The Most Expensive Homes for Sale Right Now in Naperville, Aurora, Oswego, and Plainfield

If you want to see what luxury actually costs in the western suburbs right now, this is your list. We pulled every active luxury listing across Naperville, Aurora, Oswego, and Plainfield straight from the MLS, ranked by price, so you can see exactly what today’s top of market looks like.

What Luxury Actually Costs Right Now

Prices at the top of our local market range from just over $1 million to $6 million. That is a wide spread, and it tells you something important. Location, lot size, and age of construction move the needle just as much as square footage. A brand new custom home in Plainfield can list for under $2 million, while an established estate on acreage in unincorporated Naperville can hit $6 million.

Naperville’s Priciest Listings

Naperville holds the top five spots on this list, and it is not close.

24w141 Hobson Rd, Naperville, $6,000,000. This English Manor Tudor estate sits on nearly three acres in unincorporated Naperville near Lisle. It offers over 12,000 square feet of finished space, five fireplaces, two full chef kitchens, and a private gated entry.

51 Ford Ln, Naperville, $3,285,000. Located in the Washington Woods subdivision, this riverfront estate delivers 191 feet of DuPage River access along with an infinity edge pool, spa, and a full suite of sport courts.

107 S Webster St, Naperville, $3,000,000. This is new construction in the heart of downtown Naperville’s West End, just steps from Hugo’s and the Apple Store. It offers over 5,400 square feet with a private rooftop deck.

1046 Sylvan Cir, Naperville, $2,675,000. Set in the Oak Hills subdivision near downtown Naperville, this home sits on a half acre with over $400,000 in updates completed in the past year alone.

849 E Hillside Rd, Naperville, $2,499,000. Located in the East Highlands neighborhood, this home offers more than 7,300 square feet of finished living space just a short walk from downtown Naperville.

Oswego and Plainfield’s Luxury Estates

Oswego and Plainfield offer a different kind of luxury, more land and more privacy for the price.

88 Riverwood Dr, Oswego, $1,950,000. Situated in the Riverwood subdivision on nearly three acres along the Fox River, this Frank Lloyd Wright inspired home was completely reimagined in 2023.

25846 W Prairie Hill Ln, Plainfield, $1,799,900. A proposed new build in the Rolling Acres subdivision, this custom home offers 10 foot ceilings and a walk out basement on a half acre lot.

24824 Barolo Dr, Plainfield, $1,690,000. New construction in the River Pointe Estates community, featuring 30 foot cathedral ceilings and a first floor guest suite.

22625 Marina Dr, Plainfield, $1,500,000. This Lakelands waterfront property offers 231 feet of shoreline and over 8,100 square feet of finished space with a private two slip dock.

11616 and 11640 Century Cir, Plainfield, $1,499,999 each. Two build to suit lots in the Century Trace subdivision, zoned for Neuqua Valley High School, ready for a custom design.

1502 Cherry Rd, Oswego, $1,499,000. A private 14.4 acre creekfront estate with two main level master suites and a massive four car garage plus pole barn.

4779 Lees Ct, Oswego, $1,395,000. Located in the gated Grove Estates community, this custom estate recently expanded to over 2.3 acres with new wrought iron fencing.

14 Abbeyfeale Dr, Oswego, $1,150,000. Set on 2.2 landscaped acres, this executive home includes a private pickleball court and a first floor bedroom with a chairlift for accessibility.

1542 Plainfield Rd, Oswego, $1,150,000. Known as the historic Gaylord House and Gardens, this 1865 farmhouse sits on over five acres with a barn, chicken coop, and workshop space.

Aurora’s Stonebridge Luxury Market

Aurora’s high end inventory right now is concentrated almost entirely in one community, the Stonebridge Country Club.

1585 Woodcrest Ct, Aurora, $1,350,000. Positioned along the 10th fairway in the Woodlands section of Stonebridge, this home has over 6,100 square feet with fully remodeled bathrooms.

1096 Reddington Dr, Aurora, $1,186,000. This 5,700 square foot Stonebridge home overlooks the golf course with four en suite bedrooms upstairs.

1114 Chadwick Ct, Aurora, $1,145,000. Located in Stonebridge’s Brookside neighborhood along the second tee box, this home was meticulously updated by its original owners.

2432 Legacy Dr, Aurora, $1,050,000. Also in Stonebridge, this home underwent a full rebuild after a fire, meaning every system behind the walls is brand new.

What This Means If You’re Thinking About Selling a Luxury Home

We track this level of the market every week, not just for our buyers, but so we know exactly how to position a luxury listing when a seller trusts us with one. Pricing a high end home right takes more than comparing square footage. It takes understanding what a $3 million buyer in Naperville is looking for versus what a $1.2 million buyer in Stonebridge wants, and we watch both markets closely.

Frequently Asked Questions

What is the most expensive home for sale in Naperville right now?
The most expensive active listing is a $6,000,000 English Manor Tudor estate on nearly three acres in unincorporated Naperville, offering over 12,000 square feet of finished living space.

Where can I find luxury homes for sale near me in the western suburbs of Chicago?
Naperville, Aurora, Oswego, and Plainfield all currently have active luxury listings above $1 million. Naperville holds the highest price points, while Aurora’s luxury inventory is concentrated in the Stonebridge Country Club community.

What subdivisions in Aurora have the most luxury listings right now?
Stonebridge Country Club currently holds nearly all of Aurora’s high end inventory, with four active listings ranging from just over $1 million to $1.35 million.

Are there luxury new construction homes available in Plainfield right now?
Yes. Plainfield currently has new construction and build to suit luxury listings in the Rolling Acres, River Pointe Estates, and Century Trace subdivisions.

Ready to Explore the Luxury Market or Price Your Own Home?

Whether you are dreaming about a riverfront estate in Oswego or wondering what your own home could compete for at this level, we track this market closely every single week. Search homes on Zenlist to see current listings, or book a consultation with Team Elite Realtors at Baird and Warner to talk through your options.

Ready to make your next move in the western suburbs of Chicago?

We are here to help you every step of the way, whether you are buying, selling, or just exploring your options.

Julia Corkey & Vickie Schoenfeld
Team Elite Realtors at Baird & Warner

630-286-9777 | [email protected] | www.homesbyteamelite.com

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