Rolling Oaks Estates Real Estate

Welcome to Rolling Oaks Estates, a captivating subdivision nestled in the heart of San Antonio, Texas, within the vibrant Bexar County. This enchanting community offers a perfect blend of suburban tranquility and urban convenience, making it an ideal haven for families, professionals, and retirees alike.

Rolling Oaks Estates is renowned for its picturesque landscapes, featuring beautifully manicured lawns and mature trees that provide a serene backdrop for everyday life. The neighborhood boasts a variety of stunning homes, each uniquely designed to cater to diverse tastes and lifestyles. Whether you’re seeking a cozy single-family residence or a spacious estate, you’ll find a perfect fit in this charming community.

One of the standout features of Rolling Oaks Estates is its commitment to family-friendly living. Residents enjoy access to top-rated schools, parks, and recreational facilities, ensuring that children and adults alike have plenty of opportunities for outdoor activities and community engagement. The nearby Rolling Oaks Mall offers a wide array of shopping and dining options, making it easy to enjoy a day out without venturing far from home.

For those who appreciate the arts, culture, and entertainment, San Antonio’s vibrant downtown is just a short drive away. From the historic River Walk to the lively markets and festivals, there’s always something exciting happening in this dynamic city.

In Rolling Oaks Estates, you’ll find not just a home, but a lifestyle that embraces community, convenience, and comfort. Discover the charm of this remarkable subdivision and make it your own today!

Newest Listings in Rolling Oaks Estates

$650,000

4 Beds ⋅ 3 Baths ⋅ 2021806 MLS ⋅ NEW Status

Welcome home to this spacious two-story property situated on 2 beautiful acres with many mature oak trees in Far West Bexar County! Located within the highly sought-after Northside Independent School District, this property offers the perfect combination of space, privacy, and convenience. The home features 4 bedrooms, 2.5 bathrooms, and plenty of room for comfortable living. A 2-car garage plus an additional carport provides ample covered parking for vehicles, equipment, or recreational toys. Outside, enjoy 2 acres of land shaded by mature oak trees, providing plenty of room to relax, entertain, or simply enjoy the outdoors. A 15' x 15' storage building offers additional space for tools, lawn equipment, hobbies, or storage. With generous living space, beautiful acreage, mature trees, abundant parking, and valuable outdoor storage, this property is a rare find on San Antonio's growing Far West Side. Schedule your showing today and come experience the space and possibilities this Far West Bexar County property has to offer!

13415 Sleepy Oaks Ln, San Antonio

$745,000

5 Beds ⋅ 6 Baths ⋅ 1995619 MLS ⋅ ACTIVE 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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