Winter Park, FL Short term rental properties for sale

Updated: Sep 23

12-Unit Mixed-Use Property

271 South Orlando Avenue, Winter Park, FL 32789

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12 short‑term rental units: eight studios and four one‑bedroom, one‑bath units
Street‑facing office suite fronting South Orlando Avenue
Located at 271 South Orlando Avenue in Winter Park

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Based on your search, we've compiled 5 Potential Opportunities for your consideration. Besides 1 Active listings in Winter Park, FL, we suggest exploring several alternatives: 4 properties in Nearby Cities

Opportunities in Nearby Cities

Here are 4 Similar properties we found in Nearby Locations for your consideration.

Updated Two-Unit Duplex

46 E PRINCETON Street, Orlando, FL 32804

$568,200

2,016 sqft 0.15 AC lot

Two-unit residential property with updated systems, central cooling, a private driveway, and public utilities.

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Two-Home Multifamily Property

3701 Virginia Dr, Orlando, FL 32803

$625,000

2,044 sqft

Updated primary residence with a detached ADU, separate entry, and flexible occupancy options.

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Duplex with Detached ADU

3701 VIRGINIA Drive, Orlando, FL 32803

$625,000

2,044 sqft 0.19 AC lot

Two residences share a fenced parcel with separate entrances, updated systems, and a flexible layout for rental or multigenerational use.

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Updated Duplex with In-Unit Laundry

46 E PRINCETON ST, Orlando, FL 32804

$568,200

Two-unit property with refreshed interiors, private laundry, and central access to Orlando and Winter Park destinations.

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Winter Park, FL Short Term Rental Properties for Sale

271 South Orlando Avenue, Winter Park, FL 32789