Welcome to 747 Bailey Ave, a rare find in Highland Park featuring two separate homes on one lot perfect for multi-generational living. The 1,523 sq. ft. main home offers a bright, open-concept layout with laminate flooring throughout. The spacious living area flows into a beautifully designed kitchen featuring granite countertops, stainless steel appliances, custom cabinetry, and a large peninsula with bar seating and conveniently placed electrical outlets for charging devices or powering small appliances. This main home includes 4 bedrooms, each with ceiling fans, and 2 full bathrooms. The private primary suite features a beautifully tiled walk-in shower, while the second bathroom offers a modern tiled shower, tub, and a dedicated stackable washer/dryer enclosure with connections. Enjoy relaxing mornings or peaceful evenings on the inviting partial wraparound covered porch. Upgrades completed in 2023: roof, porch, all windows, kitchen cabinets and granite, bathroom tile, flooring, and light fixtures. Upgrade completed in 2025: water softener in the attic. Tucked behind the main home is a charming 546 sq. ft. permitted, detached casita built from the ground up (2023). This thoughtfully designed space features vinyl plank flooring throughout, an open-concept living area, a full kitchen with granite countertops and stainless steel appliances, a spacious bathroom with a large tiled shower, stackable washer/dryer connections, a dedicated mini-split HVAC system, its own electrical meter, and a separate unit number making it ideal for guests or extended family. Upgrades in 2024: new mini split. Conveniently located near many of San Antonio's top destinations: Steps from VIA Bus Route #20. 2 miles to Mission Concepcion National Historical Park. 3 miles to the San Antonio River Walk. 4 miles to Frost Bank Center. 5 miles to Pearl. 6 miles to the San Antonio Zoo. 9 miles to Whole Foods Market. Whether you're looking for an investment opportunity, extra space for family, or a home that offers flexibility for years to come, 747 Bailey Ave delivers modern finishes, exceptional functionality, and an unbeatable location, all in a single property. Book your showing today. Foundation work to begin August 17th, 2026 with fully transferable warranty.