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586 Chestnut Drive, 
Oswego, IL 60543

$300,000


3

Beds


2

Baths


1,493

Sq Ft


Single Family

Pending

Listed by

Meredith Deleo

Joseph Deleo

Keller Williams Infinity

Last updated:

May 14, 2026, 07:56 AM

MLS#

12632530

Source:

MLSNI

About This Home

586 Chestnut Drive

Opportunity is knocking for the buyer who sees potential. This ranch duplex has been tenant-occupied for the past 9 years and is ready for its next chapter. Not move-in ready, but absolutely ready for it's glow up. If you're looking for a "Handyman Special" or just searching for a project with strong upside, this is it! The home offers solid bones and a functional layout, featuring vaulted ceilings in the kitchen, family room, and all bedrooms, creating an open and airy feel throughout. The main level includes a primary suite with private bath and a spacious walk-in closet, plus two additional bedrooms, a full hall bath, and convenient main living spaces. The family room centers around a fireplace and flows into the kitchen, where you'll also find a pantry and generous storage, including a large coat and linen closet. Downstairs, the partially finished basement expands the possibilities with space for a potential fourth bedroom, a wet bar, and additional storage with a crawl space. Outside, enjoy a private patio and fenced yard, along with the convenience of a 2-car attached garage. The home will require cosmetic improvements including full interior painting ( with new taping on vaulted ceilings,) wood floor refinishing, and new carpet, but presents a valuable opportunity for investors, rehabbers, or buyers looking to build equity. ******This is a limited window opportunity. If not sold, the property will be updated and reintroduced to the market at a higher price point reflecting the completed improvements. Located in a highly desirable school district 308; including Prairie Point Elementary, Traughber Junior High, and Oswego High School, with easy access to local amenities, this is a chance to create something truly special.

Home Facts

Single Family

2 Baths

3 Bedrooms

Built in 2000

Price Summary

300,000

$200 per Sq. Ft.

MLS #:

12632530

Last Updated:

May 14, 2026, 07:56 AM


Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

2

Full Bathrooms:

2

Interior

Living Area:

1,493 Sq. Ft.


Structure

Structure

Building Area:

1,493 Sq. Ft.

Year Built:

2000


Finances & Disclosures

Finances

Price:

$300,000

Price per Sq. Ft:

$200 per Sq. Ft.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.