271 S ORLANDO AVENUE, WINTER PARK, Orange, Commercial Sale – MLS #O6450599
Rare hospitality-yield opportunity in Winter Park’s Class A core, directly…
$1,550,000
Residential Income
$1,550,000
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.
MLS updated 2026-10-16. Fees are reported by MLS; confirm current charges with the association.
Rare hospitality-yield opportunity in Winter Park’s Class A core, directly…
$1,550,000
An excellent and rare opportunity to expand your existing group…
$1,379,000
An excellent and rare opportunity to expand your existing group…
$1,420,000
Prime Winter Park commercial office building with visibility of monument…
$1,350,000
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