Winding Oaks Homes for Sale

Winding Oaks Homes for Sale

Welcome to Winding Oaks, a hidden gem nestled in the vibrant city of San Antonio, Texas, within the heart of Bexar County. This charming subdivision 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 picturesque tree-lined streets, beautifully manicured lawns, and a welcoming community atmosphere. The neighborhood is known for its spacious homes, many of which feature modern designs and energy-efficient amenities, making them not only stylish but also practical. Whether you’re searching for a cozy starter home or a larger residence for your growing family, Winding Oaks has a diverse selection of homes for sale that cater to various lifestyles and budgets.

Residents of Winding Oaks enjoy easy access to a wealth of local amenities, including parks, shopping centers, and dining options that reflect San Antonio's rich cultural heritage. Families will appreciate the proximity to highly-rated schools, while outdoor enthusiasts can explore nearby recreational areas that offer hiking, biking, and nature trails.

Community spirit thrives in Winding Oaks, with numerous neighborhood events and activities that foster connections among residents. This subdivision isn’t just a place to live; it’s a place to belong.

If you’re looking to make Winding Oaks your new home, now is the perfect time to explore the available homes for sale. Embrace the opportunity to join this delightful community and experience the best of San Antonio living!

Newest Winding Oaks Homes for Sale

21007 Chestnut Cv, San Antonio
$369,900
3 Beds ⋅ 3 Baths ⋅ 2010700 MLS ⋅ ACTIVE 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
21022 Chestnut, 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
21114 Chestnut Cove, San Antonio
$429,000
4 Beds ⋅ 3 Baths ⋅ 1963096 MLS ⋅ ACTIVE Status
FHA assumable loan with an attractive 3.2% interest rate, subject to buyer qualification and lender approval! 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 with luxury vinyl plank flooring creating a bright and 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 flexible living space provide plenty of 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 enjoy gated living and outstanding 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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