Winding Oaks Real Estate

Welcome to Winding Oaks, a picturesque subdivision nestled in the heart of San Antonio, Texas, within the vibrant Bexar County. This charming community is designed for those who appreciate the perfect blend of suburban tranquility and urban convenience. With its tree-lined streets and beautifully landscaped homes, Winding Oaks offers an inviting atmosphere that feels like a retreat from the hustle and bustle of city life.

One of the standout features of Winding Oaks is its prime location. Residents enjoy easy access to major highways, making commutes to downtown San Antonio and nearby employment centers a breeze. Families will appreciate the proximity to highly-rated schools, parks, and recreational facilities, ensuring that there are plenty of options for education and outdoor fun.

Winding Oaks is more than just a place to live; it’s a community where neighbors become friends. The subdivision hosts various family-friendly events throughout the year, fostering a sense of belonging and camaraderie among residents. Whether you’re taking a leisurely stroll through the neighborhood, enjoying a picnic in the local park, or participating in community gatherings, you’ll find that Winding Oaks is a place where memories are made.

With a diverse selection of homes that cater to various lifestyles, from cozy single-family residences to spacious townhouses, there’s something for everyone in Winding Oaks. If you’re looking for a welcoming community that combines the best of suburban living with the conveniences of city life, Winding Oaks could be your perfect home. Come explore this enchanting neighborhood and discover all that it has to offer!

Newest Listings in Winding Oaks

$415,000

4 Beds ⋅ 3 Baths ⋅ 1996999 MLS

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

Listing courtesy of Listing Agent: Tracy Pankau (tracypankau@gmail.com) from Listing Office: Keller Williams Heritage.

$415,000

5 Beds ⋅ 3 Baths ⋅ 1952829 MLS

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

Listing courtesy of Listing Agent: Ashley Nicholson (ashley33nicholson@gmail.com) from Listing Office: LPT Realty, LLC.

$429,500

4 Beds ⋅ 3 Baths ⋅ 1963096 MLS

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

Listing courtesy of Listing Agent: Ivan Terrazas (ivansellssa@gmail.com) from Listing Office: Keller Williams City-View.

$387,900

4 Beds ⋅ 3 Baths ⋅ 1932584 MLS

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

Listing courtesy of Listing Agent: John Garcia (garcia.daniel@kw.com) from Listing Office: Keller Williams Heritage.

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Listings provided by LERA MLS

Based on information from California Regional Multiple Listing Service, Inc. as of . This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.