1366 Scuttle Hole Rd · Bridgehampton, NY 11976

$5,495,000

5 bd · 2.0 ba · 4,631 sqft · SingleFamily public records · 129 Days on market

Built 2012 100 ac lot $1187/sqft · 7% above area Est $5138k · 7% over

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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 +26.0/30.0
• Appreciation +9.3/10.0
• DSCR +8.8/10.0
• 1% rule +5.6/10.0
• Rent growth +5.0/5.0
• ARV discount +4.4/15.0
• Schools +4.3/10.0
• Livability +3.1/5.0
• Condition / age +2.5/5.0

Listing remarks MLS

Bridgehampton Gambrel with Private Pickel & Padel Court The Ultimate Hamptons Lifestyle. This beautifully landscaped Gambrel sits on a private 1+/- acre lot, offering 5,000+/- sq. ft. of luxury living space and a brand-new private Piakcel/Padel court. The home features a dramatic double-height living room, a gourmet chef's kitchen, and five spacious bedrooms, including a grand upstairs master suite and two convenient first-floor guest rooms. Outdoor Paradise. Designed for resort-style living, the grounds feature a pristine pool, an expansive entertaining deck, and professional-grade Padel facilities-all framed by lush, mature landscaping for ultimate privacy. Unbeatable Location. Ideally situated just minutes from the vibrant villages of Bridgehampton, Southampton, and Sag Harbor, and within easy reach of world-renowned ocean beaches.

Key facts

• Pristine pool
• Unbeatable location
• 100 acre lot

Tags

• PRIVATE PICKEL & PADEL COURT
• PRISTINE POOL
• EXPANSIVE ENTERTAINING DECK
• LUSH MATURE LANDSCAPING
• UNBEATABLE LOCATION

What this means for you Summary

Snapshot

• This is a 5-bed/2.0-bath single-family listed at $5.50M.

Deal economics

• At list price, monthly cash flow is $14k ($165k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($58k rent vs $5.50M).
• Recommended offer: $4.84M (12.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads 62/100 on livability (#874 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, schools B; Watch: amenities F, commute F, cost of living F.
• Bridgehampton Union Free School District (rural): math 50% / reading 40% proficiency, ranked #511 of 755 in NY (top 68%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Market conditions: Rents rising fast (+30.1%/yr); 52 active listings in the ZIP; 2 comparable units currently listed for rent nearby; high-income renter base; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).
• At $58,128/mo this rent would consume 387% of the median local household income ($180k/yr) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• In year one you build about $512k of equity ($38k loan paydown + $474k appreciation (8.6% local appreciation)).
• Suffolk County population projected to shrink 5% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.
• At projected returns (8.6% appreciation + 8.0% rent growth), your $1.54M cash investment doubles in ~3 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$821k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 129 days — a 12% lower offer ($4.84M) is reasonable based on typical stale-listing flexibility.
• 5 sale attempts since 14y 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 $450k; list at $5.50M implies a 1121% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• 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 $4,835,600 (12.0% below list)

Questions for the listing agent

1. It's been on market 129 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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?
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: 1.06% ✓
• Cap rate: 9.29%
• Cash-on-cash: 10.70%
• DSCR: 1.48
• GRM: 7.9

CMA / ARV

• ARV (median comp): $5,137,955
• List price: $5,495,000
• Delta: 6.95%
• Verdict: FAIR
• Comps: 7 within 2.0 mi

Projected returns pro-forma

8.63% appreciation · 8.0% rent growth · sell at horizon

5-year hold

• IRR: 31.6%
• Equity multiple: 3.38×
• Total profit: $3,665,464
• Equity at exit: $4,412,791

10-year hold

• IRR: 29.6%
• Equity multiple: 8.00×
• Total profit: $10,772,870
• Equity at exit: $8,996,731

Cash invested: $1,538,600 (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 11976

• Home prices YoY: 1.6%
• Rents YoY: 30.1%
• Active inventory: 52
• Price-to-rent: 7.9×

Monthly cashflow live

• Estimated rent: $58,128 medium
• Mortgage (P&I): −$28,816
• Tax from tax record: −$1,100 /mo · $13,205/yr
• Insurance: −$2,290
• HOA: −$0
• Vacancy / Maint / Mgmt: −$12,207
• Net cashflow: $13,715

Break-even live

Break-even rent $40,768

Max offer price $5,495,000

Occupancy floor 71%

Sensitivity live

Price	-10% $16,825	-5% $15,270	+0% $13,715	+5% $12,160	+10% $10,604
Rent	-10% $9,123	-5% $11,419	+0% $13,715	+5% $16,011	+10% $18,307
Rate	-1.0pp $16,482	-0.5pp $15,112	base $13,715	+0.5pp $12,291	+1.0pp $10,842

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: $1,373,750
• Closing costs: $164,850
• Reserves months: —
• Total cash needed: —

Rent comps 2 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
491 Butter Ln Bridgehampton, NY	5.0	5.0	4800	$30,000	$6.25	45d	1	0.81mi
189 Lumber Ln Bridgehampton, NY	5.0	3.5	3200	$50,000	$15.62	26d	1	1.47mi

Listing history 31 events

1. 2026-06-21
   days on market $5,495,000 Active 129 DOM
2. 2026-06-18
   days on market $5,495,000 Active 126 DOM
3. 2026-06-17
   days on market $5,495,000 Active 125 DOM
4. 2026-06-16
   days on market $5,495,000 Active 124 DOM
5. 2026-06-15
   days on market $5,495,000 Active 123 DOM
6. 2026-06-13
   days on market $5,495,000 Active 121 DOM
7. 2026-06-09
   days on market $5,495,000 Active 117 DOM
8. 2026-06-08
   days on market $5,495,000 Active 116 DOM
9. 2026-06-07
   days on market $5,495,000 Active 115 DOM
10. 2026-06-04
    days on market $5,495,000 Active 112 DOM
11. 2026-06-03
    days on market $5,495,000 Active 111 DOM
12. 2026-06-02
    days on market $5,495,000 Active 110 DOM
13. 2026-06-01
    days on market $5,495,000 Active 109 DOM
14. 2026-05-31
    days on market $5,495,000 Active 108 DOM
15. 2026-02-12
    listed $5,495,000 Active 850-char remark

    Show marketing remark (850 chars)

    Bridgehampton Gambrel with Private Pickel & Padel Court The Ultimate Hamptons Lifestyle. This beautifully landscaped Gambrel sits on a private 1+/- acre lot, offering 5,000+/- sq. ft. of luxury living space and a brand-new private Piakcel/Padel court. The home features a dramatic double-height living room, a gourmet chef's kitchen, and five spacious bedrooms, including a grand upstairs master suite and two convenient first-floor guest rooms. Outdoor Paradise. Designed for resort-style living, the grounds feature a pristine pool, an expansive entertaining deck, and professional-grade Padel facilities-all framed by lush, mature landscaping for ultimate privacy. Unbeatable Location. Ideally situated just minutes from the vibrant villages of Bridgehampton, Southampton, and Sag Harbor, and within easy reach of world-renowned ocean beaches.

16. 2024-12-22
    historical
17. 2024-12-07
    status Active
18. 2024-12-06
    historical
19. 2024-09-10
    price $4,999,950
20. 2024-09-05
    status Active
21. 2024-09-01
    historical
22. 2024-08-23
    price $5,195,000
23. 2024-07-09
    price $5,295,000
24. 2024-06-19
    listed $5,495,000 Active
25. 2012-11-15
    historical
26. 2012-03-15
    listed $1,595,000
27. 2002-05-08
    soldstatus $450,000
28. 2002-05-08
    soldstatus $450,000
29. 1997-01-24
    soldstatus $237,000
30. 1988-05-31
    soldstatus $255,000
31. 1986-12-31
    soldstatus $70,000

ⓘ 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: $13,205 · $1,100/mo
• Projected year-2 tax: $53,035 · $4,420/mo
• Expected delta: +$39,830/yr (+$3,319/mo · 301.6%)

ⓘ 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 ≥90°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: $697,537
• − Mortgage interest: −$307,805
• − Property taxes: −$13,205
• − Insurance: −$27,475
• − Repairs & maintenance: −$55,803
• − Management: −$55,803
• − Depreciation: −$159,855
• Taxable income: $77,591
• Est. tax owed @ 24.0%: −$18,622
• After-tax cash flow: $145,956/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: Bridgehampton Union Free School District
• NCES district ID: 3605370
• Math proficiency: 50% ▼ -10.00%
• Reading proficiency: 40% ▼ -10.00%
• Median HH income: $69,915
• Composite: 42.79/100
• National rank: #6761
• State rank: #511 of 755 in NY

Livability — Bridgehampton

• Score: 62/100
• State rank: #874
• US rank: #16891

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Bridgehampton, NY
• County: Suffolk County · 679,920 people
• City population: 725
• Metro: New York-Newark-Jersey City, NY-NJ-PA
• Population (ZIP): 2,952
• Household income: $180,250
• Rent vs Own: 6.8% rent · 93.2% own

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 (87%)
• Race & ethnicity: White 87% Hispanic / Latino 9% Two or more races 9% Asian 2%
• Hispanic origin (detail): Mexican 1% Salvadoran 2%
• Common ancestry: Romanian 16% Scotch-Irish 7% Italian 3%
• Foreign-born: 11% · Canada, China
• Languages at home: 86% English-only · Spanish 7% Other Indo-European 4% German/W. Germanic 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: ▲ 8.63%
• Current HPI: 540.0967
• Rent YoY: ▲ 30.05%
• Metro: New York-Newark-Jersey City, NY-NJ-PA
• 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

+7750.0% since first listed

17 events — show timeline

• 2026-02-12 Listed $5,495,000 OneKey® MLS as Distributed by MLS Grid
• 2024-12-22 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2024-12-07 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2024-12-06 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2024-09-10 Price Changed $4,999,950 OneKey® MLS as Distributed by MLS Grid
• 2024-09-05 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2024-09-01 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2024-08-23 Price Changed $5,195,000 OneKey® MLS as Distributed by MLS Grid
• 2024-07-09 Price Changed $5,295,000 OneKey® MLS as Distributed by MLS Grid
• 2024-06-19 Listed $5,495,000 OneKey® MLS as Distributed by MLS Grid
• 2012-11-15 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2012-03-15 Listed $1,595,000 OneKey® MLS as Distributed by MLS Grid
• 2002-05-08 Sold (Public Records) $450,000 Public Records
• 2002-05-08 Sold (Public Records) $450,000 Public Records
• 1997-01-24 Sold (Public Records) $237,000 Public Records
• 1988-05-31 Sold (Public Records) $255,000 Public Records
• 1986-12-31 Sold (Public Records) $70,000 Public Records

Property tax history

+8.1%/yr

Latest (2024): $13,205 · +0.0% YoY. Source: county tax records.