934 Route 296 · Windham, NY 12444

$329,000

4 bd · 2.0 ba · 1,582 sqft · SingleFamily · 326 Days on market

Built 1850 0.64 ac lot $208/sqft · 48% below area Est $635k · 48% 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 +15.0/15.0
• 1% rule +5.0/10.0
• DSCR +5.0/10.0
• Appreciation +4.4/10.0
• 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

Perfectly positioned between Hunter and Windham ski resorts and just down the road from the beloved Matilda restaurant and the boutique Henson Hotel, this well-loved 3-bedroom, 2-bath home offers the kind of charm and potential that's becoming increasingly rare in the Catskills. Set on a gentle rise with a classic Colonial Revival façade, a full-length front porch welcomes you with sweeping views—an ideal perch for morning coffee or golden-hour unwinding. Inside, the home is filled with warmth, literally and figuratively: wood-paneled walls, exposed beams, and a massive wood-burning stove create a cozy, lodge-like feel that radiates throughout. The layout includes a formal dining room, a bright and functional kitchen, a recently updated bath, and a main-level primary en-suite for added flexibility. Upstairs offers two more bedrooms and a large extra room—ideal as a second living space, game room, or home office. A private backyard provides space to relax or garden, while the detached outbuilding is ready to be transformed into an artist studio, writing retreat, yoga space, or workshop. A single-car garage and a large basement room add extra utility and storage. Whether you're looking for a year-round home, a ski-season base, or a Catskills getaway with serious potential, this is an exceptional value—priced to move and packed with personality.

Key facts

• Formal dining room
• Wood-paneled walls
• Exposed beams

Tags

• COLONIAL REVIVAL FAÇADE
• FULL-LENGTH FRONT PORCH
• WOOD-PANELED WALLS
• EXPOSED BEAMS
• MASSIVE WOOD-BURNING STOVE
• FORMAL DINING ROOM

What this means for you Summary

Snapshot

• This is a 4-bed/2.0-bath single-family listed at $329k.

Deal economics

• At list price, monthly cash flow is $17k ($210k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($25k rent vs $329k).
• Recommended offer: $290k (12.0% below list) — sets the bar for market timing.
• Cap rate 70.0% vs local median 3.2% 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: 29 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 97 units permitted in Greene County in 2024 (0 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-1.2%/yr); year-one equity from $2k of loan paydown is wiped out by about $4k of value loss. Plan a longer hold.
• Greene County population projected at -22% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (-1.2% appreciation + 3.0% rent growth), your $92k cash investment doubles in ~1 year — after that, you're playing with house money.

Negotiation context

• It's been on market 326 days — a 12% lower offer ($290k) is reasonable based on typical stale-listing flexibility.

Risks & watch-outs

• Watch-outs: built in 1850 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $289,520 (12.0% below list)

Questions for the listing agent

1. It's been on market 326 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 1850 — 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. 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?
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: 7.60% ✓
• Cap rate: 70.04%
• Cash-on-cash: 227.66%
• DSCR: 11.13
• GRM: 1.1

CMA / ARV

• ARV (median comp): $634,761
• List price: $329,000
• Delta: -48.17%
• Verdict: UNDERPRICED
• Comps: 9 within 1.0 mi

Projected returns pro-forma

-1.19% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: —
• Equity multiple: 12.79×
• Total profit: $1,085,819
• Equity at exit: $76,369

10-year hold

• IRR: —
• Equity multiple: 27.10×
• Total profit: $2,404,181
• Equity at exit: $77,625

Cash invested: $92,120 (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 12444

• Home prices YoY: -0.2%
• Active inventory: 29
• Price-to-rent: 1.1×

Monthly cashflow live

• Estimated rent: $25,000 medium
• Mortgage (P&I): −$1,725
• Tax est. 1.5%: −$411 /mo · $4,935/yr
• Insurance: −$137
• HOA: −$0
• Vacancy / Maint / Mgmt: −$5,250
• Net cashflow: $17,476

Break-even live

Break-even rent $2,878

Max offer price $329,000

Occupancy floor 25%

Sensitivity live

Price	-10% $17,704	-5% $17,590	+0% $17,476	+5% $17,363	+10% $17,249
Rent	-10% $15,501	-5% $16,489	+0% $17,476	+5% $18,464	+10% $19,451
Rate	-1.0pp $17,642	-0.5pp $17,560	base $17,476	+0.5pp $17,391	+1.0pp $17,304

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: $82,250
• Closing costs: $9,870
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
32 Twin Pond Rd Jewett, NY	4.0	3.0	2000	$25,000	$12.50	16d	1	1.02mi

Listing history 18 events

1. 2026-06-21
   days on market $329,000 Active 326 DOM
2. 2026-06-21
   days on market $329,000 Active 325 DOM
3. 2026-06-18
   days on market $329,000 Active 323 DOM
4. 2026-06-17
   days on market $329,000 Active 322 DOM
5. 2026-06-16
   days on market $329,000 Active 321 DOM
6. 2026-06-15
   days on market $329,000 Active 320 DOM
7. 2026-06-13
   days on market $329,000 Active 318 DOM
8. 2026-06-12
   days on market $329,000 Active 317 DOM
9. 2026-06-09
   days on market $329,000 Active 314 DOM
10. 2026-06-08
    days on market $329,000 Active 313 DOM
11. 2026-06-07
    days on market $329,000 Active 312 DOM
12. 2026-06-07
    days on market $329,000 Active 311 DOM
13. 2026-06-04
    days on market $329,000 Active 308 DOM
14. 2026-06-03
    price $329,000 Active 307 DOM
15. 2026-06-02
    days on market $385,000 Active 307 DOM
16. 2026-06-01
    days on market $385,000 Active 306 DOM
17. 2026-05-31
    days on market $385,000 Active 305 DOM
18. 2025-07-30
    listed $385,000 Active 1389-char remark

    Show marketing remark (1389 chars)

    Perfectly positioned between Hunter and Windham ski resorts and just down the road from the beloved Matilda restaurant and the boutique Henson Hotel, this well-loved 3-bedroom, 2-bath home offers the kind of charm and potential that's becoming increasingly rare in the Catskills. Set on a gentle rise with a classic Colonial Revival façade, a full-length front porch welcomes you with sweeping views—an ideal perch for morning coffee or golden-hour unwinding. Inside, the home is filled with warmth, literally and figuratively: wood-paneled walls, exposed beams, and a massive wood-burning stove create a cozy, lodge-like feel that radiates throughout. The layout includes a formal dining room, a bright and functional kitchen, a recently updated bath, and a main-level primary en-suite for added flexibility. Upstairs offers two more bedrooms and a large extra room—ideal as a second living space, game room, or home office. A private backyard provides space to relax or garden, while the detached outbuilding is ready to be transformed into an artist studio, writing retreat, yoga space, or workshop. A single-car garage and a large basement room add extra utility and storage. Whether you're looking for a year-round home, a ski-season base, or a Catskills getaway with serious potential, this is an exceptional value—priced to move and packed with personality.

ⓘ 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 (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 3/10 Moderate
• 🌡 Heat 1/10 Low 7 d/yr ≥87°F today · 16 d/yr by 30 yrs out
• 💨 Wind 2/10 Low 3% 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: $300,000
• − Mortgage interest: −$18,429
• − Property taxes: −$4,935
• − Insurance: −$1,645
• − Repairs & maintenance: −$24,000
• − Management: −$24,000
• − Depreciation: −$9,571
• Taxable income: $217,420
• Est. tax owed @ 24.0%: −$52,181
• After-tax cash flow: $157,535/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): 519

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: Majority White (59%)
• Race & ethnicity: White 59% Two or more races 38% Hispanic / Latino 34%
• Hispanic origin (detail): Cuban 3%
• Common ancestry: Romanian 12% Lithuanian 5% Subsaharan African 3%
• Foreign-born: 4%
• Languages at home: 98% English-only · Russian/Polish/Slavic 2%

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: ▼ -1.19%
• Current HPI: 483.4459
• 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

1 event — show timeline

• 2025-07-30 Listed $385,000 HVCRMLS