Winding Oaks Real Estate

Welcome to Winding Oaks, a charming subdivision nestled in the vibrant heart of San Antonio, Texas. Known for its picturesque landscapes and welcoming community atmosphere, Winding Oaks is the perfect place to call home for families, retirees, and everyone in between.

This beautifully designed neighborhood features a variety of well-appointed single-family homes, each showcasing unique architectural styles that blend seamlessly with the natural surroundings. The spacious lots provide ample room for outdoor activities, while mature trees and lush greenery create a serene environment perfect for relaxation and recreation.

Residents of Winding Oaks enjoy a wealth of amenities right at their fingertips. The community boasts well-maintained parks, walking trails, and playgrounds that encourage an active lifestyle. Families will appreciate the proximity to top-rated schools within the Northside Independent School District, ensuring children receive an excellent education.

Winding Oaks is conveniently located near major highways, making commuting to downtown San Antonio and the surrounding areas a breeze. With a variety of shopping, dining, and entertainment options just a short drive away, residents can indulge in the vibrant culture and rich history that San Antonio has to offer. From the famous River Walk to the historic Alamo, there’s always something exciting to explore.

Whether you’re looking for a peaceful retreat or a lively community, Winding Oaks provides the ideal blend of comfort, convenience, and charm. Discover your dream home in this delightful subdivision and experience the best of San Antonio living!

Newest Listings in Winding Oaks

$415,000

4 Beds ⋅ 3 Baths ⋅ 1996999 MLS ⋅ ACTIVE Status

Welcome home to this immaculate, move-in-ready 4 bedroom 3 full bath residence in a premier gated neighborhood. Meticulously maintained from top to bottom, this home boasts a light-filled open layout perfect for living and entertaining. The bright crisp island kitchen offers gas cooking and added storage. Beautiful upgraded wood flooring runs throughout the living area. The expansive primary suite features a stunningly upgraded primary bath, offering a luxurious, spa-like escape. The downstairs secondary bedroom and bath is perfect for guests or home office. Additional living space upstairs could be gameroom, playroom or media space. Outside, the beautiful and large backyard provides an incredible private sanctuary with plenty of room to play, garden, or host guests. Combining security, style, and a prime location, this pristine property is a rare find. With 4 spacious bedrooms, premium finishes, and the added security of a gated neighborhood full of amenities, this turnkey property truly checks every box. Minutes to shopping, military bases and major highways for easy commute. Located in sought after Northeast I.S.D.

5610 Ancient Ave, San Antonio

$415,000

5 Beds ⋅ 3 Baths ⋅ 1952829 MLS ⋅ PRICE CHANGE 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

$387,900

4 Beds ⋅ 3 Baths ⋅ 1932584 MLS ⋅ PRICE CHANGE Status

PRICE IMPROVED PLUS SELLER OFFERING $5,000 IN BUYER CONCESSIONS (use toward rate buy-down or closing costs, buyer's choice)! This Stunning Winding Oaks home with SOLAR PANELS (no electric bill!) Welcome to this beautifully upgraded home in the gated Winding Oaks community, featuring resort-style amenities including a pool, clubhouse, and playground. Tucked on a rare circular cul-de-sac with an HOA-owned greenbelt, this low-traffic setting offers privacy, curb appeal, and a true neighborhood feel. Inside, custom woodwork throughout adds warmth and craftsmanship, and the flexible floor plan works beautifully for everyday living, entertaining, and working from home. Outdoor living shines with a deck and covered patio, while low-maintenance turf and a front yard irrigation system keep the yard lush with minimal effort. ***Solar*** - Seller to satisfy obligation at closing OR buyer to assume existing solar agreement (ask for details). Less than a mile to the Bulverde Fire Station, shopping, and a Valero gas station, with quick access to Evans Road, Loop 1604, and major commuter routes. A rare combination of privacy, upgrades, energy efficiency, and location. Schedule your showing today!

5726 Chestnut Xing, San Antonio

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Listings provided by LERA MLS