For SaleRisky Deal44 days on market
1140 Oakley Ave
1140 Oakley Ave, Winnetka, IL 60093, Winnetka, IL 60093
$2,695,000
Listing Price
1140 Oakley Ave, Winnetka, IL 60093
Loc: Winnetka, IL
Days Listed
44
Tax Assessed
$1260k
Lot Size
0.27 acres
Type
single family
More Than Just a Property
We believe a home extends beyond its walls. That's why we help you explore the pulse of the community—from top-rated schools to essential emergency services. Your safety, well-being, and connection to the neighborhood matter to us.
4.9
Safety Score
A+
Schools
Nearby Schools
Educational options and performance ratings in the area.
10
Hubbard Woods Elementary School
K-4
0.2 mi away
8
Carleton W Washburne School
7-8
0.8 mi away
N/A
New Trier Township H S Northfield
9
2.1 mi away
Property Overview
No property narrative or remarks were supplied in the source listing records. Underwriting and financial metrics are calculated directly from public record data and MLS attributes.
Features & Amenities
colonial revivalwhite brickgated courtyardsymmetrical facadelush landscapingtraditional architecturemanicured lawnmature treesluxury residenceestateblack shutterspaver walkwaycurb appealcentral entryway
Haven AI Verdict
Recommendation
Risky
Confidence Score: 2/10
Exercise caution due to potential market volatility.
Cap Rate
5.98%
Total ROI
88.9%
Cash Flow
$-552/mo
DSCR
0.96
Was this AI Verdict accurate?
Data provided by Haven AI. Disclaimer
Haven AI
Property yields an estimated $-552/mo net cash flow with a 6.0% cap rate. Underwriting indicates risky fundamentals for long-term hold.
Strengths
- • Favorable cap rate profile (6.0%)
- • Strong rental demand in Winnetka
Considerations
- • Verify historical operating expenses and local tax assessment
- • Confirm current lease terms and tenant estoppel certificates
10-Year Price Projection
Price & Tax History
Price History
| Date | Event | Price | Price/sqft |
|---|---|---|---|
| 2026-08-10 | Listed for sale | $2,695,000 | $598 |
| 2021-07-21 | Sold | $1,650,000 | $366 |
| 2014-08-06 | Sold | $1,375,000 | $305 |
| 2014-07-15 | Pending sale | $1,379,000 | $306 |
| 2014-07-15 | Listed for sale | $1,379,000 | $306 |
| 2013-08-27 | Sold | $1,210,000 | $268 |
| 2013-06-02 | Pending sale | $1,229,000 | $273 |
| 2013-05-25 | Listed for sale | $1,229,000 | $273 |
| 2003-05-23 | Sold | $1,045,000 | $232 |
Tax History
| Year | Property Tax | Tax Assessment |
|---|---|---|
| 2024 | $30,382.17 | $126,000 |
| 2023 | $29,210.95 | $126,000 |
| 2022 | $27,500.01 | $126,000 |
| 2021 | $26,814.65 | $106,653 |
| 2020 | $26,445.79 | $106,653 |
| 2019 | $26,233.84 | $115,928 |
| 2018 | $29,182.95 | $125,103 |
| 2017 | $28,296.05 | $125,103 |
| 2016 | $27,144.56 | $125,103 |
| 2015 | $23,964.35 | $100,025 |
| 2014 | $25,789.1 | $109,687 |
| 2013 | $24,583.93 | $109,687 |
| 2012 | $23,979.57 | $112,185 |
| 2011 | $22,930.9 | $112,185 |
| 2010 | $22,275.1 | $112,185 |
| 2009 | $23,791 | $142,296 |
| 2008 | $23,515.3 | $156,460 |
| 2007 | $23,936.2 | $167,555 |
| 2006 | $22,178.2 | $121,674 |
| 2005 | $21,776.4 | $121,674 |
| 2004 | $21,116.6 | $121,674 |
| 2003 | $19,048.8 | $96,704 |
| 2002 | $17,655.8 | $96,704 |
| 2001 | $16,460 | $96,704 |
| 2000 | $15,977.7 | $87,035 |
| 1999 | $14,870.1 | $87,035 |
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