Recently Listed Open House 4/30 5pm - 7pm
586 Chestnut Drive
Oswego, IL, 60543 $ 300,000
Bedrooms3 Baths2.0 Sq 1,493 Monthly Estimate*
$ 1,847
for $300,000 with 3 bedrooms and 2 full baths. This 1,493 square foot home was built in 2000.
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.
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Open House
4/30/2026 5:00 PM - 7:00 PM
586 Chestnut Drive Oswego, IL
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
FeaturesGeneralLiving Area 1493
Sewer Public Sewer
Heating Natural Gas Forced Air
Cooling Central Air
Possession Closing
Appliances Range Microwave Dishwasher Refrigerator
HOA Fee 110
Garage Spaces 2
Association Fee Includes Insurance
Construction Materials Vinyl Siding
Pets Allowed Cats OK Dogs OK
Year Built 2000
Township Oswego
Tax Year 2024
Ownership Fee Simple w/ HO Assn.
Assoc Fee Paid Per Quarterly
County Kendall
New Construction N
Property Type Residential Attached Single
Subdivision Name Morgan Crossing
Total Rooms 8
Full Baths 2
Status New
Directions Grove to Collins to Buckskin to Chestnut
High School Oswego High School
City Oswego
High School District 308
MLS Area Oswego
Elementary School Prairie Point Elementary School
Tax Annual Amount 6771
Middle/Junior High School Traughber Junior High School
Standard Status Active
Middle/Junior School District 308
Elementary School District 308
Sub Type 1/2 Duplex
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InteriorInterior Amenities Vaulted Ceiling(s)
Basement Partially Finished Crawl Space Partial
Total Fireplaces 1
Total Stories 1
Half Baths 0
Total Bedrooms 3
Room Type Office Recreation Room Foyer Walk In Closet
Total Baths 2
Bedrooms Possible 3
Bathroom Double Sink
Total Number of Units 2
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ExteriorParking Features Asphalt Garage Door Opener Yes Garage Owned Attached Garage
Water Source Public
Total Parking 2
Lot Dimensions 176 x 111 x 141 x 16
Waterfront Y/N N
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* Excluded FeaturesList ByKeller Williams InfinityBroker
meredith@deleogroup.com;joe@deleogroup.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $1,847
- Monthly Property Taxes
- $564
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbyMulti-family listings in Oswego, IL
Average List Price $360,667
Percent of Sale Price 20%
About Oswego, IL 31,545 Population
130% Since 2002
$ 94,639 Median Income
36.59 Median Age
44% Households with Children
Trends Information provided by ATTOM Data Solutions.
1540268 Elementary School
1540506 Middle School
Oswego High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 4/29/2026 | $300,000 | | Listed Price |