151 Bay Ave · Greenport, NY 11944

$2,100,000

5 bd · 4.5 ba · 3,500 sqft · SingleFamily · 641 Days on market

Built 1897 9,583 sqft lot $600/sqft · 12% below area Est $2377k · 12% under

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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
• ARV discount +12.7/15.0
• DSCR +10.0/10.0
• 1% rule +9.7/10.0
• 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

This beautiful Queen Ann Victorian home includes a priceless location in the heart of Greenport Village. Built in 1897, many of the fine architectural detail in this home is still present today. There are 5 bedrooms in which three of them are ensuites. The property is loaded with gorgeous specimen plantings. There is a large barn behind the pergola covered courtyard. This home makes a perfect Bed and Breakfast (formerly Rubys Cove) with front and back staircases, large parlor rooms and an updated kitchen. Bay Avenue is an amazing location just steps to Main and Front Street shops, fine restaurants, and all transportation., Additional information: Appearance:Excellent,Interior Features:Lr/Dr,Separate Hotwater Heater:y

Key facts

• 9,583 sq ft lot
• Built 1897
• Listed 641 days

What this means for you Summary

Snapshot

• This is a 5-bed/4.5-bath single-family listed at $2.10M.

Deal economics

• At list price, monthly cash flow is $11k ($137k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($31k rent vs $2.10M).
• Recommended offer: $1.85M (12.0% 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.
• Zoned schools: Greenport Elementary School (math 47% / reading 62%, grade C, #908 of 2,108 statewide, top 46%, 339 students, 61% FRL); Greenport High School (math 52% / reading 54%, grade C-, #934 of 1,100 statewide, top 86%, 356 students, 63% FRL).
• Market conditions: 69 active listings in the ZIP; 6 comparable units currently listed for rent nearby; rentals lingering (median 46d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 100% 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 $15k of loan paydown is wiped out by about $63k 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 $588k cash investment doubles in ~6 years — after that, you're playing with house money.

Negotiation context

• It's been on market 641 days — a 12% lower offer ($1.85M) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 11y ago with the ask held roughly flat each time — persistent listings suggest the price (not the market) is what's stuck; bring a comps-based counter.
• Current owner paid $1.35M; list at $2.10M implies a 56% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1897 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: severe wind risk, 80% chance of damaging wind over 30y; extreme-heat days projected 7→21/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $1,848,000 (12.0% below list)

Questions for the listing agent

1. It's been on market 641 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 1897 — 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: 12.80%
• Cash-on-cash: 23.24%
• DSCR: 2.03
• GRM: 5.7

CMA / ARV

• ARV (median comp): $2,377,337
• List price: $2,100,000
• Delta: -11.67%
• Verdict: UNDERPRICED
• Comps: 9 within 1.0 mi

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
340 Robinson Rd	0.62mi	4/3.0 (-1)	3,500 (0%)	4mo	$2,500,000	$714	57

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: 16.2%
• Equity multiple: 1.65×
• Total profit: $384,510
• Equity at exit: $313,117

10-year hold

• IRR: 24.8%
• Equity multiple: 3.15×
• Total profit: $1,266,798
• Equity at exit: $181,570

Cash invested: $588,000 (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 11944

• Home prices YoY: -23.7%
• Active inventory: 69
• Price-to-rent: 5.7×

Monthly cashflow live

• Estimated rent: $30,844 medium
• Mortgage (P&I): −$11,013
• Tax from tax record: −$1,092 /mo · $13,102/yr
• Insurance: −$875
• HOA: −$0
• Vacancy / Maint / Mgmt: −$6,477
• Net cashflow: $11,388

Break-even live

Break-even rent $16,430

Max offer price $2,100,000

Occupancy floor 58%

Sensitivity live

Price	-10% $12,576	-5% $11,982	+0% $11,388	+5% $10,793	+10% $10,199
Rent	-10% $8,951	-5% $10,169	+0% $11,388	+5% $12,606	+10% $13,824
Rate	-1.0pp $12,445	-0.5pp $11,922	base $11,388	+0.5pp $10,843	+1.0pp $10,290

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: $525,000
• Closing costs: $63,000
• Reserves months: —
• Total cash needed: —

Rent comps 6 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
165 Marine Pl Greenport, NY	4.0	4.5	3800	$20,000	$5.26	46d	1	0.94mi
950 Tasker Ln Greenport, NY	4.0	3.5	3500	$36,000	$10.29	46d	1	1.16mi
64230 North Rd Greenport, NY	4.0	3.0	2800	$6,500	$2.32	46d	1	1.23mi
1000 Sound Dr Greenport, NY	5.0	4.5	3700	$45,000	$12.16	46d	1	1.29mi
2700 Sound Dr Greenport, NY	5.0	3.0	3700	$25,000	$6.76	46d	1	1.34mi
63615 North Rd Greenport, NY	4.0	4.5	3500	$7,000	$2.00	46d	1	1.37mi

Listing history 30 events

1. 2026-06-22
   days on market $2,100,000 Active 641 DOM
2. 2026-06-21
   days on market $2,100,000 Active 640 DOM
3. 2026-06-21
   days on market $2,100,000 Active 639 DOM
4. 2026-06-18
   days on market $2,100,000 Active 637 DOM
5. 2026-06-17
   days on market $2,100,000 Active 636 DOM
6. 2026-06-16
   days on market $2,100,000 Active 635 DOM
7. 2026-06-15
   days on market $2,100,000 Active 634 DOM
8. 2026-06-13
   days on market $2,100,000 Active 632 DOM
9. 2026-06-12
   days on market $2,100,000 Active 631 DOM
10. 2026-06-09
    days on market $2,100,000 Active 628 DOM
11. 2026-06-08
    days on market $2,100,000 Active 627 DOM
12. 2026-06-07
    days on market $2,100,000 Active 626 DOM
13. 2026-06-05
    days on market $2,100,000 Active 624 DOM
14. 2026-06-04
    days on market $2,100,000 Active 622 DOM
15. 2026-06-02
    days on market $2,100,000 Active 621 DOM
16. 2026-06-01
    days on market $2,100,000 Active 620 DOM
17. 2026-05-31
    days on market $2,100,000 Active 619 DOM
18. 2024-09-19
    listed $2,100,000 Active 732-char remark

    Show marketing remark (732 chars)

    This beautiful Queen Ann Victorian home includes a priceless location in the heart of Greenport Village. Built in 1897, many of the fine architectural detail in this home is still present today. There are 5 bedrooms in which three of them are ensuites. The property is loaded with gorgeous specimen plantings. There is a large barn behind the pergola covered courtyard. This home makes a perfect Bed and Breakfast (formerly Rubys Cove) with front and back staircases, large parlor rooms and an updated kitchen. Bay Avenue is an amazing location just steps to Main and Front Street shops, fine restaurants, and all transportation., Additional information: Appearance:Excellent,Interior Features:Lr/Dr,Separate Hotwater Heater:y

19. 2021-01-16
    soldstatus $1,350,000
20. 2019-07-01
    historical
21. 2019-06-30
    historical
22. 2019-03-05
    price $1,199,000
23. 2019-03-05
    price $1,999,000
24. 2018-07-16
    listed $1,350,000 New
25. 2018-07-16
    listed $1,199,000
26. 2016-11-25
    historical
27. 2016-02-28
    price $995,000
28. 2015-11-25
    listed $865,000 New
29. 2008-12-23
    soldstatus $750,000
30. 1999-12-30
    soldstatus $210,000

ⓘ 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: $13,102 · $1,092/mo
• Projected year-2 tax: $24,296 · $2,025/mo
• Expected delta: +$11,194/yr (+$933/mo · 85.4%)

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

Climate risk First Street

• 🌊 Flood 4/10 Moderate FEMA zone X (unshaded) · 17% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 6/10 Major 7 d/yr ≥90°F today · 21 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: $370,132
• − Mortgage interest: −$117,633
• − Property taxes: −$13,102
• − Insurance: −$10,500
• − Repairs & maintenance: −$29,611
• − Management: −$29,611
• − Depreciation: −$61,091
• Taxable income: $108,585
• Est. tax owed @ 24.0%: −$26,060
• After-tax cash flow: $110,590/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

+900.0% since first listed

13 events — show timeline

• 2024-09-19 Listed $2,100,000 OneKey® MLS as Distributed by MLS Grid
• 2021-01-16 Sold (Public Records) $1,350,000 Public Records
• 2019-07-01 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2019-06-30 Listing Removed — Cincy MLS
• 2019-03-05 Price Changed $1,199,000 OneKey® MLS as Distributed by MLS Grid
• 2019-03-05 Price Changed $1,999,000 OneKey® MLS as Distributed by MLS Grid
• 2018-07-16 Listed $1,199,000 Cincy MLS
• 2018-07-16 Listed $1,350,000 OneKey® MLS as Distributed by MLS Grid
• 2016-11-25 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2016-02-28 Price Changed $995,000 OneKey® MLS as Distributed by MLS Grid
• 2015-11-25 Listed $865,000 OneKey® MLS as Distributed by MLS Grid
• 2008-12-23 Sold (Public Records) $750,000 Public Records
• 1999-12-30 Sold (Public Records) $210,000 Public Records

Property tax history

+5.7%/yr

Latest (2025): $13,102 · +0.0% YoY. Source: county tax records.