Virtual TourMap

For SaleCommercial SaleActive

271 S Orlando Avenue

Winter Park, FL 32789

$1,550,000

20 Days On Site

  • 3,430Sq Ft
  • $452Per Sq Ft
  • 0.18Acres
  • 1949Built
Subdivision
Killarney Estates
County
Orange
MLS®
O6450599

Overview

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.

Listing Snapshot

Price
$1,550,000
Days On Site
20 Days
Bedrooms
N/A
Inside Area (SqFt)
3,430 sqft
Total Baths
N/A
Full Baths
N/A
Partial Baths
0
Lot Size
0.18 Acres
Year Built
1949
MLS® Number
O6450599
Status
Active
Property Tax
$11,445.21 (2026)
HOA/Condo/Coop Fees
N/A
Sq Ft Source
Public Records

Property Details

General Features

8 items
Acres
0.18
Foundation
Block, Brick/Mortar
Number Of Stories
1
Sewer
Public Sewer
SqFt Total
4,582
Utilities
Electricity Available, Water Connected
Water Source
Public
Zoning
C-3

Interior Features

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

Exterior Features

3 items
Construction Details
Block, Stucco
Road Frontage
State Road
Roof
Concrete

Community Features

4 items
MLS Area
32789 - Winter Park
Township
22
Financing Terms Available
Cash
Roads
Paved

Location

271 S Orlando Avenue, Winter Park, FL 32789 · 32789 - Winter Park

Neighborhood & Commute

ZIP Code 32789

Median household income
$110,150
Income per person
$78,898
Households
12,171
Average household size
2.08
Median age
44.5

Source: Walk Score.

Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.

Price & Status History

  1. Listing updated with changes from the MLS®
  2. Status changed to Active
  3. Listing first seen on site

Friends & Family

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Listing courtesy of SAND DOLLAR REALTY GROUP INC (407) 389-7318

Stellar MLS

Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.

Last checked: 2026-11-05 09:52 PM EST

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