506 5th St · Greenport, NY 11944

$995,000

3 bd · 1.5 ba · 1,800 sqft · SingleFamily · 103 Days on market

Built 1868 0.25 ac lot $553/sqft · at area comps Est $983k · at est. ↓ 13% since listing

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Why this score? — see what drove the B- 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
• DSCR +10.0/10.0
• 1% rule +9.7/10.0
• ARV discount +7.0/15.0
• Schools +4.5/10.0
• Livability +3.8/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

Built in 1868, this historic Greenport Village home is brimming with character and ready for its next chapter. Set on a .25-acre lot, the home features large spacious rooms, 3 bedrooms, 1.5 baths, beautiful built-ins, and a wood-burning stove. The home presents an exciting opportunity for thoughtful restoration and personalization, allowing the next owner to enhance and reimagine the space while honoring its original details. A rear deck extends the living space outdoors, while a substantial barn at the back of the property opens the door to endless potential as a studio, workshop, or inspired retreat. The expansive yard provides room to entertain, garden, or simply enjoy the privacy and openness seldom found within the village. Ideally located just a short distance to Greenport’s vibrant shops, restaurants, park, waterfront, bay beach, LIRR & Hampton Jitney. A unique opportunity to own a piece of Greenport history with space, flexibility, and an unbeatable village lifestyle.

Key facts

• Large spacious rooms
• Beautiful built-ins
• Expansive yard

Tags

• LARGE SPACIOUS ROOMS
• BEAUTIFUL BUILT-INS
• WOOD-BURNING STOVE
• REAR DECK
• SUBSTANTIAL BARN
• EXPANSIVE YARD

What this means for you Summary

Snapshot

• This is a 3-bed/1.5-bath single-family listed at $995k.

Deal economics

• At list price, monthly cash flow is $6k ($66k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($15k rent vs $995k).
• Recommended offer: $905k (9.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads 76/100 on livability (#217 in NY, #3,399 nationally) — a middle-class / working-renter tenant base. Strengths: crime A+, health & safety A+, commute B+; Watch: housing C-, cost of living F.
• Greenport Union Free School District (town): math 55% / reading 45% proficiency, ranked #450 of 755 in NY (top 60%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Market conditions: 67 active listings in the ZIP; 8 comparable units currently listed for rent nearby; rentals lingering (median 44d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 50% of comp listings sitting > 30 days — soft ceiling on asking rent; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $7k of loan paydown is wiped out by about $30k of value loss. Plan a longer hold.
• Suffolk County population projected to shrink 5% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $279k cash investment doubles in ~6 years — after that, you're playing with house money.

Negotiation context

• It's been on market 103 days — a 9% lower offer ($905k) is reasonable based on typical stale-listing flexibility.

Risks & watch-outs

• Watch-outs: built in 1868 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: severe wind risk, 80% chance of damaging wind over 30y; extreme-heat days projected 7→20/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $905,450 (9.0% below list)

Questions for the listing agent

1. It's been on market 103 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 1868 — 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. 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.
6. 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.
7. 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: 1.47% ✓
• Cap rate: 12.94%
• Cash-on-cash: 23.75%
• DSCR: 2.06
• GRM: 5.7

CMA / ARV

• ARV (median comp): $983,116
• List price: $995,000
• Delta: 1.21%
• Verdict: FAIR
• Comps: 20 within 1.0 mi

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
237 5th Ave	0.13mi	3/1.5	1,700 (-6%)	11mo	$1,250,000	$735	75
239 5th Ave	0.14mi	3/2.0	1,750 (-3%)	15mo	$895,000	$511	74
516 4th St	0.08mi	4/2.5 (+1)	1,840 (+2%)	14mo	$1,195,000	$649	72
426 Clark St	0.32mi	3/2.5	1,672 (-7%)	3mo	$1,645,000	$984	67
520 4th St	0.08mi	3/2.0	1,599 (-11%)	11mo	$890,000	$557	66
216 North St	0.41mi	3/3.5	1,724 (-4%)	0mo	$999,000	$579	66
336 2nd St	0.33mi	4/2.0 (+1)	1,800 (0%)	14mo	$578,000	$321	66
312 5th Ave	0.20mi	3/2.0	1,620 (-10%)	10mo	$875,000	$540	64
330 2nd St	0.33mi	2/2.0 (-1)	1,946 (+8%)	6mo	$675,000	$347	60
1605 Washington Ave	0.67mi	4/3.0 (+1)	1,740 (-3%)	6mo	$1,295,000	$744	47
73175 Main Rd	0.72mi	3/2.0	1,540 (-14%)	2mo	$595,000	$386	39
16 Washington Ave	0.73mi	3/1.5	1,550 (-14%)	12mo	$979,000	$632	33

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

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

5-year hold

• IRR: 16.9%
• Equity multiple: 1.68×
• Total profit: $189,678
• Equity at exit: $148,358

10-year hold

• IRR: 25.4%
• Equity multiple: 3.21×
• Total profit: $616,202
• Equity at exit: $86,029

Cash invested: $278,600 (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 11944

• Home prices YoY: -23.7%
• Active inventory: 67
• Price-to-rent: 5.7×

Monthly cashflow live

• Estimated rent: $14,620 medium
• Mortgage (P&I): −$5,218
• Tax from tax record: −$403 /mo · $4,839/yr
• Insurance: −$415
• HOA: −$0
• Vacancy / Maint / Mgmt: −$3,070
• Net cashflow: $5,514

Break-even live

Break-even rent $7,640

Max offer price $995,000

Occupancy floor 57%

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: $248,750
• Closing costs: $29,850
• Reserves months: —
• Total cash needed: —

Rent comps 8 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
248 5th Ave Greenport, NY	2.0	1.0	1306	$3,500	$2.68	43d	1	0.18mi
312 5th Ave Greenport, NY	4.0	2.0	1900	$12,000	$6.32	43d	1	0.22mi
237 6th St Greenport, NY	2.0	2.5	1452	$14,000	$9.64	11d	1	0.24mi
134 6th St Greenport, NY	3.0	2.0	1560	$18,500	$11.86	19d	1	0.39mi
131 6th St Unit G Greenport, NY	3.0	2.5	2238	$5,000	$2.23	24d	1	0.43mi
123 Sterling Ave #2 Greenport, NY	3.0	3.0	1528	$45,000	$29.45	43d	1	0.61mi
485 Sutton Pl Greenport, NY	4.0	2.5	2026	$20,000	$9.87	43d	1	1.05mi
3650 Bay Shore Rd Greenport, NY	3.0	3.0	2400	$10,000	$4.17	24d	1	1.39mi

Listing history 3 events

1. 2026-05-12
   status Pending 1001-char remark

   Show marketing remark (1001 chars)

   Built in 1868, this historic Greenport Village home is brimming with character and ready for its next chapter. Set on a .25-acre lot, the home features large spacious rooms, 3 bedrooms, 1.5 baths, beautiful built-ins, and a wood-burning stove. The home presents an exciting opportunity for thoughtful restoration and personalization, allowing the next owner to enhance and reimagine the space while honoring its original details. A rear deck extends the living space outdoors, while a substantial barn at the back of the property opens the door to endless potential as a studio, workshop, or inspired retreat. The expansive yard provides room to entertain, garden, or simply enjoy the privacy and openness seldom found within the village. Ideally located just a short distance to Greenport’s vibrant shops, restaurants, park, waterfront, bay beach, LIRR & Hampton Jitney. A unique opportunity to own a piece of Greenport history with space, flexibility, and an unbeatable village lifestyle.

2. 2026-04-07
   price $995,000 1001-char remark

   Show marketing remark (1001 chars)

   Built in 1868, this historic Greenport Village home is brimming with character and ready for its next chapter. Set on a .25-acre lot, the home features large spacious rooms, 3 bedrooms, 1.5 baths, beautiful built-ins, and a wood-burning stove. The home presents an exciting opportunity for thoughtful restoration and personalization, allowing the next owner to enhance and reimagine the space while honoring its original details. A rear deck extends the living space outdoors, while a substantial barn at the back of the property opens the door to endless potential as a studio, workshop, or inspired retreat. The expansive yard provides room to entertain, garden, or simply enjoy the privacy and openness seldom found within the village. Ideally located just a short distance to Greenport’s vibrant shops, restaurants, park, waterfront, bay beach, LIRR & Hampton Jitney. A unique opportunity to own a piece of Greenport history with space, flexibility, and an unbeatable village lifestyle.

3. 2026-01-28
   listed $1,150,000 Active 1001-char remark

   Show marketing remark (1001 chars)

   Built in 1868, this historic Greenport Village home is brimming with character and ready for its next chapter. Set on a .25-acre lot, the home features large spacious rooms, 3 bedrooms, 1.5 baths, beautiful built-ins, and a wood-burning stove. The home presents an exciting opportunity for thoughtful restoration and personalization, allowing the next owner to enhance and reimagine the space while honoring its original details. A rear deck extends the living space outdoors, while a substantial barn at the back of the property opens the door to endless potential as a studio, workshop, or inspired retreat. The expansive yard provides room to entertain, garden, or simply enjoy the privacy and openness seldom found within the village. Ideally located just a short distance to Greenport’s vibrant shops, restaurants, park, waterfront, bay beach, LIRR & Hampton Jitney. A unique opportunity to own a piece of Greenport history with space, flexibility, and an unbeatable village lifestyle.

ⓘ 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: $4,839 · $403/mo
• Projected year-2 tax: $10,827 · $902/mo
• Expected delta: +$5,988/yr (+$499/mo · 123.8%)

ⓘ 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 1/10 Low
• 🌡 Heat 5/10 Major 7 d/yr ≥90°F today · 20 d/yr by 30 yrs out
• 💨 Wind 8/10 Severe 80% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 3 unhealthy d/yr today · 4 by 30 yrs out

Taxation est. · year 1

• Rental income: $175,443
• − Mortgage interest: −$55,735
• − Property taxes: −$4,839
• − Insurance: −$4,975
• − Repairs & maintenance: −$14,035
• − Management: −$14,035
• − Depreciation: −$28,945
• Taxable income: $52,877
• Est. tax owed @ 24.0%: −$12,691
• After-tax cash flow: $53,481/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: Greenport Union Free School District
• NCES district ID: 3612840
• Math proficiency: 55% ▲ 5.00%
• Reading proficiency: 45% ▼ -5.00%
• Median HH income: $54,490
• Composite: 45.25/100
• National rank: #5759
• State rank: #450 of 755 in NY

Livability — Greenport

• Score: 76/100
• State rank: #217
• US rank: #3399

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Greenport, NY
• City population: 4,744
• Population (ZIP): 4,744

Population outlook (Suffolk County) Hauer SSP2

• Today (2025): 1,505,262 people
• By 2030: 1,498,318 · -0.5%
• By 2040: 1,471,101 · -2.3%
• By 2050: 1,424,848 · -5.3%
• By 2075: 1,337,157 · -11.2%
• By 2100: 1,217,720 · -19.1%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (69%)
• Race & ethnicity: White 69% Hispanic / Latino 23% Two or more races 6% Black 4% Asian 2%
• Hispanic origin (detail): Mexican 5% Puerto Rican 2%
• Common ancestry: Romanian 6% Lithuanian 2% Subsaharan African 2%
• Foreign-born: 19% · Canada, China
• Languages at home: 69% English-only · Spanish 22% German/W. Germanic 3% Russian/Polish/Slavic 2%

Political lean MEDSL · Suffolk

• 2024 margin: Lean R (+10.0) · D 45.0% · R 55.0%
• 2008→2024 swing: -16.0pp toward R · 2008: 6.0pp · 2024: -10.0pp
• All cycles: 2024: R+10.0 2020: R+0.0 2016: R+8.2 2012: D+2.9 2008: D+6.0

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -143.97%
• Current HPI: 462.3431
• 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

-13.5% since first listed

3 events — show timeline

• 2026-05-12 Pending — OneKey® MLS as Distributed by MLS Grid
• 2026-04-07 Price Changed $995,000 OneKey® MLS as Distributed by MLS Grid
• 2026-01-28 Listed $1,150,000 OneKey® MLS as Distributed by MLS Grid

Property tax history

+4.6%/yr

Latest (2025): $4,839 · +0.0% YoY. Source: county tax records.