Winding Oaks Homes for Sale

Welcome to Winding Oaks, a picturesque subdivision nestled in the heart of San Antonio, Texas. This charming community, located in Bexar County, offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, professionals, and retirees alike.

Winding Oaks is characterized by its lush, tree-lined streets and beautifully manicured lawns, creating an inviting atmosphere that residents are proud to call home. The neighborhood is known for its friendly community spirit, where neighbors become friends and gatherings are a common occurrence. With nearby parks and recreational facilities, families can enjoy outdoor activities and create lasting memories together.

The homes for sale in Winding Oaks are as diverse as the residents themselves. From cozy single-family homes to spacious modern designs, there’s something to suit every taste and budget. Many properties feature open floor plans, updated kitchens, and private backyards perfect for entertaining or enjoying a peaceful evening under the stars. With the real estate market in this desirable area thriving, prospective buyers will find a variety of options to explore.

Living in Winding Oaks means enjoying easy access to San Antonio’s vibrant culture, dining, and shopping experiences. Major highways and public transportation options are conveniently located, ensuring a seamless commute to work or leisure activities. Whether you're drawn to the rich history of San Antonio or the warmth of a close-knit community, Winding Oaks offers a unique lifestyle that truly feels like home. Come discover your dream home in this enchanting neighborhood today!

Newest Winding Oaks Homes for Sale

$359,900

3 Beds ⋅ 3 Baths ⋅ 2010700 MLS ⋅ PRICE CHANGE Status

$5,000 CLOSING COST INCENTIVE AND CORNER LOT!! Welcome to this beautifully maintained 3-bedroom, 2.5-bath home in Winding Oaks, ideally located within North East ISD and offering an excellent opportunity for a first-time homebuyer. From the moment you enter, rich wood flooring, abundant natural light, and an inviting open floor plan create a warm, welcoming feel. The spacious family room flows seamlessly into the kitchen and breakfast area, making everyday living and entertaining easy. The island kitchen features quartz countertops, under-cabinet lighting, gas cooking, a walk-in pantry, and plenty of workspace. The refrigerator, washer, and dryer are included, along with a programmable thermostat, video doorbell, and owned water softener. Upstairs, the massive primary suite offers a private retreat with a walk-in closet, ceiling fan, and bath with double vanity and walk-in shower. Two additional bedrooms provide flexibility for family, guests, or a home office. Outside, enjoy the covered patio, privacy-fenced yard, sprinkler system, gutters, and desirable corner-lot setting with a Texas sized driveway!! The community offers a pool, park/playground, controlled access, and sidewalks. With convenient access to major roads, shopping, dining, and everyday amenities, this home combines comfort, convenience, and value in a great Northeast San Antonio location. SEE THIS ONE TODAY!!

21007 Chestnut Cv, San Antonio

$414,000

5 Beds ⋅ 3 Baths ⋅ 1952829 MLS ⋅ ACTIVE Status

Step into this beautifully designed open-concept home offering five spacious bedrooms, three full bathrooms, and a versatile bonus room perfect for a game room, media space, or home office. The thoughtfully designed first floor features a private primary suite, complete with a walk-in shower, dual vanities, an enclosed water closet, and a generous walk-in closet. An additional first-floor bedroom with a full bath provides the perfect setup for guests or multi-generational living. At the heart of the home, the kitchen is ideal for both everyday living and entertaining, showcasing a large center island, ample counter space, and a well-appointed pantry with abundant shelving. Upstairs, you'll find three generously sized bedrooms, a full bath, and a spacious bonus room offering endless possibilities. Enjoy outdoor living with a covered patio... perfect for relaxing or entertaining-along with the added benefit of energy-efficient solar panels.

21022 Chestnut, San Antonio

$429,500

4 Beds ⋅ 3 Baths ⋅ 1963096 MLS ⋅ ACTIVE Status

Located in the gated community of Winding Oaks, this stunning stone and stucco home exudes modern elegance from the moment you arrive. Its refined exterior and designer finishes set the tone for the beautifully appointed interior, where soaring ceilings and luxury vinyl flooring create a bright, open atmosphere. At the heart of the home, the chef's kitchen showcases striking two-tone cabinetry, quartz countertops, stainless steel appliances, gas cooking, and a statement herringbone backsplash, all flowing seamlessly into the dining and living areas for effortless entertaining. The private downstairs primary suite offers a spa-inspired shower and a spacious walk-in closet. Upstairs, a versatile loft, secondary bedrooms, and flex space provide room to live, work, and unwind. Step outside to a covered patio and enjoy the privacy of a premium corner lot with no rear neighbors. Residents of Winding Oaks enjoy the security of gated living along with outstanding neighborhood amenities, including a community pool, park, playground, and walking trails. Located within the highly acclaimed NEISD and just minutes from premier shopping, dining, and major highways, this exceptional home offers the perfect blend of luxury, comfort, community, and convenience.

21114 Chestnut Cove, 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