34 Old Rd · Windham, NY 12496

$525,000

3 bd · 1.5 ba · 2,084 sqft · SingleFamily · 147 Days on market

Built 1971 2.54 ac lot $252/sqft · 31% below area Est $756k · 31% 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 +5.0/30.0
• Schools +4.3/10.0
• Livability +3.0/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +0.8/10.0
• DSCR +0.0/10.0

Listing remarks MLS

Discover an exceptional Windham, NY mountain retreat just ~2 miles from Windham Mountain, offering both lifestyle appeal and income potential. This spacious, rustic 3-bedroom, 1.5-bath home features two separate living rooms—one on the first floor and one on the second floor—providing flexible space for entertaining, relaxing, or multi-group living. A cozy fireplace, open living areas, modern comforts, and scenic mountain views create the perfect Catskills getaway for skiing, hiking, biking, and year-round adventure. Enjoy additional living space in the fully enclosed porch with fully opening windows, ideal for three-season use and indoor-outdoor enjoyment. The home sits on two separate tax parcels, offering excellent potential for future development, expansion, or additional income strategies. The expansive yard and peaceful setting provide ample room for outdoor enjoyment or creative possibilities. Notable features include two Steffes Electric Thermal Storage heaters, designed to take advantage of peak/off-peak electric pricing for efficient and economical heating. With a unbeatable proximity to Windham Mountain Resort, this is a rare opportunity to own a versatile, turn-key Catskills property with built-in upside.

Key facts

• Expansive yard
• Fully enclosed porch
• 2.54 acre lot

Tags

• TWO SEPARATE LIVING ROOMS
• FULLY ENCLOSED PORCH
• TWO SEPARATE TAX PARCELS
• EXPANSIVE YARD

What this means for you Summary

Snapshot

• This is a 3-bed/1.5-bath single-family listed at $525k.

Deal economics

• At list price, monthly cash flow is $-1k ($-15k/yr) — negative.
• To cash-flow at today's rent, offer at most $346k (34.2% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $302k (42.4% below list).
• Recommended offer: $302k (42.4% below list) — sets the bar for 1% rule.

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 $30k of equity ($4k loan paydown + $27k 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 2, paydown + projected appreciation supports a ~$48k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 147 days — a 12% lower offer ($462k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 9y ago; this cycle's ask has dropped $64k (11%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $340k; list at $525k implies a 54% gain — meaningful room to come down on a strong offer.

Recommended offer $302,418 (42.4% 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 147 days. Have you received any prior offers? Is the seller open to a 42% concession, seller financing, or rate buy-down credit?
3. Built in 1971 — 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: 0.58% ✗
• Cap rate: 3.46%
• Cash-on-cash: -10.11%
• DSCR: 0.55
• GRM: 14.5

CMA / ARV

• ARV (median comp): $755,910
• List price: $525,000
• Delta: -30.55%
• Verdict: UNDERPRICED
• Comps: 9 within 1.0 mi

Show comp detail 3 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
4992 Ny-23	0.45mi	3/2.5	2,172 (+4%)	6mo	$400,000	$184	63
122 Old Rd	0.37mi	4/2.5 (+1)	1,973 (-5%)	7mo	$715,000	$362	59
29 Martin Lane Ln	0.69mi	4/2.0 (+1)	2,116 (+2%)	17mo	$585,000	$276	44

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: 4.6%
• Equity multiple: 1.30×
• Total profit: $43,816
• Equity at exit: $299,300

10-year hold

• IRR: 7.2%
• Equity multiple: 2.36×
• Total profit: $200,094
• Equity at exit: $518,035

Cash invested: $147,000 (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: 14.5×

Monthly cashflow live

• Estimated rent: $3,024 medium
• Mortgage (P&I): −$2,753
• Tax est. 1.5%: −$656 /mo · $7,875/yr
• Insurance: −$219
• HOA: −$0
• Vacancy / Maint / Mgmt: −$635
• Net cashflow: $-1,239

Break-even live

Break-even rent $4,593

Max offer price $345,707

Occupancy floor —

Sensitivity live

Price	-10% $-876	-5% $-1,058	+0% $-1,239	+5% $-1,420	+10% $-1,602
Rent	-10% $-1,478	-5% $-1,359	+0% $-1,239	+5% $-1,120	+10% $-1,000
Rate	-1.0pp $-975	-0.5pp $-1,106	base $-1,239	+0.5pp $-1,375	+1.0pp $-1,513

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: $131,250
• Closing costs: $15,750
• Reserves months: —
• Total cash needed: —

Listing history 17 events

1. 2026-06-15
   statusdays on market $525,000 Pending 147 DOM
2. 2026-06-13
   days on market $525,000 Active 145 DOM
3. 2026-06-12
   days on market $525,000 Active 144 DOM
4. 2026-06-09
   days on market $525,000 Active 141 DOM
5. 2026-06-08
   days on market $525,000 Active 140 DOM
6. 2026-06-07
   days on market $525,000 Active 139 DOM
7. 2026-06-07
   days on market $525,000 Active 138 DOM
8. 2026-06-04
   days on market $525,000 Active 135 DOM
9. 2026-06-02
   days on market $525,000 Active 134 DOM
10. 2026-06-01
    days on market $525,000 Active 133 DOM
11. 2026-05-31
    days on market $525,000 Active 132 DOM
12. 2026-01-20
    price $525,000 1248-char remark

    Show marketing remark (1248 chars)

    Discover an exceptional Windham, NY mountain retreat just ~2 miles from Windham Mountain, offering both lifestyle appeal and income potential. This spacious, rustic 3-bedroom, 1.5-bath home features two separate living rooms—one on the first floor and one on the second floor—providing flexible space for entertaining, relaxing, or multi-group living. A cozy fireplace, open living areas, modern comforts, and scenic mountain views create the perfect Catskills getaway for skiing, hiking, biking, and year-round adventure. Enjoy additional living space in the fully enclosed porch with fully opening windows, ideal for three-season use and indoor-outdoor enjoyment. The home sits on two separate tax parcels, offering excellent potential for future development, expansion, or additional income strategies. The expansive yard and peaceful setting provide ample room for outdoor enjoyment or creative possibilities. Notable features include two Steffes Electric Thermal Storage heaters, designed to take advantage of peak/off-peak electric pricing for efficient and economical heating. With a unbeatable proximity to Windham Mountain Resort, this is a rare opportunity to own a versatile, turn-key Catskills property with built-in upside.

13. 2026-01-17
    listed $589,000 Active 1248-char remark

    Show marketing remark (1248 chars)

    Discover an exceptional Windham, NY mountain retreat just ~2 miles from Windham Mountain, offering both lifestyle appeal and income potential. This spacious, rustic 3-bedroom, 1.5-bath home features two separate living rooms—one on the first floor and one on the second floor—providing flexible space for entertaining, relaxing, or multi-group living. A cozy fireplace, open living areas, modern comforts, and scenic mountain views create the perfect Catskills getaway for skiing, hiking, biking, and year-round adventure. Enjoy additional living space in the fully enclosed porch with fully opening windows, ideal for three-season use and indoor-outdoor enjoyment. The home sits on two separate tax parcels, offering excellent potential for future development, expansion, or additional income strategies. The expansive yard and peaceful setting provide ample room for outdoor enjoyment or creative possibilities. Notable features include two Steffes Electric Thermal Storage heaters, designed to take advantage of peak/off-peak electric pricing for efficient and economical heating. With a unbeatable proximity to Windham Mountain Resort, this is a rare opportunity to own a versatile, turn-key Catskills property with built-in upside.

14. 2025-06-13
    soldstatus $340,000 Closed 834-char remark

    Show marketing remark (834 chars)

    Escape to this warm and inviting3+-bedroom, 1.5-bath home, just minutes from Windham Village and the ski slopes. Boasting a country-style kitchen with granite countertops, a cozy Harmon pellet stove insert, and beautiful hardwood floors, this home blends comfort with charm. An office space provides extra flexibility, and the laundry area can easily function as a 4th bedroom. Step outside to enjoy a wraparound deck and a spacious, beautifully landscaped yard perfect for relaxation or entertaining. Additional features include a large 2-car garage, ideal for snowy winter months, and an adjoining building lot connected to municipal sewer, offering over 1 acre of total property. Whether you're seeking a peaceful retreat or a full-time residence, this property offers the perfect balance of rural living yet close to everything. .

15. 2024-09-27
    listed $399,000 834-char remark

    Show marketing remark (834 chars)

    Escape to this warm and inviting3+-bedroom, 1.5-bath home, just minutes from Windham Village and the ski slopes. Boasting a country-style kitchen with granite countertops, a cozy Harmon pellet stove insert, and beautiful hardwood floors, this home blends comfort with charm. An office space provides extra flexibility, and the laundry area can easily function as a 4th bedroom. Step outside to enjoy a wraparound deck and a spacious, beautifully landscaped yard perfect for relaxation or entertaining. Additional features include a large 2-car garage, ideal for snowy winter months, and an adjoining building lot connected to municipal sewer, offering over 1 acre of total property. Whether you're seeking a peaceful retreat or a full-time residence, this property offers the perfect balance of rural living yet close to everything. .

16. 2018-03-15
    soldstatus $210,000
17. 2017-07-24
    listed $209,900

ⓘ 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 3/10 Moderate FEMA zone X (unshaded) · 20% chance over 30 yrs
• 🔥 Wildfire 3/10 Moderate
• 🌡 Heat 1/10 Low 8 d/yr ≥86°F today · 18 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: $36,290
• − Mortgage interest: −$29,408
• − Property taxes: −$7,875
• − Insurance: −$2,625
• − Repairs & maintenance: −$2,903
• − Management: −$2,903
• − Depreciation: −$15,273
• Taxable loss: −$24,697
• Est. tax savings @ 24.0%: +$5,927
• After-tax cash flow: $-8,941/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

+150.1% since first listed

6 events — show timeline

• 2026-01-20 Price Changed $525,000 OneKey® MLS as Distributed by MLS Grid
• 2026-01-17 Listed $589,000 OneKey® MLS as Distributed by MLS Grid
• 2025-06-13 Sold (MLS) $340,000 HVCRMLS
• 2024-09-27 Listed $399,000 HVCRMLS
• 2018-03-15 Sold (MLS) $210,000 HVCRMLS
• 2017-07-24 Listed $209,900 HVCRMLS