Windham, Derry, or Londonderry? A Buyer's Guide to Picking the Right Southern NH Town

Why these three towns get cross-shopped

Almost every buyer moving into Southern NH ends up comparing these three towns. They sit next to each other on I-93, they share Route 102 as the local spine, and on a Zillow search they look close enough to treat as interchangeable. They are not.

Windham, Derry, and Londonderry each have a different price band, a different school system, a different weekend life, and a different kind of buyer they fit best. Picking between them is usually less about square footage and more about what you want your Saturday to look like five years from now.

I show homes across all three every week. Below is the honest comparison. No town is "the best." There is a best fit for your budget, your kids, and your commute, and that is what this guide is for.

Windham, the premium

Windham is the premium and it will show up in every price search you run. Single-family median sits around $725K in 2025 data, with new construction on the north side pushing well past $1M. Older ranches near the town center still come in below that, but they move fast, often under a week, and often with multiple offers.

The school district is the draw that keeps Windham's inventory thin. Windham High scores consistently at the top of Southern NH public schools, and the feeder pattern through Golden Brook Elementary is a line families will move for. Per-pupil spending runs above the state average, class sizes stay reasonable, and the athletic and arts programs punch above the enrollment numbers.

Cobbett's Pond is the lifestyle piece. The town beach is a resident-only perk, and it matters more than people expect when they tour the area in April. In July it is swimming and kayaking. In January it is skating. There are good streets on all sides of the pond: Canobie Road runs the west shore, London Bridge Road curves along the north end, and North Lowell Road holds some of the prettier older homes near the meetinghouse. If you want a sense of the town, drive those three at dusk on a Tuesday.

The tradeoff is honest. You pay more, inventory is thin, and the seasonal turnover is slower than the other two towns. You will sometimes wait three or four months for the right listing on the side of the pond you want. If Windham fits the budget and the school draw matters, that wait is usually worth it. If you need to move in 60 days, Windham may push you into a compromise you will regret.

Derry, the middle ground

Derry is the widest price spread of the three. Starter homes still exist under $400K, particularly on the West Derry side and in the older neighborhoods off Crystal Avenue. The higher end runs up to $750K on the nicer pockets of East Derry and near the Rockingham County line. A Derry buyer on a $500K budget has real options. A Windham buyer on that budget is mostly looking at 40-year-old ranches that need work.

Pinkerton Academy is the thing every buyer asks about and nobody outside Southern NH understands. Derry K-8 is Derry public schools. High school is Pinkerton, which is technically a private academy but serves as the public high school for Derry, Auburn, Chester, Candia, and Hampstead via tuition contracts. About 3,000 students total. Some families love the scale, it means AP options, sports depth, and arts programs a small-town high school cannot match. Others find it too big and transfer to the Derry Public Charter or cross-district options. Both reactions are common. Budget a conversation about it.

Downtown Derry has been quietly reviving over the last five years. Hood Park sits right at the heart of it, with walkable access to coffee, restaurants that stay open past 8 PM, and the rail trail that runs all the way through town. East Derry, up the hill, feels older New England, stone walls and colonial porches and the original meetinghouse. West Derry, down along Broadway and the commercial corridor, is more working, more practical, more affordable. Each side feels like a different town. Tour both before you commit.

The tradeoff is mostly the Pinkerton conversation and the wider condition variation. Derry has more inventory, which means more room to negotiate, but it also means more homes that need meaningful work. A good inspection and a good agent who knows the local builders matter more here than in Windham.

Londonderry, the third way

Londonderry sits between the other two on price and runs its own school district, separate from both. Median single-family prices land roughly in the mid-$500Ks to low-$600Ks depending on the pocket. Londonderry High has its own strong reputation, feeding from Moose Hill and the other elementary schools, and it does not share the scale-concerns or the private/public complication that Pinkerton carries.

The eastern side of Londonderry is apple country. Mack's Apples has been there for generations, the orchards roll through the back roads, and in late September the town smells like cider and wood smoke. That is the Londonderry you move to if you want that New England picture without Windham's price ceiling.

The western side, closer to Manchester and Route 28, is more suburban and less scenic, but gets you closer to the airport and the Manchester commute. Woodmont Commons is the newer mixed-use development on that side, and it has changed the character of that corner of town noticeably over the last few years.

The tradeoff: Londonderry does not have Derry's downtown energy. The restaurants close earlier, the walkable commercial strip is smaller, and the weekends are quieter. Some buyers love that. Others find it isolating after a year. Know which one you are before you commit.

Schools, head to head

On pure academic ranking, the order is Windham, Londonderry, Derry. That is the consistent pattern across standardized test results, teacher-to-student ratios, and per-pupil spending data over the last several years.

Windham High runs roughly 12:1 student-to-teacher, with per-pupil spending above $19K and consistent top-tier results on NH state assessments. Londonderry High sits solidly in the upper tier, closer to 13:1 ratios, strong extracurriculars, and a well-regarded athletic program. Pinkerton, serving Derry, is harder to benchmark because of its scale and its unusual structure, but academically it competes with Londonderry on AP pass rates and college placement while offering program depth neither of the other two can match.

If your kids thrive in a smaller, tighter environment, Windham or Londonderry read better. If your kids want the scale, the sports depth, or the specialty programs (Pinkerton has a working farm and technical programs most NH high schools do not touch), Derry-to-Pinkerton can be the right answer. Visit before you commit. Tour all three if you can. Schools are the decision that ages the worst when you get it wrong.

Commute realities

All three towns sit on I-93, but not at the same exit, and not at the same distance from Boston.

Windham is Exit 3. Derry is Exit 4. Londonderry is Exit 5. Commute to Boston (North Station area) in typical morning traffic: Windham 45 to 55 minutes, Derry 50 to 60, Londonderry 50 to 65 depending on which side of town you live on and whether you are coming out of an eastern neighborhood or a western one. The spread widens significantly on snow days and on Fridays after 3 PM.

To Manchester-Boston Regional Airport, all three towns are in the 15 to 25 minute window. Londonderry is closest, Derry is middle, Windham is furthest. If you fly weekly for work, that 10-minute delta matters more than it sounds.

Route 102 runs through all three as the town-to-town local spine and will be the road you use more than you expect. Windham to Derry via Route 102 is about 30 minutes off-peak. Derry to Londonderry is about 10. For in-town errands, doctors' offices, and kids' sports practices, the three towns function almost as one extended neighborhood along that corridor. The choice is really about which end you sleep on.

How to choose

A simple decision tree, based on the patterns I see with buyers every month.

Pick Windham if: budget is comfortable over $700K for a single-family, the school district is the top-three reason you are moving, you want Cobbett's Pond as part of your weekend life, and you can wait three-plus months for the right listing. Windham rewards patience.

Pick Derry if: your budget starts at $400K to $500K and needs to stretch, you have checked out Pinkerton in person and feel good about it (or your kids are still years away from high school and you can make that call later), and you want a real downtown with actual restaurants and a walkable rail trail. Derry rewards buyers who know what they want and move fast when it shows up.

Pick Londonderry if: your budget is middle-ish ($500K to $650K), you want strong schools without Windham's price ceiling and without Pinkerton's scale, you prefer apple orchards to downtowns, and quieter weekends sound like a feature not a bug. Londonderry rewards the buyers who want the New England picture without the Windham premium.

If you are still genuinely torn between two, tour a listing in each on the same Saturday. That is the honest test. If you want to talk through your specific budget and school situation, there is a 30-minute consultation slot on the calendar. Pick one. The rest of the decision gets easier once we map your numbers to real streets.

For buyers moving up from Massachusetts, there is also the tax and registration piece to factor in. That is covered in the honest MA to NH relocation guide. And if Salem is on your shortlist alongside these three, the Salem NH neighborhood guide walks the same terrain for that town. You can also browse all of the Southern NH neighborhoods on one page.