250 Main Rd · Aquebogue, NY 11901

$1,199,000

7 bd · 3.0 ba · 3,937 sqft · MultiFamily public records · 127 Days on market

Built 1860 1.24 ac lot

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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
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• ARV discount +7.5/15.0
• Schools +3.6/10.0
• Livability +3.1/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Multi-family units

County records classify this as Multi-Family (2-4 Unit). Listing-text estimate: 2 units. confirmed

Listing remarks MLS

PRIME LOCATION FOR OPPORTUNITY Positioned along scenic Main Road in Riverhead, this rare investment opportunity combines size, style, and location on an impressive 1.24-acre parcel. This stately Colonial-style duplex offers 3,900 square feet of living space across two spacious rental units- currently generating income, with a possible 3rd that is unfinished. Inside, you'll find a total of 8 bedrooms and 4 bathrooms, offering incredible flexibility for multigenerational living, rental expansion, or creative reconfiguration. A generously sized parking lot ensures ample off-street parking for residents and guests alike. Surrounded by the charm of Long Island's North Fork, this property is moments from local farms and acclaimed vineyards, with easy access to the area’s best dining, recreation, and coastal attractions. Whether you’re looking to expand your rental portfolio or explore new development potential, 250 Main Road delivers both immediate value and long-term upside in one of Riverhead’s most desirable spots.

Key facts

• Acclaimed vineyards
• 1.24-acre parcel
• Recreation

Tags

• 1.24-ACRE PARCEL
• COLONIAL-STYLE DUPLEX
• GENEROUSLY SIZED PARKING LOT
• ACCLAIMED VINEYARDS
• EASY ACCESS TO DINING
• RECREATION

What this means for you Summary

Snapshot

• This is a 2 × 4-bed/2.0-bath units multifamily listed at $1.20M.

Deal economics

• At list price, monthly cash flow is $19k ($223k/yr) — positive. Per door: $9k/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($34k rent vs $1.20M).
• Recommended offer: $1.06M (12.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads 62/100 on livability (#887 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.
• Riverhead Central School District (suburban): math 34% / reading 48% proficiency, ranked #489 of 590 in NY (top 83%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Market conditions: 188 active listings in the ZIP; 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 $8k of loan paydown is wiped out by about $36k 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 $336k cash investment doubles in ~2 years — after that, you're playing with house money.

Negotiation context

• It's been on market 127 days — a 12% lower offer ($1.06M) is reasonable based on typical stale-listing flexibility.
• Current owner paid $35k; list at $1.20M implies a 3326% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1860 — expect roof / HVAC / electrical / plumbing capex.
• 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 $1,055,120 (12.0% below list)

Questions for the listing agent

1. It's been on market 127 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
3. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
4. Built in 1860 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
5. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
6. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
7. 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?
8. 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.
9. 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.
10. How much new apartment / multifamily construction is in the pipeline within 1–3 miles? Heavy new supply (>2% of stock underway) typically softens rents 12–24 months out; light construction supports rent growth.

Investment metrics

• 1% rule: 2.82% ✓
• Cap rate: 24.89%
• Cash-on-cash: 66.40%
• DSCR: 3.95
• GRM: 3.0

CMA / ARV

No comps found within radius.

Projected returns pro-forma

-3.0% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 65.7%
• Equity multiple: 3.95×
• Total profit: $989,321
• Equity at exit: $178,775

10-year hold

• IRR: 70.0%
• Equity multiple: 8.11×
• Total profit: $2,386,684
• Equity at exit: $103,668

Cash invested: $335,720 (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 11901

• Home prices YoY: -29.5%
• Active inventory: 188
• Price-to-rent: 5.9×

Monthly cashflow live

• Estimated rent: $33,781 medium
• Mortgage (P&I): −$6,288
• Tax from tax record: −$1,322 /mo · $15,867/yr
• Insurance: −$500
• HOA: −$0
• Vacancy / Maint / Mgmt: −$7,094
• Net cashflow: $18,577

Break-even live

Break-even rent $10,265

Max offer price $1,199,000

Occupancy floor 40%

2-unit breakdown (identical units grouped — click to expand)

Units	Beds	Baths	Est. rent
▸ 2× units	4	2	$33,780
Total (2 units)			$33,781

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: $299,750
• Closing costs: $35,970
• Reserves months: —
• Total cash needed: —

Listing history 18 events

1. 2026-06-18
   days on market $1,199,000 Active 127 DOM
2. 2026-06-17
   days on market $1,199,000 Active 126 DOM
3. 2026-06-16
   pricedays on market $1,199,000 Active 125 DOM
4. 2026-06-15
   days on market $1,250,000 Active 124 DOM
5. 2026-06-13
   days on market $1,250,000 Active 122 DOM
6. 2026-06-09
   days on market $1,250,000 Active 118 DOM
7. 2026-06-08
   days on market $1,250,000 Active 117 DOM
8. 2026-06-07
   pricedays on market $1,250,000 Active 116 DOM
9. 2026-06-04
   days on market $1,295,000 Active 113 DOM
10. 2026-06-03
    days on market $1,295,000 Active 112 DOM
11. 2026-06-02
    days on market $1,295,000 Active 111 DOM
12. 2026-06-01
    days on market $1,295,000 Active 110 DOM
13. 2026-05-31
    days on market $1,295,000 Active 109 DOM
14. 2026-04-09
    price $1,295,000 1051-char remark

    Show marketing remark (1051 chars)

    PRIME LOCATION FOR OPPORTUNITY Positioned along scenic Main Road in Riverhead, this rare investment opportunity combines size, style, and location on an impressive 1.24-acre parcel. This stately Colonial-style duplex offers 3,900 square feet of living space across two spacious rental units- currently generating income, with a possible 3rd that is unfinished. Inside, you'll find a total of 8 bedrooms and 4 bathrooms, offering incredible flexibility for multigenerational living, rental expansion, or creative reconfiguration. A generously sized parking lot ensures ample off-street parking for residents and guests alike. Surrounded by the charm of Long Island's North Fork, this property is moments from local farms and acclaimed vineyards, with easy access to the area’s best dining, recreation, and coastal attractions. Whether you’re looking to expand your rental portfolio or explore new development potential, 250 Main Road delivers both immediate value and long-term upside in one of Riverhead’s most desirable spots.

15. 2026-03-25
    price $1,375,000 1051-char remark

    Show marketing remark (1051 chars)

    PRIME LOCATION FOR OPPORTUNITY Positioned along scenic Main Road in Riverhead, this rare investment opportunity combines size, style, and location on an impressive 1.24-acre parcel. This stately Colonial-style duplex offers 3,900 square feet of living space across two spacious rental units- currently generating income, with a possible 3rd that is unfinished. Inside, you'll find a total of 8 bedrooms and 4 bathrooms, offering incredible flexibility for multigenerational living, rental expansion, or creative reconfiguration. A generously sized parking lot ensures ample off-street parking for residents and guests alike. Surrounded by the charm of Long Island's North Fork, this property is moments from local farms and acclaimed vineyards, with easy access to the area’s best dining, recreation, and coastal attractions. Whether you’re looking to expand your rental portfolio or explore new development potential, 250 Main Road delivers both immediate value and long-term upside in one of Riverhead’s most desirable spots.

16. 2026-02-04
    listed $1,475,000 Active 1051-char remark

    Show marketing remark (1051 chars)

    PRIME LOCATION FOR OPPORTUNITY Positioned along scenic Main Road in Riverhead, this rare investment opportunity combines size, style, and location on an impressive 1.24-acre parcel. This stately Colonial-style duplex offers 3,900 square feet of living space across two spacious rental units- currently generating income, with a possible 3rd that is unfinished. Inside, you'll find a total of 8 bedrooms and 4 bathrooms, offering incredible flexibility for multigenerational living, rental expansion, or creative reconfiguration. A generously sized parking lot ensures ample off-street parking for residents and guests alike. Surrounded by the charm of Long Island's North Fork, this property is moments from local farms and acclaimed vineyards, with easy access to the area’s best dining, recreation, and coastal attractions. Whether you’re looking to expand your rental portfolio or explore new development potential, 250 Main Road delivers both immediate value and long-term upside in one of Riverhead’s most desirable spots.

17. 1986-08-27
    soldstatus $35,000
18. 1986-08-27
    soldstatus $35,000

ⓘ 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: $15,867 · $1,322/mo
• Projected year-2 tax: $18,065 · $1,505/mo
• Expected delta: +$2,198/yr (+$183/mo · 13.9%)

ⓘ 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 3/10 Moderate
• 🌡 Heat 5/10 Major 7 d/yr ≥91°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 2 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $405,372
• − Mortgage interest: −$67,163
• − Property taxes: −$15,867
• − Insurance: −$5,995
• − Repairs & maintenance: −$32,430
• − Management: −$32,430
• − Depreciation: −$34,880
• Taxable income: $216,608
• Est. tax owed @ 24.0%: −$51,986
• After-tax cash flow: $170,944/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: Riverhead Central School District
• NCES district ID: 3624690
• Math proficiency: 34% ▼ -4.00%
• Reading proficiency: 48% ▲ 13.00%
• Median HH income: $61,607
• Composite: 36.38/100
• National rank: #4683
• State rank: #489 of 590 in NY

Livability — Aquebogue

• Score: 62/100
• State rank: #887
• US rank: #17213

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Aquebogue, NY
• Population (ZIP): 32,921

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: Diverse neighborhood (Simpson 0.63)
• Race & ethnicity: White 52% Hispanic / Latino 29% Two or more races 14% Black 11% Asian 3%
• Hispanic origin (detail): Mexican 4%
• Common ancestry: Romanian 8% Iranian 1% Portuguese 1%
• Foreign-born: 25% · Canada, Jamaica
• Languages at home: 68% English-only · Spanish 26% Other Indo-European 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: ▼ -182.60%
• Current HPI: 436.7781
• 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

+3600.0% since first listed

5 events — show timeline

• 2026-04-09 Price Changed $1,295,000 OneKey® MLS as Distributed by MLS Grid
• 2026-03-25 Price Changed $1,375,000 OneKey® MLS as Distributed by MLS Grid
• 2026-02-04 Listed $1,475,000 OneKey® MLS as Distributed by MLS Grid
• 1986-08-27 Sold (Public Records) $35,000 Public Records
• 1986-08-27 Sold (Public Records) $35,000 Public Records

Property tax history

+2.4%/yr

Latest (2025): $15,867 · +0.0% YoY. Source: county tax records.