Winfield offers 32 subdivisions and condo buildings, ranging from established single-family neighborhoods to townhouse and condo communities tucked closer to downtown and the Metra line. Klein Creek stands out as the largest and most active community in town, spanning single-family homes, townhouses, condos, and land parcels with a wide price spread. Buyers looking for a townhouse or condo lifestyle will find good options in Shelburne Crossing, Harper Woods, and Winfield Square, while single-family buyers gravitate toward Fredericksburg Farm, Woods of Cantigny, and Winfield Heights. For those seeking a 55+ lifestyle, Trillium Farm is the community's designated active adult option. Winfield's mix leans toward mature, resale-driven neighborhoods rather than new construction, with many communities like Churchill Woods and Timber Ridge built out decades ago and now trading based on lot size, updates, and proximity to Cantigny Park and the town center. Smaller pockets such as Garfield Court and Normandy Woods round out the inventory with limited turnover. Overall, Winfield's subdivisions serve move-up families and downsizers alike, with entry-level condos starting in the high $200,000s and executive single-family homes reaching well past $1 million.