43 Gardiners Bay Dr · Shelter Island, NY 11964

$3,625,000

5 bd · 4.5 ba · 6,106 sqft · SingleFamily · 5 Days on market

Built 1985 0.92 ac lot

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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 +30.0/30.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• ARV discount +7.5/15.0
• 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

Listing remarks MLS

Shy Acre On A Rise With A Spacious Main House As Well As Separate Guest Cottage With Living Room, Bath & 2Brs. Circular Drive, Oak Floors, Outside Shower, Vaulted Ceilings. Very Close To Beaches, Golf And Country Club. New Roof And 5 Year Old Furnace. An Ideal Summer Get-Away Or Year Round Residence., Additional information: Appearance:Excellent,Separate Hotwater Heater:Y

Key facts

• Firelit living room
• Exquisite millwork
• Light-filled foyer

Tags

• WINTER WATER VIEWS
• LIGHT-FILLED FOYER
• EXQUISITE MILLWORK
• EXPANSIVE GROUNDS
• FIRELIT LIVING ROOM
• CHEF'S KITCHEN

Property features AI

Finance

• Other: Living area reported from public records; Additional equipment includes compressor, fuel tank(s), and pool equipment/cover

Exterior

• Parking: Driveway; Garage (1 car)
• Security: Smoke detectors
• Utilities: Electric service by PSEG; Water connected; Sewer via cesspool/septic tank; Propane available; Cable available; Electricity connected
• Home design: Single family residence; Updated/remodeled condition; Two levels; Basement: full, partially finished with walk-out access; Attic access via scuttle
• Construction: Clapboard exterior; Concrete perimeter foundation; Year built/upgrades not specified
• Exterior features: In-ground outdoor pool with cover; Pool equipment and cover provided; Lighting; Playground; Rain gutters; Back yard and front yard landscaping; Corner and interior lot aspects; Level and sloped areas; Private setting with views; Stone/brick wall; Back yard fencing

Interior

• Kitchen: Chef's kitchen with cooktop; Kitchen island; Marble counters; Pantry; Eat-in kitchen; Dishwasher
• Bedrooms: Total rooms include bedrooms on two levels
• Flooring: Hardwood; Ceramic tile; Concrete; Other flooring
• Bathrooms: Four full bathrooms; One half bathroom; Primary bathroom with double vanity and soaking tub
• Heating & cooling: Central air conditioning; Forced air heating; Hot water heating; Oil heating
• Interior features: Built-in features; Cathedral ceilings; Ceiling fans; Chef's kitchen; Double vanity; Eat-in kitchen; Entertainment cabinets; Entrance foyer; High ceilings; Kitchen island; Marble counters; Natural woodwork; Open floorplan; Open kitchen; Pantry; Primary bathroom; Recessed lighting; Soaking tub; Speakers; Walk-in closets; New windows; Window screens; Covered patio and porch
• Laundry & utility: Dedicated laundry room; Washer/dryer hookups (dryer listed); Compressor and fuel tank(s)

What this means for you Summary

Snapshot

• This is a 5-bed/4.5-bath single-family listed at $3.62M.

Deal economics

• At list price, monthly cash flow is $34k ($410k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($75k rent vs $3.62M).

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: 40 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 1,366 units permitted in Suffolk County in 2024 (216 in 5+ unit buildings).

Forward outlook

• In year one you build about $96k of equity ($25k loan paydown + $71k 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.
• At projected returns (2.0% appreciation + 3.0% rent growth), your $1.01M cash investment doubles in ~2 years — after that, you're playing with house money.
• By year 3, paydown + projected appreciation supports a ~$245k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• Only 5 days on market — expect competitive offers; lowballing is unlikely to land.
• 3 sale attempts since 13y 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 $815k; list at $3.62M implies a 345% gain — meaningful room to come down on a strong offer.

Recommended offer $3,625,000

Questions for the listing agent

1. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
2. 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.
3. 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.
4. 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: 2.07% ✓
• Cap rate: 17.61%
• Cash-on-cash: 40.43%
• DSCR: 2.80
• GRM: 4.0

CMA / ARV

No comps found within radius.

Projected returns pro-forma

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

5-year hold

• IRR: 44.4%
• Equity multiple: 3.39×
• Total profit: $2,422,056
• Equity at exit: $1,423,705

10-year hold

• IRR: 45.2%
• Equity multiple: 6.74×
• Total profit: $5,823,561
• Equity at exit: $2,045,489

Cash invested: $1,015,000 (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: 40
• Price-to-rent: 4.0×

Monthly cashflow live

• Estimated rent: $75,000 medium
• Mortgage (P&I): −$19,010
• Tax est. 1.5%: −$4,531 /mo · $54,375/yr
• Insurance: −$1,510
• HOA: −$0
• Vacancy / Maint / Mgmt: −$15,750
• Net cashflow: $34,198

Break-even live

Break-even rent $31,711

Max offer price $3,625,000

Occupancy floor 49%

Sensitivity live

Price	-10% $36,704	-5% $35,451	+0% $34,198	+5% $32,946	+10% $31,693
Rent	-10% $28,273	-5% $31,236	+0% $34,198	+5% $37,161	+10% $40,123
Rate	-1.0pp $36,024	-0.5pp $35,120	base $34,198	+0.5pp $33,259	+1.0pp $32,303

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: $906,250
• Closing costs: $108,750
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
15 Montclair Ave Shelter Island, NY	6.0	4.5	4600	$75,000	$16.30	23d	1	1.40mi

Listing history 4 events

1. 2026-06-21
   days on market $3,625,000 Active 5 DOM
2. 2026-06-18
   days on market $3,625,000 Active 2 DOM
3. 2026-06-17
   remarks 687-char remark
4. 2026-06-17
   listed $3,625,000 Active 1 DOM

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Taxation est. · year 1

• Rental income: $900,000
• − Mortgage interest: −$203,056
• − Property taxes: −$54,375
• − Insurance: −$18,125
• − Repairs & maintenance: −$72,000
• − Management: −$72,000
• − Depreciation: −$105,455
• Taxable income: $374,989
• Est. tax owed @ 24.0%: −$89,997
• After-tax cash flow: $320,384/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
• 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

+322.0% since first listed

7 events — show timeline

• 2026-06-15 Listed $3,625,000 OneKey® MLS as Distributed by MLS Grid
• 2014-04-28 Sold (MLS) $815,000 MLSLI
• 2014-04-28 Sold (MLS) $815,000 OneKey® MLS as Distributed by MLS Grid
• 2014-03-13 Pending — MLSLI
• 2013-10-20 Price Changed $859,000 MLSLI
• 2013-06-06 Listed $885,000 MLSLI
• 2013-06-06 Listed $859,000 OneKey® MLS as Distributed by MLS Grid