53 Main St · Philmont, NY 12565

$299,900

6 bd · 2.0 ba · 2,962 sqft · MultiFamily · 73 Days on market

Built 1870 Fair condition 0.58 ac lot $101/sqft · 36% below area Est $472k · 36% under

---

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 +29.7/30.0
• ARV discount +15.0/15.0
• DSCR +10.0/10.0
• 1% rule +8.3/10.0
• Appreciation +4.6/10.0
• Schools +4.5/10.0
• Livability +3.0/5.0
• Rent growth +2.5/5.0
• Condition / age +2.2/5.0

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

Versatile Multi-Family Opportunity in the Heart of Philmont Discover the potential of this spacious and character-filled property, ideal for investors or owner-occupants alike. Currently configured as a two-family home, this residence also offers the flexibility to be converted back into a single-family home to suit your needs. Boasting over 3,000 square feet of living space, this impressive 6-bedroom, 3-bath home showcases charming original details dating back to 1870, including beautiful woodwork and hardwood floors throughout. While the home does require a new roof and some repairs, it presents a fantastic opportunity to add value and restore its full potential. Set on a generous 0.58-acre lot spanning three tax parcels, the property backs up to the scenic High Falls Conservation Area, offering privacy and natural beauty. The yard provides ample space for parking, gardening, outdoor entertaining, or even the possibility of adding a pool or rebuilding the garage. Located in the vibrant and evolving Village of Philmont, this property invites you to be part of a growing community with a strong sense of revitalization and charm.

Key facts

• 0.58 acre lot
• 8 parking spots
• Built 1870

What this means for you Summary

Snapshot

• This is a 6-bed/2.0-bath multifamily listed at $300k. Condition is rated fair.

Deal economics

• At list price, monthly cash flow is $1k ($13k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($4k rent vs $300k).
• Recommended offer: $282k (6.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads 60/100 on livability (#958 in NY) — a middle-class / working-renter tenant base. Strengths: housing A+, cost of living B; Watch: schools F, crime F, amenities F.
• Taconic Hills Central School District (rural): math 53% / reading 51% proficiency, ranked #335 of 590 in NY (top 57%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Market conditions: 12 active listings in the ZIP; 136 units permitted in Columbia County in 2024 (0 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-0.8%/yr); year-one equity from $2k of loan paydown is wiped out by about $2k of value loss. Plan a longer hold.
• Columbia County population projected at -22% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (-0.8% appreciation + 3.0% rent growth), your $84k cash investment doubles in ~6 years — after that, you're playing with house money.

Negotiation context

• It's been on market 73 days — a 6% lower offer ($282k) is reasonable based on typical stale-listing flexibility.
• 7 sale attempts since 16y ago; this cycle's ask has dropped $20k (6%) from the opening price — seller is motivated, your offer sets the floor, not the list.

Risks & watch-outs

• Watch-outs: built in 1870 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: moderate wildfire risk — expect insurance premiums to compound above CPI over the hold.

Recommended offer $281,906 (6.0% below list)

Questions for the listing agent

1. It's been on market 73 days. Have you received any prior offers? Is the seller open to a 6% 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 1870 — 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. Schools are F-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
7. 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?
8. 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.
9. 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.
10. 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: 1.33% ✓
• Cap rate: 10.64%
• Cash-on-cash: 15.54%
• DSCR: 1.69
• GRM: 6.2

CMA / ARV

• ARV (median comp): $471,813
• List price: $299,900
• Delta: -36.44%
• Verdict: UNDERPRICED
• Comps: 10 within 1.0 mi

Show comp detail 2 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
35 Church St	0.19mi	7/2.0 (+1)	2,668 (-10%)	1mo	$330,000	$124	69
41 Prospect St	0.22mi	6/2.5	2,664 (-10%)	6mo	$240,000	$90	66

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

-0.79% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 12.9%
• Equity multiple: 1.59×
• Total profit: $49,555
• Equity at exit: $75,387

10-year hold

• IRR: 18.6%
• Equity multiple: 2.90×
• Total profit: $159,940
• Equity at exit: $81,742

Cash invested: $83,972 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 15 Strongly Tenant-Friendly
• State New York: 15 Strongly Tenant-Friendly · D+10
• County: — inherits STATE
• City: — inherits STATE

NYC rent stabilization (~1M units); 2019 HSTPA strengthened tenant rights; courts deeply backlogged.

Methodology + full state rankings →

ZIP-level market 12565

• Home prices YoY: -0.2%
• Active inventory: 12
• Price-to-rent: 12.5×

Monthly cashflow live

• Estimated rent: $4,000 medium
• Mortgage (P&I): −$1,573
• Tax est. 1.5%: −$375 /mo · $4,498/yr
• Insurance: −$125
• HOA: −$0
• Vacancy / Maint / Mgmt: −$840
• Net cashflow: $1,087

Break-even live

Break-even rent $2,623

Max offer price $299,900

Occupancy floor 68%

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

Units	Beds	Baths	Est. rent
▸ 2× units	3	1.5	$4,000
Total (2 units)			$4,000

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: $74,975
• Closing costs: $8,997
• Reserves months: —
• Total cash needed: —

Listing history 26 events

1. 2026-06-19
   days on market $299,900 Active 73 DOM
2. 2026-06-18
   days on market $299,900 Active 72 DOM
3. 2026-06-17
   days on market $299,900 Active 71 DOM
4. 2026-06-16
   days on market $299,900 Active 70 DOM
5. 2026-06-15
   days on market $299,900 Active 69 DOM
6. 2026-06-14
   days on market $299,900 Active 67 DOM
7. 2026-06-12
   days on market $299,900 Active 66 DOM
8. 2026-06-09
   pricedays on market $299,900 Active 63 DOM
9. 2026-06-08
   days on market $319,900 Active 62 DOM
10. 2026-06-07
    days on market $319,900 Active 61 DOM
11. 2026-06-07
    days on market $319,900 Active 60 DOM
12. 2026-06-04
    days on market $319,900 Active 57 DOM
13. 2026-06-02
    days on market $319,900 Active 56 DOM
14. 2026-06-01
    days on market $319,900 Active 55 DOM
15. 2026-05-31
    days on market $319,900 Active 54 DOM
16. 2026-05-31
    days on market $319,900 Active 53 DOM
17. 2026-04-06
    listed $319,900 Active 1145-char remark

    Show marketing remark (1145 chars)

    Versatile Multi-Family Opportunity in the Heart of Philmont Discover the potential of this spacious and character-filled property, ideal for investors or owner-occupants alike. Currently configured as a two-family home, this residence also offers the flexibility to be converted back into a single-family home to suit your needs. Boasting over 3,000 square feet of living space, this impressive 6-bedroom, 3-bath home showcases charming original details dating back to 1870, including beautiful woodwork and hardwood floors throughout. While the home does require a new roof and some repairs, it presents a fantastic opportunity to add value and restore its full potential. Set on a generous 0.58-acre lot spanning three tax parcels, the property backs up to the scenic High Falls Conservation Area, offering privacy and natural beauty. The yard provides ample space for parking, gardening, outdoor entertaining, or even the possibility of adding a pool or rebuilding the garage. Located in the vibrant and evolving Village of Philmont, this property invites you to be part of a growing community with a strong sense of revitalization and charm.

18. 2026-03-31
    listed $319,900 Active 1148-char remark

    Show marketing remark (1148 chars)

    Versatile Multi-Family Opportunity in the Heart of Philmont Discover the potential of this spacious and character-filled property, ideal for investors or owner-occupants alike. Currently configured as a two-family home, this residence also offers the flexibility to be converted back into a single-family home to suit your needs. Boasting over 3,000 square feet of living space, this impressive 6-bedroom, 3-bath home showcases charming original details dating back to 1870, including beautiful woodwork and hardwood floors throughout. While the home does require a new roof and some repairs, it presents a fantastic opportunity to add value and restore its full potential. Set on a generous 0.58-acre lot spanning three tax parcels, the property backs up to the scenic High Falls Conservation Area, offering privacy and natural beauty. The yard provides ample space for parking, gardening, outdoor entertaining, or even the possibility of adding a pool or rebuilding the garage. Located in the vibrant and evolving Village of Philmont, this property invites you to be part of a growing community with a strong sense of revitalization and charm.

19. 2024-03-10
    listed $320,000
20. 2024-03-09
    listed $320,000
21. 2023-09-06
    price $489,000
22. 2023-09-06
    price $489,000
23. 2023-09-01
    listed $499,000 Active
24. 2023-08-31
    listed $499,000 Active
25. 2011-10-28
    historical
26. 2010-03-30
    listed $109,000

ⓘ 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 0% chance over 30 yrs
• 🔥 Wildfire 5/10 Major
• 🌡 Heat 3/10 Moderate 7 d/yr ≥95°F today · 16 d/yr by 30 yrs out
• 💨 Wind 3/10 Moderate 9% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 1 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $48,000
• − Mortgage interest: −$16,799
• − Property taxes: −$4,498
• − Insurance: −$1,500
• − Repairs & maintenance: −$3,840
• − Management: −$3,840
• − Depreciation: −$8,724
• Taxable income: $8,799
• Est. tax owed @ 24.0%: −$2,112
• After-tax cash flow: $10,938/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 · 13 photos

Fair 45/100 Moderate rehab

This multi-family property requires moderate renovations, including a new roof and updated kitchen and bathroom fixtures, to significantly improve its resale and rental value.

Repairs flagged

• Major roof — visible wear on roofline
• Major kitchen cabinets — dated and worn
• Major bathroom fixtures — dated and worn
• Major landscaping — overgrown and unkempt

Value-add opportunities

• Both new roof — improves both resale and rental value
• Both modern kitchen cabinets — enhances both resale and rental appeal
• Both updated bathroom fixtures — enhances both resale and rental appeal
• Both landscaping improvements — enhances curb appeal and rental value

Renovation cost estimate screening

Repair item	Severity	Est. cost
roof · visible wear on roofline	Major	$15,000–50,000
kitchen cabinets · dated and worn	Major	$15,000–50,000
bathroom fixtures · dated and worn	Major	$15,000–50,000
landscaping · overgrown and unkempt	Major	$15,000–50,000
Total estimated repair cost · 4 items		$60,000–200,000

Value-add ROI direction

• Both new roof — improves both resale and rental value ↑
• Both modern kitchen cabinets — enhances both resale and rental appeal ↑
• Both updated bathroom fixtures — enhances both resale and rental appeal ↑
• Both landscaping improvements — enhances curb appeal and rental value ↑

ⓘ 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)

• District: Taconic Hills Central School District
• NCES district ID: 3628620
• Math proficiency: 53% ▲ 10.00%
• Reading proficiency: 51% ▲ 11.00%
• Median HH income: $57,329
• Composite: 45.16/100
• National rank: #2676
• State rank: #335 of 590 in NY

Livability — Philmont

• Score: 60/100
• State rank: #958
• US rank: #18780

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Philmont, NY
• City population: 1,575
• Population (ZIP): 1,575

Population outlook (Columbia County) Hauer SSP2

• Today (2025): 58,662 people
• By 2030: 56,557 · -3.6%
• By 2040: 51,324 · -12.5%
• By 2050: 45,790 · -21.9%
• By 2075: 35,232 · -39.9%
• By 2100: 25,846 · -55.9%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (79%)
• Race & ethnicity: White 79% Black 15% Hispanic / Latino 4% Two or more races 4%
• Common ancestry: Slovak 5% Iranian 4% Romanian 3%
• Foreign-born: 10% · Canada

Political lean MEDSL · Columbia

• 2024 margin: D (+14.7) · D 57.4% · R 42.6%
• 2008→2024 swing: +1.3pp toward D · 2008: 13.4pp · 2024: 14.7pp
• All cycles: 2024: D+14.7 2020: D+16.7 2016: D+1.4 2012: D+11.7 2008: D+13.4

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -0.79%
• Current HPI: 377.9813
• Rent YoY: —
• Metro: —
• State GDP YoY: ▲ 2.60%
• F500 in state: 92

Industry mix (Fortune 500 HQ in NY)

Industry	F500 HQs	Revenue
▸Financial Services	10	$950B
▸Consumer Goods	9	$162B
▸Insurance	4	$225B
▸Telecommunications	2	$144B
▸Pharmaceuticals	2	$112B
▸Media / Entertainment	2	$69B

Price history

+193.5% since first listed

10 events — show timeline

• 2026-04-06 Listed $319,900 OneKey® MLS as Distributed by MLS Grid
• 2026-03-31 Listed $319,900 HVCRMLS
• 2024-03-10 Listed $320,000 HVCRMLS
• 2024-03-09 Listed $320,000 HVCRMLS
• 2023-09-06 Price Changed $489,000 HVCRMLS
• 2023-09-06 Price Changed $489,000 HVCRMLS
• 2023-09-01 Listed $499,000 HVCRMLS
• 2023-08-31 Listed $499,000 HVCRMLS
• 2011-10-28 Listing Removed — Global MLS
• 2010-03-30 Listed $109,000 Global MLS