66 Waterhole Rd · Springs, NY 11937

$1,349,000

4 bd · 2.0 ba · 1,600 sqft · SingleFamily · 389 Days on market

Built 1982 0.46 ac lot $843/sqft · 19% below area Est $1669k · 19% under $32/mo HOA ↓ 7% since listing

---

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
• ARV discount +15.0/15.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• Schools +5.1/10.0
• Rent growth +5.0/5.0
• Livability +3.2/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

CLOSE TO THE BAY IN CLEARWATER BEACH Located within walking distance to the beach in Clearwater Beach, a private beach and marina community, this home was renovated in 2020, and features 1600 square feet of living space with four bedrooms, two bathrooms, a finished lower level and plenty of room for expansion and a pool. The modified Saltbox architecture offers ample natural light from skylights and a double-height ceiling in the great room that features a wood-burning fireplace on one side and a recently renovated eat-in kitchen on the other. A convenient pantry/mudroom leads to the backyard via a French door. Two bedrooms, one with walkout egress, share a full bath on the main level. Upst

Key facts

• Ample natural light
• Inviting front porch
• Renovated in 2020

Tags

• RENOVATED IN 2020
• INVITING FRONT PORCH
• MODIFIED SALTBOX ARCHITECTURE
• AMPLE NATURAL LIGHT
• DOUBLE-HEIGHT CEILING
• WOOD-BURNING FIREPLACE

What this means for you Summary

Snapshot

• This is a 4-bed/2.0-bath single-family listed at $1.35M.

Deal economics

• At list price, monthly cash flow is $10k ($121k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($24k rent vs $1.35M).
• Recommended offer: $1.19M (12.0% below list) — sets the bar for market timing.
• Cap rate 15.2% vs local median 11.1% in Springs — 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 63/100 on livability (#809 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+; Watch: housing C-, schools D-, amenities F.
• Springs Union Free School District (town): math 55% / reading 60% proficiency, ranked #239 of 590 in NY (top 40%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 9% free/reduced lunch — higher-income household profile.
• Market conditions: Rents rising fast (+12.3%/yr); 135 active listings in the ZIP; 8 comparable units currently listed for rent nearby; rentals lingering (median 44d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 62% of comp listings sitting > 30 days — soft ceiling on asking rent; high-income renter base; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).
• At $23,558/mo this rent would consume 218% of the median local household income ($130k/yr) (locally 896% of renters already pay >50% of income on rent) — very limited rent-growth headroom before tenants either downsize or default.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $9k of loan paydown is wiped out by about $40k 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 + 8.0% rent growth), your $378k cash investment doubles in ~4 years — after that, you're playing with house money.

Negotiation context

• It's been on market 389 days — a 12% lower offer ($1.19M) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts; this cycle's ask has dropped $101k (7%) 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 $1,187,120 (12.0% below list)

Questions for the listing agent

1. It's been on market 389 days. Have you received any prior offers? Is the seller open to a 12% concession, seller financing, or rate buy-down credit?
2. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
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 D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
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: 1.75% ✓
• Cap rate: 15.24%
• Cash-on-cash: 31.96%
• DSCR: 2.42
• GRM: 4.8

CMA / ARV

• ARV (median comp): $1,669,121
• List price: $1,349,000
• Delta: -19.18%
• Verdict: UNDERPRICED
• Comps: 13 within 1.0 mi

Show comp detail 4 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
16 Lion Head Rock Rd	0.35mi	4/3.0	1,600 (0%)	10mo	$1,850,000	$1,156	72
18 Norfolk Dr	0.35mi	3/2.0 (-1)	1,500 (-6%)	0mo	$1,180,000	$787	68
104 Pembroke Dr	0.09mi	3/3.0 (-1)	1,697 (+6%)	14mo	$1,525,000	$899	65
51 Sherwood Ln	0.46mi	4/3.5	1,750 (+9%)	9mo	$1,575,000	$900	49

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 · 8.0% rent growth · sell at horizon

5-year hold

• IRR: 32.3%
• Equity multiple: 2.45×
• Total profit: $546,558
• Equity at exit: $201,140

10-year hold

• IRR: 41.9%
• Equity multiple: 5.94×
• Total profit: $1,867,187
• Equity at exit: $116,637

Cash invested: $377,720 (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 11937

• Rents YoY: 12.3%
• Active inventory: 135
• Price-to-rent: 4.8×

Monthly cashflow live

• Estimated rent: $23,558 medium
• Mortgage (P&I): −$7,074
• Tax from tax record: −$881 /mo · $10,577/yr
• Insurance: −$562
• HOA: −$32
• Vacancy / Maint / Mgmt: −$4,947
• Net cashflow: $10,061

Break-even live

Break-even rent $10,823

Max offer price $1,349,000

Occupancy floor 52%

Sensitivity live

Price	-10% $10,824	-5% $10,443	+0% $10,061	+5% $9,679	+10% $9,297
Rent	-10% $8,200	-5% $9,130	+0% $10,061	+5% $10,991	+10% $11,922
Rate	-1.0pp $10,740	-0.5pp $10,404	base $10,061	+0.5pp $9,711	+1.0pp $9,356

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: $337,250
• Closing costs: $40,470
• Reserves months: —
• Total cash needed: —

Rent comps 8 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
135 Pembroke Dr East Hampton, NY	4.0	2.0	2000	$30,000	$15.00	25d	1	0.21mi
1181 Springs Fireplace Rd East Hampton, NY	3.0	2.0	1600	$75,000	$46.88	44d	1	0.58mi
85 Camberly Rd East Hampton, NY	4.0	3.5	1700	$40,000	$23.53	25d	1	0.62mi
19 Pond Ln East Hampton, NY	3.0	2.0	1500	$85,000	$56.67	44d	1	0.65mi
221 Norfolk Dr East Hampton, NY	5.0	2.0	1500	$30,000	$20.00	44d	1	0.75mi
12 Underwood Dr East Hampton, NY	3.0	2.0	1600	$30,000	$18.75	19d	1	0.88mi
197 Hog Creek Rd East Hampton, NY	3.0	2.0	1700	$20,000	$11.76	44d	1	0.95mi
12 Maidstone Park Rd East Hampton, NY	3.0	3.5	1800	$75,000	$41.67	44d	1	0.98mi

HOA detail

• Monthly dues: $32 · $384/yr
• Likely covers: waterpool

Listing history 21 events

1. 2026-06-18
   days on market $1,349,000 Active 389 DOM
2. 2026-06-17
   days on market $1,349,000 Active 388 DOM
3. 2026-06-16
   days on market $1,349,000 Active 387 DOM
4. 2026-06-15
   days on market $1,349,000 Active 386 DOM
5. 2026-06-13
   days on market $1,349,000 Active 384 DOM
6. 2026-06-13
   days on market $1,349,000 Active 383 DOM
7. 2026-06-09
   days on market $1,349,000 Active 380 DOM
8. 2026-06-08
   days on market $1,349,000 Active 379 DOM
9. 2026-06-07
   days on market $1,349,000 Active 378 DOM
10. 2026-06-04
    days on market $1,349,000 Active 375 DOM
11. 2026-06-03
    days on market $1,349,000 Active 374 DOM
12. 2026-06-02
    days on market $1,349,000 Active 373 DOM
13. 2026-06-01
    days on market $1,349,000 Active 372 DOM
14. 2026-05-31
    days on market $1,349,000 Active 371 DOM
15. 2026-05-20
    historical
16. 2026-05-05
    price $1,349,000
17. 2026-02-08
    price $1,380,000
18. 2025-11-25
    status Active
19. 2025-11-20
    historical
20. 2025-08-17
    price $1,395,000
21. 2025-05-19
    listed $1,450,000 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: $10,577 · $881/mo
• Projected year-2 tax: $16,688 · $1,391/mo
• Expected delta: +$6,110/yr (+$509/mo · 57.8%)

ⓘ 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 1/10 Low
• 🌡 Heat 4/10 Moderate 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: $282,693
• − Mortgage interest: −$75,565
• − Property taxes: −$10,577
• − Insurance: −$6,745
• − Repairs & maintenance: −$22,615
• − Management: −$22,615
• − HOA: −$384
• − Depreciation: −$39,244
• Taxable income: $104,947
• Est. tax owed @ 24.0%: −$25,187
• After-tax cash flow: $95,542/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: Springs Union Free School District
• NCES district ID: 3627900
• Math proficiency: 55% ▲ 6.00%
• Reading proficiency: 60% ▲ 10.00%
• Median HH income: $75,413
• Composite: 51.42/100
• National rank: #1728
• State rank: #239 of 590 in NY

Livability — Springs

• Score: 63/100
• State rank: #809
• US rank: #15666

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Springs, NY
• County: Suffolk County · 679,920 people
• City population: 21,806
• Metro: New York-Newark-Jersey City, NY-NJ-PA
• Population (ZIP): 21,882
• Household income: $129,883
• Rent vs Own: 23.1% rent · 76.9% own
• Severe rent burden: 896.0

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: Majority White (61%)
• Race & ethnicity: White 61% Hispanic / Latino 32% Two or more races 23% Black 2% Asian 2%
• Hispanic origin (detail): Mexican 2% Puerto Rican 1%
• Common ancestry: Romanian 5% Scotch-Irish 4% Italian 2%
• Foreign-born: 25% · Canada, Guatemala, Jamaica
• Languages at home: 68% English-only · Spanish 28% Other Indo-European 1% Russian/Polish/Slavic 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: ▼ -285.21%
• Current HPI: 444.1499
• Rent YoY: ▲ 12.28%
• 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

-7.0% since first listed

7 events — show timeline

• 2026-05-20 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2026-05-05 Price Changed $1,349,000 OneKey® MLS as Distributed by MLS Grid
• 2026-02-08 Price Changed $1,380,000 OneKey® MLS as Distributed by MLS Grid
• 2025-11-25 Relisted — OneKey® MLS as Distributed by MLS Grid
• 2025-11-20 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2025-08-17 Price Changed $1,395,000 OneKey® MLS as Distributed by MLS Grid
• 2025-05-19 Listed $1,450,000 OneKey® MLS as Distributed by MLS Grid

Property tax history

+3.5%/yr

Latest (2025): $10,577 · +0.0% YoY. Source: county tax records.