Montgomery's housing reflects its layered history. The oldest homes cluster around the downtown historic district, where restored early Texas houses and structures line the streets, and the city offers a historical-district tax exemption for property owners who maintain qualifying structures. Beyond the historic core, the surrounding area is defined by a mix of ranch-style homes on larger lots, wooded acreage, and newer subdivisions that have grown up around the Lake Conroe area. Many properties sit on generous lots with mature trees, and some offer lake access or proximity to the national forest. The overall character is lower-density than nearby Conroe or The Woodlands, with a blend of small-town residences, rural homesteads, and modern single-family communities.

Montgomery is small enough that its districts are less pronounced than in a larger city, but the area breaks into a few recognizable zones. The historic downtown anchors the city with early Texas homes, the N.H. Davis Pioneer Complex, and the shops along its main streets. Immediately around the city limits, established residential streets and ranch-style homes on large lots give way to newer subdivisions on the outskirts. To the east and northeast, the Lake Conroe shoreline and its surrounding communities offer waterfront and water-access properties. To the west and north, wooded acreage and rural homesteads blend into the Sam Houston National Forest, offering seclusion and outdoor access.

Life in Montgomery centers on a relaxed, small-town rhythm. The historic downtown is the social heart, where residents gather at cafés, wine bars, and locally owned restaurants, and browse antique and boutique shops. Community identity is closely tied to Texas history, with the town's Lone Star Flag heritage and its pioneer-era buildings celebrated through museums, walking tours, and local events. The pace is quiet compared with Conroe or The Woodlands, and much of local recreation happens outdoors — on Lake Conroe, in the Sam Houston National Forest, or on the area's rural roads and trails. For dining, entertainment, and shopping on a larger scale, residents can reach Conroe or The Woodlands within a short drive.

Students in Montgomery attend Montgomery ISD, a district serving about 9,000 students across 11 campuses, with schools located in and around the city. The district covers a largely suburban and rural area of western Montgomery County and offers the full range of elementary, intermediate, junior high, and high school levels. Neighboring districts, including Conroe ISD, serve portions of the broader Lake Conroe area. For higher education, Lone Star College and Sam Houston State University in nearby Huntsville are within commuting distance, and families also have access to private school options in Conroe and The Woodlands.

Montgomery sits west of Interstate 45, the primary corridor connecting the Lake Conroe area to Houston, about 50 miles to the south. State Highways 105 and 75 and farm-to-market roads such as FM 149 and FM 1097 link the city to Conroe, Willis, and the surrounding countryside. Commuters typically reach Conroe and The Woodlands in about 15 to 30 minutes and can connect to Houston's employment centers via I-45 or the Hardy Toll Road. The city itself is compact and walkable around its historic downtown, but daily travel in the area is car-dependent, as is typical of exurban Texas. George Bush Intercontinental Airport, north of Houston, is the nearest major airport.

Montgomery is surrounded by some of the region's most substantial outdoor recreation. Lake Conroe, a roughly 21,000-acre reservoir, lies immediately to the east and offers boating, fishing, water skiing, and lakeside parks, with marinas and boat ramps around its shoreline. To the west and north, the Sam Houston National Forest spans more than 160,000 acres, with hiking, mountain biking, hunting, and camping along its trails and forest roads. W.G. Jones State Forest, just to the south, provides additional walking trails and wildlife viewing. Fernland Historical Park in downtown Montgomery combines open space with preserved pioneer structures, and the city's small-town parks host community gatherings throughout the year.