$1,550,000
Active271 S Orlando Ave, Winter Park, FL 32789
3,430 sq ft
Listing courtesy of SAND DOLLAR REALTY GROUP INC · MLS# O6450599
Listed today
Refreshed from the Stellar MLS feed . This listing’s MLS record last changed .
About this property
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.
Facts
- Property type
- Multi-Family 5+
- Year built
- 1949
- Flood zone
- X
- Annual taxes
- $11,445/yr
- Listed
- Oct 16, 2026
- MLS #
- O6450599
Commercial details
Building & site
- Building size
- 4,582 SF
- Lot size
- 0.18 acres (7,884 SF)
- Zoning
- C-3
- Road frontage
- State Road
- Buildings
- 1
- Occupancy
- Tenant-occupied
Investor metrics
- Price per SF (MLS)
- $338.28/SF
- Net operating income
- $148,222/yr
- Units
- 12
As reported by the listing broker in the MLS. Not verified by Lasbury-Tracy Realty — confirm with the listing broker before relying on them. We never estimate a cap rate.
Take a tour
Pick a day that suits you — a licensed Lasbury Tracy agent confirms personally, usually within minutes. No account needed.
271 S Orlando Ave, Winter Park, FL 32789
Listing courtesy of SAND DOLLAR REALTY GROUP INC · MLS# O6450599 · Active
Where this property is
Opens on aerial — on this coast the canal, the lot and the neighbours answer more questions than a street grid does.
