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Top places to live in Leicestershire & Rutland Oakham

As charming as the Cotswolds, but with a cheaper price tag, Oakham has fabulous shopping, great travel connections, charming buildings, beautiful country pubs and a well-heeled vibe.


A compact and characterful town largely due to its lively and quaint market place and buzzing high street. It’s a popular place for Londoners to settle down because of its laid-back country charm and good travel connections.


The Larder is a firm favourite for lunch! As well as salads and sandwiches their specials are super popular (we love the Japanese sushi bowl). Cool eatery, Orbis Oakham has moved to Mill Street and serve brunch, lunch and small plates packed with bags of flavour. For something a little quieter, there’s the rustic Hitchen’s Barn (a Bib Gourmand-winning restaurant) and Sarpech is a great Indian restaurant and wine bar. We also recommend the date and walnut sourdough bread from award-winning, Hambleton Bakery.


No visit to Oakham would be complete without a visit to Cavells, an incredible fashion boutique stocking over 100 designers with a lovely homeware section too. Look out for Prink, a fabulous new fashion boutique on the High Street. Walkers of Oakham is a lovely indie bookshop – always worth a rummage – while Nadinoo sells mindfully made clothes that are simple, comfortable and versatile. It’s also worth spending a day at Rutland Garden Village, just outside of Oakham where you can have a nose around the garden centre and stylish homewares shop, Barefoot Sunday.


Oakham Castle, is a fine example of Norman architecture and beautifully restored. At Rutland County Museum you can explore the exciting archaeology discoveries of the area and Rutland Water is a large playground for big and little kids – you can enjoy water sports, nature reserves, outdoor water adventure cycling and walking facilities.


Around £264,057 with detached properties being more popular selling for an average price of £360,843.


View house and gallery here


Oakham School is a brilliant co-ed independent school for children aged from 10 to 18. There’s also Uppingham School, Brooke Hill Primary and both Catmose College and sixth form, Harington School (state-funded) have been voted ‘Outstanding’ by Ofsted.


The Great Hall of Oakham Castle is the finest surviving example of Norman domestic architecture in Europe, built between 1180 and 1190.


Most people work in and around Leicester or Peterborough (around 45 mins drive either way). It’s 101 miles to London, which to drive, would take over two hours. Oakham Station is a few minutes drive and you can get a season ticket for just under £9,000.

View the full Top 200 Best Places to Live 

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Leicestershire & Rutland

Best Place to Live in Leicestershire & Rutland Reader Vote

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A delightful des res village that has plenty to offer families.

Kibworth Beauchamp

If you want a quaint village life, Kibworth Beauchamp is a great bet.

Ashby de la Zouch

Looking to leave city life? Tucked away deep in the National Forest, this Midlands town has good schools, a busy high street and the charming remains of an old castle.

Market Harborough leicestershire

Market Harborough

Great shopping, beautiful buildings and a growing arts and culture scene, you'll be hard pushed to find a better place to live than this pretty market town plus, it's easy to head to the city when required.

uppingham town rutland


Voted by The Sunday Times as the best place to live in the Midlands this year, Uppingham has it all.


As charming as the Cotswolds, but with a cheaper price tag, Oakham has fabulous shopping, great travel connections, charming buildings, beautiful country pubs and a well-heeled vibe.


Clarendon Park

If you want to hang out with the cool kids, there's no better spot.


Small but perfectly formed and quite possibly the most beautiful village in Rutland.

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