Is 90 Caiola Ct in Greenport West, NY a good investment?

CashFlowRE grades it B+ with a 18.7% cap rate and $17,510/mo modeled cash flow at a $1,695,000 list price. See the full underwriting and recommended offer on the page.

What is the cap rate for 90 Caiola Ct?

The modeled cap rate is 18.7% — annual NOI divided by price, using CashFlowRE's rent and expense estimates.

What would this property rent for?

Estimated market rent is $35,834/month, from CashFlowRE's rent model.

B+ Composite 79.79

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 +15.0/15.0
1% rule +10.0/10.0
DSCR +10.0/10.0
Schools +5.4/10.0
Condition / age +4.0/5.0
Livability +2.9/5.0
Rent growth +2.5/5.0
Appreciation +0.0/10.0

$1,695,000

90 Caiola Ct · Greenport West, NY 11944

4 bd · 3.0 ba · 3,392 sqft · SingleFamily · 22 Days on market

Built 2007 Good condition 0.62 ac lot 2-car garage $500/sqft · 17% below area Est $2.044M · 17% under $29/mo HOA

🖨 Deal sheet (PDF) 📄 Offer letter ✓ Due diligence

Listing remarks

Welcome to 90 Caiola Court, nestled within the highly sought-after waterfront community of Rock Cove Estates in the charming hamlet of Greenport. Built in 2007 and impeccably maintained, this Post Modern residence makes an immediate impression with its mature specimen landscaping, manicured grounds, and timeless curb appeal. Step inside to a grand, light-filled foyer featuring soaring ceilings, an elegant open staircase, and an inviting sense of scale that sets the tone for the home's thoughtfully designed interior.

Key facts

Open staircase
Formal dining room
Waterfront community

What this means for you Summary

Snapshot

This is a 4-bed/3.0-bath single-family listed at $1.70M. Condition is rated good.

Deal economics

At list price, monthly cash flow is $18k ($210k/yr) — positive.
The deal already cash-flows at list — no discount required.
Meets the 1% rule at list price ($36k rent vs $1.70M).
Recommended offer: $1.67M (1.5% below list) — sets the bar for market timing.
Cap rate 18.7% vs local median 8.0% in Greenport West — 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 58/100 on livability (#1,073 in NY) — a working-class tenant base; expect higher turnover. Strengths: crime A+, employment A+; Watch: amenities F, commute F, 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: 74 active listings in the ZIP; 6 comparable units currently listed for rent nearby; rentals lingering (median 93d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 100% of comp listings sitting > 30 days — soft ceiling on asking rent; solid renter incomes; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).
At $35,834/mo this rent would consume 538% of the median local household income ($80k/yr) (locally 21% 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 $12k of loan paydown is wiped out by about $51k 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 $475k cash investment doubles in ~3 years — after that, you're playing with house money.

Negotiation context

It's been on market 22 days — a 2% lower offer ($1.67M) is reasonable based on typical stale-listing flexibility.
2 sale attempts; this cycle's ask has dropped $90k (5%) from the opening price — seller is motivated, your offer sets the floor, not the list.
Current owner paid $846k; list at $1.70M implies a 100% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

Climate carrying-cost: severe wind risk, 80% chance of damaging wind over 30y; extreme-heat days projected 7→19/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $1,669,575 (1.5% below list)

Questions for the listing agent

What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
Schools are D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
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.
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.
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: 2.11% ✓
Cap rate: 18.69%
Cash-on-cash: 44.27%
DSCR: 2.97
GRM: 3.9

CMA / ARV

ARV (median comp): $2,043,963
List price: $1,695,000
Delta: -12.67%
Verdict: UNDERPRICED
Comps: 20 within 1.0 mi

Show comp detail 7 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
1000 Green Hill Ln	0.07mi	4/2.5	3,400 (+0%)	6mo	$1,450,000	$426	90
155 Caiola Ct	0.05mi	4/3.5	3,500 (+3%)	12mo	$1,885,000	$539	80
695 Sound Dr	0.20mi	5/3.0 (+1)	3,393 (0%)	10mo	$2,163,000	$637	77
3200 Sound Dr	0.32mi	4/3.0	3,145 (-7%)	2mo	$2,142,500	$681	71
1740 Inlet Pond Rd	0.11mi	4/3.0	3,756 (+11%)	12mo	$3,000,000	$799	66
2375 Sound Dr	0.19mi	5/5.5 (+1)	3,200 (-6%)	2mo	$2,150,000	$672	65
135 Sunset Ln	0.25mi	4/5.0	3,200 (-6%)	18mo	$975,000	$305	56

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: 41.2%
Equity multiple: 2.77×
Total profit: $840,547
Equity at exit: $252,730

10-year hold

IRR: 47.5%
Equity multiple: 5.57×
Total profit: $2,167,884
Equity at exit: $146,553

Cash invested: $474,600 (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 →

Seller's market Market conditions within 1.0 mi — comparable homes for sale

Active competition Active MLS

For sale now: 1 active · 3 under contract
Months of supply: 1.5 mo (67%/mo absorbed)
Median asking: $2,150,000 ($778/sqft)
Median days on market: 318 d
This list price: lowest-priced of the active set
ARV vs active asking: -22.5% vs current asking $/sqft

Closed sales set the value; these active listings set current market conditions and a practical price ceiling.

ZIP-level market 11944

Home prices YoY: -23.7%
Active inventory: 74
Price-to-rent: 3.9×

Monthly cashflow live

Estimated rent: $35,834 medium interval (Pro) →
Mortgage (P&I): −$8,889
Tax from tax record: −$1,175 /mo · $14,096/yr
Insurance: −$706
HOA: −$29
Lot rent: −$0
Vacancy / Maint / Mgmt: −$7,525
Net cashflow: $17,510

Break-even live

Break-even rent $13,669

Max offer price $1,695,000

Occupancy floor 46%

Sensitivity live

Price	-10% $18,470	-5% $17,990	+0% $17,510	+5% $17,030	+10% $16,551
Rent	-10% $14,679	-5% $16,095	+0% $17,510	+5% $18,926	+10% $20,341
Rate	-1.0pp $18,364	-0.5pp $17,941	base $17,510	+0.5pp $17,071	+1.0pp $16,624

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: $423,750
Closing costs: $50,850
Club membership (one-time): —
Reserves months: —
Total cash needed: —

Loan-product check · same deal, 3 products live

Conventional

25% down · 7.5% · 30yr

Cash invested: —
Monthly P&I: —
Monthly cashflow: —
DSCR: —
Eligible?: —

Personal DTI + credit; lowest rate.

DSCR

20% down · 8.5% · 30yr

Cash invested: —
Monthly P&I: —
Monthly cashflow: —
DSCR: —
Eligible?: —

No personal income docs; deal must DSCR.

Hard money

10% down · 12.0% · 12mo

Cash invested: —
Monthly P&I: —
Monthly cashflow: —
DSCR: —
Eligible?: —

Short-term bridge; refi at stabilization.

Rent comps 6 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
950 Tasker Ln Greenport, NY	4.0	3.5	3500	$36,000	$10.29	93d	1	0.19mi
1000 Sound Dr Greenport, NY	5.0	4.5	3700	$45,000	$12.16	93d	1	0.22mi
2700 Sound Dr Greenport, NY	5.0	3.0	3700	$25,000	$6.76	93d	1	0.26mi
64230 North Rd Greenport, NY	4.0	3.0	2800	$6,500	$2.32	93d	1	0.79mi
63615 North Rd Greenport, NY	4.0	4.5	3500	$7,000	$2.00	93d	1	0.87mi
165 Marine Pl Greenport, NY	4.0	4.5	3800	$10,000	$2.63	36d	1	1.35mi

Property features AI

Finance

HOA & community: Association: Rockcove EstatesAnnual association fee $350 (includes other services)

Exterior

Parking: DrivewayGarage2-car garage
Utilities: PSEG electricNatural gas availableWater connectedSewer: septic tankCable connectedPhone connectedUnderground utilities
Home design: Single family residencePartial attic with pull-down stairsFull walk-out basement
Construction: Cedar sidingFrame constructionFiberglass insulation
Exterior features: DeckFenced yardFront yardLandscaped groundsLevel lotNear golf courseNear public transitNear shopsPrivate setting

Interior

Kitchen: DishwasherElectric ovenElectric rangeExhaust fanFreezerRefrigeratorKitchen islandEat-in kitchenStone counters
Bedrooms: His and hers closets (primary suite)Walk-in closets
Flooring: TileWood
Bathrooms: 3 full bathroomsDouble vanitySoaking tubPrimary bathroom
Heating & cooling: Central airForced air heatingNatural gas heating
Interior features: Cathedral ceilingsCentral vacuumCrown moldingDouble vanityEat-in kitchenEntrance foyerFormal dining roomHigh ceilingsHigh speed internetHis and hers closetsKitchen islandPrimary bathroomRecessed lightingSoaking tubStone countersWalk-in closetsFirst floor full bath
Laundry & utility: Laundry roomWasherDryerCentral vacuum

HOA detail $29/mo · $348/yr

Likely covers: waterlandscaping

Listing history 42 events

2026-08-08

days on market $1,695,000 Active 22 DOM
2026-08-07

days on market $1,695,000 Active 21 DOM
2026-08-06

days on market $1,695,000 Active 20 DOM
2026-08-05

days on market $1,695,000 Active 19 DOM
2026-08-04

pricedays on market $1,695,000 Active 18 DOM
2026-08-03

days on market $1,785,000 Active 17 DOM
2026-07-31

days on market $1,785,000 Active 14 DOM
2026-07-29

days on market $1,785,000 Active 12 DOM
2026-07-27

days on market $1,785,000 Active 10 DOM
2026-07-25

days on market $1,785,000 Active 8 DOM
2026-07-24

days on market $1,785,000 Active 7 DOM
2026-07-23

days on market $1,785,000 Active 6 DOM
2026-07-22

days on market $1,785,000 Active 5 DOM
2026-07-21

days on market $1,785,000 Active 4 DOM
2026-07-20

days on market $1,785,000 Active 3 DOM
2026-07-18

days on marketlisting id $1,785,000 Active 1 DOM
2026-07-01

days on market $1,785,000 Active 62 DOM
2026-06-30

days on market $1,785,000 Active 61 DOM
2026-06-29

days on market $1,785,000 Active 60 DOM
2026-06-28

days on market $1,785,000 Active 59 DOM
2026-06-27

days on market $1,785,000 Active 58 DOM
2026-06-26

days on market $1,785,000 Active 57 DOM
2026-06-22

days on market $1,785,000 Active 53 DOM
2026-06-21

days on market $1,785,000 Active 52 DOM
2026-06-21

days on market $1,785,000 Active 51 DOM
2026-06-18

days on market $1,785,000 Active 49 DOM
2026-06-17

days on market $1,785,000 Active 48 DOM
2026-06-16

days on market $1,785,000 Active 47 DOM
2026-06-15

days on market $1,785,000 Active 46 DOM
2026-06-13

days on market $1,785,000 Active 44 DOM
2026-06-12

days on market $1,785,000 Active 43 DOM
2026-06-09

days on market $1,785,000 Active 40 DOM
2026-06-08

days on market $1,785,000 Active 39 DOM
2026-06-07

days on market $1,785,000 Active 38 DOM
2026-06-05

days on market $1,785,000 Active 36 DOM
2026-06-04

days on market $1,785,000 Active 34 DOM
2026-06-02

days on market $1,785,000 Active 33 DOM
2026-06-01

days on market $1,785,000 Active 32 DOM
2026-05-31

days on market $1,785,000 Active 31 DOM
2026-04-30

listed $1,785,000 Active 1295-char remark
2008-05-14

soldstatus $845,900
2002-09-26

soldstatus $140,000

ⓘ 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: $14,096 · $1,175/mo
Projected year-2 tax: $21,371 · $1,781/mo
Expected delta: +$7,274/yr (+$606/mo · 51.6%)

ⓘ 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 1/10 Low
🌡 Heat 5/10 Major 7 d/yr ≥90°F today · 19 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

Nearby sold comps map

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Walkable amenities ~0.75 mi

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Taxation est. · year 1

Rental income: $430,008
− Mortgage interest: −$94,946
− Property taxes: −$14,096
− Insurance: −$8,475
− Repairs & maintenance: −$34,401
− Management: −$34,401
− HOA: −$348
− Depreciation: −$49,309
Taxable income: $194,032

Your marginal tax rate % combined federal + state — saved on this device

Est. tax owed @ 24.0%: −$46,568
After-tax cash flow: $163,554/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.

Condition & rehab AI · 9 photos

Good 80/100 Cosmetic rehab Est. rehab $16,960–$50,880 screening

This well-maintained home in Rock Cove Estates offers a blend of privacy and comfort, with good curb appeal and fresh interior paint.

Components & finishes AI

Roof asphalt shingle · good Flooring hardwood Counters granite

Deferred maintenance Est. $2,000–$8,000 screening

Minor Roof (roof) — No visible signs of damage or wear on the roof.
Minor Windows (windows) — No visible signs of damage or wear on the windows.
Minor Electrical (electrical) — No visible signs of damage or wear on the electrical components.
Minor Plumbing (plumbing) — No visible signs of damage or wear on the plumbing.

Value-add opportunities

Resale Paint exterior — Fresh paint enhances curb appeal and home value ↑
Rental Clean gutters — Clean gutters improve drainage and reduce maintenance costs ↑

ⓘ Rehab cost is a screening estimate — Cosmetic scope × the home's square footage at US $/sqft rules of thumb (the same model as the Flip Finder). Get contractor quotes + a written scope before underwriting.

D Composite school gradezoned avg 54/100

Zoned Schools

Elementary Greenport Elementary School C NY #908/2,108 Nat'l #9,801/41,679 High Greenport High School C- NY #934/1,100 Nat'l #4,871/17,239

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

D Composite livability gradescore 58/100

Livability — Greenport West

Score: 58/100
State rank: #1073
US rank: #21520

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

Census place: Greenport West, NY
County: Suffolk · 1,505,262 people
Metro: New York-Newark-Jersey City, NY-NJ
Population (ZIP): 4,744
Household income: $79,917
Rent vs Own: 36.5% rent · 63.5% own
Severe rent burden: 21% of renters

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
#11 JPMorgan Chase New York $278.9B #21 Citigroup New York $170.8B #32 Goldman Sachs New York $126.9B #40 Morgan Stanley New York $107.3B #42 StoneX Group New York $99.9B #58 American Express New York $74.2B #98 TIAA New York $46.9B #273 Mastercard Purchase $28.2B #328 M&T Bank Buffalo $8.8B #392 Voya Financial New York $7.8B
Consumer Goods	9	$162B
#45 PepsiCo Purchase $91.9B #171 Colgate-Palmolive New York $19.5B #207 Estee Lauder New York $15.6B #246 Constellation Brands Victor $10.2B #422 PVH Corp New York $8.6B #364 Tapestry New York $6.7B #420 Ralph Lauren New York $6.6B #460 Steven Madden Long Island City $2.2B #498 Prestige Consumer Healthcare Tarrytown $1.1B
Insurance	4	$225B
#60 MetLife New York $71.0B #69 New York Life Insurance New York $62.6B #99 Travelers Companies New York $46.4B #101 AIG New York $44.9B
Telecommunications	2	$144B
#30 Verizon Communications New York $134.8B #297 Altice USA Long Island City $9.1B
Pharmaceuticals	2	$112B
#67 Pfizer New York $63.6B #94 Bristol-Myers Squibb New York $48.3B
Media / Entertainment	2	$69B
#295 Warner Bros. Discovery New York $39.9B #269 Paramount Global New York $28.9B

Price history

+1175.0% since first listed

5 events — show timeline

2026-07-17 Listed $1,785,000 OneKey® MLS as Distributed by MLS Grid
2026-07-02 Listing Removed — OneKey® MLS as Distributed by MLS Grid
2026-04-30 Listed $1,785,000 OneKey® MLS as Distributed by MLS Grid
2008-05-14 Sold (Public Records) $845,900 Public Records
2002-09-26 Sold (Public Records) $140,000 Public Records

Property tax history

+2.7%/yr

Latest (2025): $14,096 · +0.0% YoY. Source: county tax records.

Cash-flow waterfall

monthly

Sold comps — $/sqft

last 12 mo · ≤1 mi

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