OFF_MARKETRisky Deal230 days on market

11 Chestnut St

11 Chestnut St, Boston, MA 02108, Boston, MA 02108
$8,500,000
Zestimate®:$7,666,200

Listing Price

Property image 1
11 Chestnut St, Boston, MA 02108
Loc: Boston, MA
Days Listed
230
Tax Assessed
$7956k
Zestimate®
$7666k
Market Rate
Lot Size
1,740 sqft
Rent Estimate
$6,535/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.

8

Josiah Quincy Elementary School

PK-5
0.7 mi away
3

Quincy Upper School

6-12
0.7 mi away
N/A

Boston Adult Academy

11-12
0.6 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
-0.79%
Total ROI
-58.4%
Cash Flow
$-49,706/mo
DSCR
-0.13
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Data provided by Haven AI. Disclaimer

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10-Year Price Projection

Price & Tax History

Price History

DateEventPricePrice/sqft
2026-06-01Listing removed$8,500,000$1,501
2026-01-20Price change$8,500,000$1,501
2025-08-27Listed for sale$8,950,000$1,580
2025-06-30Listing removed$8,950,000$1,580
2025-04-28Price change$8,950,000$1,580
2024-09-09Price change$9,200,000$1,625
2024-04-09Listed for sale$9,700,000$1,713
2018-01-30Sold$6,700,000$1,183
2018-01-12Pending sale$7,350,000$1,298
2017-01-17Listed for sale$7,350,000$1,298
2012-07-20Listing removed$4,650,000$821
2012-04-20Listed for sale$4,650,000$821
2004-05-27Sold$2,650,000$468

Tax History

YearProperty TaxTax Assessment
2025$92,126$7,955,600
2024$78,650$7,215,600
2023$77,496$7,215,600
2022$71,141$6,538,700
2021$69,768$6,538,700
2020$67,038$6,348,300
2019$63,674$6,041,200
2018$54,461$5,196,700
2017$12,613.09$4,949,200
2016$52,414$4,764,900
2015$55,045$4,545,400
2014$54,459$4,329,000
2013$52,669$4,008,300
2012$44,138$3,384,800
2011$40,827$3,192,100
2010$35,775$3,011,400
2009$33,555$3,156,670
2008$34,590$3,153,150
2007$35,845$3,261,610
2006$34,604$3,111,900
2005$26,731$2,491,200
2004$24,317$2,395,800
2003$25,747$2,280,500
2002$25,179$2,286,900
2000$19,582$1,489,100
Nathaniel Pitchon-Getzels Logo
Getzels Group
Haven Team
CalRE #01884947
Call / Text
818.535.5337

Property Specs

Beds
5
Baths
6
Sq Ft
6,596
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: $8,500,000Rent Basis: Observed Comp Model ($6,535/mo)State Tax Benchmark: 1.23% (MA)Hazard Reserve: $2,479/mo
Haven ScoreRisky
0/ 10

Multi-factor yield grade

Cap Rate (Unleveraged)
-0.79%

NOI: $-67,218/yr

Cash-on-Cash Yield
-30.5%

On $1,955,000 invested

DSCR Ratio
-0.13x

Negative debt coverage

5-Yr Leveraged ROI
+-58.4%

Equity + cumulative cash

Financing Scenario Controls
Adjust down payment & rates to model your personalized return

Monthly Cash Flow Breakdown

Monthly Operating Deductions
Property Taxes (1.23% of basis)-$8,154/mo
Homeowner / Hazard Insurance-$2,479/mo
Vacancy Reserve (5% of rent)-$327/mo
Repairs & Maintenance (10% of rent)-$654/mo
Property Management (8% of rent)-$523/mo
Total Pure Operating Expenses-$12,137/mo
Net Investor Cash Flow
Gross Scheduled Rent+$6,535/mo
Less: Operating Expenses-$12,137/mo
Net Operating Income (NOI)+$-5,602/mo
Less: Debt Service (30yr @ 6.75%)-$44,105/mo
Net Cash Flow
$-49,706/mo
$-596,475/year
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11 Chestnut St | Boston, MA | Haven AI Analysis | Haven by ScoutHavens