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$1,550,000 Just Listed

  • For Sale
  • Active
  • Commercial
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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.

Full Property Details for 271 S Orlando Ave

General

  • Price: $1,550,000
  • Taxes: $11,445 (2026)
  • Status: Active
  • Type: Commercial
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6450599
  • Updated: 10/17/2026
  • Added to Site: 1 day(s) ago

Interior

  • Appliances: Dryer, Microwave, Refrigerator, Washer

Location

  • Area: 32789 - Winter Park
  • County: Orange
  • Development Name: 32789 - Winter Park
  • Subdivision: KILLARNEY ESTATES
  • Driving 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.

Community

  • Community Name: 32789 - Winter Park

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Electricity Available, Public, Water Connected

Structural Information

  • # Buildings: 1
  • Exterior Const.: Block, Stucco
  • Roof: Concrete
  • Square Feet: 3,430
  • Sq. Ft. Source: Public Records
  • Year Built: 1949

Lot Features

  • Lot Size (Acres): 0.18
  • Lot Size (Sq. Ft.): 7,884
  • Lot Size: 7884
  • Frontage: State Road
  • Street/Road Desc.: Paved

Financial Considerations

  • Tax Amount: $11,445.21
  • Tax Year: 2026

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • 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
  • Flood Zone Info: X
  • APN: 122229417207101
  • Property ID: 122229417207101
  • Block/Lot/Section: 7

Listed by Sand Dollar Realty Group Inc

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Listing agent

— 271 S Orlando Ave —

  • Sand Dollar Realty Group Inc

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 271 S Orlando Ave

School District:Orange County School District
NameGradesDistance
Killarney Elementary School
2401 Wellington Boulevard, Winter Park, FL 32789
PK-51 mi
College Park Middle School
1201 Maury Road, Orlando, FL 32804
6-82 mi
Edgewater High School
3100 Edgewater Drive, Orlando, FL 32804
9-122 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 271 S Orlando Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/16/2026
Listed
$1,550,000
158.33%
MLS
10/05/2017
Sold
$600,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 271 S Orlando Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$10,658
4%
$660,526
4%
2024
$10,259
6%
$637,507
5%
2023
$9,650
12%
$608,931
5%
2022
$8,644
11%
$580,350
17%
2021
$7,806
1%
$494,946
4%
2019
$7,737
-1%
$474,232
1%
2018
$7,794
79%
$470,763
75%
2017
$4,361
6%
$268,514
3%
2016
$4,103
1%
$260,824
25%
2015
$4,044
21%
$208,967
10%
2014
$3,346
-38%
$189,970
-39%
2013
$5,428
—
$309,717
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Sand Dollar Realty Group Inc

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271 S Orlando Avenue, Winter Park, FL 32789 (MLS# O6450599) is a Commercial property. 271 S Orlando Avenue is currently listed for $1,550,000 and was received on October 16, 2026. Want to learn more about 271 S Orlando Avenue? Do you have questions about finding other Commercial real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

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