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$1,550,000
New Listing
271 S ORLANDO AVENUEWINTER PARK, FL 32789
For Sale|Quadruplex|Active
4
Beds
12
Total Baths
3,430
SqFt
$452
/SqFt
1949
Built
Subdivision:
KILLARNEY ESTATES
County:
Orange
Call Now: (407) 620-6608
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(407) 620-6608
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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.
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Listing Snapshot
Price
$1,550,000
Days On Site
0 Days
Bedrooms
4
Inside Area (SqFt)
3,430 sqft
Total Baths
12
Full Baths
N/A
Partial Baths
N/A
Lot Size
0.18 Acres
Year Built
1949
MLS® Number
O6450507
Status
Active
Property Tax
$11,445.21
HOA/Condo/Coop Fees
N/A
Sq Ft Source
Public Records
Friends & Family
Recent Activity
| 3 hours ago | Listing updated with changes from the MLS® | |
| 5 hours ago | Listing first seen on site |
General Features
Acres
0.18
Foundation
BlockBrick/Mortar
Levels
One
Property Sub Type
Quadruplex
Sewer
Public Sewer
SqFt Total
4582
Utilities
Electricity ConnectedSewer ConnectedWater Connected
Water Source
Public
Zoning
C-3
Interior Features
Appliances
DryerExhaust FanMicrowaveRefrigeratorWasher
Cooling
Central Air
Heating
Central
Laundry Features
Common AreaLaundry RoomOutside
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Exterior Features
Construction Details
BlockStucco
Exterior
Awning(s)
Roof
Concrete
Community Features
MLS Area
32789 - Winter Park
Township
22
Financing Terms Available
CashConventional
Roads
AsphaltPaved
Listing courtesy of SAND DOLLAR REALTY GROUP INC (407) 389-7318
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: 2026-10-16 07:06 PM EDT
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: 2026-10-16 07:06 PM EDT
Neighborhood & Commute
Source: Walkscore
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