271 S Orlando Ave
Winter Park, FL 32789
Active
List price
$1,550,000
Listing courtesy of SAND DOLLAR REALTY GROUP INC, 407-389-7318 (Robert Arnold, Jr)
MLS# O6450599 Status Active
Listing updated October 17, 2026
- Sq ft
- 3,430
- Year built
- 1949
About this home
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.
Facts
- Property type
- Multi-Family 5+
- Year built
- 1949
- Lot
- 0.18 acres
- Stories
- 1
- Annual taxes
- $11,445
- Construction
- Completed
- Subdivision
- Killarney Estates
- County
- Orange
Virtual tour
Location
Map: OpenFreeMap, © OpenMapTiles, © OpenStreetMap contributors
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