Rolling Oaks Estates Homes for Sale

Welcome to Rolling Oaks Estates, a hidden gem nestled in the heart of San Antonio, Texas, within the vibrant Bexar County. This charming subdivision offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place to call home.

Rolling Oaks Estates is characterized by its picturesque tree-lined streets, spacious lots, and beautifully designed homes that cater to a variety of lifestyles. Whether you’re a growing family, a first-time homebuyer, or looking to downsize, this community has something for everyone. The homes for sale in Rolling Oaks Estates boast modern amenities, open floor plans, and stunning outdoor spaces, perfect for entertaining or simply enjoying the serene Texas evenings.

One of the standout features of Rolling Oaks Estates is its prime location. Residents enjoy easy access to major highways, making commutes to downtown San Antonio a breeze. The area is also surrounded by a wealth of shopping, dining, and recreational options. Families will appreciate the proximity to highly-rated schools and parks, providing ample opportunities for outdoor activities and community engagement.

As you explore the available homes for sale in Rolling Oaks Estates, you’ll discover a variety of styles and price points, ensuring that your dream home is within reach. Don’t miss the opportunity to be part of this welcoming community where neighbors become friends and memories are made. Come and experience the charm of Rolling Oaks Estates—your future home awaits!

Newest Rolling Oaks Estates Homes for Sale

$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 ⋅ PRICE CHANGE 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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