Winchester

Welcome to Winchester

The town of Winchester has lots of parks and green space; it boasts a small town feel with a vibrant center.

Winchester is a town located in the northern suburbs of Boston, Massachusetts. It is known for its historic homes, excellent schools, and picturesque downtown area. The area has a centralized location, a thriving town center, and its very own boat and country clubs. A quick eight miles northwest of Boston, this affluent town is the 7th wealthiest municipality in Massachusetts and is known throughout the Commonwealth for its large, traditional homes and quaint lifestyle.

Winchester has two “Zone 1” stops on the MBTA Commuter Rail Lowell Line: Wedgemere and Winchester Center. The stops are an easy walking distance of one another. The Lowell Line runs from Lowell to Boston’s North Station, where one can connect with the “T”, Boston’s subway system. Winchester is also served by two bus lines that can bring you to the Orange Line in Medford for connections to points all over Boston and to the popular Burlington Mall for upscale shopping.

A PLACE TO LEARN

Winchester is known for its excellent public schools, which are part of the Winchester Public Schools district and offer a wide range of academic programs and extracurricular activities for students of all ages.

The community of Winchester is home to a variety of schooling options, from reputable high schools to specialized private schools. Winchester’s children enjoy five public elementary schools, including Ambrose, Lincoln, Lynch, Muraco and Vinson-Owen. There is one middle school, McCall, and a high school, Winchester High School. There is also a town-wide public preschool program at the Lynch Elementary school. There are four private schools in Winchester, including Acera, Childrens Own School, Creative Corner Children’s Learning Center and St. Mary’s School.

Winchester’s schools boast high ratings, with most ranking between 7 and 10 out of 10. The yearly expenditure per student is $11,958, landing Winchester in the 81st percentile in the country.

In 2022, Winchester High School ranked #2 in Massachusetts on Boston Magazine’s list of top Public Schools in Greater Boston, with a graduation rate of 98.9% and also being known for its students’ superior performance on the MCAS exams.

A PLACE TO GROW

When it comes to Winchester real estate, Colonial, Cape and Victorian single-family homes dominates. The town also offers several townhome and condominium communities. Most people moving to Winchester and ones that already live in Winchester are families, as people tend to move here for the School System. Young couples who are looking to start a family consider moving to Winchester as well.

A PLACE TO CONNECT

Winchester’s small but vibrant town center is full of small town character. Its town center green is a gathering place for farmer’s markets, summer concerts and Town Day festivities each year. There are a variety of activities to do in and around Winchester, including a few of our favorite:

Visit the Winchester Discovery Center: This hands-on science museum offers interactive exhibits and activities for children of all ages.
Explore the Horn Pond: A great spot for fishing, swimming, kayaking, and picnicking with a playground and a beach area.
Take a stroll through the Winchester Town Common: This picturesque park features a playground, a pond and ducks, a bandstand, and a gazebo.
Visit the Winchester Mystery House: This famous mansion is known for its architectural oddities and features, including secret rooms and staircases that lead to nowhere.
Visit the Stone Zoo: This small zoo features a variety of animals, including otters, bears, and a large collection of reptiles.
Visit the Tufts Library: Not only it offers an extensive collection of books and resources, but also has many children’s programs and events.
Visit the Winchester farmers market: Open during the Summer and Fall, it features a variety of fresh fruits and vegetables, baked goods, and crafts.
Visit the Winchester Sports Park: A great spot for families to enjoy sports like softball, soccer, and lacrosse.
Visit the Winchester Country Club: The club offers swimming, tennis, and other activities for families.
Visit the Winchester Cultural Council: They often host family-friendly events and performances throughout the year.

A PLACE TO EXPLORE

The Middlesex Fells Conservation Area in Winchester is vast and provides visitors with several entrances to the state park. There are multiple walking paths as well as guided tours. Mountain bikers, dog owners, and families with small children all taking part in the beauty of the park.

UPPER HIGHLANDS

Upper Highlands is known for its winding roads, natural beauty, and shade trees. Shingle, Queen Anne, and Tudor style homes and some eclectic examples of these styles dominate the neighborhood. First developed in the late 1900’s, the area has seen recent new construction on subdivided/tear-down lots.

Nearby schools include McCall Middle School, Lincoln Elementary School and Children’s Own School. Nearby grocery stores are Pairings Wine & Food, Super Stop & Shop and First National Stores Inc. Nearby coffee shops include Dunkin’ Donuts, Starbucks and the FULLer CUP. Nearby restaurants include Black Horse Tavern, Comella’s and China Sky.

Residents enjoy easy access to route I-93, Winchester Hospital, Ginn Field, Dennett Park and Wadleigh Park and the recreational opportunities provided by The Middlesex Fells/Long Pond Fells.

NORTH MAIN

From an agricultural and industrial village by the mid-20th century into a predominantly residential community with some light commercial remains – and a mix of housing options, North Main neighborhood transformed from turn-of-the century duplexes and cottages to newly constructed townhouses and single family homes.

Nearby schools include Winchester High School, Lynch Elementary School and St Mary’s School. Nearby grocery stores are Super Stop & Shop, First National Stores Inc and Pairings Wine & Food. Nearby coffee shops include Gluten Free Me Bakery and Cafe, Dunkin’ Donuts and Bruegger’s Bagels. Nearby restaurants include Toscano’s Italian Kitchen, Fen Yang House and Burger King.

Residents enjoy easy access to Horn Pond and its walking path, Loring Field, north Main Street retail, NextDoor Center for the Arts/Kidstock! Theater and Winchester Indoor Lawn Tennis Center.

THE FLATS

With impressive examples of late Victorian architecture that prevailed in the area and developers who laid the streets out on a grid, not found in other areas of town in the 1890’s, The Flats is recognized as one of Boston’s first planned suburban developments. Queen Anne, Colonial Revival, and Tudor style homes also dominate this area. The land here is truly flat (thus having the name “the Flats”) and lot sizes are generally uniform in shape ranging from approximately 8,000 to 18,000 square feet.

Nearby schools include Ambrose Elementary School, Lynch Elementary School and Lincoln Elementary School. Nearby grocery stores are Pairings Wine & Food, Super Stop & Shop and First National Stores Inc. Nearby coffee shops include La Patisserie, Bruegger’s Bagels and the FULLer CUP. A few of the nearby restaurants include A Tavola and D’Agostino’s Delicatessen.

Residents enjoy the wide sidewalks and strong neighborhood spirit in the Flats, with close proximity to Winchester Center, Middlesex Park, Elliot Park, Winter Pond, Borggaard Beach, FAN Splash Park, Town Clay Tennis Courts, commuter rail station and Route 3, you can really have it all at Winchester Flats!

WEST SIDE

The rolling farmland and fields of west Winchester changed dramatically in the years following WWII. With population growth and the need for housing came speculation and development outside of the established areas closer to town. Homes on the west side are generally on bigger lots (15,000-20,000 square feet and more) than those on the east side of town and reflect the popular styles of the time when they were built, including: Split-Level, Ranch, Cape and Colonial. The Ledges, Winchester’s largest townhouse community, is located here.

Nearby schools include Ambrose Elementary School, Vinson-Owen Elementary School and Lynch Elementary School. Nearby grocery stores are Whole Foods Market, Tuesday Morning and Pairings Wine & Food. Nearby coffee shops include Dunkin’ Donuts, Allegro Coffee Company and La Patisserie. Nearby restaurants include Taqueria, Papa Gino’s and The Local Woburn.

Residents enjoy amenities including West Side Field, Robert Nutile Fields, Locke Farm, Sachem Swamp and Winchester Swim and Tennis Club (private) with close proximity to Town of Lexington/Burlington Mall/Lahey Clinic and easy access Route 128 and other major highways.

LOWER HIGHLANDS

First developed in the late 1900’s, Lower Highlands area has seen recent new construction on subdivided/tear-down lots. The neighborhood is known for its natural beauty, winding roads, and shade trees. Tudor, Shingle, and Queen Anne style homes, including some eclectic ones dominate that makes this neighborhood full of character.

Minutes walk to McCall Middle School, Lincoln Elementary School and St Mary’s School. Nearby grocery stores are Pairings Wine & Food, Super Stop & Shop and First National Stores Inc. Nearby coffee shops include Dunkin’ Donuts, Starbucks and the FULLer CUP. Nearby restaurants include China Sky, Comella’s and Pizza in Piazza.

Residents enjoy easy access to town’s commuter rail, with close proximity to Town Center, Winchester Hospital, Highland Park, Wadleigh Park, the recreational opportunities provided by the 2200+ acre Middlesex Fells/Long Pond and just minutes drive to Boston on 93.

EAST HILL

The popular neighborhood known as “East Hill” is tucked between Highland Avenue and The Fells, south of Main Street. The location offers easy access to Medford, Boston and Winchester Center as well as the Fells.

Closer to Highland Avenue, you find classic Colonials from the 1920’s. Further east are some of Winchester’s “newer” houses, Capes and Splits that came with post-war development. Because of their generous lots, some of these houses have recently been replaced with expansive Contemporaries.

Residents enjoy easy access to the city via Route 93 commuter trains, with close proximity to Ginn Field, Wadleigh Park and Winchester Community Music School.

SYMMES CORNER

This area along Main Street going towards Medford gradually developed as Winchester evolved into a residential community in the 1880’s. Several lovely 18th century houses built by the industrious Symmes family, who originally owned and worked this land (once in fact part of Medford), can still be found at the rotary. A mix of Federal, Colonial, Greek Revival, Italianate, and Colonial Revival houses are found along Main and its sloping side streets. This area is particularly popular with commuters who want easy access to both bus and train transportation.

Nearby schools include Children’s Own School, McCall Middle School and Lincoln Elementary School. Nearby grocery stores are Pairings Wine & Food, Super Stop & Shop and First National Stores Inc. Nearby coffee shops include Dunkin’ Donuts, Starbucks and La Patisserie. Nearby restaurants include Black Horse Tavern, Comella’s and D’Agostino’s Delicatessen.

Residents enjoy easy access to Winchester Town Center via Route 93 or Wedgemere commuter rail station and close proximity to Dennett Park, Wadleigh Park, Ginn Field, Middlesex Fells Reservation & Community Music School.

GROVE STREET

Grove street is a small, close-knit community that is very proud of its architectural heritage with historically significant properties that stands as a monument to town’s history and inheritance.

Nearby schools include Children’s Own School, McCall Middle School and Lincoln Elementary School. Nearby grocery stores are Pairings Wine & Food, Super Stop & Shop and First National Stores Inc. Nearby coffee shops include La Patisserie, Dunkin’ Donuts and Starbucks. Nearby restaurants include Black Horse Tavern, A Tavola and D’Agostino’s Delicatessen.

Residents enjoy easy access to Ginn Field, Dennett Park and Winchester Town Center.

MYOPIA HILL

The area known as “Myopia Hill” is found in the hills just west of Cambridge Street, overlooking upper Mystic Lake, close to the Arlington border. Its name harkens back to the late 1800’s when it was the home of the Myopia Hunt Club (named in jest for its near-sighted founders), now located in Hamilton, MA.

This part of town was not systematically developed like other parts of Winchester. Around 1900, individual citizens began to build grand homes on the wooded, sloping land that afforded lush, private settings for beautiful Federal, Colonial, and Tudor style homes. Early residents included Governor Samuel McCall and William F. Schrafft, candy company founder, whose impressive homes still stand. Large Capes and Contemporaries came later when substantial lots were subdivided.

Nearby schools include Ambrose Elementary School, M Norcross Stratton Elementary School and Vinson-Owen Elementary School. Nearby grocery store is Whole Foods Market and Tuesday Morning. Nearby coffee shops include La Patisserie, the FULLer CUP and Dunkin’ Donuts. Nearby restaurants include A Tavola, and D’Agostino’s Delicatessen.

Residents continue to enjoy the privacy provided by the generous lots as well as the beautiful setting. With close proximity to West Side Field, Mullen Playfield, Sachem Swamp, Upper Mystic Lake, Arlington Center and two private clubs – the Winchester Country Club and the Winchester Boat Club, you’ll really love living here.

WINCHESTER SCHOOLS

The Winchester Sports Foundation
Sports and fostering young athletes is very important to Winchester High School. According to their official website, “The Winchester Sports Foundation was organized in 1989 by a group of Winchester parents and sports enthusiasts as a result of severe budget cuts to the Winchester High School’s athletic budget. That year the athletic budget faced a $60,000 deficit and the high school considered instituting a $35 per student “sports and transportation fee. To negate the need for this fee, the Foundation raises money from an annual golf tournament, an annual campaign, and through individual and corporate donations.”

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