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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 is moving from Bakers Yard to Mill Street in Nov. Hurrah! They serve brunch, lunch and small plates packed with 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 that’s just opened up on the High Street. Walkers of Oakham is a lovely indy 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 the 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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