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 housing mix, a different school system, a different weekend life, and a different kind of house they do 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. Below is the honest comparison. No town is "the best." There is a best fit for your budget, your schools list, and your commute, and that is what this guide is for.

Windham, the lake town

In Windham, newer construction and older ranches near the town center sit in very different price ranges, so set your search by the house you want, not the town name.

Windham runs its own schools, from Golden Brook Elementary up through Windham High School. Rankings change every year, so look up current results on the NH Department of Education iPlatform school profiles and visit before you decide. My Windham town guide has the rest of the local detail.

Cobbett's Pond is the lifestyle piece. In July it is swimming and kayaking, and in winter it is quiet. Waterfront, water-view, and water-access homes around the pond are three different purchases, and I walk you through which one a listing really is.

The tradeoff is honest. Inventory in a small town is limited, and the right house on the side of the pond you want can take a while to come up. If you need to move on a tight deadline, tell me up front so we can widen the search early.

Derry, the middle ground

Derry is the biggest of the three and has the widest mix of housing, from older homes on the West Derry side and off Crystal Avenue to the nicer pockets of East Derry. Ask me for a current comparable analysis on the streets you like, because prices move month to month. The Derry town guide covers the rest.

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 Academy, an independent academy that serves as the high school of record for Derry and the nearby towns of Auburn, Candia, Chester, Hampstead, and Hooksett through tuition contracts. It is a large school, with a broad range of AP, sports, arts, and career programs. Budget a conversation and a campus visit.

Downtown Derry is the walkable center of town. Hood Park sits right at the heart of it, with coffee, restaurants, and the Derry Opera House nearby. East Derry, up the hill, feels older New England, stone walls and colonial porches. West Derry, along Broadway and the commercial corridor, is more commercial and practical. 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 runs its own school district, separate from both. Its 2025 total tax rate was $14.47 per $1,000, close to Windham's (NH DRA 2025 Municipal Tax Rates). Londonderry High School serves the whole town, with no tuition-contract arrangement like Pinkerton's.

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 the New England picture.

The side closer to the airport and Manchester is more suburban and less scenic, but it shortens the Manchester commute. Woodmont Commons is the newer mixed-use development by I-93, and it is still building out.

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

Rankings move every year and depend on who is doing the ranking, so I point buyers to the sources instead of handing out a number. The NH Department of Education iPlatform publishes school profiles and assessment results for Windham High School, Londonderry High School, and Pinkerton Academy, and third-party sites like Niche publish their own ratings.

The structural difference is easy to state. Windham and Londonderry are in-town public districts. Pinkerton, serving Derry, is a large independent academy that Derry students attend by tuition contract, with the program range that comes with its size.

If a smaller school is the priority, Windham or Londonderry may read better. If you want the scale and the program range, 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, and Londonderry has Exits 4 and 5, with a Boston Express bus stop at North Londonderry (Exit 5). Without traffic, from each town hall to the Massachusetts State House, OpenStreetMap routing (October 2026) puts Windham at about 45 minutes, Derry at about 50, and Londonderry at about 55. Rush hour, snow days, and Friday afternoons run longer.

To Manchester-Boston Regional Airport without traffic, Londonderry is about 15 minutes, Derry about 20, and Windham about 30. If you fly often for work, that difference adds up.

For local driving, Route 102 links Londonderry and Derry, and Route 28 and Route 111 connect Windham to its neighbors. For in-town errands, doctors' offices, and practices, the three towns function almost as one extended neighborhood. 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.

Pick Windham if: the lowest tax rate of the three matters (run it on the property tax calculator), you want Cobbett's Pond as part of your weekend life, and you can be patient for the right listing. Windham rewards patience.

Pick Derry if: you want the widest range of houses to choose from, you have checked out Pinkerton in person and feel good about it (or high school is still years away), and you want a real downtown with restaurants and a walkable center. Derry rewards buyers who know what they want and move fast when it shows up.

Pick Londonderry if: you want an in-town school district, the airport close by, apple orchards over a downtown, and quieter weekends that sound like a feature, not a bug.

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, and how I work with buyers lays out the process. 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.