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.
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.
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.
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.
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..
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.
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.
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.
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.
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.
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