Rolling Oaks Estates Real Estate

Welcome to Rolling Oaks Estates, a hidden gem nestled in the heart of San Antonio, Texas, within the vibrant Bexar County. This charming subdivision is a perfect blend of suburban tranquility and urban convenience, making it an ideal choice for families, professionals, and retirees alike.

Rolling Oaks Estates boasts beautifully landscaped streets lined with mature trees, creating a picturesque setting that invites you to take leisurely strolls or enjoy a morning jog. The homes here are a delightful mix of contemporary designs and traditional architecture, offering something for everyone. Spacious yards provide ample room for outdoor activities, gardening, or simply relaxing under the Texas sun.

One of the standout features of Rolling Oaks Estates is its strong sense of community. Neighbors often gather for seasonal events, fostering lasting friendships and a welcoming atmosphere. Families will appreciate the nearby parks and recreational facilities, perfect for weekend picnics and playdates. The area is also home to highly-rated schools, ensuring your children receive a top-notch education.

Conveniently located, Rolling Oaks Estates offers easy access to major highways, making commuting a breeze. Residents can enjoy a short drive to the bustling downtown San Antonio, where a wealth of shopping, dining, and entertainment options await. Plus, the rich cultural heritage of the city, including the famous River Walk and the historic Alamo, is just around the corner.

Experience the charm and community spirit of Rolling Oaks Estates—where your dream home awaits in the heart of San Antonio!

Newest Listings in Rolling Oaks Estates

$775,000

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

$815,000

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 for visitors, a home office, or rental income. 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

$1,449,000

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

$885,000

3 Beds ⋅ 5 Baths ⋅ 1969985 MLS ⋅ ACTIVE Status

Situated on 2.002 acres in Rolling Oak Estates with no HOA, 13439 Sunnyview Trail offers 3,943 square feet of custom Mediterranean style living designed for buyers seeking space, functionality, energy efficiency, and long term flexibility. Located in Northwest San Antonio near Potranco Road and Highway 211, the property provides convenient access to Loop 1604, Alamo Ranch shopping and dining, HEB, Costco, Walmart Supercenter, Dove Creek retail, SeaWorld San Antonio, and major commuter corridors while maintaining a private country setting. Built in 2017, this single story home includes 3 bedrooms, 4 full bathrooms, 1 half bath, a private study, flex room, two dining areas, dual laundry spaces, an oversized side entry 3 car garage, RV and boat parking, and a detached RV garage/workshop. Since 2023, the home has received more than $100,000 in updates and improvements. The chef's kitchen features custom painted cabinetry, granite countertops, an oversized island, farmhouse sink, updated lighting and fixtures, double ovens, walk in pantry storage, and a Thor Kitchen commercial grade 6 burner gas range with grill and oven. The open concept layout includes oversized living and dining areas, tray ceilings, recessed lighting, expansive windows, and a blend of tile flooring and locking bamboo engineered hardwood throughout the home. Every bedroom includes ensuite bathroom access, while the split primary suite offers a sitting area, oversized walk in closet, dual vanities, oversized walk in shower with dual shower heads, and private laundry access. The home was built with a strong focus on efficiency, durability, and self sufficiency. Features include a 35 panel 10KW solar system, solar hot water system, 6 inch spray foam insulated exterior walls, upgraded water softener and reverse osmosis system, whole house surge protection, home generator, 99 percent LED lighting, double pane windows, zoned HVAC systems, programmable thermostats, Energy Star appliances, private well, aerobic septic system, and no city taxes. Outdoor features include a gated entrance, long paved driveway, mature oak trees, covered back patio, storage buildings, open acreage, and expansive country views.

13439 Sunnyview Trail, San Antonio

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