16 Shelterlands Path · Shelter Island, NY 11964

$1,175,000

4 bd · 3.0 ba · 1,950 sqft · SingleFamily public records · 58 Days on market

Built 1988 0.93 ac lot $603/sqft · 15% below area Est $1381k · 15% under $4/mo HOA

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Why this score? — see what drove the D 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).

• ARV discount +14.2/15.0
• Cash flow +7.6/30.0
• Appreciation +6.0/10.0
• Schools +4.1/10.0
• Livability +3.0/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• DSCR +1.7/10.0
• 1% rule +1.1/10.0

Listing remarks MLS

This island classic is truly a home for all seasons. The bright and open floor plan is beautifully complemented by the natural surroundings of Shelter Island, creating an inviting atmosphere throughout the year. The spacious living room and dining room feature sliding doors that open onto surrounding decks, making summer relaxation a breeze. A cozy fireplace offers comfort on the chilliest autumn evenings, providing a warm and inviting space to unwind. The kitchen and den become the heart of the home during winter weekends with friends. Located on a quiet street and close to the hiking trails of Mashomack Preserve, making it ideal for spring adventures. The sandy shores of the nearby Wades Beach will bring you right back to summer fun and gatherings. With 3 bedrooms ,3 baths and 1950 sqft., creates ample space for visiting guests, ensuring comfort and convenience all year long. This Shelter Island retreat is truly a home for all.

Key facts

• 0.93 acre lot
• Garage
• Built 1988

What this means for you Summary

Snapshot

• This is a 4-bed/3.0-bath single-family listed at $1.18M.

Deal economics

• At list price, monthly cash flow is $-1k ($-17k/yr) — negative.
• To cash-flow at today's rent, offer at most $930k (20.8% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $720k (38.7% below list).
• Recommended offer: $720k (38.7% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads 60/100 on livability (#998 in NY) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+; Watch: amenities F, commute F, cost of living F.
• Shelter Island Union Free School District (rural): math 40% / reading 45% proficiency, ranked #546 of 755 in NY (top 72%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases; only 16% free/reduced lunch — higher-income household profile.
• Market conditions: 39 active listings in the ZIP; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).

Forward outlook

• In year one you build about $31k of equity ($8k loan paydown + $23k appreciation (2.0% local appreciation)).
• Suffolk County population projected to shrink 5% by 2050 — rents likely to lag national; underwrite the cash flow, not the appreciation.
• By year 3, paydown + projected appreciation supports a ~$79k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 58 days — a 3% lower offer ($1.14M) is reasonable based on typical stale-listing flexibility.

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 $719,994 (38.7% below list)

Questions for the listing agent

1. What do current leases actually rent for vs. the listed asking? Can we see a recent rent roll and the last 12 months of T-12 income?
2. It's been on market 58 days. Have you received any prior offers? Is the seller open to a 39% concession, seller financing, or rate buy-down credit?
3. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
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: 0.61% ✗
• Cap rate: 4.88%
• Cash-on-cash: -5.06%
• DSCR: 0.77
• GRM: 13.6

CMA / ARV

• ARV (median comp): $1,381,024
• List price: $1,175,000
• Delta: -14.92%
• Verdict: UNDERPRICED
• Comps: 9 within 1.0 mi

Projected returns pro-forma

1.97% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: -0.6%
• Equity multiple: 0.97×
• Total profit: $-10,139
• Equity at exit: $461,477

10-year hold

• IRR: 3.8%
• Equity multiple: 1.51×
• Total profit: $168,702
• Equity at exit: $663,020

Cash invested: $329,000 (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 11964

• Home prices YoY: 0.4%
• Active inventory: 39
• Price-to-rent: 13.6×

Monthly cashflow live

• Estimated rent: $7,200 medium
• Mortgage (P&I): −$6,162
• Tax from tax record: −$419 /mo · $5,029/yr
• Insurance: −$490
• HOA: −$4
• Vacancy / Maint / Mgmt: −$1,512
• Net cashflow: $-1,387

Break-even live

Break-even rent $8,955

Max offer price $930,065

Occupancy floor —

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: $293,750
• Closing costs: $35,250
• Reserves months: —
• Total cash needed: —

HOA detail

• Monthly dues: $4 · $48/yr

Listing history 6 events

1. 2026-06-04
   statusdays on market $1,175,000 Pending 58 DOM
2. 2026-06-03
   days on market $1,175,000 Active 57 DOM
3. 2026-06-02
   days on market $1,175,000 Active 56 DOM
4. 2026-06-01
   days on market $1,175,000 Active 55 DOM
5. 2026-05-31
   days on market $1,175,000 Active 54 DOM
6. 2026-04-07
   listed $1,175,000 Active 944-char remark

   Show marketing remark (944 chars)

   This island classic is truly a home for all seasons. The bright and open floor plan is beautifully complemented by the natural surroundings of Shelter Island, creating an inviting atmosphere throughout the year. The spacious living room and dining room feature sliding doors that open onto surrounding decks, making summer relaxation a breeze. A cozy fireplace offers comfort on the chilliest autumn evenings, providing a warm and inviting space to unwind. The kitchen and den become the heart of the home during winter weekends with friends. Located on a quiet street and close to the hiking trails of Mashomack Preserve, making it ideal for spring adventures. The sandy shores of the nearby Wades Beach will bring you right back to summer fun and gatherings. With 3 bedrooms ,3 baths and 1950 sqft., creates ample space for visiting guests, ensuring comfort and convenience all year long. This Shelter Island retreat is truly a home for all.

ⓘ 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: $5,029 · $419/mo
• Projected year-2 tax: $12,443 · $1,037/mo
• Expected delta: +$7,414/yr (+$618/mo · 147.4%)

ⓘ 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 2/10 Low 2 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $86,399
• − Mortgage interest: −$65,818
• − Property taxes: −$5,029
• − Insurance: −$5,875
• − Repairs & maintenance: −$6,912
• − Management: −$6,912
• − HOA: −$48
• − Depreciation: −$34,182
• Taxable loss: −$38,376
• Est. tax savings @ 24.0%: +$9,210
• After-tax cash flow: $-7,428/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: Shelter Island Union Free School District
• NCES district ID: 3626640
• Math proficiency: 40% ▼ -15.00%
• Reading proficiency: 45% ▼ -15.00%
• Median HH income: $75,456
• Composite: 41.31/100
• National rank: #7365
• State rank: #546 of 755 in NY

Livability — Shelter Island

• Score: 60/100
• State rank: #998
• US rank: #19481

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: Shelter Island, NY
• City population: 3,279
• Population (ZIP): 2,858

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 0.57)
• Race & ethnicity: White 62% Hispanic / Latino 21% Native American 15% Two or more races 7% Asian 6%
• Hispanic origin (detail): Mexican 16%
• Common ancestry: Italian 13% Romanian 5% Portuguese 1%
• Foreign-born: 15% · Canada
• Languages at home: 78% English-only · Spanish 18% Other Indo-European 3%

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: ▲ 1.97%
• Current HPI: 476.2348
• 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

1 event — show timeline

• 2026-04-07 Listed $1,175,000 OneKey® MLS as Distributed by MLS Grid

Property tax history

+1.7%/yr

Latest (2025): $5,029 · +0.0% YoY. Source: county tax records.