150 Baywater Ave

Southold, NY 11971

$850,000B+

3 bd · 4.0 ba · 2,100 sqft · Built 1900 · SingleFamily · Active · 173 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $16,871/mo
• Mortgage (P&I): −$4,457
• Tax + insurance: −$981
• HOA: −$0
• Vac / Maint / Mgmt: −$3,543
• Net cashflow: $7,889/mo
• Annual: $94,672/yr
• Cap rate: 17.43%
• Cash-on-cash: 39.78%
• DSCR: 2.77
• 1% rule: 1.98%
• Cash to close: $238,000

Investor read

• This is a 3-bed/4.0-bath single-family listed at $850k. Condition is rated poor.
• At list price, monthly cash flow is $8k ($95k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($17k rent vs $850k).
• It's been on market 173 days — a 12% lower offer ($748k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $748k (12.0% below list) — sets the bar for market timing.
• Local home prices are declining (-3.0%/yr); year-one equity from $6k of loan paydown is wiped out by about $26k of value loss. Plan a longer hold.
• Location reads 67/100 on livability (#583 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, health & safety B+; Watch: amenities F, commute F, cost of living F.
• Southold Union Free School District (town): math 46% / reading 59% proficiency, ranked #298 of 590 in NY (top 50%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 17% free/reduced lunch — higher-income household profile.
• Zoned schools: Southold Elementary School (math 37% / reading 62%, grade D, #1,085 of 2,108 statewide, top 56%, 317 students, 35% FRL); Southold Junior-Senior High School (math 52% / reading 52%, grade D+, #946 of 1,100 statewide, top 88%, 380 students, 40% FRL) — zoned schools average 38% FRL vs 17% district-wide (21 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Watch-outs: built in 1900 — expect roof / HVAC / electrical / plumbing capex.
• Market conditions: 133 active listings in the ZIP; 10 comparable units currently listed for rent nearby; rentals leasing fast (median 11d on market — plan ~1-2 weeks tenant-placement turnaround); high-income renter base; 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.
• 2 sale attempts since 3y 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 $700k; 21% above their basis — modest negotiation headroom, anchor on the comps not their cost.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $238k cash investment doubles in ~3 years — after that, you're playing with house money.
• 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.
• Cap rate 17.4% vs local median 5.8% in Southold — 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 173 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
• Have any recent inspections been done? Can we get a copy of the seller's disclosures and any deferred-maintenance estimates?
• Built in 1900 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
• Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
• Schools are A-rated — typically a magnet for longer-tenancy family renters. What's the average tenant stay here, and is there a school-zone premium baked into asking?
• 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.

Repairs flagged (vision-AI assessment)

• Major: Landscaping — Overgrown vegetation and lack of landscaping.
• Major: Fencing — No visible fencing.
• Major: Exterior Painting — No visible exterior paint condition.
• Major: Roof Inspection — No visible roof condition, but the satellite image shows a pitched roof structure.
• Major: Interior Painting — No visible interior paint condition.
• Major: Systems Inspection — No visible systems condition, but the satellite image shows a pitched roof structure.