586 Chestnut Drive — Oswego, IL 60543
Active Under Contract
Oswego, IL 60543

586 Chestnut Drive

$300,000
3 beds · 2 baths · 1,493 sqft
Listed at $300,000 32 days on market $6,771/yr taxes
01About this home

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.

02Inside the home
03By the numbers
$300,000
List price
1,493
Square feet
3
Bedrooms
2 full
Bathrooms
2000
Year built
Lot size
2
Garage spaces
$6,771
Annual taxes
Attached Single
Style
32
Days on market
04Features
Heating
Natural GasForced Air
Cooling
Central Air
Appliances
RangeMicrowaveDishwasherRefrigerator
Parking
AsphaltGarage Door OpenerGarage OwnedAttachedGarage
Construction
Vinyl Siding
Sewer
Public Sewer
05Neighborhood
This home EElementary schoolMMiddle schoolHHigh school
E Elementary school
Prairie Point Elementary School
Oswego, IL
📍0.8 mi🚗2 min🚶19 min
M Middle school
Traughber Junior High School
Oswego, IL
📍1.2 mi🚗3 min🚶28 min
H High school
Oswego High School
Oswego, IL
📍1.7 mi🚗4 min🚶40 min
  • Asadoras Argentinas Burgers 1.3 mi
  • La Cabana D'Oswego 1.3 mi
  • Shu's Sushi Bar and Grill 1.3 mi
  • Dosbro Fresh Mexican Grill Oswego 1.3 mi
  • Jimmy John's 1.3 mi
  • Roadhouse 71 "america's Saloon" 1.3 mi
  • 7-Eleven 1.4 mi
  • Andover Park 0.5 mi
  • Morgan Creek Park 0.5 mi
  • Morgan Creek Playground 0.5 mi
  • Morgan Creek Prairie and Wetland 0.6 mi
  • Lakeview Park 0.9 mi
  • Prairie Point Community Park 0.9 mi
  • Nothing surfaced nearby in our maps data.
POI data via Mapbox · OpenStreetMap contributors
06History

Every event we have for this address, straight from the MLS.

Apr 29, 2026
Listed for saleThis listing
Keller Williams Infinity
$300,000
Sourced from MRED. Older events appear here as our history backfill completes.
07Ask Dwello

Real answers about this home — pricing, schools, what to ask, anything.

08See it for yourself

Stand in the kitchen.
See the light at 4pm.

Photos can only do so much. Pick a time — we'll meet you at the door.

Connect with Ewelina, Anna, or Nadeem — real people on our team, no call centers.
09Similar homes
Listed by Keller Williams Infinity · Meredith DeLeo · 630-632-5787
MLS data provided through MLS GRID · MRED MLS · MLS# MRD12632530
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