271 S ORLANDO AVENUE WINTER PARK FL 32789 | MLS #O6450599

271 S ORLANDO AVENUE
WINTER PARK, FL, 32789
$1,550,000
Beds
0 Baths
3,430 SqFt
0.18 Acres
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MLS #O6450599 image #0
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.

Property Details

Price:
$1,550,000
MLS #:
O6450599
Status:
Active
Beds:
0
Baths:
0
Type:
Commercial
Subtype:
Multi Family (5+)
Subdivision:
KILLARNEY ESTATES
Neighborhood:
32789winterpark
Listed Date:
Oct 16, 2026
Finished Sq Ft:
3,430
Total Sq Ft:
4,582
Lot Size:
7,884 sqft / 0.18 acres (approx)
Year Built:
1949
32789 – Winter Park32789winterparkKillarney Estates

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Schools

Interior

Appliances
Dryer, Microwave, Refrigerator, Washer
Cooling
Central Air
Heating
Central

Exterior

Construction Materials
Block, Stucco
Roof
Concrete

Financial

Tax Year
2026
Taxes
$11,445

Map

Community

Subdivisions in WINTER PARK

Market Summary

Current real estate data for Commercial in WINTER PARK as of Oct 18, 2026
14
Commercial Listed
149
Avg DOM
445
Avg $ / SqFt
$1,411,571
Avg List Price

Property Summary

    Located in the KILLARNEY ESTATES subdivision, 271 S ORLANDO AVENUE WINTER PARK FL is a Commercial for sale in WINTER PARK, FL, 32789. It is listed for $1,550,000 To schedule a showing of MLS#o6450599 at 271 S ORLANDO AVENUE in WINTER PARK, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.

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broker reciprocity Courtesy of SAND DOLLAR REALTY GROUP INC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved.
Rover IDX
271 S ORLANDO AVENUE
WINTER PARK, FL