9 Pinekill Ln · Windham, NY 12496

$599,000

3 bd · 2.0 ba · 1,650 sqft · SingleFamily public records · 443 Days on market

Built 2003 2.40 ac lot $363/sqft · 20% below area Est $764k · 22% 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 +5.9/30.0
• Schools +4.3/10.0
• Livability +3.0/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +0.3/10.0
• DSCR +0.3/10.0

Listing remarks MLS

Renovated Mountain Retreat house on 2.4 landscaped acres.! This beautifully renovated 3-bedroom, 2-bath home, updated in 2022, Located within walking distance to CD Lane Park for swimming, boating, and BBQs, and close to the Catskill Forest Preserve for hiking and biking, this property is perfect for outdoor enthusiasts. Inside, you'll find a spacious open floor plan with a modern kitchen and dining area that opens onto a large rear deck and patio. The main bedroom features an ensuite bath, while two additional bedrooms, another two full baths, and a laundry room complete the home. The two-car garage and a new roof (2020) add to the convenience. Located just 6 miles from Windham Mountain and 9 miles from Hunter, this home is ideal for year-round living, a vacation getaway, or an investment property, rent as an AIRBNB house for potential income. This property is more than just a house; it's a lifestyle. Don't miss out on owning this slice of paradise-schedule your viewing today!

Key facts

• 2.4 acre lot
• Garage
• Built 2003

What this means for you Summary

Snapshot

• This is a 3-bed/2.0-bath single-family listed at $599k.

Deal economics

• At list price, monthly cash flow is $-1k ($-14k/yr) — negative.
• To cash-flow at today's rent, offer at most $392k (34.6% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $317k (47.1% below list).
• Recommended offer: $317k (47.1% below list) — sets the bar for 1% rule.
• Cap rate 3.9% vs local median 3.2% in Windham — meaningfully above typical; check what's discounted (condition, days-on-market, listing class) to confirm the premium yield is real.

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 $34k of equity ($4k loan paydown + $30k 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 ~$55k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 443 days — a 12% lower offer ($527k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 2y ago; this cycle's ask has dropped $166k (22%) from the opening price — seller is motivated, your offer sets the floor, not the list.

Risks & watch-outs

• Climate carrying-cost: moderate wildfire risk — expect insurance premiums to compound above CPI over the hold.

Recommended offer $316,705 (47.1% 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 443 days. Have you received any prior offers? Is the seller open to a 47% concession, seller financing, or rate buy-down credit?
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. 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?
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: 0.53% ✗
• Cap rate: 3.94%
• Cash-on-cash: -8.40%
• DSCR: 0.63
• GRM: 15.8

CMA / ARV

• ARV (median comp): $763,750
• List price: $599,000
• Delta: -21.57%
• Verdict: UNDERPRICED
• Comps: 5 within 1.0 mi

Projected returns pro-forma

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

5-year hold

• IRR: 6.0%
• Equity multiple: 1.39×
• Total profit: $65,003
• Equity at exit: $341,487

10-year hold

• IRR: 8.3%
• Equity multiple: 2.55×
• Total profit: $259,895
• Equity at exit: $591,054

Cash invested: $167,720 (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: 143
• Price-to-rent: 15.8×

Monthly cashflow live

• Estimated rent: $3,167 medium
• Mortgage (P&I): −$3,141
• Tax from tax record: −$285 /mo · $3,416/yr
• Insurance: −$250
• HOA: −$0
• Vacancy / Maint / Mgmt: −$665
• Net cashflow: $-1,173

Break-even live

Break-even rent $4,652

Max offer price $391,701

Occupancy floor —

Sensitivity live

Price	-10% $-834	-5% $-1,004	+0% $-1,173	+5% $-1,343	+10% $-1,513
Rent	-10% $-1,424	-5% $-1,299	+0% $-1,173	+5% $-1,048	+10% $-923
Rate	-1.0pp $-872	-0.5pp $-1,021	base $-1,173	+0.5pp $-1,329	+1.0pp $-1,487

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: $149,750
• Closing costs: $17,970
• Reserves months: —
• Total cash needed: —

Listing history 29 events

1. 2026-06-22
   days on market $599,000 Active 443 DOM
2. 2026-06-21
   days on market $599,000 Active 442 DOM
3. 2026-06-21
   days on market $599,000 Active 441 DOM
4. 2026-06-18
   days on market $599,000 Active 439 DOM
5. 2026-06-17
   days on market $599,000 Active 438 DOM
6. 2026-06-16
   days on market $599,000 Active 437 DOM
7. 2026-06-15
   days on market $599,000 Active 436 DOM
8. 2026-06-13
   days on market $599,000 Active 434 DOM
9. 2026-06-12
   days on market $599,000 Active 433 DOM
10. 2026-06-09
    days on market $599,000 Active 430 DOM
11. 2026-06-08
    days on market $599,000 Active 429 DOM
12. 2026-06-07
    days on market $599,000 Active 428 DOM
13. 2026-06-07
    days on market $599,000 Active 427 DOM
14. 2026-06-04
    days on market $599,000 Active 424 DOM
15. 2026-06-02
    days on market $599,000 Active 423 DOM
16. 2026-06-01
    days on market $599,000 Active 422 DOM
17. 2026-05-31
    days on market $599,000 Active 421 DOM
18. 2026-05-02
    price $599,000 995-char remark

    Show marketing remark (995 chars)

    Renovated Mountain Retreat house on 2.4 landscaped acres.! This beautifully renovated 3-bedroom, 2-bath home, updated in 2022, Located within walking distance to CD Lane Park for swimming, boating, and BBQs, and close to the Catskill Forest Preserve for hiking and biking, this property is perfect for outdoor enthusiasts. Inside, you'll find a spacious open floor plan with a modern kitchen and dining area that opens onto a large rear deck and patio. The main bedroom features an ensuite bath, while two additional bedrooms, another two full baths, and a laundry room complete the home. The two-car garage and a new roof (2020) add to the convenience. Located just 6 miles from Windham Mountain and 9 miles from Hunter, this home is ideal for year-round living, a vacation getaway, or an investment property, rent as an AIRBNB house for potential income. This property is more than just a house; it's a lifestyle. Don't miss out on owning this slice of paradise-schedule your viewing today!

19. 2026-03-25
    status Active 995-char remark

    Show marketing remark (995 chars)

    Renovated Mountain Retreat house on 2.4 landscaped acres.! This beautifully renovated 3-bedroom, 2-bath home, updated in 2022, Located within walking distance to CD Lane Park for swimming, boating, and BBQs, and close to the Catskill Forest Preserve for hiking and biking, this property is perfect for outdoor enthusiasts. Inside, you'll find a spacious open floor plan with a modern kitchen and dining area that opens onto a large rear deck and patio. The main bedroom features an ensuite bath, while two additional bedrooms, another two full baths, and a laundry room complete the home. The two-car garage and a new roof (2020) add to the convenience. Located just 6 miles from Windham Mountain and 9 miles from Hunter, this home is ideal for year-round living, a vacation getaway, or an investment property, rent as an AIRBNB house for potential income. This property is more than just a house; it's a lifestyle. Don't miss out on owning this slice of paradise-schedule your viewing today!

20. 2025-10-13
    price $628,000 995-char remark

    Show marketing remark (995 chars)

    Renovated Mountain Retreat house on 2.4 landscaped acres.! This beautifully renovated 3-bedroom, 2-bath home, updated in 2022, Located within walking distance to CD Lane Park for swimming, boating, and BBQs, and close to the Catskill Forest Preserve for hiking and biking, this property is perfect for outdoor enthusiasts. Inside, you'll find a spacious open floor plan with a modern kitchen and dining area that opens onto a large rear deck and patio. The main bedroom features an ensuite bath, while two additional bedrooms, another two full baths, and a laundry room complete the home. The two-car garage and a new roof (2020) add to the convenience. Located just 6 miles from Windham Mountain and 9 miles from Hunter, this home is ideal for year-round living, a vacation getaway, or an investment property, rent as an AIRBNB house for potential income. This property is more than just a house; it's a lifestyle. Don't miss out on owning this slice of paradise-schedule your viewing today!

21. 2025-08-03
    price $638,000 995-char remark

    Show marketing remark (995 chars)

    Renovated Mountain Retreat house on 2.4 landscaped acres.! This beautifully renovated 3-bedroom, 2-bath home, updated in 2022, Located within walking distance to CD Lane Park for swimming, boating, and BBQs, and close to the Catskill Forest Preserve for hiking and biking, this property is perfect for outdoor enthusiasts. Inside, you'll find a spacious open floor plan with a modern kitchen and dining area that opens onto a large rear deck and patio. The main bedroom features an ensuite bath, while two additional bedrooms, another two full baths, and a laundry room complete the home. The two-car garage and a new roof (2020) add to the convenience. Located just 6 miles from Windham Mountain and 9 miles from Hunter, this home is ideal for year-round living, a vacation getaway, or an investment property, rent as an AIRBNB house for potential income. This property is more than just a house; it's a lifestyle. Don't miss out on owning this slice of paradise-schedule your viewing today!

22. 2025-07-14
    price $655,000 995-char remark

    Show marketing remark (995 chars)

    Renovated Mountain Retreat house on 2.4 landscaped acres.! This beautifully renovated 3-bedroom, 2-bath home, updated in 2022, Located within walking distance to CD Lane Park for swimming, boating, and BBQs, and close to the Catskill Forest Preserve for hiking and biking, this property is perfect for outdoor enthusiasts. Inside, you'll find a spacious open floor plan with a modern kitchen and dining area that opens onto a large rear deck and patio. The main bedroom features an ensuite bath, while two additional bedrooms, another two full baths, and a laundry room complete the home. The two-car garage and a new roof (2020) add to the convenience. Located just 6 miles from Windham Mountain and 9 miles from Hunter, this home is ideal for year-round living, a vacation getaway, or an investment property, rent as an AIRBNB house for potential income. This property is more than just a house; it's a lifestyle. Don't miss out on owning this slice of paradise-schedule your viewing today!

23. 2025-06-18
    price $659,000 995-char remark

    Show marketing remark (995 chars)

    Renovated Mountain Retreat house on 2.4 landscaped acres.! This beautifully renovated 3-bedroom, 2-bath home, updated in 2022, Located within walking distance to CD Lane Park for swimming, boating, and BBQs, and close to the Catskill Forest Preserve for hiking and biking, this property is perfect for outdoor enthusiasts. Inside, you'll find a spacious open floor plan with a modern kitchen and dining area that opens onto a large rear deck and patio. The main bedroom features an ensuite bath, while two additional bedrooms, another two full baths, and a laundry room complete the home. The two-car garage and a new roof (2020) add to the convenience. Located just 6 miles from Windham Mountain and 9 miles from Hunter, this home is ideal for year-round living, a vacation getaway, or an investment property, rent as an AIRBNB house for potential income. This property is more than just a house; it's a lifestyle. Don't miss out on owning this slice of paradise-schedule your viewing today!

24. 2025-05-11
    status Active 995-char remark

    Show marketing remark (995 chars)

    Renovated Mountain Retreat house on 2.4 landscaped acres.! This beautifully renovated 3-bedroom, 2-bath home, updated in 2022, Located within walking distance to CD Lane Park for swimming, boating, and BBQs, and close to the Catskill Forest Preserve for hiking and biking, this property is perfect for outdoor enthusiasts. Inside, you'll find a spacious open floor plan with a modern kitchen and dining area that opens onto a large rear deck and patio. The main bedroom features an ensuite bath, while two additional bedrooms, another two full baths, and a laundry room complete the home. The two-car garage and a new roof (2020) add to the convenience. Located just 6 miles from Windham Mountain and 9 miles from Hunter, this home is ideal for year-round living, a vacation getaway, or an investment property, rent as an AIRBNB house for potential income. This property is more than just a house; it's a lifestyle. Don't miss out on owning this slice of paradise-schedule your viewing today!

25. 2024-08-30
    price $699,000 995-char remark

    Show marketing remark (995 chars)

    Renovated Mountain Retreat house on 2.4 landscaped acres.! This beautifully renovated 3-bedroom, 2-bath home, updated in 2022, Located within walking distance to CD Lane Park for swimming, boating, and BBQs, and close to the Catskill Forest Preserve for hiking and biking, this property is perfect for outdoor enthusiasts. Inside, you'll find a spacious open floor plan with a modern kitchen and dining area that opens onto a large rear deck and patio. The main bedroom features an ensuite bath, while two additional bedrooms, another two full baths, and a laundry room complete the home. The two-car garage and a new roof (2020) add to the convenience. Located just 6 miles from Windham Mountain and 9 miles from Hunter, this home is ideal for year-round living, a vacation getaway, or an investment property, rent as an AIRBNB house for potential income. This property is more than just a house; it's a lifestyle. Don't miss out on owning this slice of paradise-schedule your viewing today!

26. 2024-08-18
    listed $765,000 Active 995-char remark

    Show marketing remark (995 chars)

    Renovated Mountain Retreat house on 2.4 landscaped acres.! This beautifully renovated 3-bedroom, 2-bath home, updated in 2022, Located within walking distance to CD Lane Park for swimming, boating, and BBQs, and close to the Catskill Forest Preserve for hiking and biking, this property is perfect for outdoor enthusiasts. Inside, you'll find a spacious open floor plan with a modern kitchen and dining area that opens onto a large rear deck and patio. The main bedroom features an ensuite bath, while two additional bedrooms, another two full baths, and a laundry room complete the home. The two-car garage and a new roof (2020) add to the convenience. Located just 6 miles from Windham Mountain and 9 miles from Hunter, this home is ideal for year-round living, a vacation getaway, or an investment property, rent as an AIRBNB house for potential income. This property is more than just a house; it's a lifestyle. Don't miss out on owning this slice of paradise-schedule your viewing today!

27. 2024-08-17
    historical $765,000 995-char remark

    Show marketing remark (995 chars)

    Renovated Mountain Retreat house on 2.4 landscaped acres.! This beautifully renovated 3-bedroom, 2-bath home, updated in 2022, Located within walking distance to CD Lane Park for swimming, boating, and BBQs, and close to the Catskill Forest Preserve for hiking and biking, this property is perfect for outdoor enthusiasts. Inside, you'll find a spacious open floor plan with a modern kitchen and dining area that opens onto a large rear deck and patio. The main bedroom features an ensuite bath, while two additional bedrooms, another two full baths, and a laundry room complete the home. The two-car garage and a new roof (2020) add to the convenience. Located just 6 miles from Windham Mountain and 9 miles from Hunter, this home is ideal for year-round living, a vacation getaway, or an investment property, rent as an AIRBNB house for potential income. This property is more than just a house; it's a lifestyle. Don't miss out on owning this slice of paradise-schedule your viewing today!

28. 2022-11-30
    soldstatus $550,000
29. 2003-07-10
    soldstatus $18,000

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Tax reassessment forecast NY · Partial reset (capped growth)

• Current annual tax: $3,416 · $285/mo
• Projected year-2 tax: $6,769 · $564/mo
• Expected delta: +$3,354/yr (+$279/mo · 98.2%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 5/10 Major
• 🌡 Heat 1/10 Low 8 d/yr ≥84°F today · 20 d/yr by 30 yrs out
• 💨 Wind 3/10 Moderate 5% 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: $38,005
• − Mortgage interest: −$33,553
• − Property taxes: −$3,416
• − Insurance: −$2,995
• − Repairs & maintenance: −$3,040
• − Management: −$3,040
• − Depreciation: −$17,425
• Taxable loss: −$25,466
• Est. tax savings @ 24.0%: +$6,112
• After-tax cash flow: $-7,970/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

+3227.8% since first listed

12 events — show timeline

• 2026-05-02 Price Changed $599,000 OneKey® MLS as Distributed by MLS Grid
• 2026-03-25 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2025-10-13 Price Changed $628,000 OneKey® MLS as Distributed by MLS Grid
• 2025-08-03 Price Changed $638,000 OneKey® MLS as Distributed by MLS Grid
• 2025-07-14 Price Changed $655,000 OneKey® MLS as Distributed by MLS Grid
• 2025-06-18 Price Changed $659,000 OneKey® MLS as Distributed by MLS Grid
• 2025-05-11 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2024-08-30 Price Changed $699,000 OneKey® MLS as Distributed by MLS Grid
• 2024-08-18 Listed $765,000 OneKey® MLS as Distributed by MLS Grid
• 2024-08-17 Coming Soon $765,000 OneKey® MLS as Distributed by MLS Grid
• 2022-11-30 Sold (Public Records) $550,000 Public Records
• 2003-07-10 Sold (Public Records) $18,000 Public Records

Property tax history

+0.7%/yr

Latest (2025): $3,416 · +4.6% YoY. Source: county tax records.