542 Mitchell Hollow Rd · Windham, NY 12496

$285,000

3 bd · 1.5 ba · 1,446 sqft · SingleFamily · 163 Days on market

Built 1940 Average condition 0.50 ac lot $197/sqft · 46% below area Est $528k · 46% under

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Why this score? — see what drove the D 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).

• ARV discount +15.0/15.0
• Appreciation +7.5/10.0
• Cash flow +4.7/30.0
• Schools +4.3/10.0
• Livability +3.0/5.0
• Condition / age +2.8/5.0
• Rent growth +2.5/5.0
• 1% rule +0.6/10.0
• DSCR +0.0/10.0

Listing remarks

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.

Key facts

• 0.5 acre lot
• Built 1940
• Listed 162 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 $-706 ($-8k/yr) — negative.
• To cash-flow at today's rent, offer at most $183k (35.8% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $160k (43.9% below list).
• Recommended offer: $160k (43.9% below list) — sets the bar for 1% rule.
• Cap rate 3.3% vs local median 1.8% 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: 194 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

• 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.
• 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 163 days — a 12% lower offer ($251k) 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: built in 1940 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $160,000 (43.9% below list)

Questions for the listing agent

1. What do current leases actually rent for vs. the listed asking? Can we see a recent rent roll and the last 12 months of T-12 income?
2. It's been on market 163 days. Have you received any prior offers? Is the seller open to a 44% concession, seller financing, or rate buy-down credit?
3. Built in 1940 — 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. 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. The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
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 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: 0.56% ✗
• Cap rate: 3.32%
• Cash-on-cash: -10.61%
• DSCR: 0.53
• GRM: 14.8

CMA / ARV

• ARV (median comp): $528,090
• List price: $285,000
• Delta: -46.03%
• Verdict: UNDERPRICED
• Comps: 2 within 1.0 mi

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
4 French Park Dr Unit 1 (2a)	1.65mi	3/2.0	1,392 (-4%)	9mo	$340,000	$244	49
13 Boulder Brook Rd	0.24mi	4/2.0 (+1)	1,840 (+27%)	15mo	$521,000	$283	45
333 Begley Rd	1.09mi	3/2.0	1,568 (+8%)	10mo	$300,000	$191	41
513 County Road 10	1.73mi	3/3.0	1,870 (+29%)	0mo	$590,000	$316	34
113 Windham Ridge Rd	1.63mi	2/2.0 (-1)	1,024 (-29%)	5mo	$240,000	$234	29
63 Windham Ridge Rd Unit 16c	1.64mi	2/2.5 (-1)	1,178 (-18%)	3mo	$250,000	$212	28
770 Mitchell Hollow Rd	1.13mi	3/2.0	1,622 (+12%)	21mo	$520,000	$321	25
73 Windham Ridge Rd Unit 16h	1.63mi	2/2.5 (-1)	1,058 (-27%)	7mo	$310,000	$293	25
4 French Park Dr Dr Unit C-8	1.77mi	3/2.0	1,632 (+13%)	24mo	$395,000	$242	22
79 Windham Ridge Rd Unit 17A	1.61mi	2/2.5 (-1)	1,211 (-16%)	12mo	$269,000	$222	21
36 Loo Bridge Ln	1.69mi	2/2.5 (-1)	1,211 (-16%)	17mo	$280,000	$231	17
66 Loo Bridge Lane Ln Unit 12G	1.72mi	2/2.5 (-1)	1,211 (-16%)	24mo	$340,000	$281	11

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: 4.2%
• Equity multiple: 1.27×
• Total profit: $21,687
• Equity at exit: $162,477

10-year hold

• IRR: 6.9%
• Equity multiple: 2.30×
• Total profit: $104,091
• 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 →

Active competition Active MLS

• For sale now: 1 active
• Median asking: $639,000 ($441/sqft)
• Median days on market: 240 d
• This list price: lowest-priced of the active set
• ARV vs active asking: -17.2% vs current asking $/sqft

Closed sales set the value; these active listings set current market conditions and a practical price ceiling.

ZIP-level market 12496

• Home prices YoY: 1.2%
• Active inventory: 194
• Price-to-rent: 14.8×

Monthly cashflow live

• Estimated rent: $1,600 medium
• Mortgage (P&I): −$1,495
• Tax est. 1.5%: −$356 /mo · $4,275/yr
• Insurance: −$119
• HOA: −$0
• Vacancy / Maint / Mgmt: −$336
• Net cashflow: $-706

Break-even live

Break-even rent $2,493

Max offer price $182,903

Occupancy floor —

Sensitivity live

Price	-10% $-509	-5% $-607	+0% $-706	+5% $-804	+10% $-903
Rent	-10% $-832	-5% $-769	+0% $-706	+5% $-642	+10% $-579
Rate	-1.0pp $-562	-0.5pp $-633	base $-706	+0.5pp $-779	+1.0pp $-855

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
• Club membership (one-time): —
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
60 Bell Hill Rd Windham, NY	2.0	1.0	1024	$1,600	$1.56	6d	1	1.04mi

Property features AI

Finance

Exterior

• Parking: Driveway
• Utilities: Electricity connectedWater connectedSewer: Other
• Home design: Single family residence
• Exterior features: Frame constructionNot waterfrontNo additional parcels

Interior

• Kitchen: RangeRefrigerator
• Flooring: Hardwood flooring
• Bathrooms: 1 full bathroom1 half bathroom
• Heating & cooling: Oil heatingOther heatingNo central air
• Interior features: FireplaceOther interior featuresBasement (see remarks)Attic (see remarks)5 total rooms

Listing history 50 events

1. 2026-09-24
   days on market $285,000 Active 163 DOM
2. 2026-09-23
   days on market $285,000 Active 162 DOM
3. 2026-09-21
   days on market $285,000 Active 160 DOM
4. 2026-09-20
   days on market $285,000 Active 159 DOM
5. 2026-09-19
   days on market $285,000 Active 158 DOM
6. 2026-09-19
   days on market $285,000 Active 157 DOM
7. 2026-09-17
   days on market $285,000 Active 156 DOM
8. 2026-09-17
   days on market $285,000 Active 155 DOM
9. 2026-09-16
   days on market $285,000 Active 154 DOM
10. 2026-09-14
    days on market $285,000 Active 153 DOM
11. 2026-09-13
    days on market $285,000 Active 152 DOM
12. 2026-09-12
    days on market $285,000 Active 151 DOM
13. 2026-09-11
    days on market $285,000 Active 150 DOM
14. 2026-09-05
    days on market $285,000 Active 144 DOM
15. 2026-09-04
    days on market $285,000 Active 143 DOM
16. 2026-09-03
    days on market $285,000 Active 142 DOM
17. 2026-09-02
    days on market $285,000 Active 141 DOM
18. 2026-08-30
    days on market $285,000 Active 138 DOM
19. 2026-08-29
    days on market $285,000 Active 137 DOM
20. 2026-08-28
    days on market $285,000 Active 136 DOM
21. 2026-08-27
    days on market $285,000 Active 135 DOM
22. 2026-08-26
    days on market $285,000 Active 134 DOM
23. 2026-08-25
    days on market $285,000 Active 133 DOM
24. 2026-08-24
    days on market $285,000 Active 132 DOM
25. 2026-08-23
    days on market $285,000 Active 131 DOM
26. 2026-08-22
    days on market $285,000 Active 130 DOM
27. 2026-08-21
    days on market $285,000 Active 129 DOM
28. 2026-08-20
    days on market $285,000 Active 128 DOM
29. 2026-08-19
    days on market $285,000 Active 127 DOM
30. 2026-08-18
    days on market $285,000 Active 126 DOM
31. 2026-08-17
    days on market $285,000 Active 125 DOM
32. 2026-08-16
    days on market $285,000 Active 124 DOM
33. 2026-08-15
    days on market $285,000 Active 123 DOM
34. 2026-08-13
    days on market $285,000 Active 121 DOM
35. 2026-08-12
    days on market $285,000 Active 120 DOM
36. 2026-08-11
    days on market $285,000 Active 119 DOM
37. 2026-08-10
    days on market $285,000 Active 118 DOM
38. 2026-08-09
    days on market $285,000 Active 117 DOM
39. 2026-08-08
    days on market $285,000 Active 116 DOM
40. 2026-08-07
    days on market $285,000 Active 115 DOM
41. 2026-08-06
    days on market $285,000 Active 114 DOM
42. 2026-08-05
    days on market $285,000 Active 113 DOM
43. 2026-08-04
    days on market $285,000 Active 112 DOM
44. 2026-08-03
    days on market $285,000 Active 111 DOM
45. 2026-07-31
    days on market $285,000 Active 108 DOM
46. 2026-07-30
    days on market $285,000 Active 107 DOM
47. 2026-07-29
    days on market $285,000 Active 106 DOM
48. 2026-07-27
    days on market $285,000 Active 104 DOM
49. 2026-07-25
    days on market $285,000 Active 102 DOM
50. 2026-07-24
    days on market $285,000 Active 101 DOM

ⓘ 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 4/10 Moderate FEMA zone X (unshaded) · 24% 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: $19,200
• − Mortgage interest: −$15,964
• − Property taxes: −$4,275
• − Insurance: −$1,425
• − Repairs & maintenance: −$1,536
• − Management: −$1,536
• − Depreciation: −$8,291
• Taxable loss: −$13,827
• Est. tax savings @ 24.0%: +$3,319
• After-tax cash flow: $-5,148/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 Est. rehab $36,150–$65,070 screening

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 ↑

ⓘ Rehab cost is a screening estimate — Moderate scope × the home's square footage at US $/sqft rules of thumb (the same model as the Flip Finder). Get contractor quotes + a written scope before underwriting.

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

C Composite livability gradescore 60/100

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

• County: Greene · 44,963 people
• Population (ZIP): 1,241
• Household income: $68,173
• Rent vs Own: 12.2% rent · 87.8% own
• Severe rent burden: 38% of renters

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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%

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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%

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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

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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

Property features AI

Finance

Exterior

• Parking: Driveway
• Utilities: Electricity connectedWater connectedSewer: Other
• Home design: Single family residence
• Exterior features: Frame constructionNot waterfrontNo additional parcels

Interior

• Kitchen: RangeRefrigerator
• Flooring: Hardwood flooring
• Bathrooms: 1 full bathroom1 half bathroom
• Heating & cooling: Oil heatingOther heatingNo central air
• Interior features: FireplaceOther interior featuresBasement (see remarks)Attic (see remarks)5 total rooms

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