17 Crescent Way · Shelter Island Heights, NY 11964

$1,875,000

3 bd · 3.5 ba · 3,607 sqft · SingleFamily public records · 100 Days on market

Built 1990 0.87 ac lot $520/sqft · 13% below area Est $2146k · 13% under

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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 +26.0/30.0
• ARV discount +13.2/15.0
• DSCR +8.7/10.0
• Appreciation +6.0/10.0
• 1% rule +5.7/10.0
• Schools +4.1/10.0
• Livability +2.8/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0

Listing remarks MLS

SHELTER ISLAND CONTEMPORARY WITH POOL NEAR BEACH Located within close proximity to five sandy beach areas, this cheery, sun-filled contemporary sited on .87 acres is turn-key. The stone tiled foyer steps down to the living room which flows easily to an open floor plan to the rear of the home overlooking the outdoor entertainment deck. The area features a dining area and a kitchen with Scandinavian cabinets, seating and prep island. The hall leads to a powder room and first floor primary en-suite bedroom with spacious spa like bath. The second floor has two generously proportioned bedrooms and full bath in the hallway. The lower level is outfitted with recreation/media area, full bath and a segregated storage area. The grounds are lush with established plantings and a custom designed Gunite pool with automatic pool cover and an outdoor shower just off the wide deck. There is an attached two car garage with glass doors for the car lover in the household! Five beaches are within close proximity.

Key facts

• Open floor plan
• Spa like bath
• 0.87 acre lot

Tags

• CONTEMPORARY WITH POOL
• OPEN FLOOR PLAN
• SCANDINAVIAN CABINETS
• OUTDOOR ENTERTAINMENT DECK
• SPA LIKE BATH
• RECREATION MEDIA AREA

What this means for you Summary

Snapshot

• This is a 3-bed/3.5-bath single-family listed at $1.88M.

Deal economics

• At list price, monthly cash flow is $5k ($56k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($20k rent vs $1.88M).
• Recommended offer: $1.71M (9.0% below list) — sets the bar for market timing.

Location & tenants

• Location reads 56/100 on livability (#1,120 in NY) — a working-class tenant base; expect higher turnover. 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 $50k of equity ($13k loan paydown + $37k 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 $525k cash investment doubles in ~5 years — after that, you're playing with house money.
• By year 3, paydown + projected appreciation supports a ~$127k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 100 days — a 9% lower offer ($1.71M) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 10y ago; this cycle's ask has dropped $100k (5%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $940k; list at $1.88M implies a 99% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Climate carrying-cost: severe wind risk, 80% chance of damaging wind over 30y; extreme-heat days projected 7→18/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $1,706,250 (9.0% below list)

Questions for the listing agent

1. It's been on market 100 days. Have you received any prior offers? Is the seller open to a 9% concession, seller financing, or rate buy-down credit?
2. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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.
5. 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.
6. 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: 1.07% ✓
• Cap rate: 9.26%
• Cash-on-cash: 10.61%
• DSCR: 1.47
• GRM: 7.8

CMA / ARV

• ARV (median comp): $2,145,912
• List price: $1,875,000
• Delta: -7.96%
• Verdict: FAIR
• Comps: 5 within 1.0 mi

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
27 Country Club Dr	0.12mi	3/2.0	3,170 (-12%)	5mo	$1,725,000	$544	64

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

Projected returns pro-forma

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

5-year hold

• IRR: 14.9%
• Equity multiple: 1.80×
• Total profit: $420,452
• Equity at exit: $736,399

10-year hold

• IRR: 17.4%
• Equity multiple: 3.31×
• Total profit: $1,211,783
• Equity at exit: $1,058,011

Cash invested: $525,000 (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: 7.8×

Monthly cashflow live

• Estimated rent: $20,000 medium
• Mortgage (P&I): −$9,833
• Tax from tax record: −$544 /mo · $6,526/yr
• Insurance: −$781
• HOA: −$0
• Vacancy / Maint / Mgmt: −$4,200
• Net cashflow: $4,642

Break-even live

Break-even rent $14,124

Max offer price $1,875,000

Occupancy floor 72%

Sensitivity live

Price	-10% $5,704	-5% $5,173	+0% $4,642	+5% $4,112	+10% $3,581
Rent	-10% $3,062	-5% $3,852	+0% $4,642	+5% $5,432	+10% $6,222
Rate	-1.0pp $5,586	-0.5pp $5,119	base $4,642	+0.5pp $4,156	+1.0pp $3,662

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: $468,750
• Closing costs: $56,250
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
165 Marine Pl Greenport, NY	4.0	4.5	3800	$20,000	$5.26	45d	1	1.30mi

Listing history 26 events

1. 2026-06-21
   pricedays on market $1,875,000 Active 100 DOM
2. 2026-06-18
   days on market $1,975,000 Active 97 DOM
3. 2026-06-17
   days on market $1,975,000 Active 96 DOM
4. 2026-06-16
   days on market $1,975,000 Active 95 DOM
5. 2026-06-15
   days on market $1,975,000 Active 94 DOM
6. 2026-06-13
   days on market $1,975,000 Active 92 DOM
7. 2026-06-13
   days on market $1,975,000 Active 91 DOM
8. 2026-06-09
   days on market $1,975,000 Active 88 DOM
9. 2026-06-08
   days on market $1,975,000 Active 87 DOM
10. 2026-06-07
    days on market $1,975,000 Active 86 DOM
11. 2026-06-04
    days on market $1,975,000 Active 83 DOM
12. 2026-06-03
    days on market $1,975,000 Active 82 DOM
13. 2026-06-02
    days on market $1,975,000 Active 81 DOM
14. 2026-06-01
    days on market $1,975,000 Active 80 DOM
15. 2026-05-31
    days on market $1,975,000 Active 79 DOM
16. 2026-03-13
    listed $1,975,000 Active 1007-char remark

    Show marketing remark (1007 chars)

    SHELTER ISLAND CONTEMPORARY WITH POOL NEAR BEACH Located within close proximity to five sandy beach areas, this cheery, sun-filled contemporary sited on .87 acres is turn-key. The stone tiled foyer steps down to the living room which flows easily to an open floor plan to the rear of the home overlooking the outdoor entertainment deck. The area features a dining area and a kitchen with Scandinavian cabinets, seating and prep island. The hall leads to a powder room and first floor primary en-suite bedroom with spacious spa like bath. The second floor has two generously proportioned bedrooms and full bath in the hallway. The lower level is outfitted with recreation/media area, full bath and a segregated storage area. The grounds are lush with established plantings and a custom designed Gunite pool with automatic pool cover and an outdoor shower just off the wide deck. There is an attached two car garage with glass doors for the car lover in the household! Five beaches are within close proximity.

17. 2018-06-14
    soldstatus $940,000
18. 2016-08-03
    soldstatus $875,000
19. 2016-07-15
    soldstatus $875,000 459-char remark

    Show marketing remark (459 chars)

    Reduced To Well-Below Assessed Value! Mint Island Oasis Ready For You To Enjoy Year Round. Entry Foyer W/Granite Floors, Formal Living Room, Family Room W/Fp & 2 Skylights, Dr, Eik W/Island. 1st Floor Master Suite W/Jacuzzi & Sep Shower. Laundry, .5Ba, 2 Car Garage & Decks Across The Back For Entertaining. 2nd Floor W/2 Large Bedrooms & Full Ba. Room For A Pool And More!, Additional information: Appearance:Mint,Separate Hotwater Heater:Yes

20. 2016-07-15
    soldstatus $875,000 Closed

    Show marketing remark (459 chars)

    Reduced To Well-Below Assessed Value! Mint Island Oasis Ready For You To Enjoy Year Round. Entry Foyer W/Granite Floors, Formal Living Room, Family Room W/Fp & 2 Skylights, Dr, Eik W/Island. 1st Floor Master Suite W/Jacuzzi & Sep Shower. Laundry, .5Ba, 2 Car Garage & Decks Across The Back For Entertaining. 2nd Floor W/2 Large Bedrooms & Full Ba. Room For A Pool And More!, Additional information: Appearance:Mint,Separate Hotwater Heater:Yes

21. 2016-06-30
    status Under Contract
22. 2016-04-14
    price $879,000
23. 2016-01-21
    listed $899,000 New
24. 2016-01-21
    historical
25. 2016-01-02
    listed $899,000

    Show marketing remark (459 chars)

    Reduced To Well-Below Assessed Value! Mint Island Oasis Ready For You To Enjoy Year Round. Entry Foyer W/Granite Floors, Formal Living Room, Family Room W/Fp & 2 Skylights, Dr, Eik W/Island. 1st Floor Master Suite W/Jacuzzi & Sep Shower. Laundry, .5Ba, 2 Car Garage & Decks Across The Back For Entertaining. 2nd Floor W/2 Large Bedrooms & Full Ba. Room For A Pool And More!, Additional information: Appearance:Mint,Separate Hotwater Heater:Yes

26. 2016-01-02
    listed $879,000 459-char remark

    Show marketing remark (459 chars)

    Reduced To Well-Below Assessed Value! Mint Island Oasis Ready For You To Enjoy Year Round. Entry Foyer W/Granite Floors, Formal Living Room, Family Room W/Fp & 2 Skylights, Dr, Eik W/Island. 1st Floor Master Suite W/Jacuzzi & Sep Shower. Laundry, .5Ba, 2 Car Garage & Decks Across The Back For Entertaining. 2nd Floor W/2 Large Bedrooms & Full Ba. Room For A Pool And More!, Additional information: Appearance:Mint,Separate Hotwater Heater:Yes

ⓘ 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: $6,526 · $544/mo
• Projected year-2 tax: $19,107 · $1,592/mo
• Expected delta: +$12,581/yr (+$1,048/mo · 192.8%)

ⓘ 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 2/10 Low
• 🌡 Heat 5/10 Major 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 2/10 Low 2 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $240,000
• − Mortgage interest: −$105,029
• − Property taxes: −$6,526
• − Insurance: −$9,375
• − Repairs & maintenance: −$19,200
• − Management: −$19,200
• − Depreciation: −$54,545
• Taxable income: $26,125
• Est. tax owed @ 24.0%: −$6,270
• After-tax cash flow: $49,437/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 Heights

• Score: 56/100
• State rank: #1120
• US rank: #23056

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Shelter Island Heights, 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

+119.7% since first listed

11 events — show timeline

• 2026-03-13 Listed $1,975,000 OneKey® MLS as Distributed by MLS Grid
• 2018-06-14 Sold (Public Records) $940,000 Public Records
• 2016-08-03 Sold (Public Records) $875,000 Public Records
• 2016-07-15 Sold (MLS) $875,000 OneKey® MLS as Distributed by MLS Grid
• 2016-07-15 Sold (MLS) $875,000 MLSLI
• 2016-06-30 Pending — MLSLI
• 2016-04-14 Price Changed $879,000 MLSLI
• 2016-01-21 Listed $899,000 MLSLI
• 2016-01-21 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2016-01-02 Listed $879,000 OneKey® MLS as Distributed by MLS Grid
• 2016-01-02 Listed $899,000 OneKey® MLS as Distributed by MLS Grid

Property tax history

+2.0%/yr

Latest (2025): $6,526 · +0.0% YoY. Source: county tax records.