🎯 STRisker: Bulletin - Riverhead, NY
Online Clues Could Soon Be Enough to Flag Illegal Short-Term Rentals in Riverhead

Riverhead Moves Toward Stronger STR Enforcement Using Online Evidence

Riverhead is inching closer to a major overhaul of its short-term rental policy, and residents made sure their voices were heard. With rentals under 30 days banned for more than a decade—but still popping up across town—the proposed enforcement boost drew both applause and concern.
The biggest shift comes from how the town would determine whether a property is being used for short-term stays. Instead of needing renters to testify, enforcement officers could rely on public online evidence to establish “presumed transient use.”


A confirmed violation would mean immediate permit loss, plus fines starting at $3,000 and soaring to $30,000 for repeated offenses. Add to that possible $5,000-per-day civil penalties and the authority to force platforms to remove listings, and Riverhead is clearly signaling it's serious.
A number of speakers expressed how disruptive illegal short-term rentals have become. Bob Klein from Aquebogue described years of turmoil from a single mega-rental property that pushed limits with weddings, parties, and up to 45 guests at a time. Similar stories of noise, trash, heavy traffic, and constant guest turnover highlighted the strain STRs bring to quiet neighborhoods.
Some attendees urged the town to consider the economic and practical value of short-term rentals. Riverhead resident Zuleika Hines argued that STRs serve more than tourists—they’re a lifeline for visiting medical patients, business travelers, and families in transition. She called for exploring a 14-day minimum instead of the hard 30-day rule, but only after residents feel confident that the enforcement process is reliable and responsive.
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Residents questioned whether certain well-connected properties are receiving different oversight. Others expressed concern about accidental violations triggered by glitches within platforms like Airbnb. Monthly renter Michael Jones said the penalties felt “extreme” and warned against punishing honest homeowners over minor technical slip-ups.
Questions also arose about enforcement staffing, but the town clarified that it has a multi-person team and two open part-time positions, pushing back on the notion that there’s only one enforcement officer.
With written comments accepted until Nov. 28, the conversation isn’t done yet. Riverhead now faces a familiar challenge: finding the right balance between neighborhood stability, fairness, and real-world housing needs in the ever-shifting short-term rental landscape.
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