556 S Main St · Brattleboro, VT 05301

$270,000

6 bd · 2.0 ba · 2,112 sqft · MultiFamily · 1332 Days on market

Built 1910 6,534 sqft lot

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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 +30.0/30.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• ARV discount +7.5/15.0
• Schools +5.0/10.0
• Livability +3.4/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Multi-family units

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

Listing remarks

What a great way to start your home ownership! A tenant can help with the monthly expenses letting you build your own reserves and take a bit of pressure off the cost of home ownership! This 2 family has two-3 bedroom units, a nice yard and off street parking. Check it out and see for yourself. .. please respect the 48 hour notice for tenants, mask up! No interior photos due to tenant privacy. The vacant lot next door is not part of the offering. Seller to complete a 1031 Exchange. Owner is a Licensed Real Estate appraiser.

Key facts

• 6,534 sq ft lot
• Built 1910
• Listed 1332 days

Property features AI

Finance

• Other: Deed and tax map documents available
• Financial info: Net income reported: $12,887; Operating expenses include insurance, water/sewer, and other expenses

Exterior

• Parking: Dirt driveway
• Utilities: Public water; Public sewer; Electric service with circuit breakers; Cable and DSL/high-speed internet available; Telephone service available; Municipal trash service
• Home design: Duplex; Existing construction; Brown exterior color
• Construction: Built in 1910; Wood frame construction with asbestos exterior and shingle siding; Asphalt shingle roof; Foundation details not specified
• Exterior features: City corner lot in town with curb, sidewalks, street lights and open setting; Near shopping and public transportation; Paved public road frontage (approximately 160 ft)

Interior

• Kitchen: Water heater (electric)
• Bedrooms: Two 3-bedroom units
• Flooring: Vinyl flooring; Wood flooring
• Bathrooms: Two full bathrooms (one in each unit)
• Heating & cooling: Oil heating with forced air; No central cooling
• Interior features: Full unfinished basement with dirt floor, interior stairs, and storage space; Townhouse-style units
• Laundry & utility: Water heater (electric)

What this means for you Summary

Snapshot

• This is a 2 × 3-bed/1.0-bath units multifamily listed at $270k.

Deal economics

• At list price, monthly cash flow is $2k ($18k/yr) — positive. Per door: $769/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($4k rent vs $270k).
• Recommended offer: $238k (12.0% below list) — sets the bar for market timing.
• Cap rate 13.1% vs local median 4.5% in Brattleboro — 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 67/100 on livability (#42 in VT) — a middle-class / working-renter tenant base. Strengths: schools A+, health & safety A+, cost of living B; Watch: crime F, amenities D-, commute F.
• Market conditions: 82 active listings in the ZIP; 188 units permitted in Windham County in 2024 (0 in 5+ unit buildings).
• At $4,308/mo this rent would consume 78% of the median local household income ($66k/yr) (locally 594% 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 $8k of value loss. Plan a longer hold.
• Windham County population projected at -26% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $76k cash investment doubles in ~5 years — after that, you're playing with house money.

Negotiation context

• It's been on market 1332 days — a 12% lower offer ($238k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 4y 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.

Risks & watch-outs

• Watch-outs: built in 1910 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $237,600 (12.0% below list)

Questions for the listing agent

1. It's been on market 1332 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
3. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
4. Built in 1910 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
5. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
6. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
7. Schools are A-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?
8. Crime grade is F in this area — have there been break-ins, vandalism, or insurance claims at this property in the last 3 years? What carrier currently insures it and at what premium?
9. 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.
10. 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.
11. 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: 1.60% ✓
• Cap rate: 13.13%
• Cash-on-cash: 24.40%
• DSCR: 2.09
• GRM: 5.2

CMA / ARV

No comps found within radius.

Projected returns pro-forma

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

5-year hold

• IRR: 17.7%
• Equity multiple: 1.72×
• Total profit: $54,232
• Equity at exit: $40,258

10-year hold

• IRR: 26.2%
• Equity multiple: 3.30×
• Total profit: $173,574
• Equity at exit: $23,345

Cash invested: $75,600 (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 05301

• Home prices YoY: -19.2%
• Active inventory: 82
• Price-to-rent: 10.4×

Monthly cashflow live

• Estimated rent: $4,308 medium
• Mortgage (P&I): −$1,416
• Tax est. 1.5%: −$338 /mo · $4,050/yr
• Insurance: −$112
• HOA: −$0
• Vacancy / Maint / Mgmt: −$905
• Net cashflow: $1,537

Break-even live

Break-even rent $2,362

Max offer price $270,000

Occupancy floor 59%

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

Units	Beds	Baths	Est. rent
▸ 2× units	3	1	$4,308
Total (2 units)			$4,308

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: $67,500
• Closing costs: $8,100
• Reserves months: —
• Total cash needed: —

Listing history 6 events

1. 2026-05-22
   status Pending
2. 2025-09-05
   status Active
3. 2025-08-05
   historical
4. 2024-08-07
   status Active
5. 2024-08-06
   historical
6. 2022-08-25
   listed $270,000 Active

ⓘ 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

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 3/10 Moderate 8 d/yr ≥96°F today · 18 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 9% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 0 unhealthy d/yr today · 1 by 30 yrs out

Taxation est. · year 1

• Rental income: $51,696
• − Mortgage interest: −$15,124
• − Property taxes: −$4,050
• − Insurance: −$1,350
• − Repairs & maintenance: −$4,136
• − Management: −$4,136
• − Depreciation: −$7,855
• Taxable income: $15,046
• Est. tax owed @ 24.0%: −$3,611
• After-tax cash flow: $14,838/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)

No district data.

Livability — Brattleboro

• Score: 67/100
• State rank: #42
• US rank: #10223

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Brattleboro, VT
• County: Windham County · 16,955 people
• City population: 16,955
• Metro: nan
• Population (ZIP): 16,955
• Household income: $65,910
• Rent vs Own: 34.4% rent · 65.6% own
• Severe rent burden: 594.0

Population outlook (Windham County) Hauer SSP2

• Today (2025): 40,432 people
• By 2030: 38,472 · -4.8%
• By 2040: 33,954 · -16.0%
• By 2050: 29,774 · -26.4%
• By 2075: 22,351 · -44.7%
• By 2100: 15,961 · -60.5%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (90%)
• Race & ethnicity: White 90% Two or more races 6% Hispanic / Latino 3% Asian 2%
• Common ancestry: Lithuanian 7% Romanian 5% Italian 4%
• Foreign-born: 2% · Canada
• Languages at home: 97% English-only · Spanish 2% Other Asian/Pacific 1%

Political lean MEDSL · Windham

• 2024 margin: Solid D (+42.7) · D 69.6% · R 26.9% · Other 3.5%
• 2008→2024 swing: -5.4pp toward R · 2008: 48.1pp · 2024: 42.7pp
• All cycles: 2024: D+42.7 2020: D+47.3 2016: D+42.0 2012: D+49.2 2008: D+48.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -67.19%
• Current HPI: 283.2338
• Rent YoY: —
• Metro: nan
• State GDP YoY: —
• F500 in state: 0

Price history

6 events — show timeline

• 2026-05-22 Pending — PrimeMLS
• 2025-09-05 Relisted — PrimeMLS
• 2025-08-05 Delisted — PrimeMLS
• 2024-08-07 Relisted — PrimeMLS
• 2024-08-06 Delisted — PrimeMLS
• 2022-08-25 Listed $270,000 PrimeMLS