23 Bacon Rd · Head of the Harbor, NY 11780

$1,399,999

5 bd · 5.0 ba · 5,393 sqft · SingleFamily · 233 Days on market

Built 1960 2.38 ac lot ↓ 7% since listing

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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
• DSCR +10.0/10.0
• 1% rule +9.3/10.0
• ARV discount +7.5/15.0
• Schools +6.6/10.0
• Livability +3.2/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

BACK ON MARKET !! - ALL BINDERS ARE OFF, DEAL FELL THROUGH - HOME IS 100% AVAILABLE ! Welcome to 23 Bacon Road - The Best Value in the coveted Head of the Harbor ! This Elegant & Expansive Ranch-Style home is nestled on 2.38 beautifully landscaped acres in the heart of Head of the Harbor. Built in 1960 & designed by renowned builder Yablonski - This home offers over 5,300 square feet of exquisite living space, This one-of-a-kind gem features a first floor master bedroom, generous room sizes, a sun-drenched sun room and fully finished basement, perfect for entertaining or extended family. Each of the five oversized bedrooms offers comfort and privacy, with ample closet space thr

Key facts

• Oversized bedrooms
• Ample closet space
• Mature trees

Tags

• FIRST FLOOR MASTER BEDROOM
• SUN-DRENCHED SUN ROOM
• FULLY FINISHED BASEMENT
• OVERSIZED BEDROOMS
• AMPLE CLOSET SPACE
• MATURE TREES

What this means for you Summary

Snapshot

• This is a 5-bed/5.0-bath single-family listed at $1.40M.

Deal economics

• At list price, monthly cash flow is $6k ($72k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($20k rent vs $1.40M).
• Recommended offer: $1.23M (12.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads 64/100 on livability (#719 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, housing A+; Watch: amenities F, commute F, cost of living F.
• Smithtown Central School District (suburban): math 71% / reading 70% proficiency, ranked #86 of 590 in NY (top 15%) — strong family-tenant draw, lease renewals of 3-5y typical; only 5% free/reduced lunch — higher-income household profile.
• Zoned schools: Saint James Elementary School (math 62% / reading 67%, grade B, #591 of 2,108 statewide, top 31%, 474 students, 15% FRL); Nesaquake Middle School (math 44% / reading 67%, grade B-, #211 of 729 statewide, top 29%, 473 students, 10% FRL); Smithtown High School East (math 96% / reading 82%, grade A+, #288 of 1,100 statewide, top 27%, 1,475 students, 12% FRL).
• Market conditions: 123 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 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 $10k of loan paydown is wiped out by about $42k 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 $392k cash investment doubles in ~7 years — after that, you're playing with house money.

Negotiation context

• It's been on market 233 days — a 12% lower offer ($1.23M) 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.

Risks & watch-outs

• Climate carrying-cost: severe wind risk, 80% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Recommended offer $1,231,999 (12.0% below list)

Questions for the listing agent

1. It's been on market 233 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 1960 — 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. Schools are B-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?
6. 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.
7. 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.
8. 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: 1.43% ✓
• Cap rate: 11.41%
• Cash-on-cash: 18.27%
• DSCR: 1.81
• GRM: 5.8

CMA / ARV

• ARV (on-the-fly): $2,825,932
• Comps found: 3

Show comp detail 3 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
33 Bacon Rd	0.14mi	6/5.5 (+1)	4,900 (-9%)	3mo	$2,700,000	$551	68
17 Barn Ln	0.59mi	5/4.5	5,340 (-1%)	9mo	$2,800,000	$524	61
60 Harbor Rd	0.59mi	6/7.5 (+1)	5,800 (+8%)	1mo	$1,975,000	$341	44

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: 9.9%
• Equity multiple: 1.39×
• Total profit: $153,638
• Equity at exit: $208,744

10-year hold

• IRR: 19.1%
• Equity multiple: 2.59×
• Total profit: $624,843
• Equity at exit: $121,046

Cash invested: $392,000 (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 11780

• Active inventory: 123
• Price-to-rent: 5.8×

Monthly cashflow live

• Estimated rent: $20,000 medium
• Mortgage (P&I): −$7,342
• Tax from tax record: −$1,907 /mo · $22,884/yr
• Insurance: −$583
• HOA: −$0
• Vacancy / Maint / Mgmt: −$4,200
• Net cashflow: $5,968

Break-even live

Break-even rent $12,446

Max offer price $1,399,999

Occupancy floor 65%

Sensitivity live

Price	-10% $6,760	-5% $6,364	+0% $5,968	+5% $5,572	+10% $5,175
Rent	-10% $4,388	-5% $5,178	+0% $5,968	+5% $6,758	+10% $7,548
Rate	-1.0pp $6,673	-0.5pp $6,324	base $5,968	+0.5pp $5,605	+1.0pp $5,236

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: $350,000
• Closing costs: $42,000
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
2 Sunset Dr Saint James, NY	6.0	9.5	6500	$20,000	$3.08	2d	1	0.38mi

Listing history 6 events

1. 2026-03-12
   status Pending
2. 2026-03-10
   status Active
3. 2025-11-18
   status Active
4. 2025-06-24
   listed $1,399,999 Active
5. 2024-11-15
   historical
6. 2024-08-14
   listed $1,500,000 Active

ⓘ 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: $22,884 · $1,907/mo
• Projected year-2 tax: $23,272 · $1,939/mo
• Expected delta: +$388/yr (+$32/mo · 1.7%)

ⓘ 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 4/10 Moderate
• 🌡 Heat 4/10 Moderate 6 d/yr ≥97°F today · 14 d/yr by 30 yrs out
• 💨 Wind 8/10 Severe 80% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 3 unhealthy d/yr today · 5 by 30 yrs out

Taxation est. · year 1

• Rental income: $240,000
• − Mortgage interest: −$78,422
• − Property taxes: −$22,884
• − Insurance: −$7,000
• − Repairs & maintenance: −$19,200
• − Management: −$19,200
• − Depreciation: −$40,727
• Taxable income: $52,567
• Est. tax owed @ 24.0%: −$12,616
• After-tax cash flow: $58,999/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: Smithtown Central School District
• NCES district ID: 3627060
• Math proficiency: 71% ▼ -6.00%
• Reading proficiency: 70% ▼ -1.00%
• Median HH income: $110,009
• Composite: 65.53/100
• National rank: #473
• State rank: #86 of 590 in NY

Livability — Head of the Harbor

• Score: 64/100
• State rank: #719
• US rank: #13626

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Head of the Harbor, NY
• Population (ZIP): 15,586

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 (81%)
• Race & ethnicity: White 81% Hispanic / Latino 11% Two or more races 7% Asian 5%
• Hispanic origin (detail): Puerto Rican 2%
• Common ancestry: Romanian 5% Scotch-Irish 3% Italian 1%
• Foreign-born: 9% · Canada, China, Jamaica
• Languages at home: 89% English-only · Spanish 7% Chinese 1% Other Indo-European 1%

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: ▼ -610.91%
• Current HPI: 290.2363
• 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

-6.7% since first listed

6 events — show timeline

• 2026-03-12 Pending — OneKey® MLS as Distributed by MLS Grid
• 2026-03-10 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2025-11-18 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2025-06-24 Listed $1,399,999 OneKey® MLS as Distributed by MLS Grid
• 2024-11-15 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2024-08-14 Listed $1,500,000 OneKey® MLS as Distributed by MLS Grid

Property tax history

+2.4%/yr

Latest (2025): $22,884 · -8.5% YoY. Source: county tax records.