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uppingham town rutland

Top places to live in Leicestershire & Rutland Uppingham

Voted by The Sunday Times as the best place to live in the Midlands this year, Uppingham has it all. Traditional houses at affordable prices, excellent schools, it's quietly attractive and has lots of community spirit.


This charming market town is filled with old stone buildings, gorgeous greenery, period properties, a pretty high street and overwhelmingly friendly locals.


Make a beeline for local favourites Don Paddy’s – they serve everything from brunch through to cocktails. Scandimania is the place to go for coffee though and we absolutely love their vegan pistachio and rhubarb frangipane cake. Book dinner at the charming restaurant with rooms, The Lake Isle and you can feast on delicious seasonal produce.


Art lovers should head to Goldmark Gallery where they can marvel at everything from screen prints by Warhol to etchings and lithographs from Picasso. Mooch around Made Gallery and pick up pretty pieces of jewellery and an eclectic mix of edgy art. Meanwhile, LolaWood has elegant and stylish furniture, home accents, lighting, mirrors and gifts. Pop into the beauty haven that is Organic Ritual Beauty on the High Street where you can be pampered into oblivion.


If you’ve got the kids, explore Uppingham on a self-guided murder mystery-themed Treasure Trail. The local arts scene is small and mainly centred around Uppingham Theatre. Don’t overlook Eyebrook Reservoir that covers around 200 hectares – great for outdoorsy types.


The average price for a property in Uppingham is £317,928 and detached houses sell for around £381,322.


View house and gallery here


Uppingham School (co-ed, 13 to 18) is just off the market square. Founded in 1584, it’s a full boarding school that has a brilliant reputation.


The school’s alumni include Stephen Fry, Rick Stein and Johnny Vaughan. 


It’s 97 miles to London and to drive it would take over two hours. Oakham station is a 15-minute drive, from there you can set a season ticket for just under £9,000 and it takes one hour 48 minutes by train.

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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