In a time when many are rethinking where and how they want to live, Chesterfield is quietly emerging as a compelling relocation destination.
Recently named one of the happiest places to live by The Guardian, our historic Derbyshire market town is drawing attention for all the right reasons.
Chesterfield has also been recognised as one of the greenest towns in the UK, with over 95% of homes having access to private or nearby outdoor space, including Queens Park, Holmebrook Valley Park, and the Chesterfield Canal. Thanks to its excellent schools, strong community spirit, and access to nature, it consistently ranks among the best places to raise a family.
The town is seeing new housing developments, including a new £78 million scheme by Honey Homes, and regeneration projects like the Staveley Corridor, Chesterfield Waterside, and Spire Neighbourhood will bring more homes.
But what’s driving this momentum? We spoke to local estate agents and business leaders to understand why young professionals and families are choosing to call Chesterfield home and why now might be the perfect time to join them.
Chesterfield’s national recognition
Chesterfield’s recent national recognition hasn’t come out of nowhere. Richard Sherwood, Director of Roy Peters Estates, has seen it first hand over nearly three decades in the local property market.
“It is no surprise that Chesterfield has been identified as one of the happiest places to live in the recent Guardian article. Chesterfield is a great market town, and it continues to evolve. We are looking forward to the modernisation of the Market Square being completed. We have the Peak District on the doorstep and can be in London or either coast in two hours.”
Richard also points to the town’s independent business scene, like restaurant Bottle & Thyme and Queensbury Financial Advisors and its strong sense of community, reflected in events like the Sparkle Walk for Ashgate Hospice and the Redbrik Chesterfield 10K.
A housing market built on stability and opportunity
While many towns have seen turbulence in the housing market, Chesterfield has remained remarkably resilient. Jessica Risorto, Director at Redbrik, explains how North Derbyshire has responded to national fluctuations with confidence:
“Chesterfield’s property market has weathered the national fluctuations with resilience and growing appeal. Chesterfield has stood out by maintaining its status as an affordable place to live, especially compared to other towns of similar size and location.”
She notes a growing wave of first-time buyers entering the market in 2025, particularly young families.
“Another key trend is the rise in young families settling in Chesterfield. Our town’s schools, parks, and strong sense of community are drawing people in, and we’re even seeing extended families relocating from out of town to be closer to loved ones who’ve already made the move.”
Where people want to live — and why
Chesterfield’s appeal isn’t just about price, it’s about lifestyle. Jess highlights the west side of Chesterfield as one of the most desirable areas, thanks to its character homes, green spaces, and proximity to the Peak District. But she also sees rising interest in areas like Bolsover, Calow, and Brimington:
“These neighbourhoods are fast becoming top choices for buyers, thanks to their evolving communities, increasing investment in local infrastructure, and the quality of homes being built.”
Developers, including Honey, Woodall Homes and Stancliffe Homes, are responding to demand with thoughtfully designed new builds, especially bungalows, which are proving popular with both downsizers and families.
Regeneration with purpose
Chesterfield’s transformation is rooted in long-term thinking. Stacey Davies-Bowler, Managing Director of Pinewood Property Estates, sees the town’s regeneration as a model for sustainable, community-led growth:
“The most exciting aspect of Chesterfield’s evolution is that it isn’t driven by speculative development, but by targeted investment focused on long-term value for residents, businesses, and the wider region.”
Projects like the Waterside regeneration are reshaping the town’s economic landscape. Stacey believes these developments will create modern, mixed-use spaces that integrate homes, businesses, and leisure, with better connectivity and public realm improvements.
Adding to this, Stacey has observed a shift in what buyers and renters are looking for:
“I’ve already seen a shift in the types of properties people require. Buyers and renters want more than just a home; they want neighbourhoods that offer lifestyle, connectivity, and value. With renewed investment, we can expect smarter housing developments that blend design, sustainability, and affordability.”
A way of life
For those considering moving to Derbyshire, Chesterfield offers a great lifestyle.
Jamie Wajs, Director at Lime Living, paints a picture of a town that blends convenience with culture and nature:
“Chesterfield offers the perfect balanced lifestyle with a great mix of local amenities and a good offering of educational facilities for families, and we have easy access to open and green spaces.”
“You can enjoy an increasing variety of independent shops, bars, bistros and restaurants in the town centre and along Chatsworth Road.”
He also highlights the town’s growing cultural scene, from the Winding Wheel and the Crooked Spire to the soon-to-reopen Stephenson Memorial Hall, which is being transformed as part of a multi-million pound renovation project to create a modern visitor and cultural experience in the heart of our town centre.
And for a true local experience?
“Derbyshire v Yorkshire at cricket, soaking up the atmosphere down at Queens Park.”
Be part of the community
As Chesterfield evolves, its friendliness and community spirit are grounded in the place.
Ryan Wilkes, Destination Chesterfield Board Member, believes that’s part of what makes the town so special:
“We’re very pleased to see Chesterfield gaining further recognition as a great place to live. As a lifelong resident, it’s fantastic to see our brilliant outdoor spaces, local businesses and community spirit highlighted.
“If you’re looking to live in an area which blends a strong heritage with strong local amenities within easy reach, Chesterfield is a place that you’ll be proud to call home.”
Find out more about living in Chesterfield at: https://www.chesterfield.co.uk/about-chesterfield/living/
