27 (AKA 630) Madison St · Greenport West, NY 11944

$725,000

4 bd · 2.0 ba · 1,500 sqft · SingleFamily · 40 Days on market

Built 1965 Good condition 0.33 ac lot $483/sqft · 24% below area Est $950k · 24% 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 +15.0/15.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• Schools +4.5/10.0
• Condition / age +4.0/5.0
• Livability +2.9/5.0
• Rent growth +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

This charming cape is situated in Greenport, just minutes from Greenport Village and Beaches. The home has 4 bedrooms, 2 full bathrooms, and approximately 1500 sq ft. The eat-in kitchen has granite countertops and an awesome backsplash. The basement is unfinished with bilco doors. There is a fenced backyard and 1 car garage. The home currently has tenants, who will be leaving.

Key facts

• Bilco doors
• Granite countertops
• Fenced backyard

Tags

• GRANITE COUNTERTOPS
• FENCED BACKYARD
• BILCO DOORS

Property features AI

Exterior

• Parking: Driveway; Garage; 3 total parking spaces; 1-car garage
• Utilities: Electricity connected (PSEG); Water connected; Cesspool sewer
• Home design: Single-family residence; Two-story; Actual property condition
• Construction: Vinyl siding; Full attic; Unfinished basement with Bilco door(s)
• Exterior features: Mailbox; Fenced yard; Back yard

Interior

• Kitchen: Dishwasher; Microwave; Range; Refrigerator
• Bedrooms: Two levels (total rooms: 6)
• Bathrooms: 2 full bathrooms
• Heating & cooling: Baseboard heating; Oil heating; No central cooling
• Interior features: First-floor bedroom; First-floor full bathroom; Granite countertops; Storage space; Walk-in closet(s); Washer/dryer hookup; Porch
• Laundry & utility: Washer/Dryer hookup

What this means for you Summary

Snapshot

• This is a 4-bed/2.0-bath single-family listed at $725k. Condition is rated good.

Deal economics

• At list price, monthly cash flow is $9k ($111k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($18k rent vs $725k).
• Recommended offer: $703k (3.0% below list) — sets the bar for market timing.
• Cap rate 21.7% vs local median 8.1% 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: 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); 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 $5k of loan paydown is wiped out by about $22k 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 $203k cash investment doubles in ~3 years — after that, you're playing with house money.

Negotiation context

• It's been on market 40 days — a 3% lower offer ($703k) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 2y 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.

Recommended offer $703,250 (3.0% below list)

Questions for the listing agent

1. It's been on market 40 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
2. Built in 1965 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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?
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: 2.50% ✓
• Cap rate: 21.67%
• Cash-on-cash: 54.92%
• DSCR: 3.44
• GRM: 3.3

CMA / ARV

• ARV (median comp): $950,399
• List price: $725,000
• Delta: -23.72%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 9 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
57 (aka 400) Wilmarth Ave	0.12mi	3/1.0 (-1)	1,500 (0%)	4mo	$585,000	$390	82
16 Washington Ave	0.22mi	3/1.5 (-1)	1,550 (+3%)	12mo	$979,000	$632	67
795 Westwood Ln	0.45mi	3/2.0 (-1)	1,500 (0%)	10mo	$1,230,000	$820	66
416 West St	0.60mi	4/1.5	1,450 (-3%)	4mo	$725,000	$500	61
3400 & 3500 Sound Dr	0.64mi	3/2.0 (-1)	1,500 (0%)	8mo	$4,600,000	$3,067	58
312 5th Ave	0.65mi	3/2.0 (-1)	1,620 (+8%)	10mo	$875,000	$540	44
216 North St	0.51mi	3/3.5 (-1)	1,724 (+15%)	0mo	$999,000	$579	40
302 Monsell Pl	0.35mi	3/2.0 (-1)	1,300 (-13%)	21mo	$945,000	$727	39
237 5th Ave	0.70mi	3/1.5 (-1)	1,700 (+13%)	11mo	$1,250,000	$735	29

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: 53.2%
• Equity multiple: 3.34×
• Total profit: $474,472
• Equity at exit: $108,100

10-year hold

• IRR: 58.4%
• Equity multiple: 6.79×
• Total profit: $1,176,155
• Equity at exit: $62,685

Cash invested: $203,000 (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: 3.3×

Monthly cashflow live

• Estimated rent: $18,102 medium
• Mortgage (P&I): −$3,802
• Tax est. 1.5%: −$906 /mo · $10,875/yr
• Insurance: −$302
• HOA: −$0
• Vacancy / Maint / Mgmt: −$3,801
• Net cashflow: $9,290

Break-even live

Break-even rent $6,342

Max offer price $725,000

Occupancy floor 44%

Sensitivity live

Price	-10% $9,791	-5% $9,540	+0% $9,290	+5% $9,039	+10% $8,789
Rent	-10% $7,860	-5% $8,575	+0% $9,290	+5% $10,005	+10% $10,720
Rate	-1.0pp $9,655	-0.5pp $9,474	base $9,290	+0.5pp $9,102	+1.0pp $8,911

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: $181,250
• Closing costs: $21,750
• Reserves months: —
• Total cash needed: —

Rent comps 6 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
485 Sutton Pl Greenport, NY	4.0	2.5	2026	$20,000	$9.87	46d	1	0.20mi
312 5th Ave Greenport, NY	4.0	2.0	1900	$12,000	$6.32	46d	1	0.64mi
123 Sterling Ave #2 Greenport, NY	3.0	3.0	1528	$45,000	$29.45	46d	1	0.72mi
134 6th St Greenport, NY	3.0	2.0	1560	$18,500	$11.86	21d	1	1.23mi
131 6th St Unit G Greenport, NY	3.0	2.5	2238	$5,000	$2.23	26d	1	1.25mi
1110 Gillette Dr East Marion, NY	4.0	2.0	1500	$7,000	$4.67	21d	1	1.48mi

Listing history 25 events

1. 2026-06-22
   days on market $725,000 Active 40 DOM
2. 2026-06-21
   days on market $725,000 Active 39 DOM
3. 2026-06-21
   days on market $725,000 Active 38 DOM
4. 2026-06-18
   days on market $725,000 Active 36 DOM
5. 2026-06-17
   days on market $725,000 Active 35 DOM
6. 2026-06-16
   days on market $725,000 Active 34 DOM
7. 2026-06-15
   days on market $725,000 Active 33 DOM
8. 2026-06-13
   days on market $725,000 Active 31 DOM
9. 2026-06-12
   days on market $725,000 Active 30 DOM
10. 2026-06-09
    days on market $725,000 Active 27 DOM
11. 2026-06-08
    days on market $725,000 Active 26 DOM
12. 2026-06-07
    days on market $725,000 Active 25 DOM
13. 2026-06-05
    days on market $725,000 Active 23 DOM
14. 2026-06-04
    days on market $725,000 Active 21 DOM
15. 2026-06-02
    days on market $725,000 Active 20 DOM
16. 2026-06-01
    days on market $725,000 Active 19 DOM
17. 2026-05-31
    days on market $725,000 Active 18 DOM
18. 2026-05-13
    listed $725,000 Active 383-char remark
19. 2024-12-18
    historical $3,800
20. 2024-11-26
    listed $3,800
21. 2024-11-26
    historical $3,800
22. 2024-11-13
    listed $3,800
23. 2024-06-18
    historical $4,000
24. 2024-05-14
    price $4,000
25. 2024-04-28
    listed $4,500

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Taxation est. · year 1

• Rental income: $217,219
• − Mortgage interest: −$40,611
• − Property taxes: −$10,875
• − Insurance: −$3,625
• − Repairs & maintenance: −$17,378
• − Management: −$17,378
• − Depreciation: −$21,091
• Taxable income: $106,262
• Est. tax owed @ 24.0%: −$25,503
• After-tax cash flow: $85,976/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 · 10 photos

Good 80/100 Cosmetic rehab

This charming cape is move-in ready with good condition and fresh updates, ideal for both resale and rental.

Value-add opportunities

• Both Paint exterior — Enhances curb appeal and value
• Both Replace gutters — Improves drainage and aesthetics

Renovation cost estimate screening

Value-add ROI direction

• Both Paint exterior — Enhances curb appeal and value ↑
• Both Replace gutters — Improves drainage and aesthetics ↑

ⓘ Cost ranges are severity-bucket heuristics (US national rule-of-thumb). Get contractor quotes + a written scope before underwriting a rehab budget.

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 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
• 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

+16011.1% since first listed

8 events — show timeline

• 2026-05-13 Listed $725,000 OneKey® MLS as Distributed by MLS Grid
• 2024-12-18 Rental Removed $3,800 ONEKEY
• 2024-11-26 Listed for Rent $3,800 ONEKEY
• 2024-11-26 Rental Removed $3,800 ONEKEY
• 2024-11-13 Listed for Rent $3,800 ONEKEY
• 2024-06-18 Rental Removed $4,000 ONEKEY
• 2024-05-14 Price Changed $4,000 ONEKEY
• 2024-04-28 Listed for Rent $4,500 ONEKEY