Winding Oaks Real Estate

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

Winding Oaks is renowned for its lush, tree-lined streets and beautifully landscaped homes, which create a warm and inviting atmosphere. Residents enjoy a sense of community, with friendly neighbors and a variety of social events that foster connections and camaraderie. The subdivision features a range of housing options, from cozy single-family homes to spacious properties, catering to diverse lifestyles and preferences.

One of the standout features of Winding Oaks is its proximity to San Antonio's many attractions. Just a short drive away, you can explore the rich history and culture of the city, including the iconic Alamo, the vibrant River Walk, and an array of shopping and dining options. Outdoor enthusiasts will appreciate the nearby parks and recreational facilities, perfect for weekend picnics, jogging, or simply enjoying the beautiful Texas weather.

Families will also benefit from access to highly-rated schools within the Northside Independent School District, ensuring quality education for children of all ages. With its combination of serene living, community spirit, and convenient access to urban amenities, Winding Oaks is more than just a place to live—it's a place to thrive. Discover your dream home in this enchanting subdivision and experience the best of San Antonio living!

Newest Listings in Winding Oaks

$350,000

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

IMPECCABLE 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

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