Winchester

Explore Winchester Highland’s carefully organized residential blocks and one will find an eclectic mix of homes that share a certain grandeur no matter what era they were built. But that’s just one line on a long list of appeals here. This neighborhood opens the door to one of the best public school districts in the state, offers access to a variety of expansive outdoor recreation opportunities, is conveniently situated in relation to Winchester’s downtown and posts CAP Index crime scores much better than the national average. “Winchester is a beautiful town,” says Winchester Highlands resident Christina Larson, owner and principal of Larson Financial Planning. “And the Winchester Highlands area is very close to beautiful walking trails and forests. Winchester’s also strategically located so it’s easy to get to the highway, and the schools are superb.” The houses in Winchester Highlands include ones built in the late 19th century, others built over the course of the 20th century and even some built in recent years. Yet the homes here seem to include style elements that lend to a level of harmonious uniformity, like vibrant vinyl siding and shutters. “There’s a very diverse stock here. There are ranches, there are colonials, there are two-families. Houses here are 100 years old and there are a lot of new houses,” says Larson. Winchester Highlands features straight-line blocks accented by mature trees on spacious lots. Many of the neighborhood’s properties stretch at least 6,000 square feet, enough for both a front and back lawn. Price tags here often fall between $1 million and $2 million. Some come to the area just for the schools, Larson says. And it makes sense — the Winchester Public Schools system boasts an A-plus overall rating on Niche and is No. 10 on the site’s list of the best school districts across Massachusetts. Many of the neighborhood’s homes are within reasonable walking distance of the A-rated Muraco Elementary, which offers before- and afterschool programming through the area organization Kidsborough. Students in town can then advance to the A-plus-rated McCall Middle, whose extracurricular opportunities include everything from a Coding Club to Model UN. Winchester High School also carries an A-plus grade and features a dedicated technology department with classes on topics such as web design, robotics and engineering design. Streets around Winchester Highlands are lined with sidewalks, and it’s common to see people out and about, taking a walk on a nice day. And that’s just the tip of the iceberg when it comes to outdoor opportunities here. For one, part of the 2,200-acre Middlesex Fells Reservation spills into the neighborhood. “I would say the Middlesex Fells is probably the most important outdoor feature,” says local Realtor Naomi DeLairre, of Barrett Sotheby's International Realty. “It’s a nature preserve shared by Winchester, Medford and Stoneham. It’s acres and acres of natural reserves.” Middlesex Fells features more than 100 miles of trails to peruse. The almost 7-mile Tri-Community Greenway runs through Winchester Highlands as well, a paved path locals use for walking, jogging and biking. Winchester High is primarily residential, but it does have a couple of options for locals looking to grab a bite to eat. Eighty Eight Cafe is a well-liked Chinese takeout spot in the neighborhood. And those with a sweet tooth can enjoy The Gingerbread Construction Co. “That’s a favorite spot for wonderful cakes and muffins,” Larson says. Winchester Highlands residents can also hop in the car for a quick ride to the Winchester Center area to choose from an assortment of more restaurants, like Italian institution Lucia Ristorante or First Horse Pub, popular in part for its burgers. There’s also a Stop & Shop in the Winchester Center area, which is convenient for picking up groceries and other essentials. Among Winchester Highland’s other perks is a medical center right in the neighborhood, Winchester Hospital, which has 229 beds. Neighborhood residents can take advantage of their proximity to the Winchester Center area to quickly hop on the Massachusetts Bay Transportation Authority commuter rail. The Winchester Center station is part of the Lowell Line and can take riders down to Boston in roughly an hour. The station is currently being renovated and is scheduled for a partial reopening in July 2024. Drivers in Winchester Highlands can also hop on nearby Interstate 93 for commutes to Boston, just about 11 miles away. Winchester Highlands locals can jump down to the center of town for an annual tradition each June: Winchester Town Day. Town Day celebrates the start of summer with a Friday block party, a Saturday street fair and fireworks in the evening.

Located about 7 miles northwest of Boston, Symmes Corner attracts homebuyers seeking a strong school system, lavish homes and proximity to a quintessential New England town center. Kim Covino, resident and top agent in Winchester with Compass Real Estate, says the architecture here “has old-world charm, a lot of detail and a lot of character,” which captures the traits of the whole neighborhood. Outdoor recreation spaces surround the otherwise residential enclave, offering miles of hiking trails that lead to Middlesex Fells Reservation and the South Reservoir. The neighborhood also has a CAP Index crime score of 1, significantly lower than the national average of 4. Symmes Corner provides a suburban atmosphere within close reach of Greater Boston amenities, ideal for those who crave a quiet, slower pace by night after a commute into the city for work. Students here can attend the highly rated Winchester Public Schools. The system includes five elementary schools, one middle and one high school and has an A-plus rating from Niche. The Winchester system also ranks in the top 1% on Niche’s Best Districts in America list. Children can begin their education at Lincoln Elementary School, which earns an A, and McCall Middle School, which has an A-plus. McCall students can choose from extracurriculars including an improv club and the Heritage Singers ensemble, which performs around the state. Students at Winchester High School, which also scores an A-plus, can enroll in computer animation, forensic science and songwriting. Residents frequently utilize the paths and trailheads near the Symmes Corner neighborhood. To the west, Upper Mystic Lake features a state park, boat clubs and a 3-mile lake trail, popular for birding, hiking and running. It also has Shannon Beach, often used for rowing, sailing or relaxing on the sand. To the east of Symmes Corner, Middlesex Fells Reservation includes countless trails, beaches, viewpoints and ponds. It also features the Sheepfold Dog Park, which has an off-leash area. Covino notes that sports are another big draw for the area. “Any activity that a parent or child could want, you can find it here,” she says. Through Winchester’s Recreation Department, folks can participate in sports such as t-ball, soccer, fencing and ultimate frisbee. The department also offers children’s summer programs where kids can create board games and learn to cook. Residents have shopping and dining necessities within 1 mile at Winchester’s town center, including Stop & Shop on Main Street and The Farmstand at Mahoney’s, a family-run home and garden center stocked with local products. The town’s appreciation for high-quality food extends to its restaurant scene. Black Horse Tavern, a locally owned pub-style restaurant serves burgers, steaks, seafood and pizza from a scratch-style kitchen. “It's a great meeting spot for food, drinks and live music,” Covino says. Another option, A Tavola, serves popular family-style meals that can feed up to six people. Locals can enjoy coffee and all-day breakfast options from Caffè Nero, a popular chain throughout the Greater Boston area. Restaurants sit among various practical services, gyms and shops, such as Book Ends and Pondview Florist. Winchester also has Christian churches and the Temple Shir Tikvah nearby. With Winchester’s community calendar jam-packed full of activities, Symmes Corner residents always have a unique event on the horizon. The town hosts Winchester Town Day, an annual celebration that includes games, eating competitions and a fishing derby. The Town Common, a small green oasis in a central location, holds the Winchester Farmers Market from June through October. Seasonal events include the holiday Best in Stroll Dog Show and Trolls on the Stroll Scavenger Hunt, where participants search for gnomes inside local businesses in hopes of being first to meet Santa. Streets here feature well-groomed lawns, shaded by mature trees. Houses bear an array of architectural styles, from colonials and modest Capes to striking contemporary builds. Home prices soar past Boston’s average of about $750,000, often running between $1 million and $3 million. Still, moderately priced homes do pop up in the market. For example, on Lake Street, three-bedroom townhouses are priced just below $600,000, and on Swanton Street, one-bedroom penthouse units go for about $400,000. Most homes in Winchester are clustered into subdivisions, many of which sit within walking distance of the town center. With a location 7 miles north of Boston, proximity to Interstate 93 and Winchester’s two train stations, transportation options abound near Symmes Corner. Wedgemere and Winchester Center both fall on the Lowell Line commuter rail, which leads to North Station downtown. For air travel, Boston Logan International Airport sits about 10 miles southeast. Residents can also easily access health care about 2 miles away at Winchester Hospital.