53 High St · Middlebury, VT 05753

$275,000

3 bd · 3.0 ba · 1,740 sqft · SingleFamily · 315 Days on market

Built 1920 0.29 ac lot Est $487k · 44% under ↓ 21% since listing

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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 +19.5/30.0
• ARV discount +15.0/15.0
• DSCR +6.2/10.0
• 1% rule +5.2/10.0
• Schools +5.0/10.0
• Livability +4.0/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

Attention Buyers!! Investors, Multi-generational living, first time home buyers! HUGE Price Reduction! Great Location! This is a great opportunity to build "Sweat Equity" ! Inside you will find 2 one bedroom apartments and a third floor that needs a full rehab. The town only recognizes the lower two floors. Wonderful views and sunsets from all 3 floors looking West over Middlebury proper and the Adirondacks. A short distance to groceries and the Co-op and Chipman Hill Park is a few hundred feet away! Lots of beautiful trees were planted above the house by the current owners including 2 walnut trees, pinyon pines and a willow tree. There is enough room for terraced gardening in

Key facts

• Back yard
• Deck off the back
• 2 apartments

Tags

• 2 APARTMENTS
• MULTI-GENERATIONAL LIVING
• DECK OFF THE BACK
• BACK YARD
• TERRACED GARDENING
• SHORT DISTANCE TO GROCERIES

Property features AI

Finance

• Other: Sale includes land and building; Documents available: Deed, Property Disclosure, Tax Map

Exterior

• Parking: Dirt driveway
• Utilities: Public water; Public sewer; 100 amp electric service with circuit breakers; Cable internet available (Comcast); Cable service available
• Home design: Colonial-style duplex with tri-level layout; Walkout lower level; White exterior
• Construction: Built in 1920; Wood frame with vinyl siding; Shingle roof
• Exterior features: Country setting with mountain and open views; Hilly, sloping lot with nearby trails; View

Interior

• Kitchen: Electric range; Refrigerator
• Bedrooms: Bedrooms on levels 1 and 3
• Flooring: Carpet; Vinyl; Vinyl plank
• Bathrooms: Three full bathrooms
• Heating & cooling: Electric baseboard heat; Wall air conditioning units
• Interior features: Eight total rooms; Full walkout basement
• Laundry & utility: Electric water heater

What this means for you Summary

Snapshot

• This is a 3-bed/3.0-bath single-family listed at $275k.

Deal economics

• At list price, monthly cash flow is $312 ($4k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($3k rent vs $275k).
• Recommended offer: $242k (12.0% below list) — sets the bar for market timing.
• Cap rate 7.7% vs local median 2.2% in Middlebury — 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 81/100 on livability (#7 in VT, #1,594 nationally) — a professional / high-income tenant draw. Strengths: schools A+, health & safety A+, amenities A; Watch: cost of living D+, commute F.
• Market conditions: 41 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 104 units permitted in Addison County in 2024 (6 in 5+ unit buildings).

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.
• Addison County population projected at -12% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.

Negotiation context

• It's been on market 315 days — a 12% lower offer ($242k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts; this cycle's ask has dropped $75k (21%) from the opening price — seller is motivated, your offer sets the floor, not the list.

Risks & watch-outs

• Watch-outs: built in 1920 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $242,000 (12.0% below list)

Questions for the listing agent

1. It's been on market 315 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Built in 1920 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. 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?
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 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: 1.02% ✓
• Cap rate: 7.65%
• Cash-on-cash: 4.86%
• DSCR: 1.22
• GRM: 8.2

CMA / ARV

• ARV (on-the-fly): $487,200
• Comps found: 10

Show comp detail 10 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
98 Peterson Ter	0.54mi	3/1.0	1,772 (+2%)	15mo	$365,000	$206	52
7 High St	0.39mi	2/2.0 (-1)	1,516 (-13%)	9mo	$578,000	$381	44
23 Brookside Dr	0.64mi	2/1.5 (-1)	1,884 (+8%)	4mo	$397,100	$211	42
26 Meadowlark Ln Unit 7.5	0.59mi	2/1.5 (-1)	1,538 (-12%)	2mo	$430,000	$280	41
22 Meadowlark Ln Unit 7.4	0.59mi	2/1.5 (-1)	1,538 (-12%)	2mo	$430,000	$280	41
18 Meadowlark Ln Unit 7.3	0.59mi	2/1.5 (-1)	1,538 (-12%)	6mo	$585,000	$380	37
11 Willard St	0.42mi	3/1.5	1,526 (-12%)	22mo	$190,000	$125	36
37 Stonecrop Rd	0.57mi	2/1.5 (-1)	1,516 (-13%)	10mo	$425,000	$280	33
39 Stonecrop Rd	0.58mi	2/1.5 (-1)	1,516 (-13%)	10mo	$425,000	$280	32
47 Stonecrop Rd	0.58mi	2/1.5 (-1)	1,516 (-13%)	10mo	$425,000	$280	32

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: -8.7%
• Equity multiple: 0.68×
• Total profit: $-24,678
• Equity at exit: $41,003

10-year hold

• IRR: 0.8%
• Equity multiple: 1.05×
• Total profit: $4,232
• Equity at exit: $23,777

Cash invested: $77,000 (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 05753

• Active inventory: 41
• Price-to-rent: 8.2×

Monthly cashflow live

• Estimated rent: $2,800 medium
• Mortgage (P&I): −$1,442
• Tax est. 1.5%: −$344 /mo · $4,125/yr
• Insurance: −$115
• HOA: −$0
• Vacancy / Maint / Mgmt: −$588
• Net cashflow: $312

Break-even live

Break-even rent $2,406

Max offer price $275,000

Occupancy floor 84%

Sensitivity live

Price	-10% $502	-5% $407	+0% $312	+5% $217	+10% $121
Rent	-10% $90	-5% $201	+0% $312	+5% $422	+10% $533
Rate	-1.0pp $450	-0.5pp $381	base $312	+0.5pp $240	+1.0pp $168

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: $68,750
• Closing costs: $8,250
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
45 Bakery Ln Middlebury, VT	3.0	2.0	2100	$2,800	$1.33	44d	1	0.77mi

Listing history 8 events

1. 2026-05-01
   status Pending
2. 2026-04-30
   historical Active with Contract
3. 2026-04-10
   status Active
4. 2026-04-01
   status Pending
5. 2026-01-28
   price $275,000
6. 2025-09-16
   price $325,000
7. 2025-08-28
   price $335,000
8. 2025-06-11
   listed $350,000 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 · 0% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 2/10 Low 7 d/yr ≥94°F today · 15 d/yr by 30 yrs out
• 💨 Wind 2/10 Low 2% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 1 unhealthy d/yr today · 1 by 30 yrs out

Taxation est. · year 1

• Rental income: $33,600
• − Mortgage interest: −$15,404
• − Property taxes: −$4,125
• − Insurance: −$1,375
• − Repairs & maintenance: −$2,688
• − Management: −$2,688
• − Depreciation: −$8,000
• Taxable loss: −$680
• Est. tax savings @ 24.0%: +$163
• After-tax cash flow: $3,902/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 — Middlebury

• Score: 81/100
• State rank: #7
• US rank: #1594

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Middlebury, VT
• City population: 11,031
• Population (ZIP): 11,031

Population outlook (Addison County) Hauer SSP2

• Today (2025): 37,078 people
• By 2030: 36,688 · -1.1%
• By 2040: 34,988 · -5.6%
• By 2050: 32,561 · -12.2%
• By 2075: 27,584 · -25.6%
• By 2100: 22,720 · -38.7%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (83%)
• Race & ethnicity: White 83% Two or more races 8% Asian 5% Hispanic / Latino 4% Black 2%
• Common ancestry: Lithuanian 6% Slovak 3% Scotch-Irish 3%
• Foreign-born: 7% · Canada, China, South Korea
• Languages at home: 88% English-only · Spanish 3% Other Indo-European 2% French/Haitian/Cajun 2%

Political lean MEDSL · Addison

• 2024 margin: Solid D (+35.9) · D 66.4% · R 30.6% · Other 3.0%
• 2008→2024 swing: -3.3pp toward R · 2008: 39.2pp · 2024: 35.9pp
• All cycles: 2024: D+35.9 2020: D+39.4 2016: D+33.6 2012: D+39.7 2008: D+39.2

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -175.89%
• Current HPI: 297.6047
• Rent YoY: —
• Metro: —
• State GDP YoY: —
• F500 in state: 0

Price history

-21.4% since first listed

8 events — show timeline

• 2026-05-01 Pending — PrimeMLS
• 2026-04-30 Contingent — PrimeMLS
• 2026-04-10 Relisted — PrimeMLS
• 2026-04-01 Pending — PrimeMLS
• 2026-01-28 Price Changed $275,000 PrimeMLS
• 2025-09-16 Price Changed $325,000 PrimeMLS
• 2025-08-28 Price Changed $335,000 PrimeMLS
• 2025-06-11 Listed $350,000 PrimeMLS