Founder-led stewardship for Woodbury rental owners

Go, with conditions. The rule that decides it: Fees per the 2024 Village application: $250 first-time owner-occupied / $500 non-owner-occupied; annual renewal $125 / $250.

Permit required: unlawful to rent or advertise a short-term rental (all or part of a single-family dwelling for 30 consecutive days or less) without registering and obtaining a revocable permit; permits are annual and void on sale of the property (§§ 255-1, 255-3). Whole-home rentals allowed: the permit application has explicit Rented in Whole and Non-Owner Occupied tracks, so owner-occupancy is not required. Permit count capped: one STR permit per landlord for a 36-month probationary period (unless a 3+ year full-time resident owner), then one additional per year, with an absolute maximum of two permits (§ 255-5.G). Neighbors within 300 feet are notified of each application by mail at the applicant's cost; an objection triggers a Board of Trustees public hearing before the permit can issue (§ 255-6.B, 255-6.E). Initial plus annual fire-safety inspections, hard-wired smoke detectors in every sleeping room, $1,000,000 liability insurance with a rental endorsement (Airbnb/umbrella policies not accepted), 1 off-street parking space per bedroom, and septic pump-out proof required (§ 255-5, application checklist). The governing text is Village of Woodbury Code, Chapter 255 (Short-Term Rentals), §§ 255-1 through 255-13.

Eligible property is limited to single-family detached dwellings; two-family dwellings and all other property types cannot be STRs (§ 255-5.A.1). Occupancy capped at 2 per legal bedroom and an absolute maximum of 12 people including residents and visitors; no events (weddings, parties, concerts) and no overnight guests beyond contracted renters (§ 255-5.A.9-11, application checklist).

Violations: fines up to $500 for a first offense, escalating to $1,000-$1,500 for repeat offenses, with each day a separate violation; permits revocable, with a 1-year reapplication ban after revocation (§ 255-10).

Absentee landlords must designate a resident agent located in Orange County who can be physically at the property within 1 hour, and must run digital camera monitoring of arrivals and departures with recordings kept 30 days (§§ 255-1, 255-5.D, 255-5.I).

Workable. Confirm the current permit position with the municipality before you commit, then treat compliance as the first operating task rather than an afterthought. Most of the risk in Woodbury (Town) is administrative, not structural.