Estate & Letting Agents In Uppingham

Nestled in England’s smallest county of Rutland, Uppingham occupies an elevated position on a small plateau, giving parts of the town magnificent views across the surrounding countryside. This historic market town dates back to Anglo-Saxon times, with its name deriving from the homestead of the people on the hill.

The town gained prominence in medieval times as a trading post, but its character was truly shaped in the 17th century with the founding of Uppingham School in 1584. The school remains integral to town life, occupying substantial buildings throughout the centre and bringing families from across the country and abroad to settle in the area.

Walking through Uppingham reveals its distinctive charm – narrow lanes wind between honey-coloured stone buildings, opening onto the marketplace with its ancient butter cross. The town showcases perfect proportions, neither too large nor too small, allowing people to know their neighbours while maintaining privacy.

Uppingham boasts an appealing mix of architectural styles spanning several centuries. The town centre features handsome Georgian and Victorian properties built from local limestone, many with distinctive facades that line the historic high street.

On the outskirts, you’ll find more modern developments alongside detached country homes and substantial period farmhouses. Rutland stone features prominently throughout the older buildings, giving the town its distinctive honey-coloured appearance.

The most sought-after properties tend to be found on High Street East and West, where Georgian townhouses stand proudly with their elegant proportions. The leafy streets around Uppingham School house larger family homes with generous gardens.

Uppingham sits in an advantageous position for those who need to travel but want to maintain distance from the larger urban centres nearby…

• Car & Road: Uppingham lies at the crossroads of the A47 and A6003, providing excellent links to surrounding areas. The A47 connects to Leicester in about 30 minutes and Peterborough in roughly 45 minutes. The nearby A1 is accessible within 15 minutes, creating quick routes to London and the north. Most properties in the area come with private parking, and the town offers adequate public car parks for shoppers and visitors.
• Train: While Uppingham doesn’t have its own railway station, Oakham station is just 6 miles away, offering services to Leicester, Birmingham, and Peterborough. Corby station, about 10 miles south, provides more frequent services to London St Pancras with journey times of around 1 hour and 10 minutes.

Rutland’s smallest historic market town offers numerous points of interest within its walkable streets and beautiful surroundings…

• Uppingham School: Founded in 1584, this prestigious independent school features striking Victorian Gothic architecture designed by G.E. Street. The school buildings include the impressive chapel and the renowned theatre. (Uppingham School, High Street West, Uppingham, LE15 9QE)
• The Market Square: Dating from medieval times and still hosting weekly markets on Fridays, the square includes the 17th-century Falcon Hotel and distinctive stone-built shops. The ancient butter cross stands as a testament to the town’s long trading history.
• Uppingham Gallery: Located on Orange Street, this gallery displays works from local and national artists, with regularly changing exhibitions throughout the year. (5 Orange Street, Uppingham, LE15 9SQ)
• The Goldmark Gallery: A nationally recognised art gallery hosting exhibitions of contemporary prints, paintings, and ceramics by major international artists. (14 Orange Street, Uppingham, LE15 9SQ)

Uppingham’s job market presents a distinctive economic landscape shaped by education, small business, and rural industries. The town’s employment heartbeat comes from Uppingham School, which stands as the largest employer providing positions across education, administration, and support services.

Small independent businesses form the backbone of local employment, with the town centre’s collection of boutique shops, galleries, cafés and restaurants creating a steady flow of retail and hospitality positions. Notable among these is the renowned Goldmark Gallery, which attracts visitors from across the country. The weekly market continues its centuries-old tradition of generating economic activity.

The broader Rutland area offers agricultural work on surrounding estates and farms, while tourism-related positions spike during summer months when visitors flock to nearby Rutland Water.