Before looking at condos for sale, it’s fun to learn about this charming small town. In 1759 the site was built by the British as an outpost on the military road across Vermont, connecting forts on Lake Champlain with the Connecticut River valley and centered on excellent farmland and gentle topography. Chartered in 1761, the settlement was probably named for Rutland, Massachusetts, the home of one of the early settlers. However, another theory is that it was named by the state governor after the influential Duke of Rutland, in the hope of currying his favor. It is the home of Vermont's oldest newspaper, the Rutland Daily Herald, published continuously since 1794. In the early 19th century small high-quality marble deposits were discovered in Rutland and in the 1830s a large deposit of nearly solid marble was found in what is now West Rutland. After Rutland was incorporated as a village in 1847, railroad construction and marble quarrying stimulated growth. Coincidentally, the famous quarries of Carrara in Tuscany, Italy, became largely unworkable because of their extreme depth at this time and Rutland quickly became one of the leading producers of marble in the world. This fueled enough growth and investment that by the 1880s it was Vermont's largest municipality. In 1886, the surrounding marble-producing communities of Proctor, Rutland town and West Rutland town, withdrew and since then Rutland city, which incorporated in 1892, has been second in size to Burlington. The closing of many of the marble quarries in the 1980s and 90s led to a significant loss of jobs in the area.

Lovingly restored historic Merchant's Row dates back to the mid-19th century with interesting shops and restaurants and a lot of banks and municipal buildings.

There’s a summer Farmers' Market in downtown's Depot Park and a winter Farmers' Market in the Vermont Farmers Food Center for those keen to buy local, organic and artisanal foods.
The bandstand in the Main Street Park, opposite the Chaffee Art Center, features a well-attended Summer Concert Series.

The Paramount Theater was fully restored in 2000 after many years of abandonment. It is one of the most beautiful buildings in New England and, with 838 seats, offers an outstanding approach to live entertainment. It is a significant and valuable community resource since assuming its role as an arts, cultural and educational center.

The 275-acre Pine Hill Park offers mountain biking, hiking and other outdoor recreation. At the park's entrance is the Flip Side Skatepark, municipally operated in an open-sided closed roof arena at the Giorgetti Athletic Complex.

Nearby Pico Mountain Ski Area is one of Vermont’s first commercial ski and snowboard resorts, founded in 1937 with 57 runs. It is now operated by POWDR, one of North America’s largest ski operators. Pico has newly upgraded snow making equipment on 75 percent of its runs and the area also receives significant natural snowfall.

Deer Leap Trail is an easy one-hour hike, with a spectacular view at the top as a reward.

An area of outstanding natural beauty, Green Mountain National Forest was established in 1932 to fight uncontrolled overlogging, fire and flooding. The forest contains three nationally designated trails, three alpine ski areas, seven Nordic ski areas and approximately 900 miles of multiple-use trails for hiking, cross country skiing, snowmobiling, horseback riding and biking. The forest supports a variety of wildlife, including beaver, moose, coyote, black bear, white-tailed deer, wild turkey and ruffed grouse. Its administrative headquarters are in the city.

The Green Mountain National Golf Course, the Neshobe Golf Club and the Okemo Valley Golf Club are local golf courses.

One oddity is the Twin Covered Bridge, which is still a bridge in the structural sense, even though it has been five decades since it spanned water. Originally located on the East Creek, this bridge along with its twin, was washed off its abutment during a flood in 1947. Unfortunately, the second twin was destroyed. There has been talk about relocating the bridge to a nearby park but to date the bridge remains adrift.