239 Rokeby Rd · Red Hook, NY 12571

$650,000

4 bd · 3.5 ba · 3,045 sqft · MultiFamily public records · 92 Days on market

Built 1956 1.60 ac lot $213/sqft · at area comps Est $630k · at est.

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Why this score? — see what drove the C- 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 +18.7/30.0
• ARV discount +6.1/15.0
• DSCR +5.9/10.0
• Schools +5.1/10.0
• 1% rule +5.0/10.0
• Livability +4.5/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

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

Whether you’re building your dream home, starting your next big project, or creating your personal sanctuary, this property is the perfect foundation. Looking for endless potential and room to grow? This as-is property is the one you've been waiting for! Whether you're a contractor, artist, or simply someone looking for a space to live, work, and create, this home offers it all. Featuring a massive garage with a loft: Perfect for projects, storage, or running your business. Complete with electricity and water, it's ready for anything you can dream up! 2 Bedroom & full bath Accessory Apartment: Ideal for extra income, guests, or a private retreat. The possibilities are endless! Incredible Views & Green Space: Surrounded by forever green space, your views are serene and unobstructed. Sit on the back deck and enjoy the views. Plus, there’s a fenced-in area for pets, giving them plenty of room to roam. Spacious Home with 3 Bedrooms & 2 Full Baths. The primary bedroom features an enormous space, offering custom closet potential and a private 3/4 bath. Create your dream sanctuary! Can be entirely one level living. Huge Basement with Bar: Imagine transforming the basement into a recreation room, home office, or anything else you envision. It’s got an old bar – perfect for entertaining or creating a unique space that suits your style. Just minutes to Red Hook village, and conveniently located near Rhinebeck and Kingston – you’ll have easy access to everything while enjoying the peace and privacy of your own property. This solidly built house is waiting for you to bring your ideas and turn it into something extraordinary. Come and build your brand, live your dreams, and make this space YOURS!

Key facts

• Green space
• Huge basement
• Fenced-in area

Tags

• MASSIVE GARAGE
• ACCESSORY APARTMENT
• INCREDIBLE VIEWS
• GREEN SPACE
• FENCED-IN AREA
• HUGE BASEMENT

What this means for you Summary

Snapshot

• This is a 4-bed/3.5-bath multifamily listed at $650k.

Deal economics

• At list price, monthly cash flow is $637 ($8k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($7k rent vs $650k).
• Recommended offer: $592k (9.0% below list) — sets the bar for market timing.
• Cap rate 7.5% vs local median 2.8% in Red Hook — 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 89/100 on livability (#5 in NY, #113 nationally) — a professional / high-income tenant draw. Strengths: crime A+, commute A+, employment A+; Watch: cost of living D-.
• Red Hook Central School District (town): math 58% / reading 57% proficiency, ranked #245 of 590 in NY (top 42%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 16% free/reduced lunch — higher-income household profile.
• Market conditions: 70 active listings in the ZIP; high-income renter base; 620 units permitted in Dutchess County in 2024 (242 in 5+ unit buildings).
• At $6,525/mo this rent would consume 66% of the median local household income ($119k/yr) (locally 241% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $4k of loan paydown is wiped out by about $20k of value loss. Plan a longer hold.
• Dutchess County population projected at -11% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.

Negotiation context

• It's been on market 92 days — a 9% lower offer ($592k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts; this cycle's ask has dropped $49k (7%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $220k; list at $650k implies a 195% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1956 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $591,500 (9.0% below list)

Questions for the listing agent

1. It's been on market 92 days. Have you received any prior offers? Is the seller open to a 9% concession, seller financing, or rate buy-down credit?
2. Built in 1956 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
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. Schools are B-rated — typically a magnet for longer-tenancy family renters. What's the average tenant stay here, and is there a school-zone premium baked into asking?
6. 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.
7. 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.
8. 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: 1.00% ✓
• Cap rate: 7.47%
• Cash-on-cash: 4.20%
• DSCR: 1.19
• GRM: 8.3

CMA / ARV

• ARV (median comp): $629,806
• List price: $650,000
• Delta: 3.21%
• Verdict: FAIR
• Comps: 6 within 1.0 mi

Projected returns pro-forma

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

5-year hold

• IRR: -9.7%
• Equity multiple: 0.64×
• Total profit: $-64,653
• Equity at exit: $96,917

10-year hold

• IRR: -0.3%
• Equity multiple: 0.98×
• Total profit: $-3,606
• Equity at exit: $56,200

Cash invested: $182,000 (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 12571

• Home prices YoY: -15.6%
• Active inventory: 70
• Price-to-rent: 24.9×

Monthly cashflow live

• Estimated rent: $6,525 medium
• Mortgage (P&I): −$3,409
• Tax from tax record: −$838 /mo · $10,061/yr
• Insurance: −$271
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,370
• Net cashflow: $637

Break-even live

Break-even rent $5,719

Max offer price $650,000

Occupancy floor 85%

Sensitivity live

Price	-10% $1,005	-5% $821	+0% $637	+5% $453	+10% $269
Rent	-10% $121	-5% $379	+0% $637	+5% $895	+10% $1,152
Rate	-1.0pp $964	-0.5pp $802	base $637	+0.5pp $468	+1.0pp $297

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

Units	Beds	Baths	Est. rent
▸ 3× units	2	1	$6,525
Total (3 units)			$6,525

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: $162,500
• Closing costs: $19,500
• Reserves months: —
• Total cash needed: —

Listing history 22 events

1. 2026-06-18
   days on market $650,000 Active 92 DOM
2. 2026-06-17
   days on market $650,000 Active 91 DOM
3. 2026-06-16
   days on market $650,000 Active 90 DOM
4. 2026-06-15
   price $650,000 Active 89 DOM
5. 2026-06-15
   days on market $675,000 Active 89 DOM
6. 2026-06-14
   days on market $675,000 Active 87 DOM
7. 2026-06-13
   days on market $675,000 Active 86 DOM
8. 2026-06-10
   days on market $675,000 Active 84 DOM
9. 2026-06-09
   days on market $675,000 Active 83 DOM
10. 2026-06-08
    days on market $675,000 Active 82 DOM
11. 2026-06-07
    days on market $675,000 Active 81 DOM
12. 2026-06-05
    days on market $675,000 Active 78 DOM
13. 2026-06-03
    days on market $675,000 Active 77 DOM
14. 2026-06-02
    days on market $675,000 Active 76 DOM
15. 2026-06-01
    days on market $675,000 Active 75 DOM
16. 2026-05-31
    days on market $675,000 Active 74 DOM
17. 2026-05-30
    days on market $675,000 Active 73 DOM
18. 2026-03-18
    listed $699,000 Active 1763-char remark

    Show marketing remark (1807 chars)

    Whether you’re building your dream home, starting your next big project, or creating your personal sanctuary, this property is the perfect foundation. Looking for endless potential and room to grow? This as-is property is the one you've been waiting for! Whether you're a contractor, artist, or simply someone looking for a space to live, work, and create, this home offers it all. Featuring a massive garage with a loft: Perfect for projects, storage, or running your business. Complete with electricity and water, it's ready for anything you can dream up! 2 Bedroom & full bath Accessory Apartment: Ideal for extra income, guests, or a private retreat. The possibilities are endless! Incredible Views & Green Space: Surrounded by forever green space, your views are serene and unobstructed. Sit on the back deck and enjoy the views. Plus, there’s a fenced-in area for pets, giving them plenty of room to roam. Spacious Home with 3 Bedrooms & 2 Full Baths. The primary bedroom features an enormous space, offering custom closet potential and a private 3/4 bath. Create your dream sanctuary! Can be entirely one level living. Huge Basement with Bar: Imagine transforming the basement into a recreation room, home office, or anything else you envision. It’s got an old bar – perfect for entertaining or creating a unique space that suits your style. Just minutes to Red Hook village, and conveniently located near Rhinebeck and Kingston – you’ll have easy access to everything while enjoying the peace and privacy of your own property. This solidly built house is waiting for you to bring your ideas and turn it into something extraordinary. Come and build your brand, live your dreams, and make this space YOURS! Listed in MLS as single family too MLS #973208

19. 2026-03-18
    listed $699,000 Active 1807-char remark

    Show marketing remark (1807 chars)

    Whether you’re building your dream home, starting your next big project, or creating your personal sanctuary, this property is the perfect foundation. Looking for endless potential and room to grow? This as-is property is the one you've been waiting for! Whether you're a contractor, artist, or simply someone looking for a space to live, work, and create, this home offers it all. Featuring a massive garage with a loft: Perfect for projects, storage, or running your business. Complete with electricity and water, it's ready for anything you can dream up! 2 Bedroom & full bath Accessory Apartment: Ideal for extra income, guests, or a private retreat. The possibilities are endless! Incredible Views & Green Space: Surrounded by forever green space, your views are serene and unobstructed. Sit on the back deck and enjoy the views. Plus, there’s a fenced-in area for pets, giving them plenty of room to roam. Spacious Home with 3 Bedrooms & 2 Full Baths. The primary bedroom features an enormous space, offering custom closet potential and a private 3/4 bath. Create your dream sanctuary! Can be entirely one level living. Huge Basement with Bar: Imagine transforming the basement into a recreation room, home office, or anything else you envision. It’s got an old bar – perfect for entertaining or creating a unique space that suits your style. Just minutes to Red Hook village, and conveniently located near Rhinebeck and Kingston – you’ll have easy access to everything while enjoying the peace and privacy of your own property. This solidly built house is waiting for you to bring your ideas and turn it into something extraordinary. Come and build your brand, live your dreams, and make this space YOURS! Listed in MLS as single family too MLS #973208

20. 2025-05-07
    historical
21. 2025-03-02
    listed $699,000 Active
22. 2004-06-02
    soldstatus $220,000

ⓘ 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: $10,061 · $838/mo
• Projected year-2 tax: $10,523 · $877/mo
• Expected delta: +$462/yr (+$39/mo · 4.6%)

ⓘ 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 2/10 Low
• 🌡 Heat 4/10 Moderate 7 d/yr ≥99°F today · 15 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 10% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 1 unhealthy d/yr today · 1 by 30 yrs out

Taxation est. · year 1

• Rental income: $78,300
• − Mortgage interest: −$36,410
• − Property taxes: −$10,061
• − Insurance: −$3,250
• − Repairs & maintenance: −$6,264
• − Management: −$6,264
• − Depreciation: −$18,909
• Taxable loss: −$2,858
• Est. tax savings @ 24.0%: +$686
• After-tax cash flow: $8,328/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: Red Hook Central School District
• NCES district ID: 3624240
• Math proficiency: 58% ▼ -4.00%
• Reading proficiency: 57% ▼ -8.00%
• Median HH income: $69,040
• Composite: 50.84/100
• National rank: #1801
• State rank: #245 of 590 in NY

Livability — Red Hook

• Score: 89/100
• State rank: #5
• US rank: #113

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• County: Dutchess County · 188,048 people
• City population: 10,108
• Metro: Poughkeepsie-Newburgh-Middletown, NY
• Population (ZIP): 10,108
• Household income: $118,967
• Rent vs Own: 19.9% rent · 80.1% own
• Severe rent burden: 241.0

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 (85%)
• Race & ethnicity: White 85% Two or more races 7% Hispanic / Latino 4% Black 2% Asian 2%
• Common ancestry: Italian 5% Romanian 4% Iranian 4%
• Foreign-born: 6% · Canada, China
• Languages at home: 94% English-only · Spanish 2% Other Indo-European 1% Russian/Polish/Slavic 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: ▼ -61.80%
• Current HPI: 333.5841
• Rent YoY: —
• Metro: Poughkeepsie-Newburgh-Middletown, NY
• 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

+217.7% since first listed

5 events — show timeline

• 2026-03-18 Listed $699,000 OneKey® MLS as Distributed by MLS Grid
• 2026-03-18 Listed $699,000 OneKey® MLS as Distributed by MLS Grid
• 2025-05-07 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2025-03-02 Listed $699,000 OneKey® MLS as Distributed by MLS Grid
• 2004-06-02 Sold (Public Records) $220,000 Public Records

Property tax history

+2.8%/yr

Latest (2025): $10,061 · +3.2% YoY. Source: county tax records.