245 Hicks Hill Rd · Pine Plains, NY 12581

$169,900

4 bd · 2.5 ba · 3,444 sqft · MultiFamily public records · 154 Days on market

Built 1951 2.40 ac lot $49/sqft · 78% below area ↓ 42% since listing

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Why this score? — see what drove the A- 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 +30.0/30.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• Appreciation +10.0/10.0
• ARV discount +7.5/15.0
• Schools +4.8/10.0
• Livability +3.2/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 1 unit. estimate disagrees with records

Listing remarks MLS

Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

Key facts

• 2.4 acre lot
• Built 1951
• Listed 154 days

What this means for you Summary

Snapshot

• This is a 4-bed/2.5-bath multifamily listed at $170k.

Deal economics

• At list price, monthly cash flow is $3k ($31k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($5k rent vs $170k).
• Recommended offer: $150k (12.0% below list) — sets the bar for market timing.
• Cap rate 24.5% vs local median 2.6% in Pine Plains — 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 64/100 on livability (#746 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, housing A+, employment B+; Watch: cost of living D+, amenities F, commute F.
• Pine Plains Central School District (rural): math 55% / reading 50% proficiency, ranked #372 of 755 in NY (top 49%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Market conditions: 12 active listings in the ZIP; 620 units permitted in Dutchess County in 2024 (242 in 5+ unit buildings).

Forward outlook

• In year one you build about $18k of equity ($1k loan paydown + $17k appreciation (10.0% local appreciation)).
• Dutchess County population projected at -11% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• At projected returns (10.0% appreciation + 3.0% rent growth), your $48k cash investment doubles in ~1 year — after that, you're playing with house money.
• By year 3, paydown + projected appreciation supports a ~$46k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 154 days — a 12% lower offer ($150k) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts; this cycle's ask has dropped $44k (21%) from the opening price — seller is motivated, your offer sets the floor, not the list.

Risks & watch-outs

• Watch-outs: property tax is 3.8% of price; built in 1951 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: moderate wildfire risk — expect insurance premiums to compound above CPI over the hold.

Recommended offer $149,512 (12.0% below list)

Questions for the listing agent

1. It's been on market 154 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 1951 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Property tax is high relative to price — has the assessment been appealed recently, and will the sale trigger a re-assessment?
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. This sits on a lake — are riparian / water-frontage rights deeded with the parcel? Any dock permits, shoreline easements, or HOA water-use restrictions?
7. What's the documented flood / surge / shoreline-erosion history here (FEMA AND non-FEMA — e.g., storm surge, creek backup, septic-field saturation)?
8. Any water-quality or seasonal algae-bloom issues that affect tenant satisfaction or short-term-rental demand?
9. 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.
10. 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.
11. How much new apartment / multifamily construction is in the pipeline within 1–3 miles? Heavy new supply (>2% of stock underway) typically softens rents 12–24 months out; light construction supports rent growth.

Investment metrics

• 1% rule: 3.04% ✓
• Cap rate: 24.53%
• Cash-on-cash: 65.14%
• DSCR: 3.90
• GRM: 2.7

CMA / ARV

• ARV (median comp): $788,214
• List price: $169,900
• Delta: -78.44%
• Verdict: UNDERPRICED
• Comps: 7 within 2.0 mi

Projected returns pro-forma

10.0% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 76.7%
• Equity multiple: 6.41×
• Total profit: $257,288
• Equity at exit: $153,059

10-year hold

• IRR: 70.8%
• Equity multiple: 14.22×
• Total profit: $628,874
• Equity at exit: $330,078

Cash invested: $47,572 (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 12581

• Home prices YoY: 8.7%
• Active inventory: 12
• Price-to-rent: 5.5×

Monthly cashflow live

• Estimated rent: $5,163 medium
• Mortgage (P&I): −$891
• Tax from tax record: −$535 /mo · $6,414/yr
• Insurance: −$71
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,084
• Net cashflow: $2,582

Break-even live

Break-even rent $1,894

Max offer price $169,900

Occupancy floor 45%

Sensitivity live

Price	-10% $2,679	-5% $2,631	+0% $2,582	+5% $2,534	+10% $2,486
Rent	-10% $2,175	-5% $2,379	+0% $2,582	+5% $2,786	+10% $2,990
Rate	-1.0pp $2,668	-0.5pp $2,626	base $2,582	+0.5pp $2,538	+1.0pp $2,494

2-unit breakdown (identical units grouped — click to expand)

Units	Beds	Baths	Est. rent
▸ 2× units	2	1	$5,164
Total (2 units)			$5,163

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: $42,475
• Closing costs: $5,097
• Reserves months: —
• Total cash needed: —

Listing history 27 events

1. 2026-06-18
   days on market $169,900 Active 154 DOM
2. 2026-06-17
   days on market $169,900 Active 153 DOM
3. 2026-06-16
   days on market $169,900 Active 152 DOM
4. 2026-06-15
   days on market $169,900 Active 151 DOM
5. 2026-06-14
   days on market $169,900 Active 149 DOM
6. 2026-06-10
   pricedays on market $169,900 Active 146 DOM
7. 2026-06-09
   days on market $174,800 Active 145 DOM
8. 2026-06-08
   days on market $174,800 Active 144 DOM
9. 2026-06-07
   days on market $174,800 Active 143 DOM
10. 2026-06-05
    days on market $174,800 Active 140 DOM
11. 2026-06-03
    days on market $174,800 Active 139 DOM
12. 2026-06-02
    days on market $174,800 Active 138 DOM
13. 2026-06-01
    days on market $174,800 Active 137 DOM
14. 2026-05-31
    days on market $174,800 Active 136 DOM
15. 2026-05-30
    days on market $174,800 Active 135 DOM
16. 2026-03-24
    price $174,800 359-char remark

    Show marketing remark (359 chars)

    Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

17. 2026-03-24
    price $174,800 359-char remark

    Show marketing remark (359 chars)

    Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

18. 2026-03-19
    price $184,000 359-char remark

    Show marketing remark (359 chars)

    Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

19. 2026-03-19
    price $184,000 359-char remark

    Show marketing remark (359 chars)

    Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

20. 2026-02-23
    status Active 359-char remark

    Show marketing remark (359 chars)

    Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

21. 2026-02-23
    status Active 359-char remark

    Show marketing remark (359 chars)

    Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

22. 2026-02-23
    status Pending 359-char remark

    Show marketing remark (359 chars)

    Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

23. 2026-02-23
    status Pending 359-char remark

    Show marketing remark (359 chars)

    Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

24. 2026-01-14
    listed $213,750 Active 359-char remark

    Show marketing remark (359 chars)

    Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

25. 2025-12-06
    price $213,750 359-char remark

    Show marketing remark (359 chars)

    Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

26. 2025-11-18
    price $225,000 359-char remark

    Show marketing remark (359 chars)

    Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

27. 2025-11-05
    listed $300,000 Active 359-char remark

    Show marketing remark (359 chars)

    Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

ⓘ 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: $6,414 · $535/mo
• Projected year-2 tax: $6,414 · $535/mo
• Expected delta: $0/yr ($0/mo · 0.0%)

ⓘ 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 3/10 Moderate 7 d/yr ≥96°F today · 15 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 12% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 2 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $61,956
• − Mortgage interest: −$9,517
• − Property taxes: −$6,414
• − Insurance: −$850
• − Repairs & maintenance: −$4,956
• − Management: −$4,956
• − Depreciation: −$4,943
• Taxable income: $30,320
• Est. tax owed @ 24.0%: −$7,277
• After-tax cash flow: $23,713/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: Pine Plains Central School District
• NCES district ID: 3623040
• Math proficiency: 55% ▬ 0.00%
• Reading proficiency: 50% ▲ 1.00%
• Median HH income: $66,189
• Composite: 48.33/100
• National rank: #4688
• State rank: #372 of 755 in NY

Livability — Pine Plains

• Score: 64/100
• State rank: #746
• US rank: #14240

Category grades

Amenities F Commute F Cost of living D+ Crime A+ Employment B+ Housing A+ Health & safety D- User ratings D

Schools grade is shown separately in the Schools card above.

Census & demographics

• City population: 2,498
• Population (ZIP): 1,928

Population outlook (Dutchess County) Hauer SSP2

• Today (2025): 291,768 people
• By 2030: 287,131 · -1.6%
• By 2040: 274,881 · -5.8%
• By 2050: 259,971 · -10.9%
• By 2075: 235,366 · -19.3%
• By 2100: 208,786 · -28.4%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (81%)
• Race & ethnicity: White 81% Hispanic / Latino 11% Two or more races 5% Asian 3%
• Hispanic origin (detail): Mexican 3% Puerto Rican 8%
• Common ancestry: Romanian 4% Iranian 3% Lithuanian 3%
• Foreign-born: 6% · Canada, China
• Languages at home: 83% English-only · Spanish 10% Chinese 2% German/W. Germanic 1%

Political lean MEDSL · Dutchess

• 2024 margin: Lean D (+5.4) · D 52.7% · R 47.3%
• 2008→2024 swing: -3.2pp toward R · 2008: 8.6pp · 2024: 5.4pp
• All cycles: 2024: D+5.4 2020: D+9.6 2016: R+1.1 2012: D+6.6 2008: D+8.6

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 21.70%
• Current HPI: 270.6533
• 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

-41.7% since first listed

12 events — show timeline

• 2026-03-24 Price Changed $174,800 OneKey® MLS as Distributed by MLS Grid
• 2026-03-24 Price Changed $174,800 OneKey® MLS as Distributed by MLS Grid
• 2026-03-19 Price Changed $184,000 OneKey® MLS as Distributed by MLS Grid
• 2026-03-19 Price Changed $184,000 OneKey® MLS as Distributed by MLS Grid
• 2026-02-23 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2026-02-23 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2026-02-23 Pending — OneKey® MLS as Distributed by MLS Grid
• 2026-02-23 Pending — OneKey® MLS as Distributed by MLS Grid
• 2026-01-14 Listed $213,750 OneKey® MLS as Distributed by MLS Grid
• 2025-12-06 Price Changed $213,750 OneKey® MLS as Distributed by MLS Grid
• 2025-11-18 Price Changed $225,000 OneKey® MLS as Distributed by MLS Grid
• 2025-11-05 Listed $300,000 OneKey® MLS as Distributed by MLS Grid

Property tax history

+3.1%/yr

Latest (2025): $6,414 · +5.4% YoY. Source: county tax records.