I’m not your typical “checklist” inspector.

Keene & the Surrounding Towns

Keene is the hub of the county, and the towns ringing it each have their own building character. Keene itself mixes downtown Victorians, mid-century neighborhoods near Keene State, and newer construction on the outskirts. Marlborough, just southeast on Route 101, grew up around a granite industry and later became home to Keene State College’s satellite presence — expect a mix of older village homes and properties stretching toward Dublin Lake. Swanzey, south of Keene along Route 32 and the Ashuelot River, runs from the West Swanzey covered bridge village out to newer subdivisions, and its river-adjacent lots come with their own moisture and grading questions I check for specifically. Surry and Sullivan, just north and northeast of Keene, are smaller and quieter — older farmhouses, camps, and a lot of well and septic systems rather than municipal hookups, which changes what I’m focused on during the inspection.

Up the Connecticut River — Walpole, Westmoreland & Chesterfield

This stretch of the county runs along the Connecticut River and has its own microclimate and building stock. Walpole is the anchor — agricultural land, a strong historic village center, and homes ranging from older farmhouses to high-value river-view properties. Westmoreland sits just south, equally rural, with similar river-valley conditions and a mix of working farms and older homes that often have had additions or outbuildings added over the decades — I look closely at how those additions tie into the original structure. Chesterfield, including the West Chesterfield village along the river and the Spofford Lake area, has both classic New England farmhouses and lakefront camps and homes, each with different concerns around drainage, foundation movement, and (for the lake properties) moisture and ventilation.

Further south, Hinsdale sits at the very bottom of the county where the Connecticut and Ashuelot Rivers meet, right on the Massachusetts and Vermont lines. It’s another river-valley town with the same attention to grading, sill condition, and foundation moisture that the rest of this corridor calls for, plus its own mix of older mill-adjacent homes and more rural outlying properties.

Further north on the river, Charlestown and North Walpole sit right along the Connecticut as well, with the same older river-valley housing stock and similar attention needed around grading, sill condition, and foundation moisture from proximity to the river.

The Monadnock Towns — Jaffrey, Rindge, Troy & Fitzwilliam

This is the Mount Monadnock corner of the county, and it’s a mix of historic village centers and newer development drawn by the mountain and the lakes. Jaffrey and Rindge both have established pages with more local detail. Troy, between Jaffrey and Fitzwilliam, is a small mill-town center with older homes built close to the village and more rural property on the outskirts. Fitzwilliam, right on the Massachusetts line, has a well-preserved colonial village green and a building stock to match — older homes where understanding period construction matters as much as understanding current code.

Peterborough & the Eastern Towns

Peterborough is the commercial center on this side of the county, with its own dedicated page covering the local detail. Dublin, just west of Peterborough on Route 101, is home to Yankee Magazine and The Old Farmer’s Almanac, and the town center sits at one of the highest elevations in the state — homes here range from historic properties near Dublin Lake to newer construction on the surrounding hills. Harrisville, north of Dublin, is one of the best-preserved 19th-century mill villages in the country, with brick mill buildings and homes built right into that industrial-era footprint — a different inspection conversation than a 1990s build, and one I’m used to having.

The Quiet Hill Towns — Gilsum, Marlow, Stoddard, Nelson, Roxbury, Richmond

These are the smaller, more rural towns in the county, and they don’t get a lot of attention from inspectors who only work the bigger markets — which is exactly why I make a point of covering them well. Gilsum, built around its Stone Arch Bridge on the Ashuelot, is small and rural with a lot of older homes and camps. Marlow and Stoddard, further northeast, are lake and woodland towns — Stoddard in particular has a lot of camp-style and lakefront properties around its ponds and near Pitcher Mountain, which means moisture, ventilation, and seasonal-use construction are common themes. Nelson, one of the smallest and oldest-platted towns in the county, and Roxbury, formed out of pieces of Keene, Marlborough, and Nelson, are both rural with older, often owner-modified homes. Richmond, in the southwest corner near the Massachusetts line, is similarly rural and agricultural. I inspect in all of these towns regularly, and the lower density doesn’t mean lower complexity — older wells, older septic systems, and decades of incremental additions are the norm, not the exception.

Nearby Monadnock Region Towns

A few towns just outside Cheshire County’s official line are close enough, and similar enough in character, that they’re part of the same practical service area. Acworth and Lempster sit along the Sullivan County line northwest of Alstead and share the same rural, well-and-septic building stock as the towns around them. Washington, tucked in the hills toward the Sullivan/Hillsborough line, is one of the higher-elevation, more remote towns I cover. Antrim and Hancock, just east of the Monadnock region’s core, and New Ipswich, Greenville, and Greenfield, toward the Hillsborough County line, round out the towns where I’m regularly called for inspections even though they fall just outside Cheshire County on a map. If you’re in one of these towns and wondering whether you’re in my service area, the answer is yes.

Check out the full list of Service Areas here.