For SaleRisky Deal91 days on market
82 Woodley Rd
82 Woodley Rd, Winnetka, IL 60093, Winnetka, IL 60093
$2,785,000
Estimate®:$2,829,700$44,700 Under Market
Listing Price
82 Woodley Rd, Winnetka, IL 60093
Loc: Winnetka, IL
Days Listed
91
Tax Assessed
$1219k
Estimate®
$2830k
2% Under Valued
Lot Size
1.50 acres
Rent Estimate
$7,398/mo
Est. Cash Flow base
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
Avoca West Elementary School
K-5
1.1 mi away
9
Marie Murphy School
PK,6-8
0.3 mi away
N/A
New Trier Township H S Northfield
9
0.8 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 revivalbrick exteriorsymmetrical designdormer windowsshuttersgravel drivewaymanicured landscapingmature treesarch-top front entryluxury homeclassic architecturetraditionalgabled roof
Haven AI Verdict
Recommendation
Risky
Confidence Score: 5/10
Exercise caution due to potential market volatility.
Cap Rate
1.11%
Total ROI
-17.0%
Cash Flow
$-11,873/mo
DSCR
0.18
Was this AI Verdict accurate?
Data provided by Haven AI. Disclaimer
Haven AI
Property yields an estimated $-11,873/mo net cash flow with a 1.1% cap rate. Underwriting indicates risky fundamentals for long-term hold.
Strengths
- • Prime residential location in Winnetka, IL
- • Long-term capital appreciation corridor
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 |
|---|---|---|---|
| 2026-06-24 | Listed for sale | $2,785,000 | – |
| 2026-02-02 | Listing removed | $15,000 | – |
| 2025-07-17 | Listed for rent | $15,000 | – |
| 2022-08-11 | Listing removed | $0 | – |
| 2022-07-07 | Price change | $2,198,926 | – |
| 2022-06-20 | Price change | $2,214,000 | – |
| 2022-06-02 | Price change | $2,259,000 | – |
| 2022-05-17 | Price change | $2,328,000 | – |
| 2022-04-12 | Price change | $2,400,000 | – |
| 2022-03-18 | Listed for sale | $2,475,000 | – |
| 2020-01-15 | Listing removed | $2,850,000 | – |
| 2019-12-31 | Listed for sale | $2,850,000 | – |
| 2009-09-29 | Sold | $1,425,000 | – |
| 2009-03-22 | Price change | $1,595,000 | – |
| 2009-02-14 | Listed for sale | $1,795,000 | – |
Tax History
| Year | Property Tax | Tax Assessment |
|---|---|---|
| 2024 | $22,421.18 | $121,938 |
| 2023 | $21,603.9 | $121,937 |
| 2022 | $20,495.89 | $121,937 |
| 2021 | $25,965.08 | $133,973 |
| 2020 | $25,370 | $133,973 |
| 2019 | $30,902.09 | $182,470 |
| 2018 | $34,904.62 | $196,372 |
| 2017 | $34,101.62 | $196,372 |
| 2016 | $32,812.53 | $199,061 |
| 2015 | $29,585.24 | $162,699 |
| 2014 | $28,990.32 | $162,699 |
| 2013 | $27,561.51 | $162,699 |
| 2012 | $22,326.64 | $142,500 |
| 2011 | $21,228.6 | $142,500 |
| 2010 | $20,733.4 | $142,500 |
| 2009 | $18,489.2 | $142,500 |
| 2008 | $35,862.5 | $304,503 |
| 2007 | $33,418 | $304,503 |
| 2006 | $26,932.2 | $209,629 |
| 2005 | $26,281.4 | $209,629 |
| 2004 | $24,978.6 | $209,629 |
| 2003 | $24,433.6 | $183,449 |
| 2002 | $24,962.4 | $183,449 |
| 2001 | $20,073.5 | $183,449 |
| 2000 | $19,756.3 | $146,881 |
| 1999 | $19,756.3 | $146,881 |
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