1446 Glenside Drive Welcome home to this beautifully updated and original owner meticulously maintained residence offering more than 2, 000 square feet of stylish living space in one of Bolingbrook's most desirable locations. Combining modern updates, exceptional outdoor entertaining space, and award-winning schools, this home delivers the perfect blend of comfort, convenience, and lifestyle. From the moment you arrive, you'll appreciate the professionally landscaped curb appeal and pride of ownership throughout. Inside, the home showcases luxury vinyl flooring, updated trim and doors, fresh paint, elegant wainscoting, and a stunning coffered ceiling that elevates the dining room into a truly memorable gathering space. The updated kitchen features quartz countertops, abundant workspace, and a layout designed for both everyday living and entertaining. The real showstopper awaits outside. Step into your private backyard retreat featuring an incredible approximately 800-square-foot paver patio covered by a pergola with a massive sliding barn door, creating the ultimate outdoor living experience. Entertain family and friends around the gas firepit, gather at the walk-up bar, or spend summer days enjoying the 21-foot round pool with surrounding deck. The fully fenced yard provides privacy, functionality, and plenty of room for recreation. Backing to Claar Blvd, while protected by a built up berm and mature trees, the lot offers privacy without a direct neighbor behind. Additional highlights include a brand-new roof (2026), a partially finished basement offering added liveable square footage and a flexible living space, and a concrete slab crawl space providing exceptional storage options. Location is everything, and this home delivers. Situated within the highly regarded Plainfield 202 School District, serving Liberty Elementary, John F. Kennedy Middle School, and Plainfield East High School, you'll also enjoy convenient access to shopping, dining, and multiple major highways for an easy commute. Beyond the property itself, you'll enjoy access to some of the area's best amenities. The renowned Bolingbrook Golf Club and popular Nest Bar & Grill are within walking distance, offering championship golf, dining, community events, and the village's spectacular annual Fourth of July celebration. Residents also benefit from the award-winning Bolingbrook Park District, known for its outstanding parks, recreation programs, fitness facilities, and community events. Just minutes away is Pelican Harbor Indoor/Outdoor Aquatic Park, one of the region's premier family destinations featuring water slides, pools, splash areas, and year-round aquatic activities. This is more than a home, it's an opportunity to enjoy a highly upgraded property in a community rich with amenities, recreation, and convenience. Don't miss your chance to own one of Bolingbrook's finest move-in-ready homes. Seller is a Licensed Illinois Real Estate Broker.