$1,550,000

271 S ORLANDO AVE, WINTER PARK FL, 32789

Price per sqft$451.90

Built in1949

Property size3,430 sqft

Property typeCommercial

Courtesy of SAND DOLLAR REALTY GROUP INC, Robert Arnold, Jr Listing Contact: 407-389-7318

Overview

Active

Listed Oct 16, 2026

Updated 6h ago

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.

Additional information

MLS^® ID: O6450599

Interior Features

Bathrooms: 0
Cooling: Yes
Heating: Yes
Basement: No

Exterior Features

Lot Size: 0.18 Acres

Other Property Details

Taxes: $11,445
Tax Frequency: Annually
Association Fee Frequency: Monthly

Listings courtesy of Stellar MLS as distributed by MLS GRID

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Based on information submitted to the MLS GRID as of 10:59 AM UTC on 10/17/2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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