27 (AKA 630) Madison St

Greenport West, NY 11944

$725,000B+

4 bd · 2.0 ba · 1,500 sqft · Built 1965 · SingleFamily · Active · 40 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $18,102/mo
• Mortgage (P&I): −$3,802
• Tax + insurance: −$1,208
• HOA: −$0
• Vac / Maint / Mgmt: −$3,801
• Net cashflow: $9,290/mo
• Annual: $111,479/yr
• Cap rate: 21.67%
• Cash-on-cash: 54.92%
• DSCR: 3.44
• 1% rule: 2.50%
• Cash to close: $203,000

Investor read

• This is a 4-bed/2.0-bath single-family listed at $725k. Condition is rated good.
• 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).
• It's been on market 40 days — a 3% lower offer ($703k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $703k (3.0% below list) — sets the bar for market timing.
• 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.
• 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).
• Suffolk County population projected to shrink 5% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.
• 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.
• 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.
• 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.

Questions for listing agent

• 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?
• Built in 1965 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• 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.