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106-108 Chestnut St Duplex
B- Composite 67.1
Why this score? — see what drove the B- grade

The composite is a weighted blend of 9 inputs, each scored 0–100. Each bar is that input's sub-score; the figure is the points it added to the 100-point composite (weight × sub-score).

  • Cash flow +25.0/30.0
  • ARV discount +15.0/15.0
  • DSCR +8.1/10.0
  • 1% rule +7.2/10.0
  • Livability +3.8/5.0
  • Rent growth +3.0/5.0
  • Schools +2.5/10.0
  • Condition / age +2.5/5.0
  • Appreciation +0.0/10.0

$359,000

106-108 Chestnut St · Manchester, CT 06040
7 bd · 2.0 ba · 3,805 sqft · MultiFamily public records · 18 Days on market
Built 1905 0.28 ac lot Est $498k · 28% under

🖨 Deal sheet (PDF) 📄 Offer letter ✓ Due diligence

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 2 units. confirmed

Listing remarks

Attention investors! Opportunity awaits a 2-family property located in a desirable neighborhood, ready for your vision and in need of significant improvement. This multi-family offers a functional layout with identical floor plans in both units. One unit is oil, and the other is gas. As it Sale

Key facts

  • 0.28 acre lot
  • Built 1905
  • Listed 18 days

Neighborhood map

Property Rental comp Retail Transit Schools Stadiums Fortune 500 · Circle radius: 3.0 mi
Loading POIs…

What this means for you Summary

Snapshot

  • This is a 2 × 3-bed/1.0-bath units multifamily listed at $359k.

Deal economics

  • At list price, monthly cash flow is $780 ($9k/yr) — positive. Per door: $390/mo.
  • The deal already cash-flows at list — no discount required.
  • Meets the 1% rule at list price ($4k rent vs $359k).
  • Recommended offer: $354k (1.5% below list) — sets the bar for market timing.
  • Cap rate 8.9% vs local median 3.7% in Manchester — top-decile yield for the area; either an underpriced asset or a hidden risk that comps aren't pricing in. Stress-test before assuming the spread holds.

Location & tenants

  • Location reads 76/100 on livability (#59 in CT, #3,580 nationally) — a middle-class / working-renter tenant base. Strengths: housing A+, health & safety A+, cost of living A-; Watch: amenities D, commute F.
  • Manchester School District (suburban): math 21% / reading 32% proficiency, ranked #130 of 153 in CT (top 85%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover.
  • Market conditions: Rents rising (+2.0%/yr); 99 active listings in the ZIP; solid renter incomes; 1,867 units permitted in Capitol Planning Region in 2024 (1,399 in 5+ unit buildings).
  • At $4,390/mo this rent would consume 63% of the median local household income ($83k/yr) (locally 1839% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

  • Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $11k of value loss. Plan a longer hold.

Negotiation context

  • It's been on market 18 days — a 2% lower offer ($354k) is reasonable based on typical stale-listing flexibility.
  • 3 sale attempts since 22y ago with the ask held roughly flat each time — persistent listings suggest the price (not the market) is what's stuck; bring a comps-based counter.
  • Current owner paid $226k; list at $359k implies a 59% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

  • Watch-outs: built in 1905 — expect roof / HVAC / electrical / plumbing capex.
  • Climate carrying-cost: major wind risk, 27% chance of damaging wind over 30y; extreme-heat days projected 7→17/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.
Recommended offer $353,615 (1.5% below list)

Questions for the listing agent

  1. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
  2. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
  3. Built in 1905 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
  4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
  5. Schools are B-rated — typically a magnet for longer-tenancy family renters. What's the average tenant stay here, and is there a school-zone premium baked into asking?
  6. What's the average days-on-market for RENTAL listings here right now (not sales)? A rising rental-DOM trend means longer vacancies and softer asking-rent achievability than the comps imply.
  7. What's the recent tenant-quality profile in this submarket — average credit score on applications, eviction rate, late-payment / NSF rate, and stable-employment percentage? A property-management company in the area should have these aggregated.
  8. How much new apartment / multifamily construction is in the pipeline within 1–3 miles? Heavy new supply (>2% of stock underway) typically softens rents 12–24 months out; light construction supports rent growth.

Investment metrics

1% rule
1.22%
Cap rate
8.90%
Cash-on-cash
9.31%
DSCR
1.41
GRM
6.8

CMA / ARV

ARV (on-the-fly)
$498,455
Comps found
11
Show comp detail 11 sales within ~0.75 mi
Address Dist Beds/Ba Sqft Sold Price $/sf Match
9 Church St 0.25mi 8/4.0 (+1) 4,032 (+6%) 1mo $560,000 $139 65
39 Chestnut St 0.16mi 8/4.0 (+1) 3,882 (+2%) 21mo $550,000 $142 59
140 Bissell St 0.59mi 7/3.0 3,703 (-3%) 9mo $435,000 $117 57
203 Center St 0.23mi 8/5.0 (+1) 4,104 (+8%) 4mo $710,000 $173 56
106 Birch St 0.51mi 7/7.0 3,772 (-1%) 7mo $565,000 $150 49
52 Arch St 0.38mi 6/4.5 (-1) 4,000 (+5%) 12mo $489,000 $122 49
15 Foster St 0.54mi 7/4.0 3,902 (+2%) 20mo $465,000 $119 46
17 Lilac St 0.52mi 6/2.5 (-1) 3,365 (-12%) 7mo $300,000 $89 43
28 Lilley St 0.59mi 8/4.0 (+1) 3,600 (-5%) 15mo $415,000 $115 38
86 School St 0.56mi 7/4.0 3,437 (-10%) 23mo $450,000 $131 30
149 Bissell St 0.64mi 8/4.0 (+1) 3,520 (-8%) 21mo $580,000 $165 27

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

-3.0% appreciation · 1.97% rent growth · sell at horizon

5-year hold
IRR
-3.4%
Equity multiple
0.87×
Total profit
$-12,791
Equity at exit
$53,528
10-year hold
IRR
5.0%
Equity multiple
1.35×
Total profit
$35,533
Equity at exit
$31,040

Cash invested: $100,520 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

Overall (STATE)
27 Tenant-Leaning
State Connecticut
27 Tenant-Leaning · D+7
County
— inherits STATE
City
— inherits STATE
Strong tenant statutes; rent commissions in some towns; courts slow especially in cities.

ZIP-level market 06040

Rents YoY
2.0%
Active inventory
99
Price-to-rent
13.6×

Monthly cashflow live

Estimated rent
$4,390 high interval (Pro) →
Mortgage (P&I)
$1,883
Tax from tax record
$656 /mo · $7,868/yr
Insurance
$150
HOA
$0
Vacancy / Maint / Mgmt
$922
Net cashflow
$780

Break-even live

Break-even rent $3,402
Max offer price $359,000
Occupancy floor 77%

Sensitivity live

Price -10% $983 -5% $882 +0% $780 +5% $679 +10% $577
Rent -10% $433 -5% $607 +0% $780 +5% $954 +10% $1,127
Rate -1.0pp $961 -0.5pp $872 base $780 +0.5pp $687 +1.0pp $593

2-unit breakdown (identical units grouped — click to expand)

UnitsBedsBathsEst. rent
Total (2 units) $4,390

UW: 25.0% down · 7.5% · 30yr · 1.5% tax · 5.0% vac · 8.0% maint · 8.0% mgmt

Financing live

Cash to close

Down payment
$89,750
Closing costs
$10,770
Reserves months
Total cash needed

Loan-product check · same deal, 3 products live

Conventional

25% down · 7.5% · 30yr

Down + closing
Monthly P&I
Monthly cashflow
DSCR
Eligible?

Personal DTI + credit; lowest rate.

DSCR

20% down · 8.5% · 30yr

Down + closing
Monthly P&I
Monthly cashflow
DSCR
Eligible?

No personal income docs; deal must DSCR.

Hard money

10% down · 12.0% · 12mo

Down + closing
Monthly P&I
Monthly cashflow
DSCR
Eligible?

Short-term bridge; refi at stabilization.

Listing history 7 events

  1. 2026-04-21
    status Under Contract
  2. 2026-04-03
    status Active
  3. 2026-04-02
    historical
  4. 2026-04-01
    listed $359,000 Active
  5. 2004-12-06
    soldstatus $226,000
  6. 2004-12-03
    soldstatus $226,000
  7. 2004-09-28
    listed $225,000

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Tax reassessment forecast CT · Partial reset (capped growth)

Current annual tax
$7,868 · $656/mo
Projected year-2 tax
$7,868 · $656/mo
Expected delta
$0/yr ($0/mo · 0.0%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

  • 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
  • 🔥 Wildfire 2/10 Low
  • 🌡 Heat 5/10 Major 7 d/yr ≥95°F today · 17 d/yr by 30 yrs out
  • 💨 Wind 6/10 Major 27% chance of damaging wind over 30 yrs
  • 🫁 Air quality 3/10 Moderate 3 unhealthy d/yr today · 4 by 30 yrs out

Nearby sold comps map

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Walkable amenities ~0.75 mi

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Taxation est. · year 1

Rental income
$52,680
− Mortgage interest
−$20,110
− Property taxes
−$7,868
− Insurance
−$1,795
− Repairs & maintenance
−$4,214
− Management
−$4,214
− Depreciation
−$10,444
Taxable income
$4,035
combined federal + state — saved on this device
Est. tax owed @ 24.0%
−$968
After-tax cash flow
$8,394/yr

For passive investors: Depreciation is non-cash, so a rental often shows a tax loss while cash-flowing — sheltering income. Rental losses are passive: they offset passive income freely, and up to $25,000/yr can offset ordinary (W-2) income if you actively participate and your MAGI is under $100k (phasing out to $0 by $150k); unused losses carry forward. On sale, claimed depreciation is recaptured at up to 25%, and gains may owe capital-gains tax (a 1031 exchange can defer both). Figures are a year-1 estimate at your 24.0% rate — not tax advice; consult a CPA.

Schools (NCES district)

District
Manchester School District
NCES district ID
0902310
Math proficiency
21% ▼ -8.00%
Reading proficiency
32% ▼ -5.00%
Median HH income
$63,391
Composite
24.54/100
National rank
#7643
State rank
#130 of 153 in CT

Livability — Manchester

Score
76/100
State rank
#59
US rank
#3580

Category grades

Amenities D Commute F Cost of living A- Crime B+ Employment C+ Housing A+ Health & safety A+ User ratings B

Schools grade is shown separately in the Schools card above.

Census & demographics

Census place
Manchester, CT
County
Hartford County · 754,208 people
City population
59,635
Metro
Hartford-East Hartford-Middletown, CT
Population (ZIP)
35,813
Household income
$83,422
Rent vs Own
45.8% rent · 54.2% own
Severe rent burden
1839.0

Population outlook (Capitol County) Hauer SSP2

By 2040
1,063,519

Race, ethnicity, and origin ACS 2023

Neighborhood character
Diverse neighborhood (Simpson 0.65)
Race & ethnicity
White 53% Hispanic / Latino 18% Black 15% Asian 9% Two or more races 8%
Hispanic origin (detail)
Puerto Rican 14%
Common ancestry
Romanian 5% Lithuanian 4% Slovak 1%
Foreign-born
15% · Canada, Jamaica, China
Languages at home
81% English-only · Spanish 8% Other Indo-European 5% Other Asian/Pacific 2%

Political lean MEDSL · Capitol

2024 margin
Strong D (+21.9) · D 60.1% · R 38.2% · Other 1.7%
All cycles
2024: D+21.9

Not yet ingested

Civics

Market trends

HPI YoY
▼ -197.69%
Current HPI
190.4204
Rent YoY
▲ 1.97%
Metro
Hartford-East Hartford-Middletown, CT
State GDP YoY
▲ 1.06%
F500 in state
38

Industry mix (Fortune 500 HQ in CT)

Industry F500 HQs Revenue

Price history

+59.6% since first listed
7 events — show timeline
  • 2026-04-21 Pending Smart MLS
  • 2026-04-03 Relisted Smart MLS
  • 2026-04-02 Listing Removed Smart MLS
  • 2026-04-01 Listed $359,000 Smart MLS
  • 2004-12-06 Sold (Public Records) $226,000 Public Records
  • 2004-12-03 Sold (MLS) $226,000 Smart MLS
  • 2004-09-28 Listed $225,000 Smart MLS

Property tax history

+3.6%/yr

Latest (2025): $7,868 · +2.9% YoY. Source: county tax records.

Cash-flow waterfall

monthly

Sold comps — $/sqft

last 12 mo · ≤1 mi

Loading sold comps…