Recently Listed Open House 8/16 12pm - 2pm
1140 Oakley Avenue
Winnetka, IL, 60093 $ 2,695,000
Bedrooms4 Baths4.1 Sq 4,509 Monthly Estimate*
$ 17,017
for $2,695,000 with 4 bedrooms and 4 full baths, 1 half bath. This 4,509 square foot home was built in 1938.
A rare, fully renovated and updated home offering move-in-ready luxury and thoughtful craftsmanship throughout. The primary bath was renovated down to the studs, and now offers a generous shower, private water closet, and all-new fixtures, plumbing, and lighting, plus a huge closet/dressing room with a 7-foot quartz-topped built-in with 24 custom drawers, and floor to ceiling custom built-ins. Two bedrooms were combined into a spacious home office (larger than the primary) with hardwood floors, updated lighting, custom closet built-ins, and upgraded networking. The first-floor office was reimagined as a dramatic library, with custom maple built-ins, matching ceiling moldings, a window seat, and high-gloss lacquered finishes. The home is wired throughout for CAT6 and wifi, with home theater wiring, an upgraded security system, energy-efficient attic insulation, and improved HVAC routing - smart, efficient, and move-in ready. Owner is a Licensed Real Estate Broker.
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Open House
8/16/2026 12:00 PM - 2:00 PM
1140 Oakley Avenue Winnetka, 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 4509
Sewer Public Sewer
Heating Natural Gas
Cooling Central Air
Possession Closing
Roof Asphalt
Appliances Double Oven Range Microwave Dishwasher Refrigerator Freezer Disposal Wine Refrigerator Range Hood Water Purifier Owned
Garage Spaces 2
Association Fee Includes None
Construction Materials Vinyl Siding Brick Plaster
Year Built 1938
Electric 200+ Amp Service
Township New Trier
Tax Year 2024
Ownership Fee Simple
Community Features Sidewalks
Assoc Fee Paid Per Not Applicable
County Cook
New Construction N
Property Type Residential Detached Single
Total Rooms 10
Full Baths 4
Status Active
Directions Home is at southwest corner of Oakley and Gordon Terrace. Park on north side of Oakley.
High School New Trier Twp H.S. Northfield/Wi
City Winnetka
High School District 203
MLS Area Winnetka
Tax Annual Amount 30382
Additional Parcels Y/N N
Standard Status Active
Middle/Junior School District 36
Elementary School District 36
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InteriorInterior Amenities Walk-In Closet(s) Bookcases Granite Counters Separate Dining Room
Basement Finished Full
Flooring Hardwood
Total Fireplaces 1
Fireplace Features Wood Burning
Half Baths 1
Laundry Features Upper Level
Total Bedrooms 4
Room Type Library Recreation Room Mud Room
Total Baths 5
Bedrooms Possible 4
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ExteriorParking Features Brick Driveway Garage Door Opener Heated Garage Yes Garage Owned Attached Garage
Lot Features Corner Lot Mature Trees
Water Source Lake Michigan
Total Parking 2
Lot Dimensions 85 x 139.9
Waterfront Y/N N
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* Excluded FeaturesList ByJameson Sotheby's International RealtyBroker
amaitland@jamesonsir.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $17,017
- Monthly Property Taxes
- $2,532
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.49% 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 NearbySingle family listings in Winnetka, IL
Average List Price $3,772,230
Percent of Sale Price 40%
About Winnetka, IL 12,298 Population
-2% Since 2002
$ 182,976 Median Income
45.24 Median Age
46% Households with Children
Trends Information provided by ATTOM Data Solutions.
564877 Elementary School
567357 Middle School
New Trier Twp H.S. Northfield/Wi High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 8/10/2026 | $2,695,000 | | Listed Price |