Rolling Oaks Estates Homes for Sale

Welcome to Rolling Oaks Estates, a hidden gem nestled in the vibrant heart of San Antonio, Texas. This picturesque subdivision in Bexar County combines the charm of suburban living with the conveniences of city life, making it an ideal place for families, professionals, and retirees alike.

Rolling Oaks Estates boasts an array of beautifully designed homes that cater to a variety of tastes and lifestyles. With properties ranging from modern single-family homes to spacious two-story residences, you’re sure to find the perfect fit for your needs. Many of these homes feature open floor plans, gourmet kitchens, and beautifully landscaped yards, offering a perfect backdrop for both relaxation and entertainment.

The community is known for its welcoming atmosphere, where neighbors become friends and families create lasting memories. Residents enjoy access to well-maintained parks, walking trails, and recreational facilities, providing plenty of opportunities for outdoor activities. The nearby shopping centers, restaurants, and entertainment options further enhance the appeal of this vibrant neighborhood.

Rolling Oaks Estates is also conveniently located for easy access to major highways, making commutes to downtown San Antonio and surrounding areas a breeze. With top-rated schools and a strong sense of community, it’s no wonder that homes for sale in Rolling Oaks Estates are highly sought after.

If you’re looking for a place that combines comfort, convenience, and a sense of belonging, consider making Rolling Oaks Estates your new home. Explore the available listings today and discover the perfect property to call your own!

Newest Rolling Oaks Estates Homes for Sale

$747,500

5 Beds ⋅ 6 Baths ⋅ 1995619 MLS ⋅ ACTIVE Status

Exceptional opportunity to finish your dream estate in the highly sought-after Rolling Oaks community. Situated on approximately 4.05 private acres at the end of a quiet cul-de-sac, this impressive 4,800 sq. ft. custom home has been rebuilt from the slab up with a thoughtfully redesigned floor plan and is ready for your personal finishing touches. Designed with both luxury and functionality in mind, the home features 5 spacious bedrooms, 5 full bathrooms, and 1 half bath. The private downstairs primary suite is its own retreat, complete with a dedicated hallway leading to the bedroom, office/study, spa-inspired bath, walk-in closet, and private exterior entrance. A secondary guest suite with its own full bath is also located on the main level, along with an expansive living area and a large media room. Upstairs, you'll find three additional bedrooms, each with its own en-suite bathroom and walk-in closet. The striking stucco exterior, charcoal standing-seam metal roof, soaring ceilings, oversized windows, and open-concept design provide the perfect foundation for a truly spectacular custom home. Major improvements have already been completed, including a new standing-seam metal roof, two new HVAC systems, all-new electrical, and all-new plumbing, all completed in 2025, allowing the next owner to focus on selecting cabinetry, flooring, countertops, fixtures, paint, trim, and other interior finishes to match their own style and vision. Surrounded by mature oak trees, the property offers the peace and privacy of country living while remaining just minutes from shopping, dining, top-rated schools, and major highways. Whether you're searching for your forever home, a luxury custom project, or a one-of-a-kind investment opportunity, this property offers incredible potential in one of San Antonio's premier acreage communities. Property is being sold in its current unfinished condition. Renovation financing options, including Conventional, FHA, and VA Renovation Loans, are available through the preferred lender.

306 N Rolling Oaks Ln, San Antonio

$795,000

4 Beds ⋅ 3 Baths ⋅ 1990084 MLS ⋅ ACTIVE Status

Nestled beneath a canopy of majestic live oaks, this stunning San Antonio estate is a rare find. From the moment you arrive, the estate is framed by mature trees and stone accents which sets the tone for the exceptional experience that awaits inside. The soaring great room impresses with vaulted tongue-and-groove wood ceilings, rich floors, and a dramatic floor-to-ceiling limestone fireplace, equally suited for grand entertaining or cozy evenings at home. The chef's kitchen delivers bold granite countertops, custom cabinetry, center island, and a sunlit breakfast nook with backyard views. The expansive primary suite offers a peaceful retreat with a window seat overlooking the pool, generous built-ins, and a spa-like ensuite featuring dual vanities, soaking tub, and walk-in shower. Outside, your private resort awaits with a sparkling in-ground pool, stamped concrete surround, and an expansive deck with breathtaking views. A charming poolside guest house with French doors and stone accents provides endless possibilities. With a 2-car garage, mature landscaping, and a setting that offers both privacy and convenience, this property truly has it all.

419 S Rolling Vw, San Antonio

$1,420,000

6 Beds ⋅ 6 Baths ⋅ 1973090 MLS ⋅ ACTIVE Status

Experience exceptional Hill Country living in this stunning executive estate nestled on two lots totaling approximately three acres at the end of a private cul-de-sac in sought-after Rolling Oaks Estates. Surrounded by mature trees and natural beauty, this remarkable property offers the perfect blend of luxury, comfort, and resort-style entertaining. Designed with an open-concept layout, the home features 6 spacious bedrooms, 5.5 bathrooms, luxury wood-look vinyl plank flooring, elegant crown molding, and abundant natural light throughout. The chef's island kitchen is truly the heart of the home, showcasing granite countertops, stainless steel appliances, double refrigerators, double ovens and warming drawer, gas cooking, ice maker, and built-in wine storage-perfect for entertaining family and guests. The main level lives like a true one-story home, featuring the luxurious primary suite along with three additional bedrooms, study, living room w/fireplace and screened in patio. The walkout lower level expands the living space with a full second kitchen, stainless steel appliances, game area, media room, bonus room currently utilized as a fitness studio, additional bedrooms, and a second utility room-ideal for multi-generational living, guests, or extended entertaining. Step outside to your private backyard paradise. Enjoy the resort-style pool and spa complete with a swim-up bar, outdoor kitchen, covered patio, and outdoor fireplace. The picturesque grounds are highlighted by towering mature trees, a charming dry creek bed, gazebo and even a chicken coop, offering a unique blend of luxury and country charm. This extraordinary estate delivers privacy, flexibility, and unmatched amenities-all within minutes of San Antonio conveniences. A rare opportunity to own one of Rolling Oaks Estates' most impressive properties.

613 N Rolling Vw, San Antonio

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