436 Big Hollow Rd · Windham, NY 12496

$349,000

3 bd · 2.0 ba · 1,400 sqft · SingleFamily · 278 Days on market

Built 1959 3.90 ac lot $249/sqft · 50% below area ↓ 5% 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 +15.9/30.0
• ARV discount +7.5/15.0
• Appreciation +7.5/10.0
• DSCR +4.9/10.0
• 1% rule +4.3/10.0
• Schools +4.3/10.0
• Livability +3.0/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks MLS

Up the road from thousands of acres of state hiking trails and from CD Lane Park with swimming, kayaking, and family fun, this location is a true four-season retreat. Minutes to Windham and Hunter ski resorts, golf courses, and local venues, the setting offers year-round recreation at your doorstep. Set back from a quiet country road on nearly 4 acres, this property is all about the outdoors. A large pond with a charming footbridge creates a picture-perfect backdrop, complemented by rolling lawn, trees, and mountain air. Two sheds provide extra storage for gear and toys. The home itself offers 3 bedrooms and 2 baths with an open floor plan and a cozy wood-burning stove along with a den/office off the living room. While the house could use some cosmetic and structural updates, it's perfectly livable as-is—giving you the opportunity to enjoy it right away while planning improvements. there is a new roof on the house. If you're looking for a ''crazy pretty property'' with true country character and endless potential, this one is worth a visit. What a great investment this would be as a home or rental property for people to enjoy the country life. Seller Says: Bring Offers!!

Key facts

• Extra storage
• Charming footbridge
• Rolling lawn

Tags

• LARGE POND
• CHARMING FOOTBRIDGE
• ROLLING LAWN
• EXTRA STORAGE
• NEW ROOF

What this means for you Summary

Snapshot

• This is a 3-bed/2.0-bath single-family listed at $349k.

Deal economics

• At list price, monthly cash flow is $99 ($1k/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 $326k (6.5% below list).
• Recommended offer: $307k (12.0% below list) — sets the bar for market timing.
• Cap rate 6.9% vs local median 3.4% in Windham — 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 60/100 on livability (#964 in NY) — a middle-class / working-renter tenant base. Strengths: housing A+, employment B+; Watch: schools C-, crime D+, cost of living D+.
• Windham-Ashland-Jewett Central School District (rural): math 55% / reading 40% proficiency, ranked #517 of 755 in NY (top 68%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Market conditions: 141 active listings in the ZIP; 97 units permitted in Greene County in 2024 (0 in 5+ unit buildings).

Forward outlook

• In year one you build about $20k of equity ($2k loan paydown + $18k appreciation (5.1% local appreciation)).
• Greene County population projected at -22% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (5.1% appreciation + 3.0% rent growth), your $98k cash investment doubles in ~5 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$32k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 278 days — a 12% lower offer ($307k) is reasonable based on typical stale-listing flexibility.

Risks & watch-outs

• Watch-outs: flood insurance adds $66/mo; built in 1959 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: severe flood risk; moderate wildfire risk — expect insurance premiums to compound above CPI over the hold.

Recommended offer $307,120 (12.0% below list)

Questions for the listing agent

1. It's been on market 278 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 1959 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
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. Crime grade is D 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?
7. 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.
8. 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.
9. 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: 0.93% ✗
• Cap rate: 6.86%
• Cash-on-cash: 2.03%
• DSCR: 1.09
• GRM: 8.9

CMA / ARV

• ARV (median comp): $702,607
• List price: $349,000
• Delta: -50.33%
• Verdict: UNDERPRICED
• Comps: 3 within 1.0 mi

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
410 Big Hollow Rd	0.25mi	3/2.0	1,344 (-4%)	6mo	$425,000	$316	76

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

Projected returns pro-forma

5.06% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 14.1%
• Equity multiple: 1.90×
• Total profit: $87,946
• Equity at exit: $198,963

10-year hold

• IRR: 14.8%
• Equity multiple: 3.66×
• Total profit: $260,137
• Equity at exit: $344,370

Cash invested: $97,720 (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 12496

• Home prices YoY: 1.2%
• Active inventory: 141
• Price-to-rent: 8.9×

Monthly cashflow live

• Estimated rent: $3,262 medium
• Mortgage (P&I): −$1,830
• Tax est. 1.5%: −$436 /mo · $5,235/yr
• Insurance: −$145
• Flood insurance flood zone: −$66 /mo · $798/yr
• HOA: −$0
• Vacancy / Maint / Mgmt: −$685
• Net cashflow: $99

Break-even live

Break-even rent $3,137

Max offer price $349,000

Occupancy floor 92%

Sensitivity live

Price	-10% $340	-5% $219	+0% $99	+5% $-22	+10% $-142
Rent	-10% $-159	-5% $-30	+0% $99	+5% $228	+10% $357
Rate	-1.0pp $275	-0.5pp $188	base $99	+0.5pp $8	+1.0pp $-84

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: $87,250
• Closing costs: $10,470
• Reserves months: —
• Total cash needed: —

Listing history 17 events

1. 2026-06-18
   days on market $349,000 Active 278 DOM
2. 2026-06-18
   price $349,000 Active 277 DOM
3. 2026-06-17
   days on market $379,000 Active 277 DOM
4. 2026-06-16
   days on market $379,000 Active 276 DOM
5. 2026-06-15
   days on market $379,000 Active 275 DOM
6. 2026-06-13
   days on market $379,000 Active 273 DOM
7. 2026-06-12
   days on market $379,000 Active 272 DOM
8. 2026-06-09
   days on market $379,000 Active 269 DOM
9. 2026-06-08
   days on market $379,000 Active 268 DOM
10. 2026-06-07
    days on market $379,000 Active 267 DOM
11. 2026-06-07
    days on market $379,000 Active 266 DOM
12. 2026-06-04
    days on market $379,000 Active 263 DOM
13. 2026-06-02
    days on market $379,000 Active 262 DOM
14. 2026-06-01
    days on market $379,000 Active 261 DOM
15. 2026-05-31
    days on market $379,000 Active 260 DOM
16. 2026-05-09
    price $379,000 1196-char remark

    Show marketing remark (1196 chars)

    Up the road from thousands of acres of state hiking trails and from CD Lane Park with swimming, kayaking, and family fun, this location is a true four-season retreat. Minutes to Windham and Hunter ski resorts, golf courses, and local venues, the setting offers year-round recreation at your doorstep. Set back from a quiet country road on nearly 4 acres, this property is all about the outdoors. A large pond with a charming footbridge creates a picture-perfect backdrop, complemented by rolling lawn, trees, and mountain air. Two sheds provide extra storage for gear and toys. The home itself offers 3 bedrooms and 2 baths with an open floor plan and a cozy wood-burning stove along with a den/office off the living room. While the house could use some cosmetic and structural updates, it's perfectly livable as-is—giving you the opportunity to enjoy it right away while planning improvements. there is a new roof on the house. If you're looking for a ''crazy pretty property'' with true country character and endless potential, this one is worth a visit. What a great investment this would be as a home or rental property for people to enjoy the country life. Seller Says: Bring Offers!!

17. 2025-09-13
    listed $399,000 Active 1196-char remark

    Show marketing remark (1196 chars)

    Up the road from thousands of acres of state hiking trails and from CD Lane Park with swimming, kayaking, and family fun, this location is a true four-season retreat. Minutes to Windham and Hunter ski resorts, golf courses, and local venues, the setting offers year-round recreation at your doorstep. Set back from a quiet country road on nearly 4 acres, this property is all about the outdoors. A large pond with a charming footbridge creates a picture-perfect backdrop, complemented by rolling lawn, trees, and mountain air. Two sheds provide extra storage for gear and toys. The home itself offers 3 bedrooms and 2 baths with an open floor plan and a cozy wood-burning stove along with a den/office off the living room. While the house could use some cosmetic and structural updates, it's perfectly livable as-is—giving you the opportunity to enjoy it right away while planning improvements. there is a new roof on the house. If you're looking for a ''crazy pretty property'' with true country character and endless potential, this one is worth a visit. What a great investment this would be as a home or rental property for people to enjoy the country life. Seller Says: Bring Offers!!

ⓘ 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 8/10 Severe FEMA zone X (unshaded) · 99% chance over 30 yrs
• 🔥 Wildfire 5/10 Major
• 🌡 Heat 1/10 Low 9 d/yr ≥84°F today · 20 d/yr by 30 yrs out
• 💨 Wind 2/10 Low 4% chance of damaging wind over 30 yrs
• 🫁 Air quality 1/10 Low 0 unhealthy d/yr today · 0 by 30 yrs out

Taxation est. · year 1

• Rental income: $39,147
• − Mortgage interest: −$19,549
• − Property taxes: −$5,235
• − Insurance: −$2,542
• − Repairs & maintenance: −$3,132
• − Management: −$3,132
• − Depreciation: −$10,153
• Taxable loss: −$4,596
• Est. tax savings @ 24.0%: +$1,103
• After-tax cash flow: $2,290/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)

• District: Windham-Ashland-Jewett Central School District
• NCES district ID: 3631590
• Math proficiency: 55% ▲ 5.00%
• Reading proficiency: 40% ▼ -10.00%
• Median HH income: $46,942
• Composite: 42.57/100
• National rank: #6842
• State rank: #517 of 755 in NY

Livability — Windham

• Score: 60/100
• State rank: #964
• US rank: #18888

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Population (ZIP): 1,241

Population outlook (Greene County) Hauer SSP2

• Today (2025): 44,963 people
• By 2030: 43,126 · -4.1%
• By 2040: 38,756 · -13.8%
• By 2050: 34,913 · -22.4%
• By 2075: 28,156 · -37.4%
• By 2100: 22,296 · -50.4%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (84%)
• Race & ethnicity: White 84% Two or more races 5% Black 5% Hispanic / Latino 3% Asian 2%
• Common ancestry: Romanian 5% Hispanic 4% Lithuanian 3%
• Foreign-born: 18% · Canada
• Languages at home: 75% English-only · Russian/Polish/Slavic 10% French/Haitian/Cajun 7% Other Indo-European 4%

Political lean MEDSL · Greene

• 2024 margin: R (+17.0) · D 41.5% · R 58.5%
• 2008→2024 swing: -7.1pp toward R · 2008: -9.9pp · 2024: -17.0pp
• All cycles: 2024: R+17.0 2020: R+15.6 2016: R+27.4 2012: R+11.1 2008: R+9.9

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 5.06%
• Current HPI: 425.2138
• 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

-5.0% since first listed

2 events — show timeline

• 2026-05-09 Price Changed $379,000 HVCRMLS
• 2025-09-13 Listed $399,000 HVCRMLS