$1,550,000
271 Orlando AvenueWinter Park, FL 32789
Listing updated: October 17, 2026 at 1:02 AM ET
Listing courtesy of Sand Dollar Realty Group Inc · Robert Arnold, Jr · MLS #O6450599 · Active · 407-389-7318Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Flood zone
About this home
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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history0 days on market
- Status: ActiveOct 16, 2026
- Listed$1,550,000Oct 16, 2026
Facts & features
- Property type
- Commercial Sale
- Sub type
- Multi-Family 5+
- Status
- Active
- Days on market
- 0
- Subdivision
- Killarney Estates
- County
- Orange
- Year built
- 1949
- Living area
- 3,430 sq ft
- Price/sq ft
- $338
- Building area
- 4,582 sq ft (Public Records)
- Lot size
- 7,884 sq ft
- Lot category
- 0 to less than 1/4
- Flood zone
- X (12095C0255F)
- Annual taxes
- $11,445 (2026)
- Parcel #
- 12-22-29-4172-07-101
- Zoning
- C-3
- MLS #
- O6450599
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Interior Details
- Appliances
- Dryer, Microwave, Refrigerator, Washer
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air
Parking
- Garage spaces
- 0
HOA & Financial
- Total monthly fees
- None
- Total annual fees
- None
- Listing terms
- Cash, Commercial Financing
- Ownership
- Fee Simple
Exterior & Construction
- Construction materials
- Block, Stucco
- Roof
- Concrete
- Foundation
- Block, Brick/Mortar
- Road surface
- Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Electricity Available, Public, Water Connected
Listing Details
- Listing date
- 2026-10-16
- On market date
- 2026-10-16
- Original list price
- $1,550,000
- Occupant type
- Tenant
- MLS area
- 32789 - Winter Park
- Listing AOR
- Orlando Regional
- Status changed
- 2026-10-16
- Tax 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 risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of October 17, 2026 at 1:02 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
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