For SaleRisky Deal33 days on market
135 Oakside Drive
135 Oakside Drive, Smithtown, NY 11787, Smithtown, NY 11787
$1,325,000
Estimate®:$1,375,200$50,200 Under Market
Listing Price
135 Oakside Drive, Smithtown, NY 11787
Loc: Smithtown, NY
Days Listed
33
Tax Assessed
$8k
Estimate®
$1375k
4% Under Valued
Lot Size
1.62 acres
Rent Estimate
$5,568/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.
7
Smithtown Elementary School
K-5
2.1 mi away
7
Accompsett Middle School
6-8
2.6 mi away
10
Smithtown High School West
9-12
2.7 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
mid-century modernsplit-levelstone veneervertical wood sidingvaulted rooflineoversized windowsasymmetric entrywaydouble doorsasphalt drivewaywooded landscapenatural lightarchitectural designretro aestheticsuburban
Haven AI Verdict
Recommendation
Risky
Confidence Score: 5/10
Exercise caution due to potential market volatility.
Cap Rate
2.25%
Total ROI
7.7%
Cash Flow
$-4,395/mo
DSCR
0.36
Was this AI Verdict accurate?
Data provided by Haven AI. Disclaimer
Haven AI
Property yields an estimated $-4,395/mo net cash flow with a 2.3% cap rate. Underwriting indicates risky fundamentals for long-term hold.
Strengths
- • Prime residential location in Smithtown, NY
- • 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 |
|---|---|---|---|
| 2026-09-21 | Price change | $1,325,000 | $442 |
| 2026-09-12 | Price change | $1,350,000 | $450 |
| 2026-09-08 | Price change | $1,399,000 | $466 |
| 2026-08-28 | Price change | $1,499,000 | $500 |
| 2026-08-22 | Listed for sale | $1,750,000 | $583 |
| 2026-06-05 | Listing removed | $2,600 | $1 |
| 2026-05-02 | Listed for rent | $2,600 | $1 |
| 2025-10-21 | Listing removed | $2,800 | $1 |
| 2025-10-09 | Listed for rent | $2,800 | $1 |
| 1996-06-20 | Sold | $325,000 | $108 |
Tax History
| Year | Property Tax | Tax Assessment |
|---|---|---|
| 2025 | $0 | $7,935 |
| 2024 | $0 | $7,935 |
| 2023 | $0 | $7,935 |
| 2022 | $0 | $7,935 |
| 2021 | $0 | $8,250 |
| 2020 | $0 | $8,250 |
| 2019 | $0 | $8,250 |
| 2018 | $0 | $8,250 |
| 2017 | $17,262.9 | $8,250 |
| 2016 | $0 | $8,250 |
| 2015 | $0 | $8,250 |
| 2014 | $0 | $8,250 |
| 2013 | $0 | $8,250 |
| 2012 | $0 | $8,250 |
| 2011 | $0 | $8,250 |
| 2010 | $0 | $8,250 |
| 2009 | $0 | $8,250 |
| 2008 | $0 | $8,250 |
| 2007 | $14,340.6 | $8,250 |
| 2005 | $11,938.4 | $8,250 |
| 2004 | $11,147.5 | $8,250 |
| 2003 | $10,317.4 | $8,250 |
| 2002 | $9,569.82 | $8,250 |
| 2001 | $0 | $8,250 |
| 2000 | $9,029.87 | $8,250 |
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