271 S Orlando AvenueWinter Park, FL 32789
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Rare hospitality-yield opportunity in Winter Park's Class A core, directly in the Hillstone trade area on South Orlando Avenue. The offering consists of 12 short-term rental units — 8 studios and 4 one-bedroom/one-bath — plus a street-facing office suite fronting S. Orlando Ave. The thesis is straightforward: Winter Park generates year-round, non-theme-park demand — Rollins, Park Avenue, AdventHealth Winter Park, and the corporate and event traffic that fills the surrounding hotels at rates a 12-unit boutique operation can match without a hotel's cost structure.
| 4 weeks ago | Listing updated with changes from the MLS | |
| 4 weeks ago | Listing first seen on site |
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Last checked: 2026-11-11 12:46 PM EST

