Rolling Oaks Estates Real Estate

Welcome to Rolling Oaks Estates, a hidden gem nestled in the heart of San Antonio, Texas. This picturesque subdivision in Bexar County offers a harmonious blend of suburban tranquility and urban convenience, making it the ideal setting for families, professionals, and retirees alike.

Rolling Oaks Estates is characterized by its beautifully landscaped streets, spacious lots, and an array of charming homes that reflect a variety of architectural styles. Residents enjoy the peace of mind that comes with living in a well-planned community, complete with tree-lined sidewalks perfect for evening strolls and friendly chats with neighbors.

One of the standout features of Rolling Oaks Estates is its proximity to top-notch schools, shopping centers, and recreational facilities. Families will appreciate the access to highly-rated public and private schools, ensuring that children receive a quality education within a short commute. For shopping enthusiasts, the nearby Rolling Oaks Mall offers a diverse selection of retail options, dining experiences, and entertainment venues.

Nature lovers will also find plenty to enjoy in this vibrant community. With several parks and green spaces nearby, residents can partake in outdoor activities, from picnicking to jogging along scenic trails. Additionally, the community hosts various events throughout the year, fostering a strong sense of camaraderie and connection among neighbors.

Whether you're looking to settle down or invest, Rolling Oaks Estates promises a lifestyle of comfort and convenience in one of San Antonio's most desirable neighborhoods. Come explore the charm of this community and discover why so many call Rolling Oaks Estates home!

Newest Listings in Rolling Oaks Estates

$745,000

5 Beds ⋅ 6 Baths ⋅ 1995619 MLS ⋅ PRICE CHANGE Status

Complete your luxury dream estate in Rolling Oaks Estates on 4.05 private acres at the end of a cul-de-sac. ARV Comps are over $1 million - one of a kind investment opportunity!!! This 4,800 sq. ft. custom home features 5 bedrooms, 5.5 baths, a redesigned floor plan, and major improvements including a new standing-seam metal roof, two HVAC systems, electrical, plumbing, insulation, drywall and much more, all completed in 2025. Finish the interior to your vision while enjoying privacy. Renovation financing options, including Conventional, FHA, and VA Renovation Loans, are available through the preferred lender.

306 N Rolling Oaks Ln, San Antonio

$775,000

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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