$1.55M
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
Building size
Lot size
Price / SF
Units
Zoning
Days on market
Investment & cash flow
Figures provided by the listing broker — verify independently.
Lease terms
- Occupancy
- Tenant
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.
Virtual tour
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
- Building area
- 4,582 sq ft
- Price/sq ft
- $338
- Lot size
- 7,884 sq ft
- Units
- 12
- Buildings
- 1
- Stories
- 1
- Road frontage
- State Road
- Annual taxes
- $11K (2026)
- Parcel #
- 12-22-29-4172-07-101
- Zoning
- C-3
- MLS #
- O6450599
Utilities
- Utilities
- Electricity Available, Public, Water Connected
- Water source
- Public
- Sewer
- Public Sewer
Listing details
- Listing date
- 2026-10-16
- On market date
- 2026-10-16
- MLS area
- 32789 - Winter Park
- 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
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.
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.
Ryan Solberg, Licensed Real Estate Broker · MaxLife Realty, LLC · FL Lic. #BK3354351 · Equal Housing Opportunity · Terms · DMCA