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Shelter Island

Suffolk County, NY

STR Investment Grade

Transparent Scoring
D
39/100
⚠️ CAUTION
Score Breakdown
💰Cash-on-Cash
5/35
🏠Affordability
2/25
📅Year-Round Income
15/15
🤝Landlord Friendly
2/10
📈Room to Grow
15/15
Cash-on-Cash
-9.8%
Negative Cash Flow
Median Home
$1723K
Very Expensive
Room to Grow
15/15
Excellent Headroom

STRs Generally Permitted

STRs generally allowed with standard permits

No major restrictions known. Standard registration and tax collection may be required. Check local ordinances for specific requirements.

Permit: Moderate
AI-generated regulation data · Regulations change frequently
📋 Before You Invest
Even in STR-friendly markets, confirm the details for your specific property. Call the Shelter Island City Clerk or Planning & Zoning Department and ask:
1. Are short-term rentals (under 30 days) allowed at [your address]?
2. What permits or licenses are required?
3. Are there owner-occupancy requirements?
4. Any caps on rental nights per year or number of permits?
Regulation details vary by neighborhood and zoning district — always verify for your specific address.

Why Shelter Island?

Beach Market

What drives short-term rental demand here

🏖️
Coastal Destination

Beach proximity drives premium nightly rates and strong seasonal demand from vacationers.

🔥
High Demand Zone

Strong traveler demand supports a competitive market with proven revenue potential.

Will This Deal Work?

Investment Grade
D
Negative Cash Flow
CoC: -9.8%
Can You Pay the Bills?
Risky
May struggle with payments
THE BOTTOM LINE ⚠️

Below average. Significant challenges may impact profitability.

💵
$440
Avg ADR
📅
69%
Occupancy
💰
$9,107
Monthly Revenue
🏠
$1723K
Median Price

Market estimates · Updated Feb 2026

📊 Income by Property Size

Monthly revenue estimates by bedroom count

1BR
$5,008
2BR
$6,830
3BR
$9,107
4BR
$12,294
5BR
$15,026
6BR+
$17,758
⭐ Best

🏠 Top Amenities for This Market

Add these to boost your revenue

MUST HAVEPool
+25%
MUST HAVEOcean View
+20%
HIGH IMPACTBeach Gear
+10%
HIGH IMPACTOutdoor Shower
+8%
NICE TO HAVEBalcony/Deck
+12%

🎯 Your Next Steps

1
Search for 6BR+ properties
Best income potential at $17,758/month
2
Add a Pool
Boost revenue by +25%
3
Target $11,384/month
Top 25% performer income goal

📋 Regulation Status

LegalPermit: Moderate

Regulations vary by city and county. Always verify local STR ordinances, permit requirements, and zoning laws before purchasing.

Research Comparable Listings

See active short-term rentals in this market

View Listings on Airbnb

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Take the Next Step

Find homes, agents, and lenders in this market

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📊

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Free STR calculator with comp data for any address

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Shelter Island, New York is rated D for Airbnb investment with a score of 39/100 (CAUTION). The market has an average daily rate (ADR) of $440, 69% occupancy, and estimated monthly STR revenue of $9,107. Median home value is $1,722,880 with a cash-on-cash return of -9.8%. STR regulation status: Legal. Data powered by Edge by Teeco using estimated market data.