Chester

Average Sales Price

$727,090

Median Sales Price

$635,500

Total Listings

Population

4,710

I'm Kyle Cavanaugh, a New Hampshire native, REALTOR® and investor. What would make a Chester home feel right for your next chapter? Explore the homes and local resources below, then let's look at the property details and everyday priorities that matter to you.

Chester, New Hampshire • With Kyle Cavanaugh

A little room
for your next chapter.

What would make a Chester move feel like yours? Start there. Then let’s explore the property—and the life around it—with care.

I’m Kyle Cavanaugh, a New Hampshire native, REALTOR® and investor. I want to understand your reason for moving before we build the shortlist.

Get to know the place

Look beyond the property line.

Your connection to a place can come from something small: an outing you enjoy, a routine that works, or a way to spend time outside. Chester’s official conservation resources offer a useful starting point for exploring.

An official local resource

Forsaith Forest: follow the town’s guide.

The town describes a nature trail and boardwalk near Ledge Road that leads into an Atlantic white cedar swamp. Its page includes directions and information about the setting.

If that sounds like your kind of outing, check the town’s current information and conditions before visiting. I’m linking to the official description rather than presenting a trail as a feature of any particular home.

Read the town’s Forsaith Forest guide →

Find your own outside.

The conservation directory also connects to Spring Hill Farm and Wason Pond trail-map resources. Explore the official materials to see what fits your interests.

Browse Chester conservation resources →

Test your routine.

Work, errands, visitors and the things you enjoy doing should all have a place in your thinking. Try the routes at relevant times and make your own observations.

Tell me what matters.

Space, simplicity, a project, a different location? We can turn your reasons for moving into a focused set of priorities.

Start with your priorities →

Kyle’s field notes

Space for an idea is the start.

I’ve flipped properties, own multifamily and rental properties, and have built and sold new-construction homes. That experience reminds me to separate the appeal of an idea from the property-specific questions that need answering.

If your Chester plans involve a change of use, an addition, or a new project, start with current municipal information and the appropriate department. Chester’s Zoning Board of Adjustment page describes its role and links application instructions and downloadable forms. A process existing does not mean a particular request will be approved.

Find Chester zoning resources →

A home you can live in now.

How does the property support the way you want to use it today? Begin with the present condition and setup.

A possibility for later.

What depends on permissions, a specialist’s assessment, or more information? Put those unknowns on the table early.

A plan that belongs to you.

Your detailed project and purchase strategy should fit your priorities, timeline and the actual property. That is a conversation we can have together.

Read my construction introduction →

Let’s make it a Prideful Move

Your next chapter.
Let’s give it some thought.

Tell me what brought you to Chester and what you hope your move will change. I’ll meet you with a welcoming conversation and a practical next step.

Plan a Chester move with Kyle →Browse the Chester area page →

Explore the existing Chester neighborhood page and refine your search there. Official town resources reviewed October 30, 2026; check current conditions and property-specific requirements.

LISTINGS

More Listings

1/60 60

Open Sat 2PM-4PM

$ 539,900

2 Beds3 Baths1,999 SqFt

251 Villager RD, Chester, NH 03036

Condo

Listed by Greg Powers of Keller Williams Realty-Metropolitan
1/45 45

Open Sat 10AM-3PM

$ 1,379,900

4 Beds3 Baths3,841 SqFt

109 Crowley RD, Chester, NH 03036

Single Family Home

Listed by Keith Martel of Martel Realty Group
1/47 47

New

$ 635,000

3 Beds2 Baths1,841 SqFt

588 Candia RD, Chester, NH 03036

Single Family Home

Listed by Priscilla Webler of Coldwell Banker Realty Bedford NH Cell: 603-493-0967