Winding Oaks Real Estate

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

Winding Oaks boasts beautifully landscaped streets lined with mature oak trees, creating a picturesque environment that invites you to take leisurely strolls or enjoy outdoor activities with loved ones. The community is known for its friendly atmosphere, where neighbors become friends and every day feels like a warm welcome home.

Homes in Winding Oaks feature a variety of architectural styles, from cozy single-family residences to spacious modern designs, ensuring there’s something for everyone. Many properties come equipped with expansive yards, perfect for hosting gatherings or simply enjoying the Texas sunshine. The neighborhood is also pet-friendly, with plenty of green spaces for your furry companions to explore.

Convenience is key in Winding Oaks, as residents enjoy easy access to major highways, making commutes to downtown San Antonio and nearby attractions a breeze. The area is home to excellent schools, shopping centers, and dining options, ensuring that all your needs are just a stone's throw away.

For those who appreciate nature, Winding Oaks is close to several parks and recreational areas, offering opportunities for hiking, picnicking, and enjoying the great outdoors. With its perfect blend of charm, convenience, and community spirit, Winding Oaks is not just a place to live; it’s a place to thrive. Come discover your new home in this delightful San Antonio subdivision!

Newest Listings in Winding Oaks

$350,000

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

$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

$429,000

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

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