88 Happy Haven Rd · Wilmington, VT 05363

$389,900

5 bd · 2.0 ba · 2,168 sqft · Other public records · 2 Days on market

Built 1971 1.02 ac lot

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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 +16.5/30.0
• ARV discount +7.5/15.0
• Appreciation +6.3/10.0
• DSCR +5.1/10.0
• Schools +5.0/10.0
• 1% rule +4.0/10.0
• Livability +3.2/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks MLS

Sweet chalet on a country road. Interior features first floor great room, open concept kitchen, living and dining, 2 bedrooms, bath and a sleeping loft. Oak floors in the great room, large windows with natural light, vaulted ceilings with some exposed beams, windows overlooking the large back deck and beautifully landscaped yard w/ impeccably maintained vegetable and flower gardens. Wrap around side deck with plenty of room for entertaining. Walkout lower level 2 bedroom apartment, fully furnished and equipped for use as an Airbnb with an excellent rental history. Landscaped path to lower level deck and private entry. Close to the Village of Wilmington, Mount Snow and The Hermitage Club at Haystack Mountain offering both winter and summer activities.

Key facts

• Private road
• Walk-out lower level
• Perennial gardens

Tags

• PRIVATE ROAD
• WALK-OUT LOWER LEVEL
• SEPARATE SECOND UNIT
• PERENNIAL GARDENS
• DECK
• PEACEFUL SURROUNDINGS

Property features AI

Exterior

• Utilities: On-site well; Septic system; 100 Amp electrical service (GMP); High-speed internet available; Cable available; Oil fuel supplied by Nido
• Home design: Chalet-style home; Existing construction
• Construction: Built in 1971; Wood frame construction; Metal roof
• Exterior features: Country setting; Near shopping, skiing, and schools; Neighborhood location; Dirt driveway; Gravel private road frontage (road frontage length: 100); Sage exterior color

Interior

• Bathrooms: 2 full bathrooms
• Heating & cooling: Oil heating
• Interior features: 8 total rooms; Finished basement with interior and exterior access; Basement contains an apartment and interior stairs; Walkout basement

What this means for you Summary

Snapshot

• This is a 5-bed/2.0-bath other listed at $390k.

Deal economics

• At list price, monthly cash flow is $226 ($3k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $350k (10.2% below list).
• Recommended offer: $350k (10.2% below list) — sets the bar for 1% rule.
• Cap rate 7.0% vs local median 2.5% in Wilmington — 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 65/100 on livability (#57 in VT) — a middle-class / working-renter tenant base. Strengths: crime A+, housing A+, employment B; Watch: schools D, health & safety D, amenities F.
• Market conditions: 65 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).

Forward outlook

• In year one you build about $13k of equity ($3k loan paydown + $10k appreciation (2.6% local appreciation)).
• Windham County population projected at -26% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (2.6% appreciation + 3.0% rent growth), your $109k cash investment doubles in ~6 years — after that, you're playing with house money.
• By year 3, paydown + projected appreciation supports a ~$33k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• Only 2 days on market — expect competitive offers; lowballing is unlikely to land.
• 3 sale attempts since 25y 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 $220k; list at $390k implies a 77% gain — meaningful room to come down on a strong offer.

Recommended offer $350,000 (10.2% below list)

Questions for the listing agent

1. Built in 1971 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
2. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
3. Schools are D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
4. 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.
5. 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.
6. How much new for-sale + rental construction is in the pipeline within 1–3 miles? Heavy new supply typically softens prices + rents 12–24 months out; constrained supply supports both.

Investment metrics

• 1% rule: 0.90% ✗
• Cap rate: 6.99%
• Cash-on-cash: 2.49%
• DSCR: 1.11
• GRM: 9.3

CMA / ARV

No comps found within radius.

Projected returns pro-forma

2.65% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 8.9%
• Equity multiple: 1.50×
• Total profit: $54,242
• Equity at exit: $167,779

10-year hold

• IRR: 11.6%
• Equity multiple: 2.67×
• Total profit: $181,849
• Equity at exit: $252,854

Cash invested: $109,172 (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 05363

• Home prices YoY: 0.7%
• Active inventory: 65
• Price-to-rent: 9.3×

Monthly cashflow live

• Estimated rent: $3,500 medium
• Mortgage (P&I): −$2,045
• Tax from tax record: −$332 /mo · $3,981/yr
• Insurance: −$162
• HOA: −$0
• Vacancy / Maint / Mgmt: −$735
• Net cashflow: $226

Break-even live

Break-even rent $3,214

Max offer price $389,900

Occupancy floor 89%

Sensitivity live

Price	-10% $447	-5% $336	+0% $226	+5% $116	+10% $5
Rent	-10% $-50	-5% $88	+0% $226	+5% $364	+10% $503
Rate	-1.0pp $422	-0.5pp $325	base $226	+0.5pp $125	+1.0pp $22

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: $97,475
• Closing costs: $11,697
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
24 Look Rd Wilmington, VT	6.0	3.0	2016	$3,500	$1.74	15d	1	1.30mi

Listing history 3 events

1. 2026-06-18
   days on market $389,900 Active 2 DOM
2. 2026-06-17
   remarks 695-char remark
3. 2026-06-17
   listed $389,900 Active 1 DOM

ⓘ 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: $3,981 · $332/mo
• Projected year-2 tax: $5,695 · $475/mo
• Expected delta: +$1,713/yr (+$143/mo · 43.0%)

ⓘ 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 1/10 Low 8 d/yr ≥86°F today · 19 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 8% 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: $42,000
• − Mortgage interest: −$21,840
• − Property taxes: −$3,981
• − Insurance: −$1,950
• − Repairs & maintenance: −$3,360
• − Management: −$3,360
• − Depreciation: −$11,343
• Taxable loss: −$3,834
• Est. tax savings @ 24.0%: +$920
• After-tax cash flow: $3,633/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 — Wilmington

• Score: 65/100
• State rank: #57
• US rank: #12863

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Population (ZIP): 2,008

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 (89%)
• Race & ethnicity: White 89% Hispanic / Latino 6% Two or more races 4% Asian 1%
• Hispanic origin (detail): Mexican 3% Puerto Rican 1%
• Common ancestry: Lithuanian 4% Iranian 4% Slovak 4%
• Foreign-born: 8% · Canada, Philippines
• Languages at home: 90% English-only · Spanish 5% Other Indo-European 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: ▲ 2.65%
• Current HPI: 362.8468
• Rent YoY: —
• Metro: —
• State GDP YoY: —
• F500 in state: 0

Price history

+242.0% since first listed

8 events — show timeline

• 2026-06-16 Listed $389,900 PrimeMLS
• 2020-10-29 Sold (Public Records) $220,000 Public Records
• 2020-10-26 Sold (MLS) $220,000 PrimeMLS
• 2020-08-08 Contingent — PrimeMLS
• 2020-07-30 Price Changed $229,000 PrimeMLS
• 2020-07-08 Listed $239,000 PrimeMLS
• 2001-10-15 Sold (MLS) $110,000 PrimeMLS
• 2001-08-08 Listed $114,000 PrimeMLS

Property tax history

+20.7%/yr

Latest (2024): $3,981 · +4.3% YoY. Source: county tax records.