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522 S Osceola Avenue, Orlando

Multiple Offers - submit highest and best by September 1 at 10:00 am. Investor opportunity in Orlando’s desirable Lake Cherokee Historic District, minutes from Downtown Orlando. This 1920s duplex offers two income-producing units, each historically renting for approximately $1,800–$2,000 per month. Original wood floors, fireplaces, abundant windows and generously sized rooms preserve the property’s historic character. Each residence features its own kitchen and living spaces, while the large backyard provides additional outdoor space and privacy. The property was converted from a rooming house into a duplex in the mid-1980s through a comprehensive gut renovation that included new plumbing and electrical systems. More recent improvements include a roof replaced approximately eight to ten years ago and air-conditioning systems replaced within the past five to six years. The property needs renovation but offers significant potential through its location, flexible configuration and established rental history. Renovate and reposition the existing duplex, occupy one unit while leasing the other, explore conversion to a single-family residence, or evaluate potential redevelopment options subject to applicable historic-preservation review and governmental approvals.

4 Beds ⋅ 4 Baths ⋅ Douglass Sub SubDv. ⋅ 32801 Zip Code

Multiple Offers - submit highest and best by September 1 at 10:00 am. Investor opportunity in Orlando’s desirable Lake Cherokee Historic District, minutes from Downtown Orlando. This 1920s duplex offers two income-producing units, each historically renting for approximately $1,800–$2,000 per month. Original wood floors, fireplaces, abundant windows and generously sized rooms preserve the property’s historic character. Each residence features its own kitchen and living spaces, while the large backyard provides additional outdoor space and privacy. The property was converted from a rooming house into a duplex in the mid-1980s through a comprehensive gut renovation that included new plumbing and electrical systems. More recent improvements include a roof replaced approximately eight to ten years ago and air-conditioning systems replaced within the past five to six years. The property needs renovation but offers significant potential through its location, flexible configuration and established rental history. Renovate and reposition the existing duplex, occupy one unit while leasing the other, explore conversion to a single-family residence, or evaluate potential redevelopment options subject to applicable historic-preservation review and governmental approvals.

522 S Osceola Avenue, Orlando

310 E Anderson Street, Orlando

Fully renovated mixed-use duplex offering exceptional flexibility and income potential in the heart of Orlando. This stand-alone historical building is zoned for both commercial and residential use, creating endless opportunities for investors, business owners, or owner-occupants. Both units are currently operating as successful short-term rentals (Airbnb), generating immediate income. The downstairs unit, previously configured as an office, features three separate rooms, a kitchenette, dining area, and a full bathroom. It can continue as a short-term rental, professional space, or be converted to residential use. The upstairs unit includes two bedrooms, one full bathroom, a full kitchen, and an open-concept living and dining area, making it ideal for guests and consistent rental income. Each unit has its own private entrance and separate electrical meter. The property offers ample parking, accommodating up to seven vehicles total, with dedicated parking areas for each unit. Recent updates include a newer roof (2018). The upstairs unit is equipped with a washer and dryer. Furniture is negotiable. Ideally located just steps from the Dr. Phillips Center for the Performing Arts, Downtown Orlando, and Lake Eola Park, with easy access to dining, entertainment, and major roadways. Live in one unit and rent the other, lease both for maximum return, or operate your business while generating additional income this property offers unmatched versatility and income potential.

3 Beds ⋅ 2 Baths ⋅ Groves Sub SubDv. ⋅ 32801 Zip Code

Fully renovated mixed-use duplex offering exceptional flexibility and income potential in the heart of Orlando. This stand-alone historical building is zoned for both commercial and residential use, creating endless opportunities for investors, business owners, or owner-occupants. Both units are currently operating as successful short-term rentals (Airbnb), generating immediate income. The downstairs unit, previously configured as an office, features three separate rooms, a kitchenette, dining area, and a full bathroom. It can continue as a short-term rental, professional space, or be converted to residential use. The upstairs unit includes two bedrooms, one full bathroom, a full kitchen, and an open-concept living and dining area, making it ideal for guests and consistent rental income. Each unit has its own private entrance and separate electrical meter. The property offers ample parking, accommodating up to seven vehicles total, with dedicated parking areas for each unit. Recent updates include a newer roof (2018). The upstairs unit is equipped with a washer and dryer. Furniture is negotiable. Ideally located just steps from the Dr. Phillips Center for the Performing Arts, Downtown Orlando, and Lake Eola Park, with easy access to dining, entertainment, and major roadways. Live in one unit and rent the other, lease both for maximum return, or operate your business while generating additional income this property offers unmatched versatility and income potential.

310 E Anderson Street, Orlando

608 Highland Avenue, Orlando

NEW PRICE, REDUCED $50,000 FOR QUICK SALE! DONT MISS OUT ON THIS FANTASTIC OPPORTUNITY, PRICED DRASTICALLY BELOW APPRAISED VALUE.This beautiful FULL duplex (both sides) is located in the highly desirable Lake Eola Heights Historic District just minutes from downtown. The property has been completely renovated, offering modern updates while maintaining its classic charm. Each unit features a brand-new kitchen and updated bathrooms, along with two spacious bedrooms and 1.5 renovated baths on each side. The refinished hardwood floors and staircase add warmth and character throughout the home. Major upgrades include a new roof installed in September 2025, along with fresh interior and exterior paint for a crisp, move-in ready feel. The exterior offers a beautiful fenced yard with elegant paver walkways and driveways, creating a welcoming outdoor space for residents and guests. This is a rare opportunity to own a fully updated duplex in one of Orlando’s most charming historic neighborhoods. This is perfect for investors or owner-occupants seeking rental income. Lease Purchase option as well as possible owner financing available, call Listing agent for details

Bailey Heights SubDv. ⋅ 32801 Zip Code

NEW PRICE, REDUCED $50,000 FOR QUICK SALE! DONT MISS OUT ON THIS FANTASTIC OPPORTUNITY, PRICED DRASTICALLY BELOW APPRAISED VALUE.This beautiful FULL duplex (both sides) is located in the highly desirable Lake Eola Heights Historic District just minutes from downtown. The property has been completely renovated, offering modern updates while maintaining its classic charm. Each unit features a brand-new kitchen and updated bathrooms, along with two spacious bedrooms and 1.5 renovated baths on each side. The refinished hardwood floors and staircase add warmth and character throughout the home. Major upgrades include a new roof installed in September 2025, along with fresh interior and exterior paint for a crisp, move-in ready feel. The exterior offers a beautiful fenced yard with elegant paver walkways and driveways, creating a welcoming outdoor space for residents and guests. This is a rare opportunity to own a fully updated duplex in one of Orlando’s most charming historic neighborhoods. This is perfect for investors or owner-occupants seeking rental income. Lease Purchase option as well as possible owner financing available, call Listing agent for details

608 Highland Avenue, Orlando