Everything you need to know about living in Winchester, MA

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If you're considering moving to Winchester, MA, or researching Greater Boston suburbs with Winchester on your list, you've found the right video. We'll cover dining, shopping, housing costs, school systems, things to do, distance from Boston, and public transportation. Stick around till the end, because I'll share a tip that can greatly benefit your wallet.

Dining and Cafes: Winchester Center, which, while not huge, packs a punch. There are many dining options, but my personal favorites are Lucia Ristorante for classic Italian, First House Pub, and Black Horse Tavern. If you visit Black Horse, I recommend trying one of their flatbread pizzas. Also, if you hadn’t heard, Karma Asian Fusion will be opening their third location here in downtown. For coffee, you can choose between Starbucks, Café Nero, or the locally owned Bagel Bar. If you're into fruits or smoothies, check out Playa Bowls or Nourish Your Soul for cold-pressed juices.

Shopping: Winchester Center is home to plenty of charming shops and small businesses, particularly boutique clothing stores. There's also a great bookstore called Book Ends and a toy store for kids.

Transportation: Downtown Winchester boasts one of the top commuter rail stations (the other being the Wedgemere stop), both of which will get you into Boston and drop you off right at North Station. It's super convenient if you're planning to catch the 2024 world champion Boston Celtics in action or if you work in the city.

Proximity to Boston: Winchester is located just 9 miles from Boston, with Interstate 93 running right by it if you prefer to drive into the city. Traffic can be heavy in the mornings, taking up to 40 minutes to reach downtown, but outside of rush hour, you can expect a 20-25 minute drive.

Schools: Niche.com gives Winchester's school system an A+ ranking, and US News scored it 96.55/100, and locally is considered one of the top school systems. The town has five elementary schools, one middle school, and one high school, and For younger kids, there are preschool options, but spots are limited, and selection is done through a lottery system.

Real Estate: In 2023, Winchester was the 13th most expensive Massachusetts suburb, with a median single-family home price of $1.468 million. However, prices range widely; some homes sold in the $600,000-$700,000 range, while others climbed to the $4 million mark, especially for waterfront properties on Mystic Lakes. Generally, the northeast and southeast parts of town have smaller homes on smaller lots that are below the median price and are closer to the Fells Reservation and Winchester Hospital. In contrast, the western part of town features larger estates on bigger plots of land, such as in the "Flats" neighborhood, where homes often sell quickly.

Outdoor Activities: If you love the outdoors, Winchester is an ideal place to live. The town borders the Fells Reservation, which spans over 2,200 acres with more than 100 miles of trails for walking, hiking, biking, and horseback riding, as well as numerous bodies of water where you can rent boats, canoes, or go fishing. There are also off-leash areas for your four-legged friends. In the summer, I recommend visting Shannon Beach or Mystic Lakes State Park, both are great options for swimming.
There is also Winchester Country Club (which I believe has a waiting list to get in at the moment) but does offer swimming, tennis, an excellent restaurant, and a golf course with views of the Boston skyline. And no tour of Winchester would be complete without a visit to Mahoney’s Garden Center, a must-see destination for garden enthusiasts. Even if you’re not a gardener, like me, you'll be impressed by the vast selection of plants, trees, and flowers.

Insider Information: After years of working with clients in Winchester, Belmont, Lexington, and Arlington, I’ve noticed a trend. Winchester homes actually sell for the lowest price per square foot among these towns, closer to Medford's pricing. For example, 3,500 square foot home in Belmont would cost you about $2.45 million, while in Winchester, it would be around $1.778 million—a massive savings. So if getting a good value is something that’s important to you, Winchester does have a leg up on it’s surrounding neighbors.


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