Quick San Antonio TX MLS Search

Browse All Highland Park Properties for Sale

$135,000
2 Beds 1 Baths 2010134 MLS NEW Status
Charming San Antonio Home with Detached Garage, Workshop & Covered Patio Welcome to 306 Bailey Ave! A charming and very well-maintained San Antonio home with a unique history-it was custom-built and lovingly cared for by the same family for two generations. This completely turnkey 2-bedroom, 1-bath home features original hardwood floors, a spacious kitchen, a large living/dining area, and a separate family room filled with abundant natural light. The kitchen opens to the family room and overlooks the backyard. Recent improvements include a new roof in 2022, a remodeled bathroom in 2023 and brand new family-room carpet. The kitchen is equipped with a side-by-side stainless steel refrigerator, built-in electric oven, gas cooktop and microwave. The washer and dryer purchased in 2026 will also convey to the new owners. Outdoor living is enhanced by a 10 x 30 covered concrete patio, wood deck and steps added in 2025 and a fully fenced backyard. A major highlight is the detached 2-car garage, which includes an additional workshop and enclosed storage space offering excellent flexibility for hobbies, projects, tools, equipment, or a home business. The garage includes front and rear doors allowing access from both the street and the back alleyway. Two additional carports provide extra covered parking. If you're searching for a move-in-ready home with a workshop, two-car garage, covered patio, fenced backyard, flexible space for hobbies or a home business, and a well-equipped kitchen, 306 Bailey Ave. is worth a closer look.

306 Bailey Ave, San Antonio

$240,000
3 Beds 2 Baths 2004860 MLS PRICE CHANGE Status
Welcome to this beautifully renovated 3-bedroom, 2-bathroom home in the established Highland Park neighborhood on San Antonio's south side. Completely transformed from top to bottom, this home offers the look and feel of new construction with modern finishes, thoughtful design, and brand-new features throughout. EVERYTHING IS BRAND NEW! From the foundation to plumbing, to electrical, to HVAC, to Roof, to interior flooring, to the fresh interior, every detail has been carefully selected to create a move-in-ready home that combines style with everyday comfort. As you approach the home, you are greeted with a welcoming color palette. Walk up the steps to a built-in front porch deck, perfect for a quick cup of coffee on those busy mornings or a wind-down on these great Texas summer nights. The open layout flows into a stunning kitchen featuring elegant quartz countertops, brand-new appliances, and a clean, modern design that makes cooking and entertaining effortless. A separate laundry room with a storage closet that could double as a pantry adds convenience, while the spacious primary suite offers a private retreat complete with a beautifully finished walk-in shower and double vanity, making getting ready more convenient. The additional bedrooms provide flexibility for family, guests, or a home office. Outside, the freshly landscaped front yard creates inviting curb appeal, and the long driveway provides plenty of parking for homeowners and visitors alike. Location is another major advantage. Situated in Highland Park, you'll enjoy quick access to Downtown San Antonio, the Alamodome, Henry B. Gonzalez Convention Center, Frost Bank Center, and Brooks City Base. You're also just minutes from the San Antonio River Walk, the city's historic Missions, major highways including I-37 and I-10, and an abundance of local restaurants, shopping, and entertainment. If you've been searching for a home that offers the character of an established neighborhood with the peace of mind and style of a completely renovated interior, this Highland Park gem is one you won't want to miss.

923 Chicago Blvd, San Antonio

$294,999
5 Beds 3 Baths 2001116 MLS PRICE CHANGE Status
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.

747 Bailey Ave, San Antonio

$489,000
5 Beds 4 Baths 1973359 MLS ACTIVE Status
Welcome to this breathtakingly restored 1915 masterpiece in the highly coveted Highland Park Estates, where historic charm meets modern luxury!! Offering 5 spacious bedrooms, 3.5 beautifully appointed bathrooms, and an unbeatable location just minutes from Downtown San Antonio, The Pearl, Southtown, the Alamodome, and some of the city's finest dining and entertainment, this exceptional residence is truly one of a kind! From the moment you arrive, you'll be captivated by the home's striking curb appeal, highlighted by custom contemporary metal-and-glass double entry doors. Step inside to a dramatic foyer featuring a bold black shiplap ceiling and an elegant gold candelabra chandelier, creating an unforgettable first impression. The inviting living room blends warmth and character with a stunning brick fireplace enhanced by electric heating, providing the perfect ambiance for relaxing evenings. Designed for both everyday living and entertaining, the chef-inspired kitchen serves as the heart of the home, showcasing quartz countertops, custom cabinetry, designer fixtures, and an oversized center island with bar seating. The open-concept dining area offers incredible versatility, easily functioning as a formal dining room, secondary living space, or home office. The thoughtfully designed floor plan includes a luxurious primary suite on the main level, creating a private retreat complete with a spa-inspired ensuite featuring dual vanities and an oversized glass walk-in shower with built-in bench seating. Upstairs, you'll find four additional bedrooms, including a second primary suite ideal for guests, extended family, or multi-generational living. Each room offers its own unique character and flexibility, while the fifth bedroom can easily serve as a private office, study, or creative space. Step outside and discover your own backyard oasis. Beautifully landscaped and designed for low-maintenance enjoyment, the outdoor space features premium artificial turf, a newly installed privacy fence, and a sparkling in-ground pool, perfect for entertaining, weekend gatherings, or simply unwinding in complete privacy. Rarely does a home combine this level of craftsmanship, historic character, modern updates, and prime location. This is more than a home, it's a lifestyle. Don't miss your opportunity to own one of Highland Park Estates' most remarkable residences. Schedule your private showing today!!

505 Rigsby, San Antonio

Start Your Search

IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS.  The MLS may, at its discretion, require use of other disclaimers as necessary to protect participants and/or the MLS from liability. 

Listings provided by LERA MLS

Home Value Market Report

Get an INSTANT market report

Home Value Property Valuation

Get an INSTANT property valuation now!