Welcome to 242 N Rolling Rd where charming character meets modern comfort in a home being sold for the first time ever from the original family who built it in 1937. Nestled on an expansive lot with back yard access into N. Highland Rd and the scenic hills neighborhood, this residence offers a rare blend of classic charm and functional living space. This 4 Bd, 2 ½ BA residence perfectly balances timeless details with newer updates. The home makes a striking first impression with its classic brick-and-stone architecture, complemented by a newly paved driveway and mature landscaping of trees and green space. Inside, the foyer welcomes you with unique multi-colored slate flooring and a coat closet. The heart of the home is a spacious living room centered around a cozy fireplace with a traditional white mantel, flanked by custom built-in arched alcoves. Warm hardwood floors flow throughout the main living area. The eat-in kitchen blends rustic textures with high-end utility. It boasts all new appliances (roughly 2 ½ years old) which include a professional stainless steel gas range, a French-door refrigerator, built-in dishwasher, stand along microwave, and a textured brick feature wall, all accented by charming scalloped bulkhead details. Access to the back yard and basement are found here as well. An additional feature to the first floor is a bedroom suite. This room includes exterior access and a full bathroom and could be utilized as a primary bedroom or in-law/au-pair/home office. Upstairs, the bedrooms are all drenched in natural light, offer ample storage with floor-to-ceiling mirrored closets and a restful atmosphere. The two smaller bedrooms share access to the Juliet balcony above the garage overlooking the driveway and yard. A large hall bathroom and cedar linen closet can also be found on this level. The walk-out basement is partially finished and can be used for additional living space as well as storage. Laundry facilities, a water closet and a workbench are also available in this space. The outdoor space is a rare find, featuring a massive backyard designed for both relaxation and utility. A permanent deck sits in the middle of the yard, perfect for a firepit, while a dedicated garden plot and a separate auxiliary building offer endless possibilities for hobbies or storage. Surrounded by privacy-enhancing evergreens and a spectacular Japanese Maple. A gated fence through the hedgerow leads to the quiet, established scenic hills neighborhood. This move-in-ready home is an exceptional blend of unique personality and functional design. Other updated/bonus features include a replacement roof with 40 year guarantee, high end Anderson vinyl clad double hung replacement windows, pull through garage with electric door opener and a bonus concrete parking pad in the rear, updated 200 amp electric with natural gas whole house generator backup, ceiling fans in just about every room, top down central air, multi zone boiler, large walk-up attic with attic fan and more… Located close to Saxer avenue shops and restaurants, highly sought after Springfield Area School District and I-476 for connection to all major roads.