22 Old Trail Rd · Water Mill, NY 11976

$2,100,000

5 bd · 2.0 ba · 2,488 sqft · SingleFamily public records · 156 Days on market

Built 1973 200 ac lot Est $2110k · at est. ↓ 25% since listing

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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 +9.3/10.0
• ARV discount +7.7/15.0
• Rent growth +5.0/5.0
• Schools +4.8/10.0
• Livability +3.6/5.0
• Condition / age +2.5/5.0

Listing remarks

Welcome to 22 Old Trail Road, a charming beach cottage-style residence of 4 bedrooms plus den and 3.5 baths. It is tucked away in the tranquil town of Water Mill, NY. This home is a captivating blend of comfort and elegance, nestled on a generous 2-acre private lot. As you step into the foyer, the 17-foot high ceiling immediately captures your attention, leading you into a living room adorned with wood burning fireplace and French doors and adjacent den. The open dining room or media room has authentic rustic, shiplap, a cozy fireplace and built-in media center. The wide plank hardwood floors showcase well all styles of decor. There is a guest powder room. The gourmet chef's kitchen, equipp

Key facts

• 17 foot high ceiling
• 2 acre private lot
• Rustic shiplap

Tags

• 2 ACRE PRIVATE LOT
• 17 FOOT HIGH CEILING
• RUSTIC SHIPLAP
• COZY FIREPLACE
• BUILT IN MEDIA CENTER
• GREAT ROOM

What this means for you Summary

Snapshot

• This is a 5-bed/2.0-bath single-family listed at $2.10M.

Deal economics

• At list price, monthly cash flow is $33k ($398k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($58k rent vs $2.10M).
• Recommended offer: $1.85M (12.0% below list) — sets the bar for market timing.
• Cap rate 25.3% vs local median 10.6% in Water Mill — 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.

Location & tenants

• Location reads 71/100 on livability (#410 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, commute A-; Watch: amenities F, cost of living F, housing F.
• Southampton Union Free School District (suburban): math 53% / reading 51% proficiency, ranked #293 of 590 in NY (top 50%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Zoned schools: Southampton Elementary School (math 42% / reading 57%, grade D, #1,085 of 2,108 statewide, top 56%, 376 students, 51% FRL); Southampton Intermediate School (math 30% / reading 47%, grade F, #437 of 729 statewide, top 60%, 363 students, 44% FRL); Southampton High School (math 98%, 595 students, 48% FRL) — zoned schools average 48% FRL vs 30% district-wide (17 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: Rents rising fast (+30.1%/yr); 52 active listings in the ZIP; 5 comparable units currently listed for rent nearby; rentals at typical pace (median 22d on market — plan ~3-4 weeks tenant-placement turnaround); high-income renter base; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).
• At $57,733/mo this rent would consume 384% 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 $196k of equity ($15k loan paydown + $181k 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 $588k cash investment doubles in ~1 year — after that, you're playing with house money.
• By year 2, paydown + projected appreciation supports a ~$314k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 156 days — a 12% lower offer ($1.85M) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts; this cycle's ask has dropped $695k (25%) from the opening price — seller is motivated, your offer sets the floor, not the list.

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 $1,848,000 (12.0% below list)

Questions for the listing agent

1. It's been on market 156 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 1973 — 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. 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: 2.75% ✓
• Cap rate: 25.26%
• Cash-on-cash: 67.73%
• DSCR: 4.01
• GRM: 3.0

CMA / ARV

• ARV (on-the-fly): $2,109,824
• Comps found: 2

Show comp detail 2 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
6 Trail Ct	0.41mi	5/3.5	2,563 (+3%)	2mo	$2,000,000	$780	68
124 Bridies Path	0.47mi	4/2.5 (-1)	2,200 (-12%)	16mo	$1,865,500	$848	38

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

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

5-year hold

• IRR: 81.9%
• Equity multiple: 6.73×
• Total profit: $3,369,019
• Equity at exit: $1,686,417

10-year hold

• IRR: 78.8%
• Equity multiple: 16.27×
• Total profit: $8,979,581
• Equity at exit: $3,438,241

Cash invested: $588,000 (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 11976

• Home prices YoY: 1.6%
• Rents YoY: 30.1%
• Active inventory: 52
• Price-to-rent: 3.0×

Monthly cashflow live

• Estimated rent: $57,733 medium
• Mortgage (P&I): −$11,013
• Tax from tax record: −$534 /mo · $6,408/yr
• Insurance: −$875
• HOA: −$0
• Vacancy / Maint / Mgmt: −$12,124
• Net cashflow: $33,187

Break-even live

Break-even rent $15,724

Max offer price $2,100,000

Occupancy floor 38%

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: $525,000
• Closing costs: $63,000
• Reserves months: —
• Total cash needed: —

Rent comps 5 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
126 Middle Line Hwy Southampton, NY	4.0	4.5	3000	$80,000	$26.67	22d	1	0.21mi
1646 Noyack Rd Southampton, NY	4.0	3.0	2458	$40,000	$16.27	22d	1	0.87mi
9 Pine Tree Rd Southampton, NY	4.0	3.5	2000	$7,000	$3.50	43d	1	0.97mi
112 Laurel Valley Dr Sag Harbor, NY	4.0	3.0	2400	$20,000	$8.33	1d	1	1.04mi
17 Bayview Rd Southampton, NY	4.0	3.5	3112	$55,000	$17.67	22d	1	1.16mi

Listing history 9 events

1. 2025-11-19
   status Pending
2. 2025-10-08
   status Active
3. 2025-10-05
   historical
4. 2025-09-22
   price $2,100,000
5. 2025-09-10
   price $2,250,000
6. 2025-08-28
   price $2,345,000
7. 2025-08-08
   price $2,445,000
8. 2025-06-25
   price $2,495,000
9. 2025-06-12
   listed $2,795,000 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: $6,408 · $534/mo
• Projected year-2 tax: $20,949 · $1,746/mo
• Expected delta: +$14,541/yr (+$1,212/mo · 226.9%)

ⓘ 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 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: $692,793
• − Mortgage interest: −$117,633
• − Property taxes: −$6,408
• − Insurance: −$10,500
• − Repairs & maintenance: −$55,423
• − Management: −$55,423
• − Depreciation: −$61,091
• Taxable income: $386,315
• Est. tax owed @ 24.0%: −$92,716
• After-tax cash flow: $305,532/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: Southampton Union Free School District
• NCES district ID: 3627540
• Math proficiency: 53% ▬ 0.00%
• Reading proficiency: 51% ▲ 4.00%
• Median HH income: $85,977
• Composite: 47.9/100
• National rank: #2213
• State rank: #293 of 590 in NY

Livability — Water Mill

• Score: 71/100
• State rank: #410
• US rank: #7088

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Water Mill, NY
• County: Suffolk County · 679,920 people
• City population: 2,952
• 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

-24.9% since first listed

9 events — show timeline

• 2025-11-19 Pending — OneKey® MLS as Distributed by MLS Grid
• 2025-10-08 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2025-10-05 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2025-09-22 Price Changed $2,100,000 OneKey® MLS as Distributed by MLS Grid
• 2025-09-10 Price Changed $2,250,000 OneKey® MLS as Distributed by MLS Grid
• 2025-08-28 Price Changed $2,345,000 OneKey® MLS as Distributed by MLS Grid
• 2025-08-08 Price Changed $2,445,000 OneKey® MLS as Distributed by MLS Grid
• 2025-06-25 Price Changed $2,495,000 OneKey® MLS as Distributed by MLS Grid
• 2025-06-12 Listed $2,795,000 OneKey® MLS as Distributed by MLS Grid

Property tax history

+2.1%/yr

Latest (2022): $6,408 · +0.0% YoY. Source: county tax records.