41 VT Route 103 S · Chester, VT 05143

$295,000

None bd · None ba · 2,702 sqft · MultiFamily · 213 Days on market

Built 1900 Fair condition 0.50 ac lot $109/sqft · 27% above area Est $232k · 27% over ↓ 1% since listing

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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 +28.5/30.0
• DSCR +10.0/10.0
• Appreciation +10.0/10.0
• 1% rule +7.9/10.0
• Schools +5.0/10.0
• Livability +3.6/5.0
• Rent growth +2.5/5.0
• Condition / age +2.2/5.0
• ARV discount +0.0/15.0

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 1 unit. estimate disagrees with records

Listing remarks MLS

Here's a great opportunity to own a property on Chester's busy Main Street, Route 103 and Route 11. Situated between the Jiffy Mart and the General Dollar Store, there are many possibilities here for a commercial enterprise. Or you can use one unit for a nice business office and continue to rent the other two existing apartments. There is good road frontage for plenty of parking. Consider the options here and take a look today!

Key facts

• Main street location
• Plenty of parking
• Good road frontage

Tags

• MAIN STREET LOCATION
• GOOD ROAD FRONTAGE
• PLENTY OF PARKING

What this means for you Summary

Snapshot

• This is a multifamily listed at $295k. Condition is rated fair.

Deal economics

• At list price, monthly cash flow is $963 ($12k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($4k rent vs $295k).
• Recommended offer: $260k (12.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads 72/100 on livability (#30 in VT) — a middle-class / working-renter tenant base. Strengths: crime A+, housing A+, health & safety A+; Watch: amenities F, commute F.
• Market conditions: 50 active listings in the ZIP; 339 units permitted in Windsor County in 2024 (240 in 5+ unit buildings).

Forward outlook

• In year one you build about $32k of equity ($2k loan paydown + $30k appreciation (10.0% local appreciation)).
• Windsor County population projected at -21% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (10.0% appreciation + 3.0% rent growth), your $83k cash investment doubles in ~2 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$51k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 213 days — a 12% lower offer ($260k) is reasonable based on typical stale-listing flexibility.

Risks & watch-outs

• Watch-outs: built in 1900 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $259,600 (12.0% below list)

Questions for the listing agent

1. It's been on market 213 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Have any recent inspections been done? Can we get a copy of the seller's disclosures and any deferred-maintenance estimates?
3. Built in 1900 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
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: 1.29% ✓
• Cap rate: 10.21%
• Cash-on-cash: 13.98%
• DSCR: 1.62
• GRM: 6.5

CMA / ARV

• ARV (median comp): $231,874
• List price: $295,000
• Delta: 27.22%
• Verdict: OVERPRICED
• Comps: 3 within 1.0 mi

Projected returns pro-forma

10.0% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 34.6%
• Equity multiple: 3.69×
• Total profit: $222,026
• Equity at exit: $265,759

10-year hold

• IRR: 29.8%
• Equity multiple: 8.33×
• Total profit: $605,736
• Equity at exit: $573,120

Cash invested: $82,600 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 41 Moderately Tenant-Leaning
• State Vermont: 41 Moderately Tenant-Leaning · D+15
• County: — inherits STATE
• City: — inherits STATE

Just-cause in Burlington (2022); strong habitability.

Methodology + full state rankings →

ZIP-level market 05143

• Home prices YoY: 7.7%
• Active inventory: 50
• Price-to-rent: 19.4×

Monthly cashflow live

• Estimated rent: $3,799 medium
• Mortgage (P&I): −$1,547
• Tax est. 1.5%: −$369 /mo · $4,425/yr
• Insurance: −$123
• HOA: −$0
• Vacancy / Maint / Mgmt: −$798
• Net cashflow: $963

Break-even live

Break-even rent $2,581

Max offer price $295,000

Occupancy floor 70%

Sensitivity live

Price	-10% $1,166	-5% $1,064	+0% $963	+5% $861	+10% $759
Rent	-10% $662	-5% $812	+0% $963	+5% $1,113	+10% $1,263
Rate	-1.0pp $1,111	-0.5pp $1,038	base $963	+0.5pp $886	+1.0pp $808

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

Units	Beds	Baths	Est. rent
▸ 3× units	1	1	$3,798
Total (3 units)			$3,799

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: $73,750
• Closing costs: $8,850
• Reserves months: —
• Total cash needed: —

Listing history 18 events

1. 2026-06-21
   days on market $295,000 Active 213 DOM
2. 2026-06-18
   days on market $295,000 Active 211 DOM
3. 2026-06-17
   days on market $295,000 Active 210 DOM
4. 2026-06-16
   days on market $295,000 Active 209 DOM
5. 2026-06-15
   days on market $295,000 Active 208 DOM
6. 2026-06-15
   days on market $295,000 Active 207 DOM
7. 2026-06-13
   days on market $295,000 Active 206 DOM
8. 2026-06-12
   days on market $295,000 Active 205 DOM
9. 2026-06-09
   days on market $295,000 Active 202 DOM
10. 2026-06-08
    days on market $295,000 Active 201 DOM
11. 2026-06-08
    days on market $295,000 Active 200 DOM
12. 2026-06-07
    days on market $295,000 Active 199 DOM
13. 2026-06-03
    days on market $295,000 Active 196 DOM
14. 2026-06-02
    days on market $295,000 Active 195 DOM
15. 2026-06-01
    days on market $295,000 Active 194 DOM
16. 2026-05-31
    days on market $295,000 Active 193 DOM
17. 2026-05-14
    price $295,000 431-char remark

    Show marketing remark (431 chars)

    Here's a great opportunity to own a property on Chester's busy Main Street, Route 103 and Route 11. Situated between the Jiffy Mart and the General Dollar Store, there are many possibilities here for a commercial enterprise. Or you can use one unit for a nice business office and continue to rent the other two existing apartments. There is good road frontage for plenty of parking. Consider the options here and take a look today!

18. 2025-11-19
    listed $299,000 Active 431-char remark

    Show marketing remark (431 chars)

    Here's a great opportunity to own a property on Chester's busy Main Street, Route 103 and Route 11. Situated between the Jiffy Mart and the General Dollar Store, there are many possibilities here for a commercial enterprise. Or you can use one unit for a nice business office and continue to rent the other two existing apartments. There is good road frontage for plenty of parking. Consider the options here and take a look today!

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

Climate risk First Street

• 🌡 Heat 2/10 Low
• 🫁 Air quality 1/10 Low 0 unhealthy d/yr today · 0 by 30 yrs out

Taxation est. · year 1

• Rental income: $45,588
• − Mortgage interest: −$16,525
• − Property taxes: −$4,425
• − Insurance: −$1,475
• − Repairs & maintenance: −$3,647
• − Management: −$3,647
• − Depreciation: −$8,582
• Taxable income: $7,288
• Est. tax owed @ 24.0%: −$1,749
• After-tax cash flow: $9,801/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.

Condition & rehab AI · 6 photos

Fair 45/100 Moderate rehab

This property requires moderate renovations, including landscaping and fencing repairs, to improve its curb appeal and value.

Repairs flagged

• Major landscaping — Overgrown bushes need trimming
• Major fencing — Decaying wooden fence needs replacement

Value-add opportunities

• Both landscaping — Aesthetic improvement and increased curb appeal
• Both fencing — Safety and property boundary enhancement

Renovation cost estimate screening

Repair item	Severity	Est. cost
landscaping · Overgrown bushes need trimming	Major	$15,000–50,000
fencing · Decaying wooden fence needs replacement	Major	$15,000–50,000
Total estimated repair cost · 2 items		$30,000–100,000

Value-add ROI direction

• Both landscaping — Aesthetic improvement and increased curb appeal ↑
• Both fencing — Safety and property boundary enhancement ↑

ⓘ Cost ranges are severity-bucket heuristics (US national rule-of-thumb). Get contractor quotes + a written scope before underwriting a rehab budget.

Schools (NCES district)

No district data.

Livability — Chester

• Score: 72/100
• State rank: #30
• US rank: #6451

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Chester, VT
• Population (ZIP): 4,916

Population outlook (Windsor County) Hauer SSP2

• Today (2025): 53,235 people
• By 2030: 51,269 · -3.7%
• By 2040: 46,517 · -12.6%
• By 2050: 41,859 · -21.4%
• By 2075: 33,298 · -37.5%
• By 2100: 24,523 · -53.9%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (96%)
• Race & ethnicity: White 96% Two or more races 2% Black 1%
• Common ancestry: Romanian 8% Lithuanian 6% Slovak 6%
• Foreign-born: 4% · Canada
• Languages at home: 97% English-only · French/Haitian/Cajun 2%

Political lean MEDSL · Windsor

• 2024 margin: Solid D (+35.6) · D 66.3% · R 30.7% · Other 2.9%
• 2008→2024 swing: -4.1pp toward R · 2008: 39.7pp · 2024: 35.6pp
• All cycles: 2024: D+35.6 2020: D+38.9 2016: D+32.1 2012: D+38.1 2008: D+39.7

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 25.13%
• Current HPI: 352.8055
• Rent YoY: —
• Metro: —
• State GDP YoY: —
• F500 in state: 0

Price history

-1.3% since first listed

2 events — show timeline

• 2026-05-14 Price Changed $295,000 PrimeMLS
• 2025-11-19 Listed $299,000 PrimeMLS