About This Home

This 0-bedroom, 0-bathroom commercial at 271 S ORLANDO Avenue in Winter Park, FL is listed for $1,550,000 ($452 per sqft). Built in 1949, the home offers 3,430 sqft of living space on a 0.18 acres lot.

Key Features

  • Built in 1949
  • 0.18 acre lot

Property Details

1 story
1949

Amenities

A/C
Listing Description

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.

Monthly Cost Estimate

$8,290/mo

20% down · 6.5% · 30 years

Principal$1,121
Interest$6,717
Insurance$452

Estimates only. Actual payments may vary.

Location

271 S ORLANDO Avenue

Winter Park, FL 32789

KILLARNEY ESTATES

Property Details

Construction

Block Stucco

Heating

Central

Cooling

Central Air

Appliances

DryerMicrowaveRefrigeratorWasher

Questions & Answers

This 0-bedroom, 0-bathroom commercial at 271 S ORLANDO Avenue is listed at $1,550,000 ($452/sqft). The estimated monthly payment is $8,290 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1949, 0.18 acre lot.

This property is listed by Robert Arnold, Jr.

RJ

Robert Arnold, Jr

Agent at Sand Dollar Realty Group Inc

Listed by Sand Dollar Realty Group Inc · Broker phone: (407) 389-7318 · Broker website

MLS# O6450599· Source: Stellar MLS· 16 days on PropertySimple

Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

271 S ORLANDO Avenue, Winter Park, FL 32789

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