OFF_MARKETRisky Deal11 days on market
66 School St
66 School St, Boston, MA 02129, Boston, MA 02129
66 School St, Boston, MA 02129
Loc: Boston, MA
Days Listed
11
Tax Assessed
$1219k
Zestimate®
$1276k
Market Rate
Lot Size
1,041 sqft
Rent Estimate
$5,545/mo
Est. Cash Flow base
Type
single family
More Than Just a Property
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4.9
Safety Score
A+
Schools
Nearby Schools
Educational options and performance ratings in the area.
8
Warren-Prescott K-8 School
PK-8
0.1 mi away
3
Charlestown High School
7-12
0.2 mi away
N/A
Horace Mann School For The Deaf
PK-12
0.2 mi away
Property Overview
A stunning investment opportunity in a prime location. This property features modern amenities, spacious living areas, and strong rental potential.
Features & Amenities
Open Floor PlanHardwood FloorsModern KitchenStainless Steel AppliancesCentral Heat/AirLarge BackyardParkingNear Transit
Haven AI Verdict
Recommendation
Pending...
Confidence Score: 0/10
Exercise caution due to potential market volatility.
Cap Rate
2.24%
Total ROI
7.5%
Cash Flow
$-4,647/mo
DSCR
0.36
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10-Year Price Projection
Price & Tax History
Price History
| Date | Event | Price | Price/sqft |
|---|---|---|---|
| 2026-05-01 | Sold | $1,275,000 | $713 |
| 2026-03-30 | Contingent | $1,339,000 | $748 |
| 2026-03-18 | Price change | $1,339,000 | $748 |
| 2026-02-24 | Listed for sale | $1,399,000 | $782 |
| 2021-03-31 | Sold | $1,030,000 | $576 |
| 2021-03-01 | Pending sale | $1,060,000 | $593 |
| 2021-02-15 | Contingent | $1,060,000 | $593 |
| 2021-01-28 | Listed for sale | $1,060,000 | $593 |
| 2021-01-19 | Listing removed | $0 | – |
| 2021-01-04 | Price change | $1,060,000 | $593 |
| 2020-11-13 | Price change | $1,065,000 | $595 |
| 2020-10-28 | Price change | $1,070,000 | $598 |
| 2020-10-13 | Listed for sale | $1,085,000 | $606 |
| 2017-12-05 | Sold | $940,000 | $525 |
| 2017-10-20 | Pending sale | $925,000 | $517 |
| 2017-10-12 | Listed for sale | $925,000 | $517 |
| 2014-08-22 | Sold | $665,000 | $372 |
| 2012-07-25 | Sold | $520,000 | $291 |
| 2012-03-15 | Listed for sale | $525,000 | $293 |
| 2010-09-15 | Listing removed | $499,000 | $279 |
| 2010-04-25 | Listed for sale | $499,000 | $279 |
| 2009-11-03 | Sold | $500,000 | $279 |
| 2009-09-19 | Listed for sale | $499,000 | $279 |
| 2007-07-30 | Sold | $466,500 | $261 |
| 2001-02-02 | Sold | $284,000 | $159 |
| 2000-07-05 | Sold | $200,865 | $112 |
| 1996-07-29 | Sold | $145,000 | $81 |
Tax History
| Year | Property Tax | Tax Assessment |
|---|---|---|
| 2025 | $13,317 | $1,150,000 |
| 2024 | $11,813 | $1,083,800 |
| 2023 | $11,087 | $1,032,300 |
| 2022 | $10,244 | $941,500 |
| 2021 | $9,849 | $923,100 |
| 2020 | $9,720 | $920,500 |
| 2019 | $9,508 | $902,100 |
| 2018 | $8,486 | $809,700 |
| 2017 | $1,374.39 | $749,400 |
| 2016 | $7,459 | $678,100 |
| 2015 | $7,149 | $590,300 |
| 2013 | $6,307 | $480,000 |
| 2012 | $6,000 | $460,100 |
| 2011 | $5,768 | $451,000 |
| 2010 | $5,411 | $455,500 |
| 2009 | $4,762 | $448,000 |
| 2008 | $5,190 | $473,100 |
| 2007 | $5,471 | $497,800 |
Institutional Underwriting Ledger
Investment Numbers & Operating Model
Standardized cash flow underwriting modeled with state tax schedules, regional insurance hazard risk, and disciplined operating reserves.
Data Sources:MLS List Price: $1,399,000Rent Basis: Observed Comp Model ($5,545/mo)State Tax Benchmark: 1.23% (MA)Hazard Reserve: $408/mo
Haven ScoreRisky
0/ 10
Multi-factor yield grade
Cap Rate (Unleveraged)
2.24%
NOI: $31,344/yr
Cash-on-Cash Yield
-17.3%
On $321,770 invested
DSCR Ratio
0.36x
Negative debt coverage
5-Yr Leveraged ROI
+7.5%
Equity + cumulative cash
Financing Scenario Controls
Adjust down payment & rates to model your personalized returnMonthly Cash Flow Breakdown
Monthly Operating Deductions
Property Taxes (1.23% of basis)-$1,250/mo
Homeowner / Hazard Insurance-$408/mo
Vacancy Reserve (5% of rent)-$277/mo
Repairs & Maintenance (10% of rent)-$555/mo
Property Management (8% of rent)-$444/mo
Total Pure Operating Expenses-$2,933/mo
Net Investor Cash Flow
Gross Scheduled Rent+$5,545/mo
Less: Operating Expenses-$2,933/mo
Net Operating Income (NOI)+$2,612/mo
Less: Debt Service (30yr @ 6.75%)-$7,259/mo
Net Cash Flow
$-4,647/mo
$-55,766/year
Underwrite with Acquisition CalculatorsTransfer this property's exact numbers into dedicated underwriting tools:
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