Welcome to Winchester

Nestled among lakes and pristine nature reserves, Winchester offers tranquil living and majestic architecture


Winchester is a quiet, picturesque community eight miles from Boston. Once known as Waterfield due to the Aberjona river running through the town and the many lakes dotting the area, Winchester has long served as a tranquil haven just outside the bustle of city life. Magnificent Victorian architecture gives Winchester a sublime, historical charm, and with an easy commute to Boston via car or MTBA, Winchester locals enjoy the best of both worlds.


Ideal for an active outdoor life, Winchester is bordered by Middlesex Fells, a 2,200-acre preserve featuring over 100 miles of trails for hiking, biking, horse riding, and cross-country skiing. In Winchester, you can enjoy fine Italian food and wine at A Tavola or a fine steak at Capital Grille.



What to Love

  • Miles of tranquil hiking trails traversing pristine conservation areas scattered with lakes, ponds, and streams
  • Proximity to Boston’s busy cosmopolitanism and rich cultural scene
  • The Winchester Country Club’s 18-hole golf course with magnificent views of Mystic Lakes
  • Summer swimming at Borggaard Beach and Splash Park in Wedge Pond, in the heart of Winchester

Local Lifestyle

Largely a bedroom community, Winchester is home to many Boston commuters who take advantage of its incredible landscapes for outdoor activities and enjoy spending quality family time in nature. Notwithstanding its provincial ambiance, Winchester is an upscale community offering a country lifestyle with all the trappings. The Winchester Country Club and the Winchester Boat Club provide members with pristine facilities for sports, socializing, and general recreation. The surrounding area of Winchester has more golf links and upscale recreation clubs. The community-focused Wright-Locke Farm offers a bit of everything. It is where residents can enjoy a friends’ night out with high-quality farm-to-table dinners made by visiting chefs in a relaxed outdoor setting. Or patrons can join a workshop, attend a lecture, or pick raspberries on a summer’s day. Winchester is bordered by small towns, each offering its own flavor to local life. Stoneham's climbing gym is three miles away, the neighboring communities have plenty of craft breweries and there are historic sites dotted throughout the area commemorating histories of the Revolutionary War and beyond. 



Dining, Entertainment & Shopping

Winchester’s cozy, small-town atmosphere wouldn’t be complete without delicious locally grown and small-batch craft foods. From June to late October, the vibrant Winchester Farmers Market is where the community gathers for coffee, local vendors, and live music. 


Downtown Winchester has the favored Mamadou’s Artisan Bakery with acclaimed pastries and French bread. Cold-pressed juice from Nourish Your Soul will replenish your body and your spirit. At Capital Grille, you can enjoy world-class wines and dine on the Grille’s signature dry-aged steaks and delectable seafood creations.


Free from the traffic of large towns, Winchester has everything residents need, a supermarket, farmstand stores, some specialty foods stores, and a handful of cafes and restaurants. 



Things to Do

A hundred miles of woodland trails at Middlesex Fells provide peaceful horse rides and easy walks, as well as more challenging hikes and biking. The area’s parks have outdoor fun for the whole family, with kids’ playgrounds, tennis courts, basketball courts, and soccer fields. 


The favored fishing spot is found at the glorious Mystic Lakes. Whether you catch a bass or not, you will enjoy the water from your boat. Upper Mystic Lake is home to the Winchester Boat Club, which hosts social events, and provides sailing, kayaking, swimming, and paddleboarding. 


A notable hub of Winchester’s cultural life is the Griffin Museum of Photography, which hosts frequent exhibitions, artist talks, and events. Locals can also take a variety of classes dedicated to the art of photography, from histories of photography to photography writing, portraiture, and digital editing. 




The Winchester Public School District serves five Elementary Schools, one Middle School, and one High School. There are three private Elementary Schools and one private High School in Winchester.


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