542 Mitchell Hollow Rd · Windham, NY 12496

$285,000

3 bd · 1.5 ba · 1,446 sqft · SingleFamily · 68 Days on market

Built 1940 Average condition 0.50 ac lot $197/sqft · 48% below area Est $548k · 48% under

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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 +23.6/30.0
• ARV discount +15.0/15.0
• DSCR +7.6/10.0
• Appreciation +7.5/10.0
• 1% rule +6.1/10.0
• Schools +4.3/10.0
• Livability +3.0/5.0
• Condition / age +2.8/5.0
• Rent growth +2.5/5.0

Listing remarks MLS

Welcome to 542 Mitchell Hollow Road, Windham, NY, a charming home set on a beautifully maintained property in the heart of the Catskills. This inviting residence offers a wonderful combination of comfort, space, and natural surroundings, making it ideal as a full-time home, weekend retreat, or investment opportunity. Expansive decking provides excellent outdoor living space for relaxing, entertaining, or enjoying the peaceful setting. Inside, the home features hardwood floors, a striking brick fireplace, abundant natural light, and a functional open layout that works well for both everyday living and hosting guests. Conveniently located just minutes from Windham Mountain, this property offers easy access to skiing, hiking, golf, and year-round recreation, while still being close to town amenities. Approximately 2.5 hours from New York City. Photos are virtually staged.

Key facts

• 0.5 acre lot
• Built 1940
• Listed 68 days

What this means for you Summary

Snapshot

• This is a 3-bed/1.5-bath single-family listed at $285k. Condition is rated average.

Deal economics

• At list price, monthly cash flow is $483 ($6k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($3k rent vs $285k).
• Recommended offer: $268k (6.0% below list) — sets the bar for market timing.
• Cap rate 8.6% 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: 143 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 $16k of equity ($2k loan paydown + $14k 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 $80k cash investment doubles in ~4 years — after that, you're playing with house money.
• By year 3, paydown + projected appreciation supports a ~$40k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 68 days — a 6% lower offer ($268k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts since 2y ago; this cycle's ask has dropped $15k (5%) from the opening price — seller is motivated, your offer sets the floor, not the list.

Risks & watch-outs

• Watch-outs: flood insurance adds $56/mo; built in 1940 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: severe flood risk — expect insurance premiums to compound above CPI over the hold.

Recommended offer $267,900 (6.0% below list)

Questions for the listing agent

1. It's been on market 68 days. Have you received any prior offers? Is the seller open to a 6% concession, seller financing, or rate buy-down credit?
2. Built in 1940 — 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: 1.11% ✓
• Cap rate: 8.56%
• Cash-on-cash: 8.10%
• DSCR: 1.36
• GRM: 7.5

CMA / ARV

• ARV (median comp): $548,203
• List price: $285,000
• Delta: -48.01%
• Verdict: UNDERPRICED
• Comps: 3 within 1.0 mi

Projected returns pro-forma

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

5-year hold

• IRR: 19.2%
• Equity multiple: 2.22×
• Total profit: $97,452
• Equity at exit: $162,477

10-year hold

• IRR: 19.1%
• Equity multiple: 4.36×
• Total profit: $267,785
• Equity at exit: $281,219

Cash invested: $79,800 (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: 143
• Price-to-rent: 7.5×

Monthly cashflow live

• Estimated rent: $3,175 medium
• Mortgage (P&I): −$1,495
• Tax est. 1.5%: −$356 /mo · $4,275/yr
• Insurance: −$119
• Flood insurance flood zone: −$56 /mo · $666/yr
• HOA: −$0
• Vacancy / Maint / Mgmt: −$667
• Net cashflow: $483

Break-even live

Break-even rent $2,563

Max offer price $285,000

Occupancy floor 80%

Sensitivity live

Price	-10% $680	-5% $582	+0% $483	+5% $385	+10% $286
Rent	-10% $232	-5% $358	+0% $483	+5% $609	+10% $734
Rate	-1.0pp $627	-0.5pp $556	base $483	+0.5pp $409	+1.0pp $334

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: $71,250
• Closing costs: $8,550
• Reserves months: —
• Total cash needed: —

Listing history 20 events

1. 2026-06-21
   days on market $285,000 Active 68 DOM
2. 2026-06-21
   days on market $285,000 Active 67 DOM
3. 2026-06-18
   days on market $285,000 Active 65 DOM
4. 2026-06-17
   days on market $285,000 Active 64 DOM
5. 2026-06-16
   days on market $285,000 Active 63 DOM
6. 2026-06-15
   days on market $285,000 Active 62 DOM
7. 2026-06-13
   days on market $285,000 Active 60 DOM
8. 2026-06-12
   days on market $285,000 Active 59 DOM
9. 2026-06-09
   days on market $285,000 Active 56 DOM
10. 2026-06-08
    days on market $285,000 Active 55 DOM
11. 2026-06-07
    days on market $285,000 Active 54 DOM
12. 2026-06-07
    days on market $285,000 Active 53 DOM
13. 2026-06-04
    days on market $285,000 Active 50 DOM
14. 2026-06-02
    days on market $285,000 Active 49 DOM
15. 2026-06-01
    days on market $285,000 Active 48 DOM
16. 2026-05-31
    days on market $285,000 Active 47 DOM
17. 2026-05-19
    price $285,000 881-char remark

    Show marketing remark (881 chars)

    Welcome to 542 Mitchell Hollow Road, Windham, NY, a charming home set on a beautifully maintained property in the heart of the Catskills. This inviting residence offers a wonderful combination of comfort, space, and natural surroundings, making it ideal as a full-time home, weekend retreat, or investment opportunity. Expansive decking provides excellent outdoor living space for relaxing, entertaining, or enjoying the peaceful setting. Inside, the home features hardwood floors, a striking brick fireplace, abundant natural light, and a functional open layout that works well for both everyday living and hosting guests. Conveniently located just minutes from Windham Mountain, this property offers easy access to skiing, hiking, golf, and year-round recreation, while still being close to town amenities. Approximately 2.5 hours from New York City. Photos are virtually staged.

18. 2026-04-14
    listed $300,000 Active 881-char remark

    Show marketing remark (881 chars)

    Welcome to 542 Mitchell Hollow Road, Windham, NY, a charming home set on a beautifully maintained property in the heart of the Catskills. This inviting residence offers a wonderful combination of comfort, space, and natural surroundings, making it ideal as a full-time home, weekend retreat, or investment opportunity. Expansive decking provides excellent outdoor living space for relaxing, entertaining, or enjoying the peaceful setting. Inside, the home features hardwood floors, a striking brick fireplace, abundant natural light, and a functional open layout that works well for both everyday living and hosting guests. Conveniently located just minutes from Windham Mountain, this property offers easy access to skiing, hiking, golf, and year-round recreation, while still being close to town amenities. Approximately 2.5 hours from New York City. Photos are virtually staged.

19. 2024-12-22
    historical $1,800
20. 2024-11-20
    listed $1,800

ⓘ 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 9/10 Extreme FEMA zone X (unshaded) · 99% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 1/10 Low 8 d/yr ≥87°F today · 18 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: $38,099
• − Mortgage interest: −$15,964
• − Property taxes: −$4,275
• − Insurance: −$2,092
• − Repairs & maintenance: −$3,048
• − Management: −$3,048
• − Depreciation: −$8,291
• Taxable income: $1,382
• Est. tax owed @ 24.0%: −$332
• After-tax cash flow: $5,466/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

Average 55/100 Moderate rehab

This home requires moderate renovations to improve its condition and increase its resale value. Key areas for improvement include the kitchen, bathrooms, and roof.

Repairs flagged

• Moderate kitchen cabinets — dated and in need of updating
• Moderate bathroom fixtures — dated and in need of updating
• Moderate roof — visible wear

Value-add opportunities

• Resale paint interior walls — Fresh paint can make a significant difference in the home's appearance
• Resale replace kitchen cabinets — New cabinets can greatly enhance the kitchen's functionality and aesthetic
• Resale update bathroom fixtures — Modern fixtures can make the bathroom more appealing and functional
• Resale repair roof — A repaired roof can add value and ensure the home is in good condition

Renovation cost estimate screening

Repair item	Severity	Est. cost
kitchen cabinets · dated and in need of updating	Moderate	$3,000–15,000
bathroom fixtures · dated and in need of updating	Moderate	$3,000–15,000
roof · visible wear	Moderate	$3,000–15,000
Total estimated repair cost · 3 items		$9,000–45,000

Value-add ROI direction

• Resale paint interior walls — Fresh paint can make a significant difference in the home's appearance ↑
• Resale replace kitchen cabinets — New cabinets can greatly enhance the kitchen's functionality and aesthetic ↑
• Resale update bathroom fixtures — Modern fixtures can make the bathroom more appealing and functional ↑
• Resale repair roof — A repaired roof can add value and ensure the home is in good condition ↑

ⓘ 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: 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

+15733.3% since first listed

4 events — show timeline

• 2026-05-19 Price Changed $285,000 OneKey® MLS as Distributed by MLS Grid
• 2026-04-14 Listed $300,000 OneKey® MLS as Distributed by MLS Grid
• 2024-12-22 Rental Removed $1,800 TURBOTENANT
• 2024-11-20 Listed for Rent $1,800 TURBOTENANT