Winding Oaks Real Estate

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

Winding Oaks is renowned for its lush landscapes and beautifully designed homes that reflect a variety of architectural styles. The tree-lined streets create a serene atmosphere, inviting residents to take leisurely strolls or enjoy evening bike rides. With an array of amenities at your doorstep, including parks, playgrounds, and walking trails, Winding Oaks is designed for those who appreciate an active lifestyle.

Families will find Winding Oaks particularly appealing, as it is served by some of the top-rated schools in Bexar County. The community fosters a strong sense of belonging, with friendly neighbors and a variety of community events that encourage interaction and camaraderie among residents.

Conveniently located, Winding Oaks provides easy access to major highways, making commutes to downtown San Antonio and surrounding areas a breeze. Residents can enjoy the vibrant culture, dining, and entertainment options that San Antonio has to offer, from the historic River Walk to the bustling markets and festivals.

Whether you're looking for your first home or seeking a peaceful retreat, Winding Oaks is a hidden gem in San Antonio that promises a welcoming environment and a lifestyle filled with joy and convenience. Come explore the possibilities of making Winding Oaks your new home!

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

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