OFF_MARKETRisky Deal5 days on market

285 Chestnut Ave

285 Chestnut Ave, Jamaica Plain, MA 02130, Jamaica Plain, MA 02130
$1,525,000
Zestimate®:$1,715,300$190,300 Under Market

Listing Price

Property image 1
285 Chestnut Ave, Jamaica Plain, MA 02130
Loc: Jamaica Plain, MA
Days Listed
5
Tax Assessed
$1595k
Zestimate®
$1715k
11% Under Valued
Lot Size
6,160 sqft
Rent Estimate
$2,776/mo
Est. Cash Flow base
Type
multi 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.

4

Curley K-8 School

PK-8
0.4 mi away
N/A

Community Academy

9-12
0.4 mi away
4

Margarita Muniz Academy

7-12
0.5 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
0.05%
Total ROI
-40.2%
Cash Flow
$-7,855/mo
DSCR
0.01
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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
2026-05-21Sold$1,715,000$342
2026-04-16Contingent$1,525,000$304
2026-04-09Listed for sale$1,525,000$304

Tax History

YearProperty TaxTax Assessment
2025$18,467$1,594,700
2024$17,986$1,650,100
2023$17,722$1,650,100
2022$16,777$1,542,000
2021$15,377$1,441,100
2020$15,188$1,438,300
2019$13,779$1,307,300
2018$12,687$1,210,600
2017$3,054.43$1,210,600
2016$12,218$1,110,700
2015$11,242$928,300
2014$10,122$804,600
2013$9,616$731,800
2012$8,987$689,200
2011$8,815$689,200
2010$8,271$696,200
2009$7,144$672,100
2008$7,373$672,100
2007$7,939$722,400
Nathaniel Pitchon-Getzels Logo
Getzels Group
Haven Team
CalRE #01884947
Call / Text
818.535.5337

Property Specs

Beds
10
Baths
3
Sq Ft
5,013
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: $1,525,000Rent Basis: Observed Comp Model ($2,776/mo)State Tax Benchmark: 1.23% (MA)Hazard Reserve: $445/mo
Haven ScoreRisky
0/ 10

Multi-factor yield grade

Cap Rate (Unleveraged)
0.05%

NOI: $695/yr

Cash-on-Cash Yield
-26.9%

On $350,750 invested

DSCR Ratio
0.01x

Negative debt coverage

5-Yr Leveraged ROI
+-40.2%

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)-$1,635/mo
Homeowner / Hazard Insurance-$445/mo
Vacancy Reserve (5% of rent)-$139/mo
Repairs & Maintenance (10% of rent)-$278/mo
Property Management (8% of rent)-$222/mo
Total Pure Operating Expenses-$2,718/mo
Net Investor Cash Flow
Gross Scheduled Rent+$2,776/mo
Less: Operating Expenses-$2,718/mo
Net Operating Income (NOI)+$58/mo
Less: Debt Service (30yr @ 6.75%)-$7,913/mo
Net Cash Flow
$-7,855/mo
$-94,259/year
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