Winding Oaks Real Estate

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

Winding Oaks is known for its beautifully landscaped streets lined with mature oak trees, creating a serene and inviting atmosphere. The subdivision boasts a diverse range of homes, from cozy single-family residences to spacious modern designs, catering to various lifestyles and preferences. With an emphasis on community spirit, residents enjoy a warm, neighborly vibe that fosters lasting friendships and a sense of belonging.

One of the standout features of Winding Oaks is its proximity to top-rated schools, parks, and recreational facilities. Families can take advantage of the nearby outdoor spaces, perfect for picnics, jogging, or simply enjoying the Texas sunshine. Additionally, the community is conveniently located near major highways, providing easy access to downtown San Antonio, where an array of dining, shopping, and entertainment options await.

For those who appreciate a blend of nature and convenience, Winding Oaks offers the best of both worlds. With its welcoming atmosphere, beautiful homes, and ideal location, this subdivision is not just a place to live; it’s a place to thrive. Discover the charm of Winding Oaks and experience the vibrant lifestyle that San Antonio has to offer. Your dream home awaits in this delightful community!

Newest Listings in Winding Oaks

$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

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