Living in Oakham: An Area Guide

Oakham consistently appears on lists of the best places to live in England, and the reasons are clear to see. It’s a genuinely self-contained market town in a county small enough that almost nothing feels far away, yet it sits within reasonable reach of Leicester, Nottingham, and Peterborough. For buyers weighing up whether a move considerably far from a major city makes practical sense, it is worth exploring how Oakham can meet your lifestyle goals.

The town is the county town of Rutland, England’s smallest county, with a population of around 12,000. It sits roughly 25 miles east of Leicester and 23 miles northwest of Peterborough, with Rutland Water, one of the largest man-made reservoirs in Europe, immediately to its east.

The Sunday Times named Oakham among the best places to live in the UK in 2025, describing it as “just as pretty as neighbouring Uppingham but far more practical.” That balance of character and practicality is what tends to attract buyers who benefit from a vibrant market town with an independent high street, strong schools, and countryside on the doorstep, without the premium attached to better-known Cotswold or Home Counties equivalents.

Why Live in Oakham?

Living in Oakham provides a fairly unique offering of rural charm without compromising on amenities. The high street has retained independent traders, there’s a twice-weekly market, and the town has its own cultural and sporting life rather than depending on a larger neighbouring city for everything. Rutland Water is a major attraction for outdoors enthusiasts with varied interests. This large reservoir has cycling trails, sailing activities, and nature reserves that most market towns of this size don’t have on their doorstep.

The town’s long heritage is another draw for buyers. Oakham Castle’s great hall dates to the late 12th century and holds a collection of over 200 commemorative horseshoes, which relates to a local custom, enforced for over 500 years, requiring visiting royalty and peers of the realm to forfeit a horseshoe to the town. All Saints’ Church, with its 14th-century spire restored by Sir George Gilbert Scott in the 1850s, is a Grade I listed building and one of the most recognisable landmarks in the East Midlands. These aren’t just visitor attractions, they give the town a sense of history that newer settlements lack.

On the education front, Oakham School is one of the country’s leading co-educational independent schools, and the state secondary provision is solid. For buyers with school-age children, that combination of strong independent and state options in the same small town is a significant draw.

Who Is Oakham Best Suited To?

Oakham is particularly suited to families and retirees but remote workers and young professionals also appreciate what the town has to off. The table below sets out the pros and cons for different types of buyers and tenants.

Oakham Property Market & Prices

Oakham’s property market has a large proportion of period stone-built terraces and Victorian semis in the town centre, with a broader mix of post-war and newer detached housing on the outskirts. The town has seen steady interest from buyers relocating from Leicester, Nottingham, and further afield, attracted by the combination of market-town character and relatively accessible entry prices compared to equivalent towns in the Cotswolds or Chilterns.

Over the last decade, the Rutland house market has an increase in average house prices from around £220,000 to over £300,000 according to Land Registry data. Rutland consistently records among the higher average sold prices in the East Midlands, reflecting its desirability and constrained supply.

The county’s planning position adds a layer of context to the house value picture: the government’s revised national planning policy framework has more than doubled Rutland’s annual housing target, from 123 to 266 homes per year, and the authority currently cannot demonstrate a five-year land supply. New sites are coming forward, including a plan submitted in June 2026 for a 70-home development south of Stamford Road, with 21 classed as affordable housing, but supply remains tight relative to demand, which underpins values.

For detail on specific streets, property types, and the architectural character of the town’s different pockets, see our guides on Key Streets & Locations and Property & Architecture guides.

Transport in Oakham

Oakham is served by rail but not motorway. The town sits on the Oakham line connecting Leicester to Peterborough via Stamford, with trains running regularly throughout the day. Road access is via the A606, which links north to Nottingham and south towards Stamford and the A1.

There have been recent improvements to bus services, including Rutland County Council launching the first phase of its Local Link transport initiative in March 2025, introducing demand-responsive and fixed-route services across the county. The second phase includes converting Jules House in Oakham into a community transport hub, due for completion by the end of 2026, funded as part of a £22.95m UK Government Rural Innovation in Action package.

Cycling infrastructure around Rutland Water is excellent for leisure, though the town’s cycle connections to neighbouring areas are limited.

Schools & Education in Oakham

Oakham has a range of schooling options for a town of its size, from primary through to sixth form. The presence of Oakham School, one of the country’s leading co-educational independent schools, is a significant factor for many families considering the area.

Note: Ofsted ratings should be verified directly on the Ofsted website, as inspection dates and outcomes are updated on a rolling basis. Ratings above reflect the most recently published outcomes at the time of writing.

Catmose College is the main state secondary for the town and has a broadly positive reputation locally. Oakham School, founded in 1584, reported a 99% A-level pass rate in 2025, a 100% IB Diploma pass rate with an average of 34.1 points, and three-year highs across all GCSE grade measures according to the Oakham School wesbite). For families considering the independent route, it is one of the stronger options in the East Midlands and draws pupils from across Rutland and beyond.

Local Amenities & Shopping in Oakham

Oakham works as a self-contained market town rather than relying on access to a larger centre, which is part of its appeal. The high street runs through the town centre and retains a good proportion of independent retailers alongside the usual national chains. A twice-weekly market operates in the market place, a short walk from the castle.

The town has a number of major supermarkets, including Tesco Superstore and Aldi. There are also several smaller convenience stores and specialist independents covering food, gifts, and homeware. The nearest leisure facilities are in Stamford and Melton Mowbray.

Oakham’s library remains open and the town has a small cinema with just 12 seats. For larger retail options, Peterborough and Leicester are both accessible by train for a day trip.

Restaurants, Pubs & Bars in Oakham

Oakham has a food and drink scene that punches above its weight for a town of 12,000. The Grainstore Brewery, based in a converted Victorian grain warehouse on Station Road, is one of the most distinctive independent breweries in the East Midlands and operates a tap room and bar on site. It forms a strong part of community, serving food, hosting quiz nights and live entertainment.

The Lord Nelson pub on Market Place is a long-established town-centre venue. Several independent cafés and restaurants operate along the high street, with the offer leaning towards traditional British and European cooking rather than anything more adventurous. The Sunday Times’ 2025 recognition of Oakham specifically cited its local businesses as a contributing factor to the town’s quality of life, and the food and drink scene is part of that picture.

Uppingham, seven miles to the south, broadens the options further for those willing to make a short drive.

Local Health & Medical Provision in Oakham

GP provision in Oakham is delivered through surgeries in the town centre, with the main practice being Oakham Medical Practice, which serves a large registered patient list across Rutland. As with many rural areas, access to same-day GP appointments can be pressured, though the town is better served than more isolated parts of the county.

The nearest A&E department is at Leicester Royal Infirmary, approximately 25 miles west, or Peterborough City Hospital to the east. Rutland Memorial Hospital in Oakham provides some outpatient services and minor procedures but does not operate a full emergency department. For dental provision, both NHS and private practices operate in the town, though NHS availability is limited, as is common across the East Midlands.

The CQC and NHS websites carry current ratings and registration information for local practices.

Parks & Green Spaces in Oakham

Rutland Water is the dominant green and blue space asset for Oakham, and it’s an exceptional one. The reservoir covers around 3,100 acres and is encircled by a 25-mile cycling and walking trail. The Rutland Water Nature Reserve, managed by the Leicestershire and Rutland Wildlife Trust, is one of the most important inland bird reserves in England, particularly for osprey. The reservoir also supports sailing, windsurfing, and fishing, and Normanton Church — now a museum — sits at the water’s edge.

Within the town itself, Cutts Close is a public park adjacent to the castle, providing open green space, a children’s play area, and a venue for local events. The park is central, well maintained, and genuinely used by residents rather than being a token green patch. Berrybut Lane and the surrounding meadow areas on the town’s eastern edge offer informal walking routes connecting to the wider countryside.

For families with dogs or young children, the combination of town park and Rutland Water means outdoor space is a genuine strength of living here.

Cost of Living in Oakham

Rutland has historically carried one of the higher council tax rates in the East Midlands, a consequence of the county’s very small tax base spread across a wide rural area.

However, the practical cost of living in Oakham is moderated by the town’s walkability. A car is useful for reaching the wider countryside, but day-to-day errands, schools, and GP appointments are all reachable on foot or by bicycle for most residents. Parking in the town centre is generally available and inexpensive compared to a city.

Rental prices are moderate by national standards, though stock is limited, which keeps vacancy rates low. Landlords benefit from consistent demand, particularly from families seeking good schools and professionals working in Peterborough or Leicester who prefer a rural base.

Community & Lifestyle in Oakham

Oakham has a strong sense of its own identity, which is unusual for a town of this size. Part of that comes from Rutland itself: England’s smallest county has a reputation for fiercely defending its independent status (it was briefly absorbed into Leicestershire before being restored as a unitary authority in 1997), and that civic pride filters down to the town level.

The town calendar includes a range of events tied to its market and heritage functions. The Rutland Ride and Stride, an annual sponsored walk visiting historic churches, raised nearly £30,000 in 2025. The Oakham Arts Centre and various community groups run a cultural programme through the year.

Alongside the Grainstore Brewery, there are independent food shops, bookshops, and specialist retailers that give the high street a character distinct from a generic market town.

Frequently Asked Questions

Looking to Buy or Rent in Oakham?

King West covers Oakham and the wider Rutland area across sales and lettings, with local knowledge that goes beyond the headline figures. Whether you’re buying a home to live in, acquiring an investment property, or looking to rent, contact us to discuss what’s available, or register as a buyer or tenant to be kept informed as new properties come to market.