33 Oak St · Brattleboro, VT 05301

$495,000

None bd · None ba · 4,116 sqft · MultiFamily public records · 49 Days on market

Built 1860 0.40 ac lot Est $560k · 12% under

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Why this score? — see what drove the C- 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 +15.0/30.0
• ARV discount +12.7/15.0
• 1% rule +5.0/10.0
• DSCR +5.0/10.0
• 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 (5+ Unit). Listing-text estimate: 1 unit. estimate disagrees with records

5+ unit building — per-unit beds/baths from public records are typically unavailable; the breakdown below (if shown) is an estimate from the listing text.

Listing remarks

This is a rare opportunity to take over a multi-family project in the heart of Brattleboro. The 0.40-acre site features a vacant three-story building that has already been gutted and fully remediated for lead paint. With town zoning already approved to expand from 8 to 13 units and full architect plans included, the heavy lifting and permitting phase is already behind you. Upon completion, the complex will offer roughly 11,183 square feet of high-demand housing. The financial incentives currently lined up for this project are significant. The sale includes access to VHIP funds : 8 original units $130,000 and the 5 new units $187,500. Additionally, there is a $125,000 Downtown State Tax Cred

Key facts

• Low vacancy rate
• Town zoning approved
• 0.4 acre lot

Tags

• VACANT THREE-STORY BUILDING
• TOWN ZONING APPROVED
• ARCHITECT PLANS INCLUDED
• DOWNTOWN STATE TAX CREDIT
• WEATHERIZATION INCENTIVES
• LOW VACANCY RATE

Property features AI

Exterior

• Parking: Gravel driveway parking
• Utilities: Public water; Public sewer; Electric service with circuit breakers and original knob-and-tube wiring; No internet service indicated; Electric service provided by GMP
• Home design: Multi-family building; Existing property; Originally built in 1860
• Construction: Wood frame construction; Roof includes corrugated metal and slate
• Exterior features: City lot; Level lot; Gravel driveway; Public road frontage

Interior

• Bedrooms: Eight-unit building with 2 one-bedroom units, 3 two-bedroom units, and 3 three-plus bedroom units
• Heating & cooling: Oil heating; Hot water heating; No central cooling
• Interior features: Full walk-up basement with dirt floor

What this means for you Summary

Snapshot

• This is a multifamily listed at $495k.

Deal economics

• At list price, monthly cash flow is $15k ($175k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($23k rent vs $495k).
• Recommended offer: $480k (3.0% below list) — sets the bar for market timing.
• Cap rate 41.6% 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; 1 comparable units currently listed for rent nearby; 188 units permitted in Windham County in 2024 (0 in 5+ unit buildings).
• At $22,677/mo this rent would consume 413% 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 $3k of loan paydown is wiped out by about $15k 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 $139k cash investment doubles in ~1 year — after that, you're playing with house money.

Negotiation context

• It's been on market 49 days — a 3% lower offer ($480k) is reasonable based on typical stale-listing flexibility.
• Current owner paid $350k; 41% above their basis — modest negotiation headroom, anchor on the comps not their cost.

Risks & watch-outs

• Watch-outs: built in 1860 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $480,150 (3.0% below list)

Questions for the listing agent

1. It's been on market 49 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
2. Built in 1860 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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?
5. 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?
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: 4.58% ✓
• Cap rate: 41.60%
• Cash-on-cash: 126.08%
• DSCR: 6.61
• GRM: 1.8

CMA / ARV

• ARV (on-the-fly): $559,776
• Comps found: 2

Show comp detail 2 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
79 Putney Rd	0.32mi	—/4.0	4,087 (-1%)	14mo	$399,000	$98	72
145 High St	0.08mi	—/—	4,345 (+6%)	22mo	$589,000	$136	68

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 · 3.0% rent growth · sell at horizon

5-year hold

• IRR: —
• Equity multiple: 7.12×
• Total profit: $847,589
• Equity at exit: $73,806

10-year hold

• IRR: —
• Equity multiple: 14.95×
• Total profit: $1,933,589
• Equity at exit: $42,799

Cash invested: $138,600 (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: 23.6×

Monthly cashflow live

• Estimated rent: $22,677 medium
• Mortgage (P&I): −$2,596
• Tax from tax record: −$550 /mo · $6,602/yr
• Insurance: −$206
• HOA: −$0
• Vacancy / Maint / Mgmt: −$4,762
• Net cashflow: $14,563

Break-even live

Break-even rent $4,243

Max offer price $495,000

Occupancy floor 31%

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

Units	Beds	Baths	Est. rent
▸ 13× units	3	1	$22,672
Total (13 units)			$22,677

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: $123,750
• Closing costs: $14,850
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
63-73 Main St Unit A Brattleboro, VT	3.0	2.0	3236	$4,550	$1.41	14d	1	0.33mi

Listing history 18 events

1. 2026-06-18
   days on market $495,000 Active 49 DOM
2. 2026-06-17
   days on market $495,000 Active 48 DOM
3. 2026-06-16
   days on market $495,000 Active 47 DOM
4. 2026-06-15
   days on market $495,000 Active 46 DOM
5. 2026-06-14
   days on market $495,000 Active 44 DOM
6. 2026-06-13
   days on market $495,000 Active 43 DOM
7. 2026-06-10
   days on market $495,000 Active 41 DOM
8. 2026-06-09
   days on market $495,000 Active 40 DOM
9. 2026-06-08
   days on market $495,000 Active 39 DOM
10. 2026-06-07
    days on market $495,000 Active 38 DOM
11. 2026-06-03
    pricedays on market $495,000 Active 34 DOM
12. 2026-06-02
    days on market $535,000 Active 33 DOM
13. 2026-06-01
    days on market $535,000 Active 32 DOM
14. 2026-05-31
    days on market $535,000 Active 31 DOM
15. 2026-05-31
    days on market $535,000 Active 30 DOM
16. 2026-05-12
    price $535,000
17. 2026-04-30
    listed $550,000 Active
18. 2023-06-16
    soldstatus $350,000

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

Tax reassessment forecast VT · Partial reset (capped growth)

• Current annual tax: $6,602 · $550/mo
• Projected year-2 tax: $8,003 · $667/mo
• Expected delta: +$1,402/yr (+$117/mo · 21.2%)

ⓘ 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 1/10 Low
• 🌡 Heat 3/10 Moderate 7 d/yr ≥94°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: $272,124
• − Mortgage interest: −$27,728
• − Property taxes: −$6,602
• − Insurance: −$2,475
• − Repairs & maintenance: −$21,770
• − Management: −$21,770
• − Depreciation: −$14,400
• Taxable income: $177,380
• Est. tax owed @ 24.0%: −$42,571
• After-tax cash flow: $132,180/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

+52.9% since first listed

3 events — show timeline

• 2026-05-12 Price Changed $535,000 PrimeMLS
• 2026-04-30 Listed $550,000 PrimeMLS
• 2023-06-16 Sold (Public Records) $350,000 Public Records

Property tax history

-3.9%/yr

Latest (2024): $6,602 · +11.7% YoY. Source: county tax records.