69 Hillside Dr E · Sag Harbor, NY 11963

$1,490,000

3 bd · 2.0 ba · 3,843 sqft · SingleFamily · 429 Days on market

Built 1954 10,019 sqft lot

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Why this score? — see what drove the A- 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
• Appreciation +9.6/10.0
• ARV discount +7.5/15.0
• Schools +5.6/10.0
• Rent growth +5.0/5.0
• Livability +3.5/5.0
• Condition / age +2.5/5.0

Listing remarks

Brand new construction in Sag Harbor Village from renowned Hamptons architect Peter Cook, 69 Hillside Drive has an enviable location and inspired design ready to deliver the best of luxury living in the Hamptons. Just moments from Main Street and with Nineveh Beach access, this prime property offers both convenience and coastal charm with a chic contemporary style home boasting 3,843 +/- sq. ft. (including the fully finished lower level), 5 bedrooms, 5 full baths and 2 half baths, 10'x'20 pool and pool house. Enter to an elegant open-concept floorplan with large windows that beam light from the rear grounds. The main level includes a large eat-in kitchen, dedicated dining space, large great

Key facts

• Large windows
• Private beach access
• 0.23 acre lot

Tags

• BRAND NEW CONSTRUCTION
• CHIC CONTEMPORARY STYLE
• LARGE WINDOWS
• OPEN-CONCEPT FLOORPLAN
• PRIVATE BEACH ACCESS
• NEARBY MARINAS AND GOLF

What this means for you Summary

Snapshot

• This is a 3-bed/2.0-bath single-family listed at $1.49M.

Deal economics

• At list price, monthly cash flow is $9k ($112k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($23k rent vs $1.49M).
• Recommended offer: $1.31M (12.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads 70/100 on livability (#427 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, health & safety A; Watch: amenities F, commute F, cost of living F.
• Sag Harbor Union Free School District (suburban): math 54% / reading 70% proficiency, ranked #175 of 590 in NY (top 30%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 8% free/reduced lunch — higher-income household profile.
• Zoned schools: Sag Harbor Elementary School (math 47% / reading 72%, grade B-, #745 of 2,108 statewide, top 39%, 426 students, 22% FRL); Pierson Middle/High School (math 61% / reading 72%, grade B, #763 of 1,100 statewide, top 69%, 525 students, 25% FRL) — zoned schools average 24% FRL vs 8% district-wide (16 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: Rents rising fast (+10.8%/yr); 65 active listings in the ZIP; high-income renter base; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).
• At $22,932/mo this rent would consume 215% of the median local household income ($128k/yr) (locally 95% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• In year one you build about $147k of equity ($10k loan paydown + $137k appreciation (9.2% 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 (9.2% appreciation + 8.0% rent growth), your $417k cash investment doubles in ~2 years — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$236k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 429 days — a 12% lower offer ($1.31M) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts since 2y ago; this cycle's ask has dropped $105k (7%) from the opening price — seller is motivated, your offer sets the floor, not the list.

Risks & watch-outs

• Watch-outs: built in 1954 — expect roof / HVAC / electrical / plumbing capex.
• 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 $1,311,200 (12.0% below list)

Questions for the listing agent

1. It's been on market 429 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 1954 — 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 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?
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: 1.54% ✓
• Cap rate: 13.81%
• Cash-on-cash: 26.85%
• DSCR: 2.19
• GRM: 5.4

CMA / ARV

No comps found within radius.

Projected returns pro-forma

9.19% appreciation · 8.0% rent growth · sell at horizon

5-year hold

• IRR: 46.1%
• Equity multiple: 4.46×
• Total profit: $1,444,360
• Equity at exit: $1,254,848

10-year hold

• IRR: 42.6%
• Equity multiple: 10.75×
• Total profit: $4,067,105
• Equity at exit: $2,618,160

Cash invested: $417,200 (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 11963

• Home prices YoY: 1.9%
• Rents YoY: 10.8%
• Active inventory: 65
• Price-to-rent: 5.4×

Monthly cashflow live

• Estimated rent: $22,932 medium
• Mortgage (P&I): −$7,814
• Tax from tax record: −$348 /mo · $4,178/yr
• Insurance: −$621
• HOA: −$0
• Vacancy / Maint / Mgmt: −$4,816
• Net cashflow: $9,334

Break-even live

Break-even rent $11,117

Max offer price $1,490,000

Occupancy floor 54%

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: $372,500
• Closing costs: $44,700
• Reserves months: —
• Total cash needed: —

Listing history 9 events

1. 2026-01-22
   status Pending
2. 2025-09-09
   price $1,490,000
3. 2025-05-28
   status Active
4. 2025-04-29
   price $1,695,000
5. 2024-10-29
   listed $1,595,000 Active
6. 2022-04-20
   soldstatus $1,475,000
7. 2021-11-19
   soldstatus $999,000
8. 2000-11-15
   soldstatus $150,000
9. 1988-11-02
   soldstatus $187,000

ⓘ 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: $4,178 · $348/mo
• Projected year-2 tax: $14,680 · $1,223/mo
• Expected delta: +$10,501/yr (+$875/mo · 251.3%)

ⓘ 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 2/10 Low
• 🌡 Heat 4/10 Moderate 7 d/yr ≥90°F today · 18 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: $275,187
• − Mortgage interest: −$83,463
• − Property taxes: −$4,178
• − Insurance: −$7,450
• − Repairs & maintenance: −$22,015
• − Management: −$22,015
• − Depreciation: −$43,345
• Taxable income: $92,721
• Est. tax owed @ 24.0%: −$22,253
• After-tax cash flow: $89,752/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: Sag Harbor Union Free School District
• NCES district ID: 3625380
• Math proficiency: 54% ▼ -13.00%
• Reading proficiency: 70% ▲ 7.00%
• Median HH income: $81,547
• Composite: 55.69/100
• National rank: #1222
• State rank: #175 of 590 in NY

Livability — Sag Harbor

• Score: 70/100
• State rank: #427
• US rank: #7428

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Sag Harbor, NY
• County: Suffolk County · 679,920 people
• City population: 8,390
• Metro: New York-Newark-Jersey City, NY-NJ-PA
• Population (ZIP): 8,390
• Household income: $127,746
• Rent vs Own: 16.3% rent · 83.7% own
• Severe rent burden: 95.0

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 (78%)
• Race & ethnicity: White 78% Hispanic / Latino 13% Two or more races 11% Asian 4% Black 2%
• Hispanic origin (detail): Mexican 8%
• Common ancestry: Scotch-Irish 4% Romanian 3% Italian 2%
• Foreign-born: 13% · Canada, China, Jamaica
• Languages at home: 81% English-only · Spanish 9% Other Indo-European 5% French/Haitian/Cajun 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: ▲ 9.19%
• Current HPI: 499.3304
• Rent YoY: ▲ 10.76%
• 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

+696.8% since first listed

9 events — show timeline

• 2026-01-22 Pending — OneKey® MLS as Distributed by MLS Grid
• 2025-09-09 Price Changed $1,490,000 OneKey® MLS as Distributed by MLS Grid
• 2025-05-28 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2025-04-29 Price Changed $1,695,000 OneKey® MLS as Distributed by MLS Grid
• 2024-10-29 Listed $1,595,000 OneKey® MLS as Distributed by MLS Grid
• 2022-04-20 Sold (Public Records) $1,475,000 Public Records
• 2021-11-19 Sold (Public Records) $999,000 Public Records
• 2000-11-15 Sold (Public Records) $150,000 Public Records
• 1988-11-02 Sold (Public Records) $187,000 Public Records

Property tax history

+1.4%/yr

Latest (2025): $4,178 · +0.0% YoY. Source: county tax records.