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Living a Mountain Lifestyle in Winchester, New_Hampshire

Winchester is a small town in southern New Hampshire home to Sheep Hill summit and Gap Mountain. Winchester is a community of less than 2,000 people. Keene and Brattleboro are the nearest towns. Outdoor activities like hiking, snow shoeing, and good skiing are all relatively close.

Photo of Congregational Church in 1910 courtesy of Wikipedia and Hugh Manatee.

Where to Retire in Winchester and Home Prices

The median home value was $205,754 in mid-2021, according to Zillow.

What Is Special about Winchester

Winchester is a small town in southern NH. Pisgah State Park is nearby.

What Is Not Special about Winchester

It is a small town where the cost of living is above average and the winters are cold.

Climate and Physical Environment

Winchester is near the Mass. border and east of the Connecticut River.  The average July high temperature is 84 and the average January high is 34 (the average low is 11). The wettest month is May (4").

Restaurants & Cultural Scene

There is a pickle festival every September. Sheridan House (1870), the Winchester Historical Society Museum. The Conant Library Museum.


The Crime rate is a little above the national average.

Medical Facilities

The nearest hospitals are in Brattleboro and Keene.


Winchester is about 10 miles from I 91, and the same distance from the AMTRAK station in Brattleboro. Hartford's Bradley Field is one of the closest big airports.

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