and one-of-a-kind custom builds—are , even as most buyers pull back.

Most people can't afford high-end homes, although they're still fun to dream about. So, to highlight where luxury real estate is commanding the highest prices, Redfin analyzed the most expensive neighborhoods in the Chicago metro area—and showcased a few of the area's standout listings (when possible).

Note: Redfin's analysis focused on metro areas, meaning some neighborhoods fell within smaller nearby cities. Listings and data were gathered on October 15, 2025.

#1. Downtown Hinsdale (Hinsdale, IL)

13 S Elm St, Hinsdale, IL 60521
- List price: $3,995,000
- Beds: 5 | Baths: 4.5 | Square feet: 6,074
- See 13 S Elm St, Hinsdale, IL 60521 on

28 S Clay St, Hinsdale, IL 60521
- List price: $1,100,000
- Beds: 3 | Baths: 3.5 | Square feet: 2,701
- See 28 S Clay St, Hinsdale, IL 60521 on

6 S Elm St, Hinsdale, IL 60521
- List price: $2,995,000
- Beds: 5 | Baths: 5.5 | Square feet: 4,340
- See 6 S Elm St, Hinsdale, IL 60521 on

#2. Timber Trails (Western Springs, IL)

5903 Timber Trails Blvd, Western Springs, IL 60558
- List price: $1,698,420
- Beds: 5 | Baths: 4.5 | Square feet: 5,000
- See 5903 Timber Trails Blvd, Western Springs, IL 60558 on

5912 Cottonwood Ct, Western Springs, IL 60558
- List price: $1,599,900
- Beds: 5 | Baths: 4.5 | Square feet: 4,850
- See 5912 Cottonwood Ct, Western Springs, IL 60558 on

6008 Burr Oak Dr, Western Springs, IL 60558
- List price: $1,599,900
- Beds: 5 | Baths: 4.5 | Square feet: 4,850
- See 6008 Burr Oak Dr, Western Springs, IL 60558 on

#3. Lakeshore (Evanston, IL)

1120 Forest Ave, Evanston, IL 60202
- List price: $2,699,000
- Beds: 7 | Baths: 6 | Square feet: 8,360
- See 1120 Forest Ave, Evanston, IL 60202 on

1319 Forest Ave, Evanston, IL 60201
- List price: $3,995,000
- Beds: 5 | Baths: 6 | Square feet: 5,418
- See 1319 Forest Ave, Evanston, IL 60201 on

202 Greenwood St, Evanston, IL 60201
- List price: $2,995,000
- Beds: 7 | Baths: 6.5 | Square feet: 7,500
- See 202 Greenwood St, Evanston, IL 60201 on

225 Hamilton St, Evanston, IL 60202
- List price: $2,095,000
- Beds: 6 | Baths: 5 | Square feet: 5,416
- See 225 Hamilton St, Evanston, IL 60202 on

#4. Horner Park (Chicago, IL)

2415 W Belle Plaine Ave, Chicago, IL 60618
- List price: $1,325,000
- Beds: 5 | Baths: 4.5 | Square feet: 3,900
- See 2415 W Belle Plaine Ave, Chicago, IL 60618 on

#5. Ashwood Park (Naperville, IL)

4052 Teak Cir, Naperville, IL 60564
- List price: $1,249,900
- Beds: 5 | Baths: 5 | Square feet: 6,094
- See 4052 Teak Cir, Naperville, IL 60564 on

4215 Chinaberry Ln, Naperville, IL 60564
- List price: $1,000,100
- Beds: 4 | Baths: 3 | Square feet: 3,500
- See 4215 Chinaberry Ln, Naperville, IL 60564 on

4240 Chinaberry Ln, Naperville, IL 60564
- List price: $1,300,000
- Beds: 5 | Baths: 5 | Square feet: 3,338
- See 4240 Chinaberry Ln, Naperville, IL 60564 on

4447 Sassafras Ln, Naperville, IL 60564
- List price: $1,349,900
- Beds: 5 | Baths: 4.5 | Square feet: 4,883
- See 4447 Sassafras Ln, Naperville, IL 60564 on