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271 S ORLANDO AVENUE Winter Park, FL $ 1,550,000
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271 S ORLANDO AVENUE
$ 1,550,000
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271 S ORLANDO AVENUE

Winter Park, FL, 32789
$ 1,550,000
Bedrooms-- Baths-- Sq 3,430

Monthly Estimate*

$ 10,705

271 S ORLANDO AVENUE, Winter Park, FL 32789 - Image 1
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Commercial Property for sale in Winter Park, FL

for $1,550,000. This 3,430 square foot building was built in 1949 on a lot size of 0.18.

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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Commercial Active

Price

$ 1,550,000

Property Type

Commercial

Taxes

$ 11,445

Style

Multi Family (5+)

Lot Size

0.18

Year Built

1949

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

O6450599
Features
General
Sewer Public Sewer
Heating Central
Cooling Central Air
Utilities Electricity Available Public Water Connected
Roof Concrete
Appliances Dryer Microwave Refrigerator Washer
Zoning C-3
Garage Spaces 0
Construction Materials Block Stucco
Year Built 1949
Property Subtype Multi Family (5+)
Tax Year 2026
Ownership Fee Simple
County Orange
New Construction false
Property Type Commercial Sale
Subdivision Name KILLARNEY ESTATES
Status Active
Directions From I-4 take Exit 87 (Fairbanks Ave) east approx. 1.5 miles to US 17-92 / S Orlando Ave. Turn left (north) on S Orlando Ave; property is on the left (west side) just south of Hillstone at 271 S Orlando Ave.
City WINTER PARK
Number Of Units Total 12
MLS Area 32789 - Winter Park
Lot Size Units Square Feet
Lot Size Square Feet 7884
Carport Spaces 0
Listing Terms Cash
Tax Annual Amount 11445.21
Property Condition Completed
Additional Parcels Y/N false
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6450599
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Tenant
Tax Lot 10
Legal Description KILLARNEY ESTATES RESURVEY L/9 LOT 10 (LESS N 3 FT OF W 40 FT & LESS E 10 FT & R/W ACROSS SE COR) & E 10 FT OF S 62 FT OF LOT 7 BLK 7
Water Access Y/N false
Water View Y/N false
Flood Zone Code X
Flood Zone Code X Y
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Interior
Total Stories 1
Air Conditioning Y/N true
Heating Y/N true
Total Baths 0
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Exterior
Water Source Public
Lot Size Area 7884
Foundation Details Block Brick/Mortar
Number of Buildings 1
Building Area Total 4582
Lot Size Acres 0.18
Road Surface Type Paved
Waterfront Y/N false
Covered Spaces 0
Road Frontage Type State Road
Road Responsibility Public Maintained Road
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* Excluded Features
List By
Sand Dollar Realty Group Inc

Broker

robert@sdrhouses.com

Email

Affordability Calculator

$11,659
Per Month
92%
8%
0%
Monthly Principal & Interest
$10,705
Monthly Property Taxes
$954
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4827338 Elementary School
4827337 Middle School
Unknown High School High School
See complete school information
Pricing History
DatePricePrice ChangeDescription
10/16/2026$1,550,000 Listed Price

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271 S ORLANDO AVENUE, Winter Park, FL, 32789 is a Commercial Property for sale at $1,550,000 with 3,430 sqft and a lot size of 0.18. 271 S ORLANDO AVENUE was built in 1949. The property's zip code is 32789 which is in Winter Park, FL

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